Prologue
Early Life
My parents were totally involved in the family winery biologics business when I grew up, so my older sister became the "go to" babysitter.
Happily for me, my sister figured out that I was more sister than brother so in simple child logic, when we played dress up games she played mommy and I became her daughter, Chrissie.
She always had a lot of clothes for me and I jumped to the chance to play dress up whenever we had the opportunity. When we were in her room would she play "mommy" and wag her finger and sternly order me to me take off my dirty outdoor clothes and "dress like a lady"!
Then she would mother me and lay out things to help me to put on, which would usually be a dress or nightgown of some sort and maybe some Barbie socks or tights and then she put some barrettes in my hair. She would dress me up as she playfully scolded me for being a bad girl for not knowing how to dress appropriately. Then when I was "dressed properly" we would sit and watch TV or read her girl's magazines. We'd point and talk about what outfits were the prettiest, and giggle as we pointed at who we thought was the cutest boy.
As I turned about ten, my sister got a Barbie make up set with all manner of blushes, eyeliners and lipsticks, nail polish. The works! I loved make up!
Mom or dad would check on us "girls" and see me happily playing in my sisters nighty and pink socks, complete with make up and pink nails and glitter. They would smile and roll their eyes, but I loved it!
About that time she got me to wear her panties as part of our play. She always told me how pretty I looked in them, and how silly looking my "boy panties" were. I loved to wear panties whenever I had the chance.
She didn't seem to mind me wearing hers, but a couple of weeks later she told me to ask mom to buy me some panties of my own. She seemed to think mom would be OK with it but I saw no problem just wearing hers. Shortly after that, a package of pretty Barbie panties appeared in my sisters drawer that she said were just for me!
One night I absent mindedly sat down with mom, dad, and my sister to watch TV before bedtime. I had on one of my sister's nightgowns that I had claimed as my own. I had on the pink Barbie panties and socks that went with it. I didn't feel the slightest bit uncomfortable about the way I was dressed when I joined them.
It was the first time I left my sisters bedroom in her nighty. It just felt so natural, I guess I forgot. Mom and dad looked at me, but didn't say a word. They must have understood by now that I was not going to outgrow being interested in girl things. Oddly, When it was bed time rather than just mom or dad, they both came in together and kissed me goodnight. I began to wear a nighty to bed every night every night.
There was many a night when dad was working late or out of town that my sister and I snuggled up on either side of mom and watched TV. Mom would sometimes comb my hair into a playful style and put in a couple of barrettes.
She would put pull up a blanket and put her arms around us, and we would watch TV in our night gowns. I remember how nice it felt to snuggle up to mom and get a kiss on the top of my head with a special snuggle as she rubbed my arm while we watched the program. I'd usually fall asleep with my head resting on her soft boob when she gently woke us up for bed.
When I was around eleven, Mom and I were at Sears one day and she got me some jeans and a couple of shirts in the boy's department. When we were about to leave, she paused and asked me if I needed anything else.
I told mom I wanted a new nightgown of my own. She thought for few seconds and then escorted me to the girls sleepwear section where I spent quite a few minutes looking for something I liked oblivious to being in boy clothes. Finally, I picked out a pink nightgown with puffy gossamer sleeves that flared out and came to my mid calf.
She checked the size and got one size larger, adding: "You probably need some panties, too."
She took me to the girls underwear section where I picked out a package of "Hipster" panties in assorted colors and showed them to mom.
"Honey, those are the wrong size. You wear a girls size 7/8" she said, getting the right size and putting it in the basket.
"You need some socks, too. The ones you have been wearing are getting worn out." she said, kindly.
I picked a package of some frilly ones in various colors.
"Those are too small, Honey. I think you need a medium." she said as I found a package that was the correct size.
From then on mom and I would shop for boy clothes, then we'd go into the girls department and she would let me pick out a thing or two.
And so Mom and dad took the path of least resistance and started treating me like a daughter on the one hand, and a boy on the other. Mom arranged a drawer in my room so when she did laundry so she had some place to put my "pretties" as she called them. It wasn't long and I needed two drawers and extra hangers! I could wear girl clothes in the house when I wanted, but the firmest rule was: No girl clothes outside, ever!
When I was in middle school I became glued at the hip with a certain boy named Brian. She asked me about him and I got evasive. With some motherly persistence, she came to the conclusion that I had a crush on him. Mom kept probing and finally dragged out of me that he and I stopped off at his house on the way from school and played in his room.
His mom worked so I lied that we had touched each other but nothing more. She was really concerned and wanted to know if he had an older brother or if there were other boys in the house. Since he did not, mom seemed to relax and said it was OK if I stopped there for a few minutes, but not to say very long unless I call her first. When my sister was babysitting me I had a lot more leeway to play with Brian.
Once out of the blue, Brian's mom invited me to spend the night at his house. When I asked mom if I could go, she and his mom had a long chat and decided it was OK as long as I wore boy's pajamas.
His mom was really nice, and his dad didn't live there with them. There was one bed in his room and his mom said we would have to share it, which was cool. He and I mostly played with our toys, but when his mom fell asleep on the couch, she awoke and went off to bed as if she forgot about me.
That gave us the chance to get serious about exploring each others bodies. We did a little kissing, but mostly got naked and sucked each others cocks. I don't remember ever coming, but I remember I really enjoyed sucking his cock!
In fact, we both seemed to like it, and it seemed perfectly OK to us. As time went on we spent a lot of time sucking and getting naked and playing in his mother's panties and nighties.
I snuck over there a lot after school when my sister was in charge and mom was working. In fact, Brian and I were pretty much each others only friend in school. Both mom's probably knew what we were really doing and relaxed the rules a bit. Mom's are like that. It's not like pregnancy is an issue.
After I turned about thirteen, my mom and I had "The Talk". Mom told me she wanted to talk about "boys". My dad decided to let mom handle it, which was fine by me.
My parents knew most of everything that was going on with me, and it was getting harder and harder to pretend like everything would keep going on as they were. Even though mom knew I was gay and feminine, I was very defensive and evasive at first. Once I started talking, I could not hold back. I told her everything.
I confessed that I avoided doing the things the other boys did particularly when they played sports. I didn't like getting thrown around and getting bruised up. She drew out of me that the other boys teased me and called me "gay" and that I was afraid they might hurt me, so I stayed with Brian or close to the girls when I could. She asked me if there were any girls I might like to kiss.
"Not really." I replied.
She smiled when we discussed my dressing in girls clothes and my sister a bit, and I admitted I liked it. I agreed that it would be fun to dress as a girl if that meant I could be treated like one by other girls and the boys wouldn't beat me up.
Circling like a hawk, she finally pried my confession out of me that I found myself getting aroused by some boys but not others, but especially by Brian. When she asked me if I had let him kiss me on the lips, I blushed bright red and smiled. Then I nodded my head "yes". She asked me if we got naked together, and I admitted we did, and that I had worn his mother's nighties and we got in his bed together.
Thankfully, she didn't ask for details and ended our conversation with: "Thats OK, honey. Thank you for being honest with me about it. I can't be a good mother if you hide things like this from me. It's OK to like boys, just be cool about it."
Look back, I'm sure mom just wanted me to admit it to her to get it off my chest and let her reinforce that she loved me and she was OK with me being gay. After that she openly talked to me about girl things, boys, and being gay.
I continued to live at home, go to school, and work in our lab and in the plant, and learn the family business.
Socially, I was nowhere. I was a big zero. The feeling of despondency led to me to experiment with hormones when I was eighteen and still living at home.
I had naturally grown two nicely formed, womanly nipples and noticeable breast tissue by time I was thirteen! I actually felt OK about it and was a bit obsessed about my development and peeked at my mom or sister when I could.
When I graduated from high school, I had still not grown the wide shoulders like most boys did. Instead I grew hips. I could wear and pretty much fill one of my sisters old 34AA bras. It may not seem like much to a female, but to me it was a lot! My nipples were at least 3/8" across, and my areolas were 1". I could play with my nipples and nearly reach orgasm!
It so happened that I stumbled into a relationship with a boyfriend who studying to be an RN and was working in a clinic. I was not very manly to begin with, and he was attracted to my femininity. As we got to know each other, he asked me if I ever had my testosterone tested. I had not, so he took to a gender clinic and I gave a blood sample and had it tested. I also gave them a sperm sample. My testosterone was very low, and my sperm count was almost in the infertile range.
One conversation led to another, and finally confided in him I wanted to be less manly and wanted to "soften up". I had been studying the hormones necessary to make some changes, but I didn't know how to get started. Considering nature seemed to have taken me part way, I felt I could go a little bit farther!
He suggested estrogen injections, combined with anti-androgen pills to inhibit testosterone production because they both were available on line. Shots were simpler and safer and he could show me how to administer the weekly shots when he wasn't available.
First we went to the clinic and got a blood test. My testosterone level was 105 and was considered to be low. He told me we would lower my testosterone with the anti-androgens, making the estrogen more effective. He also said he would check into adding a progesterone if my blood tests are normal. I will need to get a blood test from time to time at the gender clinic.
I told him I was interested in doing it.
It was quite simple. He worked out the types and the dosages and then I ordered all three on line and had them delivered to his apartment. I immediately took 1/2 of the anti-androgen pill and saved the other half for bedtime. He gave me a quick shot in the butt, and about two hours later I could tell it wasn't a placebo due to a bit of nausea. It only lasted for a week or so, and it was hard to sleep at first. During the day I felt as if I had an eternal, low grade coffee energy buzz and I was in a very positive mood.
After my first month's blood test my testosterone was quite low and everything else was normal, so we added the progesterone.
As the days marched on, I felt really good.
In the second month I was tested again. It showed my free testosterone level at a female level of 30 and estrogen at a female level of 150. The progesterone was a 12, which is good. The doctor said that I was in a good place to be and he'd see me in six months.
I noticed I didn't think about sex much, and didn't get hard easily, but I was overall happier and more mellow and had a positive outlook to what I was doing. I've always been a crybaby, but now it was easier and I had to be sure to see it coming lest I embarrass myself.
I also noticed that my face began to fill out a bit, and my already girly hips got a bit more padded. I never grew facial hair anyway, but my body hair seemed thinner. I noticed my body odor seemed to change. If I wasn't careful using deodorant, I smelled like my mom when she was working or stressed.
After about four months, I began to notice a lot of little differences and saw some subtle results. My nipples and my breasts were tender and sore and I had a very tender bump behind my nipples. My areolas got larger and a darker pink and for a short period, my nipples began to itch like the dickens like when I was an early teenager.
I already had a pretty fleshy chest and feminine nipples. Now my boobs are slightly bigger and fuller above my breast. It was especially evident when I bent down in front of the mirror.
Before hormones, my nipples didn't stick out much even when I was aroused, but now they stuck out a good 1/2" and my nipples grew to 1/2 inch across, and my areolas enlarged to 1 1/4 inches. They looked just as breasts should look on a fairly flat chested girl. When I got cold or aroused, they were very noticable and I felt compelled to hide them. I was learing the down side of growing real breasts!
The most unexpected difference was although I was less interested in sex, I was still interested but I had to be more comfortable and in the mood.
When I did want an orgasm, my nipples seemed to be connected to my pleasure spots in my groin. My orgasm was a lot different than before. It was longer lasting and quite intense, and was more of a tingling throughout my body. If I ejaculated at all, a little bit of almost clear liquid oozed out, but the afterglow stayed with me a lot longer and was quite pleasant.
I was aware that my testicles seemed to be shrinking a bit, but I didn't care about that since they were in the way. I really wonder sometimes if I need them at all. The process was beginning to worry me a bit. I wasn't sure how far I wanted to go, or when to stop!
Mom started to notice things and began asking questions. I dodged and weaved, and lied, and evaded.
One morning mom and I were having coffee and she asked me how I was doing. I told her I was fine, all was well. Then she dropped the bomb:
"Honey, are you taking hormones?" she asked.
"Uh, no. Why do you ask?" I lied, wondering if it was my areolas that gave me away. Crap.
"I've noticed some changes in your appearance, among other things, since you started dating that nurse guy."
"Oh, Mom. Really?" I blurted, feigning outrage, but knowing my blush was giving me away.
"Really. All I'm going to say is if you are under a doctors care, that's one thing. And we should discuss it. After all, I am your mother. And female. If not, then stop before you hurt yourself."
My mom has always been so supportive of me and my gayness. I felt like hell, and tried to stop the tears from flowing.
"I just wanted to soften up a little." I said quietly.
"I love you Honey, but I think you need to get smart about this. Personally, I don't think a transition to female is in your best interests. You just need to meet the right guy. I'll see you at work." she said sharply as she kissed me on the cheek.
I felt really horrible, being busted by my mother. But at least our talk was short and sweet, and mom didn't carry on about it, thank God.
So I made up my mind to stop, and dropping my malpracticing boyfriend was the first step. The only sort of good thing that came out of it was that he helped me experiment with hormones for awhile and enjoyed it! And I learned how to do it and get blood tests for free!
Not all of the changes have left me. I now get tingly very easily when I get aroused. My ejaculations are still weak and wimpy and my orgasms are much different than before. They are less intense but last longer and leave me tingling. My nipple development has not reverted, and I'm happy about that. And my boobs are pretty much the same. I don't know if it's my imagination or not, but I feel there have been other permanent changes.
Now that I'm out on my own, every now and then I restart for a few months when I start smelling like a man or I think I need a boost.
Prologue
Being a sales and service technician in the family winery service company, I spend every work week in and around the wine country of Santa Rosa, CA. As a partner in the business I have the benefit of autonomy and a good income.
Now that I'm on the road and a bit older and
more mature at the wise age of 24, I much prefer to hide my fetishes in a hotel room. I prefer to put on my nightgown and bathrobe, and go out on my secluded deck and paint my toenails.
To put it plainly: My grown up life pretty much sucks.
However, I am not a total recluse. In safe places like malls and nice department stores, I do love the erotic thrill I get from shopping for women's "pretties". I've found that for the most part the younger girls are closer to my age and tend not to be judgemental, and go out of their way to make me feel welcome to shop there.
Besides, it's sure better than me saying: "This are for my girlfriend, who just happens to be my size."
Mom and my sister have walked in on me a time or two, as I have done to them. There was no mistaking my breast and nipple growth after around 13 years old when I started covering up. I didn't want to have a doctor treat me for "that" and I discussed it with Mom at length explaining that I was fine with it. After much went on that I didn't completely understand, she must have talked to the doctor because I never heard anymore about it, and she was fine with it.
My mother and father are full blooded Irish and I inherited their very pale and translucent skin with light freckles and red hair. I never grew whiskers and have hardly any hair on my body at all. I got most of my physical traits from my mother. I have her squarish hips with a plump and fleshy butt with a perfect 45 degree spine angle that makes my butt stick out.
It would do any sexy young woman proud!
Mom often told me how lucky I was to "be pretty" and have "lovely lips and shapely hips". My sister was more graphic telling me I had a better ass than she did and that I had a nice "wiggle" and a good waist to hip ratio for child bearing if I ever could find a way.
My nipples are very sensitive and reactive, and harden easily, and can light me right up if I get too aroused or play with them! Today, with a push up bra I'm able to easily fill a 36 A and still have some jiggle and bounce.
I'm probably on bit of a downer right now because I just came off a round of hormones. Every few months so far, I get the urge to do a round of hormones for six months or so, then I stop for a while. I'm fine with the idea of doing hormones in cycles to maintain what I have. Maybe someday I will go all the way.
When I'm in my work role, I wear an undersized tight t shirt, then a regular one over it, then a shirt to keep things under control.
My sister was most helpful to me in dealing with my femininity all through my teens. She helped me with clothing that was "cross-over" and unisex. She was always on the lookout for boys that might be interested in me. It was she who suggested the tight t shirt with a looser one over to hide my nipples. We were actually like sisters.
Since we had played dolls and make up since I was little, there wasn't much that surprised her. Mom and my sister often included me in their "girl talk" and I got my share of comments about my feminine features. They both encouraged and reassured me that I very definitely had assets that many gay men like. All in all, they included me as one of them knowing that I too needed to land a man some day.
Fortunately for me, this body is a good fit for the way I feel about myself as an adult now. I'm lucky that my parents accept me as I am and how I live my role in the world. I hope someday I will find the right guy for me.
Chapter One
It was lunch time and I was leaving a service call for the day.
I was about to lift some test equipment into my car and I noticed one of the inside techs was heading my way. I assumed he was heading to his car, so I ignored him and got back to loading my gear.
"May I help you with some of your things?" he said kindly.
I glanced up at him. My stomach quivered a bit as I reacted to the sudden ambush, startled to find a man in my gay o'sphere. I was hoping he didn't spot me rocking my girly ass to some tune in my head!
Even though I recognized him since I had worked with him a time or two, I immediately went on guard and became more cautious.
"No, I think I have it handled." I replied, timidly.
"I'd be happy to help. I'm from the plant. I know you from the work you do inside." he said with a gentle smile.
Somewhat startled, but appreciating his persistence, I replied:
"Ah, I thought I recognized you from the lab." I lied. I had been checking him out for sometime now.
"Sure, that would be helpful if you have time. I have trouble with the heavy items." I replied with my perky but gentle "I'm interested" voice.
He was a pretty big guy at maybe 6'2" and a trim 200 lbs. He seemed to be around my age, or maybe a year or two older.
When I had scoped him out before, I thought he was cute but probably straight.
I could handle my things of course, but I didn't want to deny him the opportunity to help me. I'd much prefer to stand aside and look cute while a handsome man helps me! I would love it if he would rescue me from those dirty boxes, so I can furtively check out his manly body while he wiggles his cute self about!
So, I stood aside and let him get to it. I've learned that a man's protective instincts are either sex based or they aren't. Now that he has played his opening gambit, I need to carefully give him a subtle clue so he will feel safe should he be interested in me. I just hope he isn't an ax-murderer, or spreads shit about me to my customers. I'm wary about being attracted to people who can hurt me.
And maybe being an unapproachable bitch is why I am alone.
I'm not very big at 5'7" and 150 lbs, and I'm careful to hide my more obviously girly features. I do have to be submissive enough to interest the right kind of guy who might be attracted to me, but I still have to project a reasonably manly persona so I don't get myself in trouble.
It's complicated.
I could tell by his gentle voice and the softness of his eye contact that he might be letting me know he was interested. There was certainly the possibility that he just might be being nice and is putting me at ease. I needed to find out which one. I could have just asked him if he was hitting on me, but that was too transactional for me and might scare him off.
Pondering his opening I decided instead to allow my passive personality to creep out just a tiny bit to make sure I'm not misreading him.
I decided to lift a large but light box up and ungracefully fumble with it.
"Here, that's too heavy. Let me do it. You can just tell me where you want it." he said sweetly, as if careful to not hurt my feelings.
"OK." I said with a slight lilt, appreciating the double en tendre.
He smiled sweetly and looked into my eyes for a long instant, which I answered with sweet smile and a slight blush.
Sensing a positive vibe, as he got back to work I moved to where we were standing very close together and almost touching as I pretended to find a way to be helpful. When we touched, I was thrilled that he did not recoil! We touched again, then we were almost touching, then we were touching again! I could smell his masculinity and I could feel his body radiating heat. My heart rate was increasing and I was beginning to perspire, which led to me blushing even more brightly. I knew what I was feeling.
I was feeling like prey. Hopefully, challenging prey. Well, not too challenging.
We reached a rhythm and pretty quickly finished up with me doing the small stuff and him taking care of the larger things.
Since we were done and I could still flee if I read him wrong. I decided to make my move by allowing the pitch of my voice to go up a bit as I thanked him:
"Thank you for coming to my rescue. I'm usually worn out by the time I get it all in! I'm very grateful for your help." I replied with a soft, almost but not quite feminine inflection.
"It was a pleasure." he replied.
"I'm Chris. By the way." I said, holding out my little hand.
"I'm pleased to meet you. I'm Robert." he said as we shook hands.
He continued to hold my hand after the hand shake as my hand's firmness dissipated, causing me to blush. Here we were actually holding hands, which I found very exciting in my otherwise dull love life.
"Oh gosh, I'm sorry." he said, stammering and blushing a little as he released my hand.
"That's quite OK. My fault." I said smiling sweetly at him wishing our hand holding could have continued.
"Can I invite you out to lunch?"
"Sure, I'd like that." I replied.
I was still in a blush as I weighed the possibilities of suddenly grabbing a bull by the horns and getting laid today. What ever happened to my measured, careful, date by date romance with Mr. Right, I mused?
"I'm off for the afternoon." he said.
"Same here! Would you mind if I dropped my van off at the hotel and we took your car?" I proffered making damn sure I at least got in the car with him before he blew me off as some sissy fag he shouldn't get mixed up with. You know, 'all that drama and shit'.
"Absolutely. I'll follow you." he replied.
I parked my van near my entry door and got in his car.
"Nice hotel."
"Yup. I don't pay for it, and my van is always there in the morning!" I commented with a smile.
"It's got a kitchen, two bathrooms, living room. Just like an apartment. I book by the week since I like the extra space." I added.
He took me to the Ca'Bianca Restaurant in Santa Rosa, one of my favorites. He definitely had good tastes and good manners. That was a plus!
After we parked, I stalled for a few seconds by fumbling with my phone and as I had hoped, he opened the car door for me. He had me walk ahead of him and I paused for him to open the restaurant door for me.
As I went in ahead of him, I warmed a bit when I felt his hand touch my butt as he shepherded me inside. He gave the receptionist his name while I stood slightly behind him, invisible.
As the waiter led us to the dining area, Robert thoughtfully asked for a table in a quiet area so we wouldn't be on top of the other diners. I was impressed by his thoughtfulness.
We both ordered very light and had coffee instead of wine, neither of us wanting the other to think we were raging gay alcoholic narcissists! We thoroughly enjoyed each others company and finally his charm disarmed me enough that I felt safe letting my guard down so I could enjoy myself.
"I'm gay, you know. Is that OK with you?" I asked, ignoring what I thought was obvious.
"Yes. Absolutely."
Thank God we didn't have to tip toe around that anymore!
He confessed that it was hard for him to meet a decent guy since he's not a person who likes to meet men in bars.
"I know what you mean." I said, relieved that the obvious had been entered into the record.
I admitted that it's been years since I've had anyone in my life, and summed it up to a couple of unserious boyfriends.
I was wondering if my cross dressing might be an issue, but if we progressed I could introduce it gradually. I was definitely liking this guy.
"I'd love to find the perfect man to fall in love with someday. " I said, something I had struggled with for years.
"Me too." He replied as he reached across the table and put his hand over mine, adding:
"We will someday. That's what keeps romantics like us going!" he said with a warm smile as he withdrew his hand. I missed the touch of his hand instantly.
I smiled and blushed again as if on que, thinking that I'm really liking this guy assuming he's for real and not just playing me along.
He had on short sleeves and had no tattoos that I could see, and from what I could see he wasn't very hairy and seemed to be in good physical shape. That was a plus for me. I was very interested in him and actually, he was making me feel that ambiguous "want" that I've struggled with for years. It's not just "horny", or just wanting release, or blowing someone. It's bigger and more complicated and has kept me out of relationships for years. I want a man to want me, but I want to be courted. In fact, I expected to be courted.
Weighing the factors that brought us together today, I was comfortable with him because we had seen each other around the winery for a couple of years, and had worked in proximity at times and I didn't get creeped out by him. In fact, thinking back he seemed to pop up a lot where I was working and I never dropped my guard enough to encourage him to approach me. Now, I feel quite safe with him since he seems like a responsible person with a good job and I know where he works.
I was wary, but my love life has been barren as a desert. I'm thinking to myself "What am I waiting for?". I decided to go for it. I invited him to my suite for a glass of wine and he quickly agreed.
Chapter two
We drove back to the Marriott where we took the elevator to the top floor. I could tell he was impressed. I always tried to book the same two room extended stay suite partly because it had a large patio that no one could see into. It overlooked an easement and a vineyard, and the workers were far enough away that they weren't a problem even if I accidentally gave them a show!
I have spent many tearful and lonely nights out there dressed in my "pretties" with just me and the occasional mosquito.
I unlocked the room, thankful that the room had been serviced and the air conditioner set. I turned on the light but immediately dimmed it a bit, not wanting to disturb the thoroughly guest tested atmosphere of a nice calm, temperature perfect, quiet, dimly lit room that might be conducive to a nooner.
I excused myself to go to the bathroom, and pointed out the other one if he needed it. I removed the tight t-shirt I wear to disguise my little boobs, and the regular one, and just wore the lighter polo shirt, untucked. I brushed my teeth and put on some chap stick and some fresh deodorant, and did a thorough crotch wash just in case.
When he came out I showed him to the couch and turned on soft music on the TV while I fetched the wine and two glasses.
I sat on the middle cushion and kicked off my shoes, putting my legs under me. I was facing him with one arm on the back rest struggling to think of a question to ask him to break the ice.
"I feel a bit funny all of a sudden inviting you over since we just met, but I don't consider you a stranger since we sort of work together." I said, nervously making a ringlet in my longish red hair.
I didn't know what to do from here.
Whit a smile, he said "I'm just happy that we can get to know each other without people around. I've been trying to catch your eye for a long time, but we never had the chance to work in close enough proximity for me to hit on you!"
"Well, I certainly noticed you. I've been fantasizing about how to get you alone in someone else's winery without getting arrested!" I said with a girlish rhythm.
"That would have been worth it by me! Honestly, I couldn't bear to see you walk out that door one more time and not at least throw my self at your feet just once!."
"Oh, that's very sweet of you." I replied in a sweet voice, putting my hand on his knee hoping to encourage him to keep going.
I looked up into his eyes as he gently pulled me to him. As he moved closer and his lips touched mine he engaged me in small light kisses as he gently rubbed my arm, increasing my arousal.
When we disengaged from our first kiss I looked into his eyes and licked my lips, parting them slightly and leaning back a little to encourage him come to me. As he approached my waiting mouth, my lips welcomed his and we kissed again. After a couple more small kisses, he gently probed with his tongue. I let his tongue pass as he pulled me into his embrace.
He was aggressive and strong and in charge, and I communicated my submissive status proudly.
Thus, began the first surrender of many that I would make to him.
As we broke from our second kiss, I was mindful that we both had worked all day and hadn't showered. His odor was light and masculine, and was turing me on. I hope I was OK.
As he kissed my ears and my neck, I let out a passionate breath as he moved his ticklish kisses down my neck and along my shoulders. I began to breathe heavily as he slipped his hand under my polo shirt and caressed my sensitive nipples with his fingers.
His rolled them gently between his fingers sending me into shameless spasms of delight as I rubbed his larger than life cock through his pants. After many kisses, I was frustrated that we had done about as much as we could with our clothes on, and I was uneasy that we may have reached an impasse on a lumpy hotel couch.
"Can I invite you into my bedroom?" I asked timidly, not sure what to do if he declined.
"I'd like that." he replied.
I took him by the hand and led him in to the bedroom and dimmed the harsh light. I put my arms around his neck again and got up on my toes to kiss him. He put his arms around me and moved his hands under my shirt, and gently caressed me along my ticklish sides from my underarms to my waist. Then he unbuckled my belt and then the top button of my pants. He slid his hands inside my underwear and began to caress my naked butt as my zipper lowered itself as if my magic.
He continued to kiss my ears and neck with ticklish kisses before returning to my lips. I broke off from our kisses with a smile.
I stepped back and looked him in the eyes and began to undress. He took the hint and started doing the same, pretending not to watch me. I did my best to make my movements as sexy and feminine as possible without over doing it.
I took off my top while facing him so he could see my fat, pink nipples perched atop my breasts. Slowly I turned my back partly toward him as I bent down with my legs closed, and slowly removed my bottoms so he could gaze on my girly butt, yet not see my little cock.
When I turned back around to face him he was naked and gloriously hard! He was totally shaved except he had a patch on the front of each ball and square patch above his cock.
I could not help staring at his big cock. It had a good sized head and then his shaft thickened markedly toward the middle, then tapered down again as it reached his body. It reminded me of a bowling pin. My little cock was a dwarf compared to his! Then I was struck with the sobering thought that it could end up inside of me!
I reached up again and put my arms around his neck and kissed him deeply. As we kissed and held our naked bodies tightly together I could feel his big cock pressing against my stomach leaving cool damp kisses as he guided us down to the bed.
We kissed some more and I maneuvered to be on my side so my breasts would sag a bit and be more interesting to him. Taking the invitation, he slid down and took my nipple in his mouth as I rubbed his back and shoulders and moaned with passion.
"Chrissie, you are wonderful." he said quietly. Can I call you Chrissie?
"Oh, God yes.". I breathed out passionately as I warmed to being called Chrissie again. My sister nicknamed me that, and Mom often used it, too.
"And it's a delightful name, too." he added as he returned his lips to my nipple.
"Ohhhh!" I moaned as girlishly, losing myself in passion. I rubbed his broad shoulders as encouragement.
He certainly knew how to turn me on! His touches and kisses were electric, and in my ache for affection, I was ready to go wherever he wanted to take me.
He began to kiss his way down my stomach, gently rubbing my nipples with his dampened fingertips. As he spread my legs, he put his forearms under my knees and lifted gently. I shamelessly pulled my knees up and opened up all the way for him.
He began gently kissing and licking the ticklish skin of my thighs, as his gentle kisses traveled to my bald crotch and little balls, driving my passion to lip biting levels. He licked and kissed my cock then sucked my dysfunctional little balls into his mouth one at a time, then both, to give them a sensuous sucking.
"I love your little balls, they are so cute!"
I responded by yielded to his predominance and becoming more submissive and feminine. In that quick instant, I eagerly shed any pretense of maleness as Robert seemed to enforce my femininity.
He moved to my cock, and gave it little licks and kisses as he continued to massage my swollen nipples with his fingertips. He took my little cock in his mouth again and gently and slowly explored it with his tongue.
He continued to rub my nipples causing me to heave and pant with passion.
"Oh baby, I'm so close." I moaned as my hips writhed shamelessly on the bed like some harlot in a dime store novel!
"That's OK, honey. Let it come."
He kept on working his tongue on the buttons below my cock head with the tiniest movements of his mouth. I tired to hold back but everything seemed beyond my control as my body began to tickle and tingle in an escalating undulation of orgasmic intensity.
Suddenly and too quickly I began oozing my juice into his mouth, letting out the girliest of squeals as my orgasm crested and then plateaued, with every nerve ending in my body alive with energy.
He held me close and worked my cock in and out of his mouth as my orgasm slowly tapered off into a sea of orgasmic spasms and breathy moans as my girly orgasm slowly faded.
When I had softened, he came up and kissed me deeply, sharing the remnants of my watery boy juice.
"Would you be offended if I said you are very girly in bed and I love it!" he said.
"It's been a long time for me, and things slip out. I'm sorry if I made you uncomfortable." I replied.
I was feeling somewhat exhausted and feebleminded, and still tingling from my climax. I was embarrassed that I didn't pulse much any more, but the hormones ended that but ignited other sensations.
"Just be yourself. I love it!" he replied.
"I can get kind of girly if I'm not careful." I said happily still quite buzzed from my orgasm.
"Then be your girly self. It's wonderful." he said as he kissed me again.
I gave him a nudge to roll on his back. Not wanting to waste a second, I began rubbing his big cock and kissing his nipples. I slid down and began gently licking his cock, appreciating how big it was. I took the head in my mouth and began taking in as much of the shaft as I could. I licked the head carefully and slowly and ran my tongue along the bottom to his balls.
I took one ball into my mouth, then the other as I sucked on them gently one at a time thrilled that after all these years I finally had a cock to suck!
"Here, hon. Lets take our time and do it this way." he said and he put me on my back.
He took the pillow and put it under my head and straddled my chest. I suspected he must have felt the needed to show his dominance. It certainly worked. I felt very vulnerable being held down with his dick pointed in my face, even though I was dying to suck it!
He aimed his cock at my lips and as he moved it closer, I licked and kissed the head. I was trying to crane my neck to get it into my mouth, but I could tell he was enjoying teasing me and making me work for it by dragging it all over my smooth face.
"I'm really close, honey. Just kiss it for now. Let's take it slow." he said sweetly.
I was appreciating the game we were playing and was intoxicated with lust as I got to service him as a good little sissy should. He moved his cock up and dragged it lovingly across my lips letting me kiss and lick along the shaft as he presented it to me.
He brought his balls up to my mouth again, and I sucked on them properly as a sissy should.
"That feels good. Just like that, honey."
I inhaled the musk from his balls, eager to bond with his mild yet tangy masculine scent. He let his cock head rest on my lips. I gave it gentle kisses and tickled the bottom buttons with my tongue, catching a drop of precum as it oozed out.
I slowly opened my mouth as I looked into his eyes. He slid the tip in slowly and then stopped when the head was mostly in giving me the honor of licking all over and around the head. The head was nice and fat, but not so much as to prevent me from using my tongue. I was glad that it didn't begin to widen until about an inch or so past the head so I had plenty of cock to work with.
My body was still tingling from my orgasm and now my lips joined in and began to tickle, adding to my pleasure as he moved his cock in and out. I wondered if he would think less of me if he knew how much pleasure I received from the almost orgasmic feeling of his cock sliding over my sensitive lips. I was delighted to let him seek his pleasure in my eager mouth.
With small gentle movements he began to work his cock in and out, each time a little deeper until I couldn't take any more.
Slowly and deliberately he worked his cock in and out of my mouth as I sucked and then paused so I could use my lips and tongue to give him maximum pleasure. If he went too deep, he pulled back and as soon as I regained my composure, we tried again.
"Oh honey, I am so close. Do you want me stop?" he panted, almost teasing.
"No baby. Please. I want it. All of it." I pleaded shamelessly, afraid I might be denied after all these years.
I reached behind him and nudged him toward me so I could move my head better and take more of his cock. He moved forward a bit more but was still making me work for every bit of cock I got my lips around! Finally, I brought him to the edge of orgasm as he tried mightily to control himself. He was nearly motionless as I paused and ran my tongue over all of the head, lovingly licking the sensitive buttons on the bottom.
I took my time as I gradually brought him to the knife edge of climax. At this point I owned his pleasure, and felt privileged to be able to decide the moment of his climax! I felt his cock getting stiffer, and the head beginning to swell as I teased the head and the bottom buttons with my tongue!
Finally my teasing got the best of him and without as much as another tiny stroke, his body stiffened and he let out a groan as his cum burst into my mouth followed by several more powerful pulses as he delivered his bounty with manly determination.
He moved in and out carefully with each wave of pleasure. My lips were pursed as I nursed on his cock and greedily swallowed every bit of cum that he gave me as I massaged his balls. As the pulses slowly tapered off, I kept him in my mouth as long as he would let me so as to get every last sperm.
Neither of the boyfriends I had put out anything near what Robert did. It was all I could do to contain it! Crikey! I never realized how much of a sexual difference there was between a grown, powerful man like Robert and myself with my meager dribble.
"You are a wonderful lover." he said, moving up on top of me as he kissed me. I brought my knees up to receive him, allowing me to feel his weight on my soft body.
We wiggled around a bit more and got rearranged so I could put my head on his chest with his nipple at eye level.
"Why did we wait so long to find each other?" I asked hopefully.
"So we could make our mistakes with someone else?" he replied philosophically.
"That is probably very true." I replied, smiling.
I got out of bed first and sat on the edge of the bed with my back to him.
"I think I need a shower." I said.
"Can I join you?" he said.
"I'd like that." I replied.
I turned on the water in the oversized shower and got out an extra towel for him. I had a large tee shirt I sometimes used for sleeping and a pair of my men's underwear to put out for him, and then hung a hotel bathrobe on the peg by the vanity. I'm not all that sure what else he might need, but this was the best I could do right now.
As soon as we got in the shower he held me in his arms from behind, playfully letting his cock slide around my crack as the water cascaded down our bodies. It was the first time I had ever been in a naked embrace with a man. I felt impishly content as well as tiny and safe in his embrace. I was getting very excited by his big cock brushing my boypussy as I held his arms with my hands.
He turned me around and held me close and kissed me, running his hands over my butt cheeks and pressing himself to me. As he enveloped me in his masculine embrace, I shamelessly pushed my pelvis letting him know I welcomed more.
I was still aroused and tingling after my climax and feeling lovingly submissive. I took the opportunity to go "all in" and used my soapy hands to wash him gently all over, not missing a square inch.
I washed his front, gently squeezing his nipples and lovingly kissing each one. I knelt down and washed each leg carefully, mindful that his cock was hovering within kissing distance of my face. I kissed his cock gently, pleased that it was enjoying my attention as much as I enjoyed giving it.
He didn't balk when I washed his balls and unbeknownst to him, I was inspecting them. I was thrilled that there were no scars from a vasectomy. It was important, albeit selfish of me, that he gives me living sperm.
I returned to his cock and gently washed it, feeling the heft of it and gently kissing and running my tongue around the head. It began to swell a bit, so I decided I'd better leave it alone for now. I washed his front and his underarms, kissing each one when I was done. I tweaked his nipples before giving each one a kiss and a generous suckle.
I turned him around and washed his back, reaching around again to play with his nipples, and let him feel my little cock touching him. I knelt down to wash his legs, then while still kneeling I spread his cheeks and with the pad of my thumb I massaged his anus carefully as if to clean it. Then as a final tribute, I spread his cheeks and licked gently, working my tongue in as far as it would go. I could tell he was enjoying that!
I hope he will see my submissiveness as my way of honoring him and showing him what a good partner I can be if he wants me.
As I washed the soap off, I kissed him again in many sensuous places. I could feel the juices stirring, but I had other things on my mind other than sex. And as my sister used to remind me: "We don't get pretty by accident.".
As I made a bit of a show of washing my hair, he watched me with curiosity. My elbows were out and I was unafraid to reveal my shaved underarms, should he notice. I was also aware that my little boobs were bouncing and wiggling, and my little cock was wiggling.
"You are really beautiful, honey. Can I say 'beautiful'? he said as he took a wash cloth and soaped it up.
"Sometimes." I said, with my sexiest smile in a melodious voice.
With one hand he applied the soap to my skin, and washed me with his soft bare hands. He used his thumbs to graze over my nipples, teasing them to become fully erect, then kissing each one as his hands traveled down over my cock and balls. He massaged my hardening cock, and then took my balls in his hand and squeezed them just enough.
"I love your cute little balls. They feel so nice." he said.
I knew he would soon figure out that when he would redirect my attention to my balls, I instinctively became more submissive, almost admitting that I didn't need the worthless things at all.
He turned me around again and using his bare hands, he sensuously soaped my back and butt and let his fingers graze over my crack. I could feel his hardening cock constantly touching and sliding around on my soapy butt. I was rapidly heading back into a cloud of passion and losing control.
"You have a lovely body." he said quietly.
"Ohh." I breathlessly replied.
As he rubbed my globes with his soapy hands, my hips rocked with carnal urgency as he used his thumb to massage my tight little hole.
He pushed in a little and my mouth instinctively flew open in a gasp as I arched my back and pushed my rear toward him. He continued to rub inside the opening of my boy pussy as he rubbed my left nipple.
I began to lose control, panting vocally with lust.
"Oh, Robert." I moaned, breathlessly.
He moved his cock up to my opening and pushed just enough to begin to enter me. I pushed back at this first attempt, causing him to push and hold himself in just far enough to where I could feel the beginning of the stretching pain that would be the prelude to my breeding.
Suddenly, I regained my wits about me and turned around facing him before he could go in any farther.
"I'm sorry, baby. Not right now. I'm still a virgin and I'm not ready to do that yet!" I sniveled, turning around to face him, afraid that I may have already gone too far to stop him.
"I'm sorry. I got carried away." he said apologetically.
"Whew." I thought to myself.
"We need to take a break, big guy." I said to him as I kissed him, still fidgety and sexually excited, as well as conflicted by the stark symbolism of my first little bit of penetration, and the myriad of lascivious feelings it generated.
"That's OK. It was my fault for not controlling myself!" I replied contritely as I reached up and kissed him on the cheek, blushing hotly due to a very passionate near miss.
He sensed my unease and hugged me tightly.
We got out and began to dry off.
"I put some things for you on the counter. You can use any of my toiletries, and the blue toothbrush is new and you can have that. I have a thing or two left to do." I replied.
"I'm sorry, honey." he said again, apologetically.
I stopped and faced him, and replied:
"It's OK. I really was tempted, you know. It's all good." I said as I kissed him gently.
What I needed to do was get my bathroom back.
I wanted to test him by changing into something a little more feminine to bring him along gently. Also, I needed some personal space to finish up and dress.
"OK," he said contritely, taking the hint as he stepped out and took his toiletries and things to the other bathroom.
Chapter Three
I busied myself with getting back in the shower and tidying up my landing strip and reshaving my legs and underarms. My feet were fine since yesterday morning's dilatory was good for a week or more. I didn't want him to see me doing these things. We don't know each other that well. Someday maybe, but not now.
I rubbed myself with a very lightly scented vanilla honey body lotion so I'd smell nice and my legs would look nice and smooth.
I wanted to be subtle with some hints of femininity while we got used to each other, but I was unable to plan my clothing since I didn't expect to bring home a visitor. The only loungy thing I had that would work were some woven yoga shorts. They rode quite low on my hips and were snug enough to show my girly butt off nicely. They had small front pockets stitched with pink thread as an accent, and had a pink string tie.
They fit perfectly, and always made me feel sexy.
But I had a problem: all of my underwear and panties were in the living room where Robert was waiting, so I decided "what the hell" and decided to go "commando" since I was small enough down there that things won't creep out and I'm not trying to hide anything. Better commando than looking stupid by going in the other room looking for underwear.
I'm thinking: "Enter, say hello, find underwear, get it without him seeing, say bye, come back." I think not.
For a top I had a white vee neck blouse that would show some midriff and allow me some swing and jiggle, and was thin enough to show my nipples.
I combed my longish hair straight back so that when it dried it would fall and look more feminine.
I decided to put on my short white kimono style bathrobe that came up to my mid thigh, since I didn't feel comfortable going in the front room without a wrap just yet. Besides, I think short bathrobes are sexy!
When I came up to the couch he looked at me quizzically.
"I'm sorry. Did you want the short one?" I asked playfully as I loosened up the tie and sat down with him, forgetting all of my fears.
"NO, you are quite beautiful in that one. It's perfect." he gasped.
I snuggled close to him and pulled my freshly shaved legs under me and leaned into him so he would put his arm around me. He gently rubbed my leg as I put my head on his shoulder pretending to watch TV while I explored his thigh with my fingers.
"Did you shave your legs? They are very smooth and sexy. I really like that." he said.
"We can't let girls have all the fun, can we?" I quipped as I lifted my head and we met for a kiss.
He pulled me to him and kissed me again. We began to kiss more deeply, and our hands began to explore inside our robes. He unexpectedly put his hand in my stretchy yoga shorts to rub my butt.
"Hmm, did someone forget their panties today?." he asked cutely.
Well, that cat finally charged out of the bag, I thought to myself.
"I didn't have any with me this trip." I lied, knowing I had two pairs in my dresser.
"Would you like me to buy you some tomorrow?" he said.
"I'll buy them if you want me to wear them for you. But that is very thoughtful." I chirped girlishly.
"I'd like that. I love your femininity." he said.
"I'm very relieved, and I think it's sexy to hear you say it!" I replied.
"You are sexy." he replied.
"I don't mean to be too forward, but I'm here all week and you can spend every night if you wish all the way through next Friday night. I have to go home next Saturday afternoon back to Oakland, then back here on Monday." I asked, hopefully.
"I'd like that, but I have to leave tonight to do some things Saturday." he said.
"Can't you spend tonight with me and leave tomorrow?" I asked, meekly.
"No, I can't. I have to leave tonight, but I will be able to come back tomorrow." he insisted.
"Really?" I said, disappointingly.
"Yes. I'll be back in the morning."
"Crap. I knew it." I said to myself.
I probably scared him off by being too forward.
I wanted him to spend the night tonight since we made love for the first time today, then he could leave tomorrow if he must leave then come back in the afternoon so we could spend Saturday night, plus all of our other nights together in an unbroken string until I had to go back to Oakland next Saturday night. Then we could be back together on Monday!
I don't know how I lost control of the situation, but I did. I expected him to actually be thrilled to spend the night with me. We could have cuddled and kissed and maybe even had more sex, and then woke up in the morning cuddling like a couple of newlyweds.
He's probably pissed because I wouldn't let him fuck me.
"I should be here all morning." I told him as sweetly as I could manage, as I gave him his fucking key.
He gave me a kiss and a hug and off he went, leaving me with that empty, sinking feeling that maybe I blew it already and it was over. I felt more alone than ever, already missing the companionship and the kisses and loving touches that came from the man who popped into my life, however briefly.
I smiled a painful smile as a thought entered my head that this was one of the few times I can remember that I was actually lonely. But not just ordinary lonely, but lonely for "him". And what do I have to show for it? A peck on the lips and an empty bed.
I'm surprised at myself for letting my emotions lead me out on a limb. Now I'm wondering if he just sawed it off.
His departure made me feel unloved and rejected. He obviously didn't seem to care enough about my feelings to understand how much it would have meant to me if he would have spent the night.
I'm wondering if I made a mistake and he was just some lousy bastard who used me.
As I got more melancholy and the walls began to close in, I poured myself a glass of wine and sat out on the patio in a pair of panties and the under shirt he wore today, hoping to relive our closeness.
After another glass of wine, I said "the hell with it" and changed into my super sexy white tights, no panties, and a short black chiffon camisole.
I brought out my nail polish and painted my toenails a nice shade of reddish pink and drew a little flower on each big toe. I don't care if he likes it or not. If he does, great, if not too bad!
I was an emotional wreck, but I suppose I should be happy that at least I got to give him a blow job as a consolation prize and with any luck his sperm found a nice place to spend the night, even if he didn't.
I poured myself another short glass of wine and got all weepy. I changed back into panties and his t-shirt and went to bed at 10:00 o'clock. I massaged my nipples and cock for a bit but got nowhere. Finally I said "fuck it" and cried my eyes out.
I was up at eight Saturday and poured my self a Pepsi for breakfast to wash down my energy bar. I felt better this morning after a good nights sleep, albeit a lonesome one.
A few minutes later, Robert called to see if I needed anything. He was on his way from Novato!
I felt wonderful. I was happy and joyful, and down right giddy. I cleaned up my messes and got my clothes reorganized. I made two drawers ready and made room in the closet for him, just in case.
I knew there was a reason I couldn't accept that he would not come back to me!
I jumped into the shower and washed up and shaved my legs and underarms and touched up my landing strip, and then shaved the rest of the area while the dilatory went to work on my feet.
I didn't want to look like I had gone to extra trouble after getting out of bed. I quickly changed back into a pair of sleeping shorts, and put on my tank top with the large arm openings, leaving little left to the imagination! My boobs could be peeked at from the sides or the top, and every movement I made caused my breasts jiggle and sway like bait on a hook.
I combed my hair straight back and put a scrunchie in it and pulled down some bangs.
He came to the door Saturday right on time. He was wearing shorts and sexy tight top that showed off his physique. I was impressed and I was showing it. I was getting hard and wanted to jump his bones as soon as he dropped his suitcase!
He took me in his arms and gave me a wonderful kiss! He was hard and so was I! Oh how I loved his hands rubbing my bottom as he pulled me into him!
"Good morning, honey. I like your toes." he said quietly into my ear.
"I did them to surprise you sweetie." I whispered back.
He started to waltz our embrace toward the bedroom, when I suggested we should have a nice breakfast since I didn't know when housekeeping was coming. Plus, I liked that if we could put off sex right away, I'd be buzzing with lust all day and hopefully, so would he.
I called room service for a breakfast to be sent up.
In short order, breakfast arrived and Robert graciously intercepted the waiter and signed the ticket and took care of the tip. The young man gave me a hungry look as I smiled sheepishly at him, thankful that Robert was here to deal with him. He blushed and smiled, and retreated as if he was afraid that Robert was going to bite him!
I wished I wasn't dressed like a little tart but it would have to do. I could tell Robert was OK with it. I smiled as I noticed that Robert's eyes were all over me.
Chapter Four
After breakfast we lounged around a bit, with me fighting off Robert's attempts to take me to bed. I wanted him to be good and horny insuring that he would pay lots of attention to me. I suggested we go to the Coddington mall and comeback after housekeeping was done.
I changed into mostly normal "manwear" but put on a pair of women's low rise "Wedgie Jeans" I picked up at "Forever 21". They fit me perfectly, and the seam seperated and lifted my butt cheeks like a delicious peach! For a top I chose a simple, loose button up shirt with a thin t shirt under it and loafers with pink sox. To be complete, I put on a thin gold chain with a cross and a couple of bracelets on each wrist.
As we wondered around the mall, Robert was very affectionate, and doted on me, touching me often making me feel very special and secure.
Robert steered me to a Victoria's Secret window display and we gazed at the lingerie clad manikin. My heart began beating faster as I visualized wearing some of that sexy lingerie and being pretty for Robert.
Standing very close to me as lovers do, he moved his hand and stroked me ever so gently on the inside of my elbow where I'm ticklish in a strangely erotic way.
"Have you gotten any panties yet, honey?" he asked, quietly into my ear.
"No, not yet." I replied, only partly lying.
I felt my cock stir this time when he called me "honey" as he touched me. I was beginning to feel very warm and tingly as his breath tickled my hair.
"Let's browse around. I'll help you pick some out. It will be fun." he said softly into my ear, giving me more erotic goose bumps on top of my other goose bumps!
He put his hand on my bottom and guided me in, as I'm thinking, "Oh, crap. I am actually going into Victoria's Secret shopping with my boyfriend!"
We went in and started looking around together. This wasn't my first rodeo but I'd never been to Victoria's Secret before, and never, ever shopped with a man beside me. Being in here with Robert was turning me on and yet I was shaking like a leaf to boot.
Robert wasn't shy at all.
"What size are you, honey?" he asked, too loudly for my comfort.
"Size 7." I practically whispered, hoping he'd catch the hint.
This shopping trip was rapidly becoming an erotic extension of our bedroom.
He continued to call me "honey" regardless of who was nearby. He touched me when and where he felt like it, just as any man might touch his girlfriend.
A subtle bump to my hip with his ample cock, reminded me of another reason why I was in this relationship in the first place!
"Just relax, honey. No one cares. Couples like us are probably in here every day." he said quietly.
I knew he was really telling me to stop trying to be in control and let him take the lead as a man should. I had nothing to gain and everything to lose by not knowing my place.
"OK. I'm fine. It just takes me awhile to adjust." I replied, apprehensively.
"Just pretend you are my girlfriend." he said, with a quiet smile.
He took me over to the panty displays and we took our time as he pointed out several pairs he thought I'd like.
I was thankful that Robert stayed very close to me as we looked around. Our touching closeness was comforting to me even if it drew a few glances. Most were friendly, and a few met my eyes with a knowing smirk.
The whole experience was getting me hot. I was buzzing with the excitement of being a couple and being proud to be just another sissy out lingerie shopping with his man.
I was soon lost in the moment, tuning everyone out but Robert. I guiltlessly looked and touched, and held up a pair of pink hipster panties that were especially interesting and gazed tenderly up at Robert for approval.
We looked around a bit more and we chose three more pairs of panties in different styles and colors. They were really sexy and I love panties that have lots of cheek peek. I suspect Robert does, too.
By now, I was well turned on and was enjoying myself. I picked up a pair of black panty thongs, and a black pair with a lace up affair in the rear. In front of a pair of twenty something women standing next to me, I asked him playfully:
"Honey, can I get these, too?" using my gay lilt.
"Of course you can, sweetie. I can't wait to see you in them." I could tell by his smile, he was relishing the taste of victory!
I started looking around more when Robert noticed me gazing toward the lingerie section.
"Let's check that section out, honey." he said as he affectionately rubbed my butt as he directed me there.
He noticed my interest in a pink fly a way baby doll nighty.
"That would look cute on you. Would you like to try it on?" he asked.
"No, and please, no." I replied, softly.
He took it off the rack and held it up to me!
"You'll look so hot in that! Let's get it!" he said.
On the way to the check out, he saw a sexy top.
"Check this out." he said.
It was a white blouse that was thin and sheer with delicate lace trim. It was literally transparent and certainly designed to be worn with a bra and camisole in public. Robert was grinning like a Cheshire cat.
"Really?" I said
"I think you'd be a knockout in it." he said.
"OK. For you I'll do it. Just don't ask me to wear it out in public." I said, not even caring that the sales clerk was right next to me, smiling.
"Shall I add this to your purchase?" she said, kindly.
"Yes, but I need to find a white cropped mini cami." I said, getting totally into it as she set my purchases aside.
I quickly found a thin white one that hung down just below my breasts and ended with a lace fringe. It was unlined and sheer to the point of being translucent. Perfect! I like them short and loose with no elastic on the bottom, almost if they were a drape.
I added it to my pile, and she began ringing things up holding and folding every purchase for everyone to see.
"Will this be all today?" the clerk asked with a friendly smile.
"Yes, thank you." I replied, with my sweetest gay lilt.
She ran my credit card and handed it back to me. When she handed me the bag, she said
"Thank you, honey."
I smiled at her pleasantly, wondering if my name on my credit card had been changed to "Honey", but I gave her my best gay "You're welcome", knowing all in all it was a nice experience I wouldn't mind having again.
On the way to his car he asked, "That went well. Were you nervous?"
"Yes, but I'm glad you pushed me along. I couldn't have bought all of that by myself." I replied, still fidgety with nervousness.
"Yeah, we should do that again." he said.
"True." I replied, still somewhat puzzled at why he outed me like that.
"Let's go have dinner and go home." he said.
I nodded and smiled at the term "home".
"Take me home, Robert!" I replied in a twitter.
Robert had me so totally figured out. He inspired me to embrace my lingerie fetish right there in Victoria's Secret knowing I would not want to lose face in front of him.
When we got back to the hotel, I opened a bottle of wine and led Robert out to the patio. I suggested to him that I needed to change into something more comfortable and excused myself. He indicated that he was going to go put on a bathrobe.
I decided to keep it simple and sexy since it was getting close to bedtime. I put on some fresh deodorant and cleaned my bottom. I decided on my white cheeky panties and no top. I put my hair up into a high bun and held it together with a pink scrunchie.
I put on my shorty bathrobe and went out on the patio to join Robert, making sure my ties were loose enough that it would "accidentally" end up partly open in the front.
"Honey, you look beautiful." he said.
"I'll bet you say that to all the boys!" I quipped.
"No, just my one and only sweetieboy!" he said with a smile.
I was feeling horny as hell.
I leaned over him for a kiss and as planned, my bathrobe opened up all the way revealing my almost pendulous boobs dangling and wiggling, and my new panties with an outline of my cute little hard on.
"I'm getting a wonderful view, honey."
"Thank you, baby." I replied melodiously.
"It's close to bed time, isn't it?" He asked.
"It is, isn't it?" I replied sweetly.
We went into the bed room and dropped our bathrobes. Robert was completely naked, but I elected to stay in my panties fir modesty as we slipped into the cold bed. He immediately wrapped me in his warmth and kissed me gently, as his hard cock touched and probed me as his ample precum left cool damp little kisses as if to remind me of it's ultimate mission.
Robert moved his lips to my nipple and rubbed my cock though my panties with his other hand as I squirmed with passion. He rolled my panties off and kissed his way down between my legs. He opened me as wide as possible, and began kissing and licking all over down there.
He pushed my legs up farther and began licking at my boy pussy. It was wonderful!
"Ohhh, baby." I moaned excitedly as I pulled my legs and hips up to help his access.
I had my legs almost up to my chest when he licked my boy pussy a bit, then took my cock in his mouth.
"Honey, I'm too close. Let me do you a bit, please?" I whined, as I guided him on top of me not wanting to cum first.
Sneakily, he pulled my legs up with him, leaving my defenseless boy pussy open to him as we kissed some more as he teased me with his cock slipping up and down near my hole until it found it's goal.
He began to push gently.
"Honey. Please, no. I'm not ready." I whispered, yet still wanting to revisit that wonderful feeling of him testing limits I had not yet set for myself.
"Just a little sweetheart, I'll be careful." he said.
As I tensed up when I felt the stretching as he pressed into me, he stopped pushing and let his cock rest where it was. When it stopped hurting I pushed back a little more before I admitted to myself that I really liked what we were doing, but I was actually being a dick teasing little bitch by leading him on.
He answered by pushing a little bit more.
"Let's stop." I said, deciding it was time to stop before it was too late.
He rolled over on his back and I started kissing him again, moving down to his cock knowing he was disappointed.
I began licking all over and around his cock and after some teasing, took him in my mouth. He was really on fire! As soon as he entered my mouth he began gently thrusting his hips to meet me, using my mouth as his personal boypussy. I kept up as much stimulation and pressure as I could, and my tongue was as busy as I could make it, as Robert worked his cock in and out of my mouth.
Sensing that he really needed to cum quickly, I reached up and rolled his nipples gently between my fingers. He was practically convulsing as I slowed down the blow job just a bit to keep him on the edge, until he couldn't hold it back any longer.
With a groan of relief, his seed gushed into my mouth in strong, manly pulses with each burst sending another surge of seed. I kept him in my mouth and swallowed every bit as he slowly softened.
After he softened, I moved up to be close to him as we both began to drift off to sleep. I rolled over with my back to him so we could spoon. I reached down and took his semi soft cock and placed it up against my hole so he could feel it. I wanted to give him hope.
He pushed playfully against my boy pussy as we both drifted off to sleep as I fantasized that his little sperms were marching five by five into me as we slept.
Chapter Five
I woke up snuggled in to him with my face nearly in his underarm. For whatever reason I didn't mind it at all. I liked it. I snuggled in closer feigning sleep and breathed carefully through my nose with my eyes closed bonding with my mate.
I was intrigued that we will be together for another five consecutive nights! I'm looking forward to being a couple and going to bed and waking up day after day, sharing each other.
I'm eager to see if my needs are simply fantasies or realty, and if I can be unselfish enough to give myself up to man who will undoubtedly change my life in unexpected ways.
It's certainly a win for me. I will get to live my fantasy of "wifing" him as much as he will let me. I want it to be my job to cook for him and serve him his food, and take care of his clothes and things, as well as his sexual needs, just as a loving wife would do. I don't know how far he will let me go just yet, but I'd really like it if he will let me get it out of my system when we are together and I can find out if he likes it.
In short order, we blissfully surrounded ourselves with a rhythm that matched our uncommon sexuality. As a bonus, he was perfectly content to let me "be myself", and be as femininely submissive as I wanted.
One night after we had been together for two months and spending five or six nights per week together, we were on the patio quaffing some wine and he said he wanted to have a "chat".
"OK." I replied, nervously.
"Honey, I want to have intercourse with you. We've been together for awhile now." he said hopefully, adding, "I promise to be slow and careful and use a condom, and make sure I don't hurt you."
"No condom." I replied.
The look on his face was priceless.
Then I added, "I'm open to that someday, but we should get tested because it's the right thing to do given the intimacy we have. We should have done it already." I said, flatly.
"It's been awhile since I've been tested, but I'm sure I'm clean." he said.
"I want us both to get tested together, and then maybe some special day it will happen." I replied cryptically.
"There must be a testing place in Santa Rosa." I added.
Intercourse has been on my mind a lot lately and I'm glad he brought it up first.
I had been Googleing a bit and came away with the impression that generally the more manly the man the more they need this activity. It is important for them to validate their manliness in the relationship and they feel they need to constantly prove their virility to their partner.
Hell yeah! I'm so looking forward to experiencing my "manimal" at his most basic level.
"OK. Let me see what I can work out." he said.
The next Sunday when we got back together for the week we went out on the patio to catch up. He was pretty smiley. He said he found a place for couples testing. We go in together, test together, and get the results together. He said he had a couple of ideas to make it a memorable occasion.
He told me that he would like us to go as a married gay couple and he wanted me to wear his late mothers wedding rings.
He also wanted me to "fem up" a bit for the occasion so it would be obvious that I was his feminine wife.
I agreed that I sounded like a cool idea. Hell, after the trip to Victoria's Secret, this was easy!
I figured the testing places see all kinds of people, so it would be safe to "fem up" there.
With the closeness we had I felt that maybe we were almost to the point of considering marriage or something close to it someday. There was precious little I would not do for Robert if he asked.
In fact, if he asked, I'd probably say "Yes".
As our plan developed we decided that after our tests in Santa Rosa, we would plan a three day "honeymoon" of sorts at the Highlands Resort in Guerneville. The Highlands is a gay resort for fun and frolic with a suite for us overlooking the clothing optional pool .
The week before the test he produced the wedding rings. They were beautiful. He had them polished and sized for me, and wanted me to wear them when ever we were together in an appropriate situation.
"I want you to be proud to be seen with me as my feminine partner." he said.
"Honey, are you proud enough to also be my girlyboy and wear my mothers rings?" he added somewhat formally.
"Of course I am, sweetie." I said eagerly.
He got on his knees as if proposing, then asked me:
"Chris honey, will you marry me?"
"For Real" I asked excitedly.
"For real." he replied.
"Yes. Robert. I will!" My eyes began to tear up, and I couldn't get the words out fast enough.
He took my hand and slipped the rings on my finger one after the other. My eyes were watering, and I was beginning to cry with tears of joy.
"I can't wait until we get married." he said.
"I need to ease the family into it." I said. "But, exclusivity is most important to me."
"It is to me, too. How about I arrange a commitment ceremony at the resort but without the paperwork? We can save that for the actual marriage if you are OK with that."
"I like it, sweetie." I purred with my most feminine inflection, really getting into it. "But we can wait on that. Let's wait for the wedding." I added, buoyed enough by his commitment.
He was really into my feminine side, and I enjoyed playing into it. When he would buy me sexy things to wear, I enjoyed reacting with girly glee for every thing he bought me, eager to tease and tantalize him with them.
I was pleasantly aware that other than being straight at work, I was living the other 16 hours as Roberts "gender flexible" boyfriend! Now that a true, enduring relationship is on the horizon, I'm looking forward to our honeymoon and losing my virginity while letting Robert breed me proper, over and over anytime he wants it!
"We should start shopping for our engagement vacation, which I would prefer to call our first honeymoon." he said.
"That sounds like fun!"
"I'd like you to dress a little fem for me so you can get used to going out in public at the resort." he replied.
"Oh, boy. That's a little scary. I've never gone that far out in public, really." I said, hopefully.
"We'll go to San Francisco and start in the Castro. We'll just take it easy. Everything is cool there." he said.
"OK. I think I can deal with the Castro." I replied, casting my eyes downward as I caved in.
"Come on honey, the whole idea is for you to be comfortable for our testing and our honeymoon. We don't have to play it down for anyone around there." he reminded me.
When he left me alone, I began staring into my closet visualizing a "look" and putting things on the bed that might work.
I decided on my tight pair of tailored white women's jeans I bought some time ago. They fit my hips well and the back seam dives in to separate and define my butt cheeks. The high center seam helps me to tuck pretty well. Plus, it had a pretty sliver dangly metal belt to go with it.
For a top I chose a white blouse with pink horizontal stripes that was fairly tight and showed my breasts and nipples somewhat. I decided to wear my ladies leather jacket. It was a bit short so I would leave the shirt tucked. I could adjust the jacket zipper to control my jiggle if I have to.
OK. Jacket, blouse, pants.
He wanted me to wear my women's sandals and a pink toenail polish since this would be my first time dressing in public, and he thought pink wouldn't show that much.
I got out the lightest pink shade that I had, and when I was done, it was bright and obvious! I could plainly see it and was there for anyone else to see. He said it was not that obvious. He was full of it. I could see it in the mirror across the room!
So rather than be difficult, I decided to go all in and put on my pair of blingy sandals to set off my pretty feet. I really had no choice now but to trust his judgment. After all, who looks at feet in the Castro? Sheeiiitttt...
I did put on some very light eyeliner and light shadow, then added some blush to my cheeks, and some light lipstick. Light, light, light... subtle all the way to help me get used to feeling comfortable being a pretty boy for Robert.
Hair was easy. I pulled my hair back with a white scrunchie, but higher than a straight guy would do and piled it up on my head and brought along my cute little newsboy hat, just in case.
I did a slow pirouette around my mirror and concluded that unless if I spoke softly, no one would know I was a guy.
Shopping in the Castro was a comfortable experience. I see why Robert brought me here. Many same sex couples were holding hands and being very touchy-feely. It really helped me to calm down. It was an area where I could be totally free to be gay and express my femininity through my clothing. Before long I turned my wedding rings around so the diamonds were facing out.
I latched onto Roberts arm and let them sparkle for the world to see!
We found a women's casual clothing and sportswear shop, and Robert suggested we look for a bathing suit for me there.
We wandered over to the bathing suits. A sales girl came up and asked Robert if he could be helpful. Robert asked her where the bathing suits were.
"They are in that room to the right."
"Honey, why don't you browse around a bit while I look for a surprise for you." he said.
While he went looking at bathing suits I browsed around looking mostly at the various ensembles they had on the manikins to get some ideas. I liked the way they mix denim and white blouses with neck scarves. Other than the scarves, I can do that.
I went to another area and tried on a pair of denim shorts that fit perfectly, and has the deep back seam that makes them look sexy. Plus, these allowed the bottom of my butt cheeks to peek out just a bit, so I decided to buy them while I had them in front of me.
"Didn't find anything, eh?" I asked.
"I did, but they have to do an alteration and will ship it to us."
"Uh, what did you buy me?"
"It's a surprise for our vacation." He said, finally.
"Honey, can we go home now? I've had enough for one day. I want to start packing. I have a lot to do." I said, too tired to wonder what he bought me since he'll be sure I wear it anyway.
Chapter Six
Today is the day! We are going to get our HIV/STD tests. I'm so tickled I can't stop grinning!
I wore some unremarkable clothes and a wide neck athletic shirt since Robert made arrangements for me to get my hair and make up done before we head off for the resort. I don't care what the stylist sees, or thinks. She is just there to do my hair, and make up, probably someone else will do my pedi and nails
Robert and I drove to a salon where he had made arrangements for them to open up early for me so I could get pretty for our appointment without a lot of people around. From our tests we were going straight to the resort.
I slipped into a quiet reverie as we drove to the salon and put some thought into my situation.
After we get cleared on our tests, I can be pretty sure my virginity will be long gone before tomorrows sun comes up!
I confess that I'm apprehensive about it hurting given Robert's size, so I've been trying to stretch a bit to avoid that. For genetic reasons, I don't express my needs the same way Robert does, but I do understand that men like Robert have a need to express their masculinity this way, and I want him to do it with me and not someone else. And the idea of us finally being joined and him filling me with his living sperm is a thought that makes me shiver with lust!
I just hope I like it as much as Google says I will, because I will probably be getting it again and again whenever the mood strikes us, all through our honeymoon and beyond!
"Honey, we also have a pedicure and a manicure booked for you before our test. I'd like them do your make up if you are OK with that." he said, waking me from my thoughtful reverie.
We arrived at the nail salon where I had my manicure and pedicure by a cute guy who I hope was gay. He didn't have a lot to say, but he got right to work. I expected a woman, but who cares?
He scrubbed my feet and make them look and feel really nice. I did a dilatatory on my feet last night so he would have less to do. He shaped and filed my toenails to get them just right. I chose to go with Barbie pink on my toes and my fingernails for our special day.
When we were done, he asked me to put on my top so it wouldn't mess up my hair when I put it on. So I went into the ladies room and quickly put on the button up blouse and my mini cami.
He combed my longish hair back and braided in some "peasant curls", then added regular curls and extensions to my longish hair. Then end result was very feminine, and sexy, yet didn't look trashy.
When it was time for make up I was a little hesitant. The guy said I had very feminine features, and that under the circumstances I should take advantage of them.
I decided given what all was going on, I might as well go all out! It certainly would be an experience.
He went to work on me and within a few minutes I was done, complete with sexy eyebrows, curled eyelashes, and tasteful make up and lipstick. Thank God, he didn't make me look like a drag queen!
When Robert returned after I was done, he stopped mid stride when he saw me in make up. He told me I was beautiful. If he only knew how it makes me purr when he says that! When I finally got to look in a mirror, I was impressed!
I noticed he used light touches of make up and made me look quite nice and not the least bit slutty.
Then Robert opened up a bag and showed me a cute pair of women's sandals he bought me that had a bit of "bling" on the straps. Given the nature of our couples testing, I had no problems putting them on right now and showing off my piggies!
He opened up another small bag and produced a toe ring that looked like a wedding set with faux diamonds. He produced another bag that had a necklace with a gold chain with a gold key on it.
The salon let me change there, so we could save some time and get to the testing place.
I put on the toe ring and Robert helped me with the necklace.
I had my outfit packed on top and all ready to go, so dressing was pretty easy.
I wore my tightest white wedgie pants with my panty thong, and tucked myself into it creating a passable camel toe with my balls on each side of the seam and my little cock down the back. I put on my loose pink blouse with a thin mini cami under it so I'd still have some wiggle and jiggle.
Suddenly as an afterthought, I decided not to pretend and to let my small package show. I left my balls tucked but untucked my cock and allowing me to be seen as a guy tastefully dressed em fem with his lover.
I added my sandals and a couple of bracelets and I was good to go.
When I stepped out and took Roberts arm, the stylist smiled, and wished us well.
Next stop was the testing facility. As we walked from the parking lot, I walked slowly and let my hips undulate sexually. Robert smiled proudly at me for drawing attention to my femininity since we were here for only one reason, and that was to reach that final level of intimacy.
It was fairly crowded and everyone seemed to be sneaking glances at me, but I didn't care. I was here with Robert and we were in love, and that was all that counted.
The looks I got I felt were complimentary and admiring, and probably had nothing to do with my hard nipples pushing out my cami and denting my blouse!
Robert treated me really special and I was very excited that he held my hand as we went in together and checked in. At the counter he leaned in to me a little so I could feel his cock. I wiggled my hips to get a bit closer to it, not caring that people could see. I'll never be seeing them again.
The guy took our information and we sat down. I crossed my legs letting my sandal dangle, and leaned into Robert as we looked at "Out" magazine. I kept stealing glances at my pretty toes and my reflection in the windows as I tingled and squirmed in the chair, more conscious of my boy pussy than ever!
Suddenly the receptionist called Robert's last name and a guy led us into a room. Thankfully, Robert didnt let go of my hand. During the questionnaire part, I couldn't stop squirming, and I was getting hard, so I put my hands in my lap to cover my little dick, and Robert thoughtfully put his hand on top of mine and smiled at me.
As soon as our tests were taken, we went into a small waiting room. After many long minutes, the guy came back and we were given our happy results.
From there, we headed off to the Highlands Resort knowing we were biologically safe for each other.
We took our time getting settled in. I cleaned up my "landing strip" again and reshaved my underarms, and did an enema and lubed up my hole again. I got myself into the habit of having a clean and lubed hole and I feel dirty and incomplete now if I don't take care of it.
Robert checked and fussed with my hair so it would look nice. Together we touched up my make up, including rebending my eyelashes with the eyelash curler.
"I have a present for you, Honey. Close your eyes." he said.
I knew he bought me a swimsuit, but I hadn't seen it.
I closed my eyes and he laid it out on the bed. It was bright white and very brief!
"Whoa! That's skimpy!" I blurted.
"Will you wear it? This place is OK. I know you will be beautiful in it."
"I don't know about that. It's way skimpy."
"Come on Honey, go for it. We are at our special place! You are beautiful and I love you. Buy the way, I had a little gaff pocket sewed in it for you." he replied as he kissed me sweetly on the neck.
"Well, I admit I was afraid something might sneak out and embarrass me." I blurted shamelessly, knowing I had no choice but to wear it.
I laid it out and it had two skimpy triangles on top, but that was OK. I'm not all that big but I'll certainly show well enough in this. It had a tie at the neck and back, and both sides of the bottoms. The bottoms rode low on my butt, and just covered my crack. The front was the same as the back, only it was wide enough that I could tuck my parts into the little gaff pocket sewn in and gently cinch the retainer leaving me with a suspicious but nondescript bulge that stayed put. It should work well enough here considering. The bottoms almost didn't quite cover the top of my landing strip, so I shaved it 1/2" shorter, just to be safe.
I felt very vulnerable should something come untied. The whole affair was held together by four little string ties. Not being a Boy Scout, my knot tying is suspect, yet here are little bow ties just waiting to untie themselves!
It took me a good fifteen minutes to get the strings even and correct for my size. There wasn't a lot of swimming suit there. Finally I got it all together, and tucked my little wienie and balls into the pocket and cinched it and that pushed them back between my legs as I got into the suit. The top was confusing but easy. I tied the back part in front of me so I could see what I was doing, then spun it around so the tie was in back where it belonged. Then I lifted it up over my head then worked my boobs in.
I looked in the mirror and was surprised to see a cute little feminine bulge with a nice pair of breasts.
Being completely into my girly role, I asked Robert, "I feel naked. Do I look OK?" as I spun around slowly.
"Honey, you are absolutely, stunningly gorgeous."
Robert saying that made me feel like a runway model!
Robert took my hand and we went out to the pool for some nude sunbathing. No one was there so we both took a quick dip in the pool and got out to sunbathe. He got totally nude, and I went topless. I was wary of a tan line but I had to try to be in the shade anyway since I burned easily and got darker freckles, not that it mattered at his point in my life.
People were very nice, and I returned lots of smiles. My wedding rings sparkled, and I felt pretty! I noticed through my sunglasses that people first glanced at my finger nails, then my toenails adorned with my cute toe ring, then to my crotch and boobs, and finally to my wedding rings and necklace. Then back to my crotch.
Laying in the warm sun, I took advantage of the quiet and began to drift into a half asleep twilight and began to think about my first successful relationship.
Robert is my man and I've learned when to be in the role as his boyfriend, his girlfriend, or when to simply be a submissive and feminine version of either. Or both. Neither of us wants me to try to be the alpha male in our relationship.
Tonight, it's feminine and submissive as usual. There are no more excuses. I want to get it over with. I want it hot and hard, and I want him to fuck me as if his life depended on it.
Given everything I have been immersed in the last few days, it's all like a big dream.
Jostled out of my reverie by some noise of some sort, my mind slipped back to the here and now at the pool. I suspect many guests weren't sure if I was a guy or maybe just a girl with small boobs! But I was a little jealous that a couple of guys were checking out my muscular daddy, wishing I weren't here.
It was beginning to cool, so we decided to come in and have some more wine. I put on my top, and we gathered up our things. We had brought food for the first night with us in case we decided to eat in and enjoy a romantic evening.
We soon treated ourselves to a lovely kissing and lovemaking session on the couch while still in our bathing suits.
Like a kid with a new toy Robert untied the strings on my top, one by one, letting it gradually fall away. He gently rubbed my nipples as we kissed as he untied one side of my bottoms. Robert was as hard as I have ever known him to be!
"Lets check out the bedroom, Honey." he said as he led me to bedroom.
I gasped as I saw that the bed had been turned down and sprinkled with rose petals, and little tea lights were winking everywhere!
"Oh, Robert! It's beautiful." I replied.
I noticed that our suitcases had been unpacked and things hung up or put away in the drawers, and there was champaign on ice and two glasses.
Robert untied the last string on my bathing suit and it fell away leaving me naked. I quickly slid onto the sumptuous bed.
As soon as Roberts trunks hit the floor, he joined me and kissed me deeply.
"Just remember that I love you sweetheart." he replied.
I could sense he said that to play down my fears. I knew that bearing a fire, dam break, or medical emergency, come hell or high water nothing was going to stop my studly stallion now!
As he held me, he caressed and kissed my naked body, slowly taking his time as my passion increased.
He began to shift more of his weight on top of me as we kissed. He caressed my naked body, running his fingers gently along my sides starting from my underarms, then grazing my breasts, and down to my hips and along my thighs. I never felt so naked in my life. I was mewing and twittering like a teenaged schoolgirl.
As his weight centered on me I pulled my legs up to receive him, and as he came forward, I pulled my legs up to his sides and put my arms around his neck, pulling him to my lips.
He slid down again and suckled on each of my nipples and then traveled down where he kissed and licked my cock, and took my balls in his mouth. He fondled them with his tongue, gently grinding the cords between his teeth causing me to instantly open my mouth in a quiet seductive groan. He released them from his mouth, then forced my little balls up into my body cavity. While holding them in with his thumbs, he sucked on my loose empty pouch. It was a totally surreal and sexy new feeling as I imagined they were gone!
I was in a fog of submission and tingling with lust. He moved back to my cock and took just the head in his mouth, and rubbed his tongue across the sensitive buttons below the head. I began to pant and thrust with a tingling wave of passion and had to push him away before I climaxed!
He got up on his knees and hiked my butt up on his thighs and put a pillow under me. He used his slippery shaft to rub lube on my hole before placing his stiff cock at my entrance. We both began gently rocking, pausing as the relentless pressure on my tight opening began to get uncomfortable. As he sensed the discomfort had abated, he changed to using tiny little thrusts as he applied gentle pressure again.
Each nudge went a little deeper than the last and then sensing my discomfort, he paused to let me adjust. Sensing I was ready, he began his advance again and gained a few more millimeters.
He kept up the gentle pressure until almost unexpectantly, I cried out slightly as my outer barrier yielded and his cockhead slipped in past the first sphincter and pressured the second.
He kept up his gentle and gradual in and out penetration, as I pushed back to receive him, yet trying not to give in to my discomfort. Each time I could tell he was deeper in me until I cried out as he pushed past the last rampart and his cockhead was completely in me.
He held me tightly as I adjusted to his size, then he began rocking in and out, getting me used to the bigger inches to come. He pulled out all the way and added lube, and painlessly slipped back in. I think I now know how it feels to have a baby!
He held my thighs back as he rocked in and out, ever so gently, as the wide middle part of his cock began it's impatient passage home as I threw my head back mouthing a haltingly silent scream as I was stretched even more. Finally, the pain tapered off and vanished, as the wide part passed and my boypussy enveloped his cock in a gentle embrace, and his balls rested on my butt cheeks.
Resting with his cock fully inside me, I allowed myself to appreciate the true measure of my submission to him. I felt complete knowing that we were joined, and eager for what lie ahead. I could actually feel the beat of his heart transmitted through his cock. He squeezed himself larger and I squeezed back, as if we had made a secret covenant soon to be sealed with his seed.
Gradually, he began to work his cock in and out a little at a time. I held on tightly and bravely returned his kisses each time I needed to stretch a bit as he withdrew. Soon, my boy pussy seemed to be at peace with it's new role, and I felt wonderfully loose down there as my pussy dilated and contracted to match the contours of his cock as he slowly moved in and out.
Sensing I was ready, he made several complete, slow, deliberate in and out cycles. His oversized cock's upward slope augmented my it's substantial bulge in the middle, filled me completely as my hole dilated fully and then contracted again, ready to dilate again as each penetration cycle created tingling spasms of delight inside me as he began to find our rhythm.
His wonderful lovemaking skills were sending me over the edge as I began experiencing a wonderful tingling all over that gradually increased to where I felt as if I was suspended in an orgasm that kept increasing in intensity, but wouldn't quite go over the top! I squeezed my hole more tightly trying to cultivate this new and overwhelming sensation! My toes were flexing open and closed and my hands made little fists. I began panting lustily, lost in the search for relief as his balls slapped audibly on me with each thrust.
Instinctively, I squeezed him tighter and pulled myself closer to him as I squeezed my pussy as tightly as I could, desperately trying to ride his thrusts over the waterfall to my climax! I breathlessly panted and mewed like a teenage virgin as he methodically plunged his rigid cock in and out of me as I tried with every fiber to reach my elusive climax.
He began to push harder and faster until suddenly, he froze and held himself tightly in side of me and let out a loud triumphant groan as I felt his cock pulse as jets of his seed spewed deep inside me. As he began to thrust and hold again, I felt him pulsing as he delivered more and more surges of seed in side me. I pulled him as tightly to me as I could to bring him in as deep as possible.
As he began another series of thrusts, I clung to him with all my might. I froze in ecstasy as my skin began tingling and tickling, and my body became rigid in pursuit of my orgasm.
I held him tightly like a teenage virgin as he plunged in and out, forcing girly little high pitched "oohs" and "ahhs" in time with his thrusts. I cared not one bit that people could probably hear us all the way to the office. I am not going to be denied my climax!
Finally, the tingling could go no higher and I began quivering inside and began to shiver with electric pulses as the ecstasy of my orgasm washed over me!
It was wonderful. We've finally mated and I'm seeded and fertilized and had a special orgasm to boot! I had a climax better I have ever imagined possible. I even started giggling as spasms of pleasure coursed through my body!
He continued to kiss me as he told me how much he loves me as he rocked gently in and out of my wet and gushy hole until be began to soften.
We rolled on our sides and he made remained in me for as long as he could.
I rolled over on my stomach and faced him, hoping I only oozed a tiny little mess. He rubbed my butt gently with his hand.
Teasingly he asked me, "Are we going to have a baby?" he asked in his kindest voice.
"I hope so, honey." I replied in the most sweet and feminine voice I could muster.
"Good girl. It could happen, you know. I want my sperm in you all the time." he replied with loving finality.
"I love that idea."
"How about I give you a little kiss." he said as he got upright and lay between my legs.
I spread my legs to make room for him, and he began licking my hole. I was a wonderful act of love, and was a most calming and sexual experience ever. I'd been worrying about my hole after this experience, but now in my mind, all was well and good!
I felt wonderful. When he was done, we took a nap.
After a bit, it was time to get up and dress for hor d' oeurves tonight with other guests. As I began to think about dressing for the occasion, Robert came up to me and gave me a big hug and a kiss.
I was so lost in the moment during his sudden embrace, I neglected to intercept a little rivulet of semen that escaped and slowly made it's way down my leg, tickling every inch of the way. It felt very sexy!
"Oops. I should take a shower." I said, noticing my dribble.
"No, you're just fine. I think it's cute that you had a little dribble."
"But I smell like sex, too." I answered.
"I know. I like it. I'm proud of you, Honey."
And that was that, so I began to lay out my clothes for the community happy hour.
I decided to wear my black, below the belly leggings and a my black panty thongs. The leggings are nice and tight but ride fairly low. For a top I put on a thin white fluffy blouse with a mini cami under it, giving me some modesty in case I take off my spa jacket. I plan to wear it unzipped so I can show some jiggle under my blouse. I combed my hair back and held it with a rainbow scrunchie, then slipped into my pink flip flops with plastic flowers so I could show my pretty toes.
I lightly retouched my make up and realized how happy I felt being able to dress for Robert, especially knowing Robert's seed was inside me.
We joined the people milling about sampling hors d' oeuvres and wine.
As we stood around and made chit chat, I noticed that the more manly partners seemed to wander away and separate from us less manly partners. Robert gave me a nudge, so I stayed with "my" group.
This separation I learned was the custom here and soon we eight guys were all in a gaggle. One guy started acting out and talking with a very gay and girly inflection. After a couple of glasses of wine, we were all doing it and making feminine gestures and carrying on. We were soon all hinting about sexual things our partners liked, and how much we loved to do this and that.
I was the only one dressed this fem, but the guys appreciated that and remarked positively about what I was wearing. We all made little jokes and some shared that they often wore feminine things underneath, or to parties and, of course to bed.
We all got to giggling stupidly as we kept our wine glasses full. It was really fun being one of them and for the first time in my life, enjoying "coming out" into a different sexual identity. I really did feel like a blushing bride!
With more wine we began to get more silly, all of us at least hinting that we just came from an afternoon of having powerful sex with our alpha males!
After my second glass of wine, I noticed Robert looking in my direction. That meant it was time for me to leave my new friends. As I left the gaggle, I couldn't help but notice "My" group did act like a bunch of silly girls! I smiled proudly to myself.
We went to the restaurant and had two nice steaks and more wine. I felt completely different. I felt comfortable dressed the way I was, I enjoyed being with the other "boys" tonight, and I feel really great that I've crossed the Rubicon and am carrying Robert's seed. I felt happy, loved, and complete.
But, I was about done in and ready to go back to the room.
We got back to the room and poured a glass of wine.
"I'm beat. I can't wait to get to bed." I said.
"Me too."
We went in the bathroom and maneuvered around each other until he got done and left. I lubed my tender hole again just in case and put on my sheer baby doll nighty with the frilly panties and got into bed with Robert, who was nude.
I snuggled up to him and gave him a kiss, then turned my back to him to spoon with him. He put his arm over me to comfort me, then moved it under my nighty and gently rubbed my breasts and nipples before coming to rest on my stomach.
"That's my sweetieboy. Do you feel OK, honey?" he asked me, kissing my neck.
"Will it always hurt?" I asked.
"Not really. After this vacation, you should be used to it. The more we do it, the easier it becomes. Are you hurting?"
"It hurt at first, but it's not bad now."
"It a matter of me being careful, and you getting used to it."
"How do you know that?" I asked, too quickly.
"Google, honey."
"I think I'm looking forward to that." I said, careful to not give the wrong impression.
He reached under my nighty and began playing with my nipples again. I could feel him poking me with his cock, so I reached back and lowered my panties and kicked them off. Then I put his cock up to my lubed hole. I was hoping we could do it again! Get that baby in shape!
With very little discomfort, he was balls deep inside me.
He pulled out and rolled me over and lifted me so I would be on my knees. I widened my legs, pushing back to present my boy pussy to him as he painlessly reentered me. He began working in and out, holding my hips to him, as I enjoyed each thrust.
"Oh, honey. You are wonderful. You make me feel so good. I love you." he whispered to me.
I was fascinated my the slapping of his butt and balls on me as he grasped my hips and pounded deeply in me.
I squeezed my pussy tightly as my skin began to tingle and my cock began twitching and oozing as he plunged in and out of me. He grunted and I felt him twitching gently as he gave me another measure of his feminizing liquid for me to absorb.
We gradually sunk into the bed with Robert on top of me.
In a few minutes of gentle kisses, he rolled off of me and kissed me gently.
"That was wonderful. Good night, honey." he said.
"Good night, sweetie." I replied.
I was thinking, "Wow. My first quickie!"
We quickly dozed off after that. I was beat. But, boy howdy, the dreams I had.
Chapter Seven
I woke up early and did my thing. There was no semen that I could see in the toilet so happily it all soaked in and I didn't jettison any of Robert's sperm. I went ahead and did a douche and shot a bit of silicone lube up me. I took a shower and felt around a little back there. I was only slightly sore but I was definitely looser down there than before. Other than that I was I was pleased to find myself in a very happy mood.
There wasn't much to do in Guerneville, so we had a leisurely breakfast at a local bar/restaurant. I really had a case of the grins. I don't know what got into me, but I felt as if I was the happiest person in the world. I couldn't help but wonder, "What is in that stuff besides sperm? Tranquilizers?"
Finally, we each got the same idea and decided to head back to the resort. Robert decided to call to have the room made up so we could go to the pool again and not get in the way of housekeeping. Since I got a bit of sunburn on my nipples yesterday, this time I had little choice but to wear my top, and accept my tan lines as being part of who I am.
As we began undressing we took our time and when we were both naked, he gathered me up in his arms and maneuvered me onto a sitting position on the bed.
"Did you think I forgot about my sweetieboy?" he said as he moved my legs out of the way and knelt down on the carpet and began to kiss and lick my little cock.
He slowly licked along the side and the bottom and around the head, then licked all around my crotch. I began to breathe heavily as he took my cock in his mouth. He slowly sucked on me and massaged all around the head with this tongue, causing me to feel as if I was getting tickled by a thousand butterflies as I crept close to a climax. As I writhed with passion, he knowingly licked the head as if it were a clitoris until I had the most wonderful slow motion climax imaginable, as my thin semen dribbled into this mouth.
"Oh, baby. That was wonderful." I said, breathlessly.
"Hummm.... I love you, honey." he replied.
I climbed back on the bed and rested for a bit waiting for the tingling of my orgasm to subside while he softly rubbed my sides and my stomach.
We kissed deeply for a few moments, and then he scooted down between my legs. He lubed up his cock and wiped some on my hole and pushed my legs up. I widened my legs more and reached down to guide him to my opening.
"Careful, baby, she's still a little tender down there.".
"I'll be gentle, my love." he replied.
I was in worried disbelief that he went in so easy with just a few gentle thrusts, and almost no pain. I felt his heavy balls bouncing off my buttocks, as he began to work himself in and out slowly and purposefully.
As he began to pick up the pace of his thrusts, he lay fully down on top of me. We began kissing as I got my hips in motion to match his thrusts and held him tightly, buffeted by his earnest pounding. I squeezed as tightly as I could in time to his thrusts in the hope of achieving a climax. The harder I squeezed the better it felt and the closer I came.
As I worked my hips and my tired sphincter began to slacken, I strived to hurry my climax by pleading in his ear. Since we have been having a lot of sex lately, our sessions have become longer and less frantic until right at the end when he really goes for it. If I climax, that's when it happens.
"Oh, baby. I am so close!"
He started thrusting more powerfully, and I held on tightly as I changed my angle a bit, greedy for my pleasure! My little cock oozed and quivered gently in sync with the slow rolling waves of pleasure sweeping over me as Robert thrust expertly to bring me to my special climax, realizing now that my orgasm was born of a different process than his.
"Arrrgh!" came out of his mouth as he began pulsing inside me just as my climax came and waves of pleasure wracked through my body. I held him tightly, feeling every twitch of his cock as I tingled from every pore and nerve ending in my body as if each had it's own personal climax.
He rested on top of me thrusting gently as I greedily took every iota of pleasure I could. When we regained our composure and rolled over, I felt loose, wet, and messy, and very loved as I rolled face down to keep from leaking.
"How are feeling, honey." he asked.
"Absolutely wonderful." I replied.
"Ready to go to the pool?" he asked as he gently rubbed my butt.
"Sure, in a bit." I lied. I was still foggy headed and buzzing from my climax.
After we rested a bit, we put on our suits and headed for the pool. The shady chairs were taken, so I had to take the sun until it moved.
I smiled and nodded to guys I met the other night when we "boys" all got together for a giggle. We all had secrets to share.
After two hours, it was time to go in. I was getting cooked!
We went back to the room and I took off my clothes and we took a nice cool shower together. Robert was getting frisky again, and I was wondering if maybe I could give him head and give my boy pussy a break.
We got out of the shower and the first thing out of my mouth, was "Oh, wow!". I had a serious and obvious top and bottom tan line, if you consider darkened freckles a tan. I didn't know how to feel about that, except that it was obvious I have been wearing a two piece womans bathing suit. Oh well.
We both lay on the cool sheets, naked and spent.
We went to dinner in a nice up scale restruant, then went back to the resort and began packing and went to bed. I missed getting the dick. I know he probably thinks I don't want it all the time, but I do. And besides that, his semen seems like a drug. Really. I feel better than I have ever felt and different in a positive way.
We woke up early, and I got in the shower and douched and lubed. I got my travel mirror and positioned it so I could look at my boy pussy. It looked like a coin slot. It was not a round, tight little sphincter anymore. Not that it matters, I guess. All in all, it's fair to say, I've changed.
So I slipped back into bed. Robert was stirring, and gave me several sweet "morning breath" kisses which I gladly accepted.
And with that, he began kissing me again, and for the first time in my life I mouthed the words:
"Please fuck me, honey!"
It seems so dirty and unlike me, but today and the last few days have been really special!
I turned my back to him and put his rigid cock up against my hole and pushed toward him. He was inside me in a second.
He rolled me face down, and began pounding his cock into me.
"Let's turn around, honey." he said as he withdrew and rolled my on my back.
He pushed my legs up all they way to where I could rest them on his shoulders and entered me again. I pushed my hips up to help him go as deeply as possible, as he put his arms outside my legs pinning me, allowing my boy pussy to be pummeled.
I began to cry out in my most uninhibited and feminine of voices, and egged him on by panting and huffing like a dime store harlot.
"Oh baby, please." I cried as the tingling began to take over and I began to come close to my orgasm.
"That's my girl. Daddy knows you what you need." he said as he pounded into me, constantly changing positions so as to hit the places inside me that got me over the edge.
"Oh, baby!" I cried out, seconds away from my orgasm.
"Oh!" I almost screamed as my orgasm washed over me with a the force of a Tsunami!
"Oh honey, that's a good girl, let it come." he said as he kept on thrusting into me. I clamped my arms and legs around him so tightly, we became one. He finally let out a roar for all to hear as I felt his familiar pulsing as he released another flood of his feminizing potion deep within me.
"Oh, honey. That was really special." he replied.
"That was wonderful." I said as I rolled over to let his juice soak in.
He began rubbing my butt again, then moved down to play with my little balls and asked me,
"Do you really need to keep these, honey? The hormones would work better." he said.
I replied, "I should probably keep them for now, honey. I don't know if there is much demand for a story about that!"
And after that, we checked out and on the drive back to the hotel we began to talk seriously about matrimony, and agreed to come back again as soon as we had time.
Prologue
Early Life
My parents were totally involved in the family winery biologics business when I grew up, so my older sister became the "go to" babysitter.
Happily for me, my sister figured out that I was more sister than brother so in simple child logic, when we played dress up games she played mommy and I became her daughter, Chrissie.
She always had a lot of clothes for me and I jumped to the chance to play dress up whenever we had the opportunity. When we were in her room would she play "mommy" and wag her finger and sternly order me to me take off my dirty outdoor clothes and "dress like a lady"!
Then she would mother me and lay out things to help me to put on, which would usually be a dress or nightgown of some sort and maybe some Barbie socks or tights and then she put some barrettes in my hair. She would dress me up as she playfully scolded me for being a bad girl for not knowing how to dress appropriately. Then when I was "dressed properly" we would sit and watch TV or read her girl's magazines. We'd point and talk about what outfits were the prettiest, and giggle as we pointed at who we thought was the cutest boy.
As I turned about ten, my sister got a Barbie make up set with all manner of blushes, eyeliners and lipsticks, nail polish. The works! I loved make up!
Mom or dad would check on us "girls" and see me happily playing in my sisters nighty and pink socks, complete with make up and pink nails and glitter. They would smile and roll their eyes, but I loved it!
About that time she got me to wear her panties as part of our play. She always told me how pretty I looked in them, and how silly looking my "boy panties" were. I loved to wear panties whenever I had the chance.
She didn't seem to mind me wearing hers, but a couple of weeks later she told me to ask mom to buy me some panties of my own. She seemed to think mom would be OK with it but I saw no problem just wearing hers. Shortly after that, a package of pretty Barbie panties appeared in my sisters drawer that she said were just for me!
One night I absent mindedly sat down with mom, dad, and my sister to watch TV before bedtime. I had on one of my sister's nightgowns that I had claimed as my own. I had on the pink Barbie panties and socks that went with it. I didn't feel the slightest bit uncomfortable about the way I was dressed when I joined them.
It was the first time I left my sisters bedroom in her nighty. It just felt so natural, I guess I forgot. Mom and dad looked at me, but didn't say a word. They must have understood by now that I was not going to outgrow being interested in girl things. Oddly, When it was bed time rather than just mom or dad, they both came in together and kissed me goodnight. I began to wear a nighty to bed every night every night.
There was many a night when dad was working late or out of town that my sister and I snuggled up on either side of mom and watched TV. Mom would sometimes comb my hair into a playful style and put in a couple of barrettes.
She would put pull up a blanket and put her arms around us, and we would watch TV in our night gowns. I remember how nice it felt to snuggle up to mom and get a kiss on the top of my head with a special snuggle as she rubbed my arm while we watched the program. I'd usually fall asleep with my head resting on her soft boob when she gently woke us up for bed.
When I was around eleven, Mom and I were at Sears one day and she got me some jeans and a couple of shirts in the boy's department. When we were about to leave, she paused and asked me if I needed anything else.
I told mom I wanted a new nightgown of my own. She thought for few seconds and then escorted me to the girls sleepwear section where I spent quite a few minutes looking for something I liked oblivious to being in boy clothes. Finally, I picked out a pink nightgown with puffy gossamer sleeves that flared out and came to my mid calf.
She checked the size and got one size larger, adding: "You probably need some panties, too."
She took me to the girls underwear section where I picked out a package of "Hipster" panties in assorted colors and showed them to mom.
"Honey, those are the wrong size. You wear a girls size 7/8" she said, getting the right size and putting it in the basket.
"You need some socks, too. The ones you have been wearing are getting worn out." she said, kindly.
I picked a package of some frilly ones in various colors.
"Those are too small, Honey. I think you need a medium." she said as I found a package that was the correct size.
From then on mom and I would shop for boy clothes, then we'd go into the girls department and she would let me pick out a thing or two.
And so Mom and dad took the path of least resistance and started treating me like a daughter on the one hand, and a boy on the other. Mom arranged a drawer in my room so when she did laundry so she had some place to put my "pretties" as she called them. It wasn't long and I needed two drawers and extra hangers! I could wear girl clothes in the house when I wanted, but the firmest rule was: No girl clothes outside, ever!
When I was in middle school I became glued at the hip with a certain boy named Brian. She asked me about him and I got evasive. With some motherly persistence, she came to the conclusion that I had a crush on him. Mom kept probing and finally dragged out of me that he and I stopped off at his house on the way from school and played in his room.
His mom worked so I lied that we had touched each other but nothing more. She was really concerned and wanted to know if he had an older brother or if there were other boys in the house. Since he did not, mom seemed to relax and said it was OK if I stopped there for a few minutes, but not to say very long unless I call her first. When my sister was babysitting me I had a lot more leeway to play with Brian.
Once out of the blue, Brian's mom invited me to spend the night at his house. When I asked mom if I could go, she and his mom had a long chat and decided it was OK as long as I wore boy's pajamas.
His mom was really nice, and his dad didn't live there with them. There was one bed in his room and his mom said we would have to share it, which was cool. He and I mostly played with our toys, but when his mom fell asleep on the couch, she awoke and went off to bed as if she forgot about me.
That gave us the chance to get serious about exploring each others bodies. We did a little kissing, but mostly got naked and sucked each others cocks. I don't remember ever coming, but I remember I really enjoyed sucking his cock!
In fact, we both seemed to like it, and it seemed perfectly OK to us. As time went on we spent a lot of time sucking and getting naked and playing in his mother's panties and nighties.
I snuck over there a lot after school when my sister was in charge and mom was working. In fact, Brian and I were pretty much each others only friend in school. Both mom's probably knew what we were really doing and relaxed the rules a bit. Mom's are like that. It's not like pregnancy is an issue.
After I turned about thirteen, my mom and I had "The Talk". Mom told me she wanted to talk about "boys". My dad decided to let mom handle it, which was fine by me.
My parents knew most of everything that was going on with me, and it was getting harder and harder to pretend like everything would keep going on as they were. Even though mom knew I was gay and feminine, I was very defensive and evasive at first. Once I started talking, I could not hold back. I told her everything.
I confessed that I avoided doing the things the other boys did particularly when they played sports. I didn't like getting thrown around and getting bruised up. She drew out of me that the other boys teased me and called me "gay" and that I was afraid they might hurt me, so I stayed with Brian or close to the girls when I could. She asked me if there were any girls I might like to kiss.
"Not really." I replied.
She smiled when we discussed my dressing in girls clothes and my sister a bit, and I admitted I liked it. I agreed that it would be fun to dress as a girl if that meant I could be treated like one by other girls and the boys wouldn't beat me up.
Circling like a hawk, she finally pried my confession out of me that I found myself getting aroused by some boys but not others, but especially by Brian. When she asked me if I had let him kiss me on the lips, I blushed bright red and smiled. Then I nodded my head "yes". She asked me if we got naked together, and I admitted we did, and that I had worn his mother's nighties and we got in his bed together.
Thankfully, she didn't ask for details and ended our conversation with: "Thats OK, honey. Thank you for being honest with me about it. I can't be a good mother if you hide things like this from me. It's OK to like boys, just be cool about it."
Look back, I'm sure mom just wanted me to admit it to her to get it off my chest and let her reinforce that she loved me and she was OK with me being gay. After that she openly talked to me about girl things, boys, and being gay.
I continued to live at home, go to school, and work in our lab and in the plant, and learn the family business.
Socially, I was nowhere. I was a big zero. The feeling of despondency led to me to experiment with hormones when I was eighteen and still living at home.
I had naturally grown two nicely formed, womanly nipples and noticeable breast tissue by time I was thirteen! I actually felt OK about it and was a bit obsessed about my development and peeked at my mom or sister when I could.
When I graduated from high school, I had still not grown the wide shoulders like most boys did. Instead I grew hips. I could wear and pretty much fill one of my sisters old 34AA bras. It may not seem like much to a female, but to me it was a lot! My nipples were at least 3/8" across, and my areolas were 1". I could play with my nipples and nearly reach orgasm!
It so happened that I stumbled into a relationship with a boyfriend who studying to be an RN and was working in a clinic. I was not very manly to begin with, and he was attracted to my femininity. As we got to know each other, he asked me if I ever had my testosterone tested. I had not, so he took to a gender clinic and I gave a blood sample and had it tested. I also gave them a sperm sample. My testosterone was very low, and my sperm count was almost in the infertile range.
One conversation led to another, and finally confided in him I wanted to be less manly and wanted to "soften up". I had been studying the hormones necessary to make some changes, but I didn't know how to get started. Considering nature seemed to have taken me part way, I felt I could go a little bit farther!
He suggested estrogen injections, combined with anti-androgen pills to inhibit testosterone production because they both were available on line. Shots were simpler and safer and he could show me how to administer the weekly shots when he wasn't available.
First we went to the clinic and got a blood test. My testosterone level was 105 and was considered to be low. He told me we would lower my testosterone with the anti-androgens, making the estrogen more effective. He also said he would check into adding a progesterone if my blood tests are normal. I will need to get a blood test from time to time at the gender clinic.
I told him I was interested in doing it.
It was quite simple. He worked out the types and the dosages and then I ordered all three on line and had them delivered to his apartment. I immediately took 1/2 of the anti-androgen pill and saved the other half for bedtime. He gave me a quick shot in the butt, and about two hours later I could tell it wasn't a placebo due to a bit of nausea. It only lasted for a week or so, and it was hard to sleep at first. During the day I felt as if I had an eternal, low grade coffee energy buzz and I was in a very positive mood.
After my first month's blood test my testosterone was quite low and everything else was normal, so we added the progesterone.
As the days marched on, I felt really good.
In the second month I was tested again. It showed my free testosterone level at a female level of 30 and estrogen at a female level of 150. The progesterone was a 12, which is good. The doctor said that I was in a good place to be and he'd see me in six months.
I noticed I didn't think about sex much, and didn't get hard easily, but I was overall happier and more mellow and had a positive outlook to what I was doing. I've always been a crybaby, but now it was easier and I had to be sure to see it coming lest I embarrass myself.
I also noticed that my face began to fill out a bit, and my already girly hips got a bit more padded. I never grew facial hair anyway, but my body hair seemed thinner. I noticed my body odor seemed to change. If I wasn't careful using deodorant, I smelled like my mom when she was working or stressed.
After about four months, I began to notice a lot of little differences and saw some subtle results. My nipples and my breasts were tender and sore and I had a very tender bump behind my nipples. My areolas got larger and a darker pink and for a short period, my nipples began to itch like the dickens like when I was an early teenager.
I already had a pretty fleshy chest and feminine nipples. Now my boobs are slightly bigger and fuller above my breast. It was especially evident when I bent down in front of the mirror.
Before hormones, my nipples didn't stick out much even when I was aroused, but now they stuck out a good 1/2" and my nipples grew to 1/2 inch across, and my areolas enlarged to 1 1/4 inches. They looked just as breasts should look on a fairly flat chested girl. When I got cold or aroused, they were very noticable and I felt compelled to hide them. I was learing the down side of growing real breasts!
The most unexpected difference was although I was less interested in sex, I was still interested but I had to be more comfortable and in the mood.
When I did want an orgasm, my nipples seemed to be connected to my pleasure spots in my groin. My orgasm was a lot different than before. It was longer lasting and quite intense, and was more of a tingling throughout my body. If I ejaculated at all, a little bit of almost clear liquid oozed out, but the afterglow stayed with me a lot longer and was quite pleasant.
I was aware that my testicles seemed to be shrinking a bit, but I didn't care about that since they were in the way. I really wonder sometimes if I need them at all. The process was beginning to worry me a bit. I wasn't sure how far I wanted to go, or when to stop!
Mom started to notice things and began asking questions. I dodged and weaved, and lied, and evaded.
One morning mom and I were having coffee and she asked me how I was doing. I told her I was fine, all was well. Then she dropped the bomb:
"Honey, are you taking hormones?" she asked.
"Uh, no. Why do you ask?" I lied, wondering if it was my areolas that gave me away. Crap.
"I've noticed some changes in your appearance, among other things, since you started dating that nurse guy."
"Oh, Mom. Really?" I blurted, feigning outrage, but knowing my blush was giving me away.
"Really. All I'm going to say is if you are under a doctors care, that's one thing. And we should discuss it. After all, I am your mother. And female. If not, then stop before you hurt yourself."
My mom has always been so supportive of me and my gayness. I felt like hell, and tried to stop the tears from flowing.
"I just wanted to soften up a little." I said quietly.
"I love you Honey, but I think you need to get smart about this. Personally, I don't think a transition to female is in your best interests. You just need to meet the right guy. I'll see you at work." she said sharply as she kissed me on the cheek.
I felt really horrible, being busted by my mother. But at least our talk was short and sweet, and mom didn't carry on about it, thank God.
So I made up my mind to stop, and dropping my malpracticing boyfriend was the first step. The only sort of good thing that came out of it was that he helped me experiment with hormones for awhile and enjoyed it! And I learned how to do it and get blood tests for free!
Not all of the changes have left me. I now get tingly very easily when I get aroused. My ejaculations are still weak and wimpy and my orgasms are much different than before. They are less intense but last longer and leave me tingling. My nipple development has not reverted, and I'm happy about that. And my boobs are pretty much the same. I don't know if it's my imagination or not, but I feel there have been other permanent changes.
Now that I'm out on my own, every now and then I restart for a few months when I start smelling like a man or I think I need a boost.
Prologue
Being a sales and service technician in the family winery service company, I spend every work week in and around the wine country of Santa Rosa, CA. As a partner in the business I have the benefit of autonomy and a good income.
Now that I'm on the road and a bit older and
more mature at the wise age of 24, I much prefer to hide my fetishes in a hotel room. I prefer to put on my nightgown and bathrobe, and go out on my secluded deck and paint my toenails.
To put it plainly: My grown up life pretty much sucks.
However, I am not a total recluse. In safe places like malls and nice department stores, I do love the erotic thrill I get from shopping for women's "pretties". I've found that for the most part the younger girls are closer to my age and tend not to be judgemental, and go out of their way to make me feel welcome to shop there.
Besides, it's sure better than me saying: "This are for my girlfriend, who just happens to be my size."
Mom and my sister have walked in on me a time or two, as I have done to them. There was no mistaking my breast and nipple growth after around 13 years old when I started covering up. I didn't want to have a doctor treat me for "that" and I discussed it with Mom at length explaining that I was fine with it. After much went on that I didn't completely understand, she must have talked to the doctor because I never heard anymore about it, and she was fine with it.
My mother and father are full blooded Irish and I inherited their very pale and translucent skin with light freckles and red hair. I never grew whiskers and have hardly any hair on my body at all. I got most of my physical traits from my mother. I have her squarish hips with a plump and fleshy butt with a perfect 45 degree spine angle that makes my butt stick out.
It would do any sexy young woman proud!
Mom often told me how lucky I was to "be pretty" and have "lovely lips and shapely hips". My sister was more graphic telling me I had a better ass than she did and that I had a nice "wiggle" and a good waist to hip ratio for child bearing if I ever could find a way.
My nipples are very sensitive and reactive, and harden easily, and can light me right up if I get too aroused or play with them! Today, with a push up bra I'm able to easily fill a 36 A and still have some jiggle and bounce.
I'm probably on bit of a downer right now because I just came off a round of hormones. Every few months so far, I get the urge to do a round of hormones for six months or so, then I stop for a while. I'm fine with the idea of doing hormones in cycles to maintain what I have. Maybe someday I will go all the way.
When I'm in my work role, I wear an undersized tight t shirt, then a regular one over it, then a shirt to keep things under control.
My sister was most helpful to me in dealing with my femininity all through my teens. She helped me with clothing that was "cross-over" and unisex. She was always on the lookout for boys that might be interested in me. It was she who suggested the tight t shirt with a looser one over to hide my nipples. We were actually like sisters.
Since we had played dolls and make up since I was little, there wasn't much that surprised her. Mom and my sister often included me in their "girl talk" and I got my share of comments about my feminine features. They both encouraged and reassured me that I very definitely had assets that many gay men like. All in all, they included me as one of them knowing that I too needed to land a man some day.
Fortunately for me, this body is a good fit for the way I feel about myself as an adult now. I'm lucky that my parents accept me as I am and how I live my role in the world. I hope someday I will find the right guy for me.
Chapter One
It was lunch time and I was leaving a service call for the day.
I was about to lift some test equipment into my car and I noticed one of the inside techs was heading my way. I assumed he was heading to his car, so I ignored him and got back to loading my gear.
"May I help you with some of your things?" he said kindly.
I glanced up at him. My stomach quivered a bit as I reacted to the sudden ambush, startled to find a man in my gay o'sphere. I was hoping he didn't spot me rocking my girly ass to some tune in my head!
Even though I recognized him since I had worked with him a time or two, I immediately went on guard and became more cautious.
"No, I think I have it handled." I replied, timidly.
"I'd be happy to help. I'm from the plant. I know you from the work you do inside." he said with a gentle smile.
Somewhat startled, but appreciating his persistence, I replied:
"Ah, I thought I recognized you from the lab." I lied. I had been checking him out for sometime now.
"Sure, that would be helpful if you have time. I have trouble with the heavy items." I replied with my perky but gentle "I'm interested" voice.
He was a pretty big guy at maybe 6'2" and a trim 200 lbs. He seemed to be around my age, or maybe a year or two older.
When I had scoped him out before, I thought he was cute but probably straight.
I could handle my things of course, but I didn't want to deny him the opportunity to help me. I'd much prefer to stand aside and look cute while a handsome man helps me! I would love it if he would rescue me from those dirty boxes, so I can furtively check out his manly body while he wiggles his cute self about!
So, I stood aside and let him get to it. I've learned that a man's protective instincts are either sex based or they aren't. Now that he has played his opening gambit, I need to carefully give him a subtle clue so he will feel safe should he be interested in me. I just hope he isn't an ax-murderer, or spreads shit about me to my customers. I'm wary about being attracted to people who can hurt me.
And maybe being an unapproachable bitch is why I am alone.
I'm not very big at 5'7" and 150 lbs, and I'm careful to hide my more obviously girly features. I do have to be submissive enough to interest the right kind of guy who might be attracted to me, but I still have to project a reasonably manly persona so I don't get myself in trouble.
It's complicated.
I could tell by his gentle voice and the softness of his eye contact that he might be letting me know he was interested. There was certainly the possibility that he just might be being nice and is putting me at ease. I needed to find out which one. I could have just asked him if he was hitting on me, but that was too transactional for me and might scare him off.
Pondering his opening I decided instead to allow my passive personality to creep out just a tiny bit to make sure I'm not misreading him.
I decided to lift a large but light box up and ungracefully fumble with it.
"Here, that's too heavy. Let me do it. You can just tell me where you want it." he said sweetly, as if careful to not hurt my feelings.
"OK." I said with a slight lilt, appreciating the double en tendre.
He smiled sweetly and looked into my eyes for a long instant, which I answered with sweet smile and a slight blush.
Sensing a positive vibe, as he got back to work I moved to where we were standing very close together and almost touching as I pretended to find a way to be helpful. When we touched, I was thrilled that he did not recoil! We touched again, then we were almost touching, then we were touching again! I could smell his masculinity and I could feel his body radiating heat. My heart rate was increasing and I was beginning to perspire, which led to me blushing even more brightly. I knew what I was feeling.
I was feeling like prey. Hopefully, challenging prey. Well, not too challenging.
We reached a rhythm and pretty quickly finished up with me doing the small stuff and him taking care of the larger things.
Since we were done and I could still flee if I read him wrong. I decided to make my move by allowing the pitch of my voice to go up a bit as I thanked him:
"Thank you for coming to my rescue. I'm usually worn out by the time I get it all in! I'm very grateful for your help." I replied with a soft, almost but not quite feminine inflection.
"It was a pleasure." he replied.
"I'm Chris. By the way." I said, holding out my little hand.
"I'm pleased to meet you. I'm Robert." he said as we shook hands.
He continued to hold my hand after the hand shake as my hand's firmness dissipated, causing me to blush. Here we were actually holding hands, which I found very exciting in my otherwise dull love life.
"Oh gosh, I'm sorry." he said, stammering and blushing a little as he released my hand.
"That's quite OK. My fault." I said smiling sweetly at him wishing our hand holding could have continued.
"Can I invite you out to lunch?"
"Sure, I'd like that." I replied.
I was still in a blush as I weighed the possibilities of suddenly grabbing a bull by the horns and getting laid today. What ever happened to my measured, careful, date by date romance with Mr. Right, I mused?
"I'm off for the afternoon." he said.
"Same here! Would you mind if I dropped my van off at the hotel and we took your car?" I proffered making damn sure I at least got in the car with him before he blew me off as some sissy fag he shouldn't get mixed up with. You know, 'all that drama and shit'.
"Absolutely. I'll follow you." he replied.
I parked my van near my entry door and got in his car.
"Nice hotel."
"Yup. I don't pay for it, and my van is always there in the morning!" I commented with a smile.
"It's got a kitchen, two bathrooms, living room. Just like an apartment. I book by the week since I like the extra space." I added.
He took me to the Ca'Bianca Restaurant in Santa Rosa, one of my favorites. He definitely had good tastes and good manners. That was a plus!
After we parked, I stalled for a few seconds by fumbling with my phone and as I had hoped, he opened the car door for me. He had me walk ahead of him and I paused for him to open the restaurant door for me.
As I went in ahead of him, I warmed a bit when I felt his hand touch my butt as he shepherded me inside. He gave the receptionist his name while I stood slightly behind him, invisible.
As the waiter led us to the dining area, Robert thoughtfully asked for a table in a quiet area so we wouldn't be on top of the other diners. I was impressed by his thoughtfulness.
We both ordered very light and had coffee instead of wine, neither of us wanting the other to think we were raging gay alcoholic narcissists! We thoroughly enjoyed each others company and finally his charm disarmed me enough that I felt safe letting my guard down so I could enjoy myself.
"I'm gay, you know. Is that OK with you?" I asked, ignoring what I thought was obvious.
"Yes. Absolutely."
Thank God we didn't have to tip toe around that anymore!
He confessed that it was hard for him to meet a decent guy since he's not a person who likes to meet men in bars.
"I know what you mean." I said, relieved that the obvious had been entered into the record.
I admitted that it's been years since I've had anyone in my life, and summed it up to a couple of unserious boyfriends.
I was wondering if my cross dressing might be an issue, but if we progressed I could introduce it gradually. I was definitely liking this guy.
"I'd love to find the perfect man to fall in love with someday. " I said, something I had struggled with for years.
"Me too." He replied as he reached across the table and put his hand over mine, adding:
"We will someday. That's what keeps romantics like us going!" he said with a warm smile as he withdrew his hand. I missed the touch of his hand instantly.
I smiled and blushed again as if on que, thinking that I'm really liking this guy assuming he's for real and not just playing me along.
He had on short sleeves and had no tattoos that I could see, and from what I could see he wasn't very hairy and seemed to be in good physical shape. That was a plus for me. I was very interested in him and actually, he was making me feel that ambiguous "want" that I've struggled with for years. It's not just "horny", or just wanting release, or blowing someone. It's bigger and more complicated and has kept me out of relationships for years. I want a man to want me, but I want to be courted. In fact, I expected to be courted.
Weighing the factors that brought us together today, I was comfortable with him because we had seen each other around the winery for a couple of years, and had worked in proximity at times and I didn't get creeped out by him. In fact, thinking back he seemed to pop up a lot where I was working and I never dropped my guard enough to encourage him to approach me. Now, I feel quite safe with him since he seems like a responsible person with a good job and I know where he works.
I was wary, but my love life has been barren as a desert. I'm thinking to myself "What am I waiting for?". I decided to go for it. I invited him to my suite for a glass of wine and he quickly agreed.
Chapter two
We drove back to the Marriott where we took the elevator to the top floor. I could tell he was impressed. I always tried to book the same two room extended stay suite partly because it had a large patio that no one could see into. It overlooked an easement and a vineyard, and the workers were far enough away that they weren't a problem even if I accidentally gave them a show!
I have spent many tearful and lonely nights out there dressed in my "pretties" with just me and the occasional mosquito.
I unlocked the room, thankful that the room had been serviced and the air conditioner set. I turned on the light but immediately dimmed it a bit, not wanting to disturb the thoroughly guest tested atmosphere of a nice calm, temperature perfect, quiet, dimly lit room that might be conducive to a nooner.
I excused myself to go to the bathroom, and pointed out the other one if he needed it. I removed the tight t-shirt I wear to disguise my little boobs, and the regular one, and just wore the lighter polo shirt, untucked. I brushed my teeth and put on some chap stick and some fresh deodorant, and did a thorough crotch wash just in case.
When he came out I showed him to the couch and turned on soft music on the TV while I fetched the wine and two glasses.
I sat on the middle cushion and kicked off my shoes, putting my legs under me. I was facing him with one arm on the back rest struggling to think of a question to ask him to break the ice.
"I feel a bit funny all of a sudden inviting you over since we just met, but I don't consider you a stranger since we sort of work together." I said, nervously making a ringlet in my longish red hair.
I didn't know what to do from here.
Whit a smile, he said "I'm just happy that we can get to know each other without people around. I've been trying to catch your eye for a long time, but we never had the chance to work in close enough proximity for me to hit on you!"
"Well, I certainly noticed you. I've been fantasizing about how to get you alone in someone else's winery without getting arrested!" I said with a girlish rhythm.
"That would have been worth it by me! Honestly, I couldn't bear to see you walk out that door one more time and not at least throw my self at your feet just once!."
"Oh, that's very sweet of you." I replied in a sweet voice, putting my hand on his knee hoping to encourage him to keep going.
I looked up into his eyes as he gently pulled me to him. As he moved closer and his lips touched mine he engaged me in small light kisses as he gently rubbed my arm, increasing my arousal.
When we disengaged from our first kiss I looked into his eyes and licked my lips, parting them slightly and leaning back a little to encourage him come to me. As he approached my waiting mouth, my lips welcomed his and we kissed again. After a couple more small kisses, he gently probed with his tongue. I let his tongue pass as he pulled me into his embrace.
He was aggressive and strong and in charge, and I communicated my submissive status proudly.
Thus, began the first surrender of many that I would make to him.
As we broke from our second kiss, I was mindful that we both had worked all day and hadn't showered. His odor was light and masculine, and was turing me on. I hope I was OK.
As he kissed my ears and my neck, I let out a passionate breath as he moved his ticklish kisses down my neck and along my shoulders. I began to breathe heavily as he slipped his hand under my polo shirt and caressed my sensitive nipples with his fingers.
His rolled them gently between his fingers sending me into shameless spasms of delight as I rubbed his larger than life cock through his pants. After many kisses, I was frustrated that we had done about as much as we could with our clothes on, and I was uneasy that we may have reached an impasse on a lumpy hotel couch.
"Can I invite you into my bedroom?" I asked timidly, not sure what to do if he declined.
"I'd like that." he replied.
I took him by the hand and led him in to the bedroom and dimmed the harsh light. I put my arms around his neck again and got up on my toes to kiss him. He put his arms around me and moved his hands under my shirt, and gently caressed me along my ticklish sides from my underarms to my waist. Then he unbuckled my belt and then the top button of my pants. He slid his hands inside my underwear and began to caress my naked butt as my zipper lowered itself as if my magic.
He continued to kiss my ears and neck with ticklish kisses before returning to my lips. I broke off from our kisses with a smile.
I stepped back and looked him in the eyes and began to undress. He took the hint and started doing the same, pretending not to watch me. I did my best to make my movements as sexy and feminine as possible without over doing it.
I took off my top while facing him so he could see my fat, pink nipples perched atop my breasts. Slowly I turned my back partly toward him as I bent down with my legs closed, and slowly removed my bottoms so he could gaze on my girly butt, yet not see my little cock.
When I turned back around to face him he was naked and gloriously hard! He was totally shaved except he had a patch on the front of each ball and square patch above his cock.
I could not help staring at his big cock. It had a good sized head and then his shaft thickened markedly toward the middle, then tapered down again as it reached his body. It reminded me of a bowling pin. My little cock was a dwarf compared to his! Then I was struck with the sobering thought that it could end up inside of me!
I reached up again and put my arms around his neck and kissed him deeply. As we kissed and held our naked bodies tightly together I could feel his big cock pressing against my stomach leaving cool damp kisses as he guided us down to the bed.
We kissed some more and I maneuvered to be on my side so my breasts would sag a bit and be more interesting to him. Taking the invitation, he slid down and took my nipple in his mouth as I rubbed his back and shoulders and moaned with passion.
"Chrissie, you are wonderful." he said quietly. Can I call you Chrissie?
"Oh, God yes.". I breathed out passionately as I warmed to being called Chrissie again. My sister nicknamed me that, and Mom often used it, too.
"And it's a delightful name, too." he added as he returned his lips to my nipple.
"Ohhhh!" I moaned as girlishly, losing myself in passion. I rubbed his broad shoulders as encouragement.
He certainly knew how to turn me on! His touches and kisses were electric, and in my ache for affection, I was ready to go wherever he wanted to take me.
He began to kiss his way down my stomach, gently rubbing my nipples with his dampened fingertips. As he spread my legs, he put his forearms under my knees and lifted gently. I shamelessly pulled my knees up and opened up all the way for him.
He began gently kissing and licking the ticklish skin of my thighs, as his gentle kisses traveled to my bald crotch and little balls, driving my passion to lip biting levels. He licked and kissed my cock then sucked my dysfunctional little balls into his mouth one at a time, then both, to give them a sensuous sucking.
"I love your little balls, they are so cute!"
I responded by yielded to his predominance and becoming more submissive and feminine. In that quick instant, I eagerly shed any pretense of maleness as Robert seemed to enforce my femininity.
He moved to my cock, and gave it little licks and kisses as he continued to massage my swollen nipples with his fingertips. He took my little cock in his mouth again and gently and slowly explored it with his tongue.
He continued to rub my nipples causing me to heave and pant with passion.
"Oh baby, I'm so close." I moaned as my hips writhed shamelessly on the bed like some harlot in a dime store novel!
"That's OK, honey. Let it come."
He kept on working his tongue on the buttons below my cock head with the tiniest movements of his mouth. I tired to hold back but everything seemed beyond my control as my body began to tickle and tingle in an escalating undulation of orgasmic intensity.
Suddenly and too quickly I began oozing my juice into his mouth, letting out the girliest of squeals as my orgasm crested and then plateaued, with every nerve ending in my body alive with energy.
He held me close and worked my cock in and out of his mouth as my orgasm slowly tapered off into a sea of orgasmic spasms and breathy moans as my girly orgasm slowly faded.
When I had softened, he came up and kissed me deeply, sharing the remnants of my watery boy juice.
"Would you be offended if I said you are very girly in bed and I love it!" he said.
"It's been a long time for me, and things slip out. I'm sorry if I made you uncomfortable." I replied.
I was feeling somewhat exhausted and feebleminded, and still tingling from my climax. I was embarrassed that I didn't pulse much any more, but the hormones ended that but ignited other sensations.
"Just be yourself. I love it!" he replied.
"I can get kind of girly if I'm not careful." I said happily still quite buzzed from my orgasm.
"Then be your girly self. It's wonderful." he said as he kissed me again.
I gave him a nudge to roll on his back. Not wanting to waste a second, I began rubbing his big cock and kissing his nipples. I slid down and began gently licking his cock, appreciating how big it was. I took the head in my mouth and began taking in as much of the shaft as I could. I licked the head carefully and slowly and ran my tongue along the bottom to his balls.
I took one ball into my mouth, then the other as I sucked on them gently one at a time thrilled that after all these years I finally had a cock to suck!
"Here, hon. Lets take our time and do it this way." he said and he put me on my back.
He took the pillow and put it under my head and straddled my chest. I suspected he must have felt the needed to show his dominance. It certainly worked. I felt very vulnerable being held down with his dick pointed in my face, even though I was dying to suck it!
He aimed his cock at my lips and as he moved it closer, I licked and kissed the head. I was trying to crane my neck to get it into my mouth, but I could tell he was enjoying teasing me and making me work for it by dragging it all over my smooth face.
"I'm really close, honey. Just kiss it for now. Let's take it slow." he said sweetly.
I was appreciating the game we were playing and was intoxicated with lust as I got to service him as a good little sissy should. He moved his cock up and dragged it lovingly across my lips letting me kiss and lick along the shaft as he presented it to me.
He brought his balls up to my mouth again, and I sucked on them properly as a sissy should.
"That feels good. Just like that, honey."
I inhaled the musk from his balls, eager to bond with his mild yet tangy masculine scent. He let his cock head rest on my lips. I gave it gentle kisses and tickled the bottom buttons with my tongue, catching a drop of precum as it oozed out.
I slowly opened my mouth as I looked into his eyes. He slid the tip in slowly and then stopped when the head was mostly in giving me the honor of licking all over and around the head. The head was nice and fat, but not so much as to prevent me from using my tongue. I was glad that it didn't begin to widen until about an inch or so past the head so I had plenty of cock to work with.
My body was still tingling from my orgasm and now my lips joined in and began to tickle, adding to my pleasure as he moved his cock in and out. I wondered if he would think less of me if he knew how much pleasure I received from the almost orgasmic feeling of his cock sliding over my sensitive lips. I was delighted to let him seek his pleasure in my eager mouth.
With small gentle movements he began to work his cock in and out, each time a little deeper until I couldn't take any more.
Slowly and deliberately he worked his cock in and out of my mouth as I sucked and then paused so I could use my lips and tongue to give him maximum pleasure. If he went too deep, he pulled back and as soon as I regained my composure, we tried again.
"Oh honey, I am so close. Do you want me stop?" he panted, almost teasing.
"No baby. Please. I want it. All of it." I pleaded shamelessly, afraid I might be denied after all these years.
I reached behind him and nudged him toward me so I could move my head better and take more of his cock. He moved forward a bit more but was still making me work for every bit of cock I got my lips around! Finally, I brought him to the edge of orgasm as he tried mightily to control himself. He was nearly motionless as I paused and ran my tongue over all of the head, lovingly licking the sensitive buttons on the bottom.
I took my time as I gradually brought him to the knife edge of climax. At this point I owned his pleasure, and felt privileged to be able to decide the moment of his climax! I felt his cock getting stiffer, and the head beginning to swell as I teased the head and the bottom buttons with my tongue!
Finally my teasing got the best of him and without as much as another tiny stroke, his body stiffened and he let out a groan as his cum burst into my mouth followed by several more powerful pulses as he delivered his bounty with manly determination.
He moved in and out carefully with each wave of pleasure. My lips were pursed as I nursed on his cock and greedily swallowed every bit of cum that he gave me as I massaged his balls. As the pulses slowly tapered off, I kept him in my mouth as long as he would let me so as to get every last sperm.
Neither of the boyfriends I had put out anything near what Robert did. It was all I could do to contain it! Crikey! I never realized how much of a sexual difference there was between a grown, powerful man like Robert and myself with my meager dribble.
"You are a wonderful lover." he said, moving up on top of me as he kissed me. I brought my knees up to receive him, allowing me to feel his weight on my soft body.
We wiggled around a bit more and got rearranged so I could put my head on his chest with his nipple at eye level.
"Why did we wait so long to find each other?" I asked hopefully.
"So we could make our mistakes with someone else?" he replied philosophically.
"That is probably very true." I replied, smiling.
I got out of bed first and sat on the edge of the bed with my back to him.
"I think I need a shower." I said.
"Can I join you?" he said.
"I'd like that." I replied.
I turned on the water in the oversized shower and got out an extra towel for him. I had a large tee shirt I sometimes used for sleeping and a pair of my men's underwear to put out for him, and then hung a hotel bathrobe on the peg by the vanity. I'm not all that sure what else he might need, but this was the best I could do right now.
As soon as we got in the shower he held me in his arms from behind, playfully letting his cock slide around my crack as the water cascaded down our bodies. It was the first time I had ever been in a naked embrace with a man. I felt impishly content as well as tiny and safe in his embrace. I was getting very excited by his big cock brushing my boypussy as I held his arms with my hands.
He turned me around and held me close and kissed me, running his hands over my butt cheeks and pressing himself to me. As he enveloped me in his masculine embrace, I shamelessly pushed my pelvis letting him know I welcomed more.
I was still aroused and tingling after my climax and feeling lovingly submissive. I took the opportunity to go "all in" and used my soapy hands to wash him gently all over, not missing a square inch.
I washed his front, gently squeezing his nipples and lovingly kissing each one. I knelt down and washed each leg carefully, mindful that his cock was hovering within kissing distance of my face. I kissed his cock gently, pleased that it was enjoying my attention as much as I enjoyed giving it.
He didn't balk when I washed his balls and unbeknownst to him, I was inspecting them. I was thrilled that there were no scars from a vasectomy. It was important, albeit selfish of me, that he gives me living sperm.
I returned to his cock and gently washed it, feeling the heft of it and gently kissing and running my tongue around the head. It began to swell a bit, so I decided I'd better leave it alone for now. I washed his front and his underarms, kissing each one when I was done. I tweaked his nipples before giving each one a kiss and a generous suckle.
I turned him around and washed his back, reaching around again to play with his nipples, and let him feel my little cock touching him. I knelt down to wash his legs, then while still kneeling I spread his cheeks and with the pad of my thumb I massaged his anus carefully as if to clean it. Then as a final tribute, I spread his cheeks and licked gently, working my tongue in as far as it would go. I could tell he was enjoying that!
I hope he will see my submissiveness as my way of honoring him and showing him what a good partner I can be if he wants me.
As I washed the soap off, I kissed him again in many sensuous places. I could feel the juices stirring, but I had other things on my mind other than sex. And as my sister used to remind me: "We don't get pretty by accident.".
As I made a bit of a show of washing my hair, he watched me with curiosity. My elbows were out and I was unafraid to reveal my shaved underarms, should he notice. I was also aware that my little boobs were bouncing and wiggling, and my little cock was wiggling.
"You are really beautiful, honey. Can I say 'beautiful'? he said as he took a wash cloth and soaped it up.
"Sometimes." I said, with my sexiest smile in a melodious voice.
With one hand he applied the soap to my skin, and washed me with his soft bare hands. He used his thumbs to graze over my nipples, teasing them to become fully erect, then kissing each one as his hands traveled down over my cock and balls. He massaged my hardening cock, and then took my balls in his hand and squeezed them just enough.
"I love your cute little balls. They feel so nice." he said.
I knew he would soon figure out that when he would redirect my attention to my balls, I instinctively became more submissive, almost admitting that I didn't need the worthless things at all.
He turned me around again and using his bare hands, he sensuously soaped my back and butt and let his fingers graze over my crack. I could feel his hardening cock constantly touching and sliding around on my soapy butt. I was rapidly heading back into a cloud of passion and losing control.
"You have a lovely body." he said quietly.
"Ohh." I breathlessly replied.
As he rubbed my globes with his soapy hands, my hips rocked with carnal urgency as he used his thumb to massage my tight little hole.
He pushed in a little and my mouth instinctively flew open in a gasp as I arched my back and pushed my rear toward him. He continued to rub inside the opening of my boy pussy as he rubbed my left nipple.
I began to lose control, panting vocally with lust.
"Oh, Robert." I moaned, breathlessly.
He moved his cock up to my opening and pushed just enough to begin to enter me. I pushed back at this first attempt, causing him to push and hold himself in just far enough to where I could feel the beginning of the stretching pain that would be the prelude to my breeding.
Suddenly, I regained my wits about me and turned around facing him before he could go in any farther.
"I'm sorry, baby. Not right now. I'm still a virgin and I'm not ready to do that yet!" I sniveled, turning around to face him, afraid that I may have already gone too far to stop him.
"I'm sorry. I got carried away." he said apologetically.
"Whew." I thought to myself.
"We need to take a break, big guy." I said to him as I kissed him, still fidgety and sexually excited, as well as conflicted by the stark symbolism of my first little bit of penetration, and the myriad of lascivious feelings it generated.
"That's OK. It was my fault for not controlling myself!" I replied contritely as I reached up and kissed him on the cheek, blushing hotly due to a very passionate near miss.
He sensed my unease and hugged me tightly.
We got out and began to dry off.
"I put some things for you on the counter. You can use any of my toiletries, and the blue toothbrush is new and you can have that. I have a thing or two left to do." I replied.
"I'm sorry, honey." he said again, apologetically.
I stopped and faced him, and replied:
"It's OK. I really was tempted, you know. It's all good." I said as I kissed him gently.
What I needed to do was get my bathroom back.
I wanted to test him by changing into something a little more feminine to bring him along gently. Also, I needed some personal space to finish up and dress.
"OK," he said contritely, taking the hint as he stepped out and took his toiletries and things to the other bathroom.
Chapter Three
I busied myself with getting back in the shower and tidying up my landing strip and reshaving my legs and underarms. My feet were fine since yesterday morning's dilatory was good for a week or more. I didn't want him to see me doing these things. We don't know each other that well. Someday maybe, but not now.
I rubbed myself with a very lightly scented vanilla honey body lotion so I'd smell nice and my legs would look nice and smooth.
I wanted to be subtle with some hints of femininity while we got used to each other, but I was unable to plan my clothing since I didn't expect to bring home a visitor. The only loungy thing I had that would work were some woven yoga shorts. They rode quite low on my hips and were snug enough to show my girly butt off nicely. They had small front pockets stitched with pink thread as an accent, and had a pink string tie.
They fit perfectly, and always made me feel sexy.
But I had a problem: all of my underwear and panties were in the living room where Robert was waiting, so I decided "what the hell" and decided to go "commando" since I was small enough down there that things won't creep out and I'm not trying to hide anything. Better commando than looking stupid by going in the other room looking for underwear.
I'm thinking: "Enter, say hello, find underwear, get it without him seeing, say bye, come back." I think not.
For a top I had a white vee neck blouse that would show some midriff and allow me some swing and jiggle, and was thin enough to show my nipples.
I combed my longish hair straight back so that when it dried it would fall and look more feminine.
I decided to put on my short white kimono style bathrobe that came up to my mid thigh, since I didn't feel comfortable going in the front room without a wrap just yet. Besides, I think short bathrobes are sexy!
When I came up to the couch he looked at me quizzically.
"I'm sorry. Did you want the short one?" I asked playfully as I loosened up the tie and sat down with him, forgetting all of my fears.
"NO, you are quite beautiful in that one. It's perfect." he gasped.
I snuggled close to him and pulled my freshly shaved legs under me and leaned into him so he would put his arm around me. He gently rubbed my leg as I put my head on his shoulder pretending to watch TV while I explored his thigh with my fingers.
"Did you shave your legs? They are very smooth and sexy. I really like that." he said.
"We can't let girls have all the fun, can we?" I quipped as I lifted my head and we met for a kiss.
He pulled me to him and kissed me again. We began to kiss more deeply, and our hands began to explore inside our robes. He unexpectedly put his hand in my stretchy yoga shorts to rub my butt.
"Hmm, did someone forget their panties today?." he asked cutely.
Well, that cat finally charged out of the bag, I thought to myself.
"I didn't have any with me this trip." I lied, knowing I had two pairs in my dresser.
"Would you like me to buy you some tomorrow?" he said.
"I'll buy them if you want me to wear them for you. But that is very thoughtful." I chirped girlishly.
"I'd like that. I love your femininity." he said.
"I'm very relieved, and I think it's sexy to hear you say it!" I replied.
"You are sexy." he replied.
"I don't mean to be too forward, but I'm here all week and you can spend every night if you wish all the way through next Friday night. I have to go home next Saturday afternoon back to Oakland, then back here on Monday." I asked, hopefully.
"I'd like that, but I have to leave tonight to do some things Saturday." he said.
"Can't you spend tonight with me and leave tomorrow?" I asked, meekly.
"No, I can't. I have to leave tonight, but I will be able to come back tomorrow." he insisted.
"Really?" I said, disappointingly.
"Yes. I'll be back in the morning."
"Crap. I knew it." I said to myself.
I probably scared him off by being too forward.
I wanted him to spend the night tonight since we made love for the first time today, then he could leave tomorrow if he must leave then come back in the afternoon so we could spend Saturday night, plus all of our other nights together in an unbroken string until I had to go back to Oakland next Saturday night. Then we could be back together on Monday!
I don't know how I lost control of the situation, but I did. I expected him to actually be thrilled to spend the night with me. We could have cuddled and kissed and maybe even had more sex, and then woke up in the morning cuddling like a couple of newlyweds.
He's probably pissed because I wouldn't let him fuck me.
"I should be here all morning." I told him as sweetly as I could manage, as I gave him his fucking key.
He gave me a kiss and a hug and off he went, leaving me with that empty, sinking feeling that maybe I blew it already and it was over. I felt more alone than ever, already missing the companionship and the kisses and loving touches that came from the man who popped into my life, however briefly.
I smiled a painful smile as a thought entered my head that this was one of the few times I can remember that I was actually lonely. But not just ordinary lonely, but lonely for "him". And what do I have to show for it? A peck on the lips and an empty bed.
I'm surprised at myself for letting my emotions lead me out on a limb. Now I'm wondering if he just sawed it off.
His departure made me feel unloved and rejected. He obviously didn't seem to care enough about my feelings to understand how much it would have meant to me if he would have spent the night.
I'm wondering if I made a mistake and he was just some lousy bastard who used me.
As I got more melancholy and the walls began to close in, I poured myself a glass of wine and sat out on the patio in a pair of panties and the under shirt he wore today, hoping to relive our closeness.
After another glass of wine, I said "the hell with it" and changed into my super sexy white tights, no panties, and a short black chiffon camisole.
I brought out my nail polish and painted my toenails a nice shade of reddish pink and drew a little flower on each big toe. I don't care if he likes it or not. If he does, great, if not too bad!
I was an emotional wreck, but I suppose I should be happy that at least I got to give him a blow job as a consolation prize and with any luck his sperm found a nice place to spend the night, even if he didn't.
I poured myself another short glass of wine and got all weepy. I changed back into panties and his t-shirt and went to bed at 10:00 o'clock. I massaged my nipples and cock for a bit but got nowhere. Finally I said "fuck it" and cried my eyes out.
I was up at eight Saturday and poured my self a Pepsi for breakfast to wash down my energy bar. I felt better this morning after a good nights sleep, albeit a lonesome one.
A few minutes later, Robert called to see if I needed anything. He was on his way from Novato!
I felt wonderful. I was happy and joyful, and down right giddy. I cleaned up my messes and got my clothes reorganized. I made two drawers ready and made room in the closet for him, just in case.
I knew there was a reason I couldn't accept that he would not come back to me!
I jumped into the shower and washed up and shaved my legs and underarms and touched up my landing strip, and then shaved the rest of the area while the dilatory went to work on my feet.
I didn't want to look like I had gone to extra trouble after getting out of bed. I quickly changed back into a pair of sleeping shorts, and put on my tank top with the large arm openings, leaving little left to the imagination! My boobs could be peeked at from the sides or the top, and every movement I made caused my breasts jiggle and sway like bait on a hook.
I combed my hair straight back and put a scrunchie in it and pulled down some bangs.
He came to the door Saturday right on time. He was wearing shorts and sexy tight top that showed off his physique. I was impressed and I was showing it. I was getting hard and wanted to jump his bones as soon as he dropped his suitcase!
He took me in his arms and gave me a wonderful kiss! He was hard and so was I! Oh how I loved his hands rubbing my bottom as he pulled me into him!
"Good morning, honey. I like your toes." he said quietly into my ear.
"I did them to surprise you sweetie." I whispered back.
He started to waltz our embrace toward the bedroom, when I suggested we should have a nice breakfast since I didn't know when housekeeping was coming. Plus, I liked that if we could put off sex right away, I'd be buzzing with lust all day and hopefully, so would he.
I called room service for a breakfast to be sent up.
In short order, breakfast arrived and Robert graciously intercepted the waiter and signed the ticket and took care of the tip. The young man gave me a hungry look as I smiled sheepishly at him, thankful that Robert was here to deal with him. He blushed and smiled, and retreated as if he was afraid that Robert was going to bite him!
I wished I wasn't dressed like a little tart but it would have to do. I could tell Robert was OK with it. I smiled as I noticed that Robert's eyes were all over me.
Chapter Four
After breakfast we lounged around a bit, with me fighting off Robert's attempts to take me to bed. I wanted him to be good and horny insuring that he would pay lots of attention to me. I suggested we go to the Coddington mall and comeback after housekeeping was done.
I changed into mostly normal "manwear" but put on a pair of women's low rise "Wedgie Jeans" I picked up at "Forever 21". They fit me perfectly, and the seam seperated and lifted my butt cheeks like a delicious peach! For a top I chose a simple, loose button up shirt with a thin t shirt under it and loafers with pink sox. To be complete, I put on a thin gold chain with a cross and a couple of bracelets on each wrist.
As we wondered around the mall, Robert was very affectionate, and doted on me, touching me often making me feel very special and secure.
Robert steered me to a Victoria's Secret window display and we gazed at the lingerie clad manikin. My heart began beating faster as I visualized wearing some of that sexy lingerie and being pretty for Robert.
Standing very close to me as lovers do, he moved his hand and stroked me ever so gently on the inside of my elbow where I'm ticklish in a strangely erotic way.
"Have you gotten any panties yet, honey?" he asked, quietly into my ear.
"No, not yet." I replied, only partly lying.
I felt my cock stir this time when he called me "honey" as he touched me. I was beginning to feel very warm and tingly as his breath tickled my hair.
"Let's browse around. I'll help you pick some out. It will be fun." he said softly into my ear, giving me more erotic goose bumps on top of my other goose bumps!
He put his hand on my bottom and guided me in, as I'm thinking, "Oh, crap. I am actually going into Victoria's Secret shopping with my boyfriend!"
We went in and started looking around together. This wasn't my first rodeo but I'd never been to Victoria's Secret before, and never, ever shopped with a man beside me. Being in here with Robert was turning me on and yet I was shaking like a leaf to boot.
Robert wasn't shy at all.
"What size are you, honey?" he asked, too loudly for my comfort.
"Size 7." I practically whispered, hoping he'd catch the hint.
This shopping trip was rapidly becoming an erotic extension of our bedroom.
He continued to call me "honey" regardless of who was nearby. He touched me when and where he felt like it, just as any man might touch his girlfriend.
A subtle bump to my hip with his ample cock, reminded me of another reason why I was in this relationship in the first place!
"Just relax, honey. No one cares. Couples like us are probably in here every day." he said quietly.
I knew he was really telling me to stop trying to be in control and let him take the lead as a man should. I had nothing to gain and everything to lose by not knowing my place.
"OK. I'm fine. It just takes me awhile to adjust." I replied, apprehensively.
"Just pretend you are my girlfriend." he said, with a quiet smile.
He took me over to the panty displays and we took our time as he pointed out several pairs he thought I'd like.
I was thankful that Robert stayed very close to me as we looked around. Our touching closeness was comforting to me even if it drew a few glances. Most were friendly, and a few met my eyes with a knowing smirk.
The whole experience was getting me hot. I was buzzing with the excitement of being a couple and being proud to be just another sissy out lingerie shopping with his man.
I was soon lost in the moment, tuning everyone out but Robert. I guiltlessly looked and touched, and held up a pair of pink hipster panties that were especially interesting and gazed tenderly up at Robert for approval.
We looked around a bit more and we chose three more pairs of panties in different styles and colors. They were really sexy and I love panties that have lots of cheek peek. I suspect Robert does, too.
By now, I was well turned on and was enjoying myself. I picked up a pair of black panty thongs, and a black pair with a lace up affair in the rear. In front of a pair of twenty something women standing next to me, I asked him playfully:
"Honey, can I get these, too?" using my gay lilt.
"Of course you can, sweetie. I can't wait to see you in them." I could tell by his smile, he was relishing the taste of victory!
I started looking around more when Robert noticed me gazing toward the lingerie section.
"Let's check that section out, honey." he said as he affectionately rubbed my butt as he directed me there.
He noticed my interest in a pink fly a way baby doll nighty.
"That would look cute on you. Would you like to try it on?" he asked.
"No, and please, no." I replied, softly.
He took it off the rack and held it up to me!
"You'll look so hot in that! Let's get it!" he said.
On the way to the check out, he saw a sexy top.
"Check this out." he said.
It was a white blouse that was thin and sheer with delicate lace trim. It was literally transparent and certainly designed to be worn with a bra and camisole in public. Robert was grinning like a Cheshire cat.
"Really?" I said
"I think you'd be a knockout in it." he said.
"OK. For you I'll do it. Just don't ask me to wear it out in public." I said, not even caring that the sales clerk was right next to me, smiling.
"Shall I add this to your purchase?" she said, kindly.
"Yes, but I need to find a white cropped mini cami." I said, getting totally into it as she set my purchases aside.
I quickly found a thin white one that hung down just below my breasts and ended with a lace fringe. It was unlined and sheer to the point of being translucent. Perfect! I like them short and loose with no elastic on the bottom, almost if they were a drape.
I added it to my pile, and she began ringing things up holding and folding every purchase for everyone to see.
"Will this be all today?" the clerk asked with a friendly smile.
"Yes, thank you." I replied, with my sweetest gay lilt.
She ran my credit card and handed it back to me. When she handed me the bag, she said
"Thank you, honey."
I smiled at her pleasantly, wondering if my name on my credit card had been changed to "Honey", but I gave her my best gay "You're welcome", knowing all in all it was a nice experience I wouldn't mind having again.
On the way to his car he asked, "That went well. Were you nervous?"
"Yes, but I'm glad you pushed me along. I couldn't have bought all of that by myself." I replied, still fidgety with nervousness.
"Yeah, we should do that again." he said.
"True." I replied, still somewhat puzzled at why he outed me like that.
"Let's go have dinner and go home." he said.
I nodded and smiled at the term "home".
"Take me home, Robert!" I replied in a twitter.
Robert had me so totally figured out. He inspired me to embrace my lingerie fetish right there in Victoria's Secret knowing I would not want to lose face in front of him.
When we got back to the hotel, I opened a bottle of wine and led Robert out to the patio. I suggested to him that I needed to change into something more comfortable and excused myself. He indicated that he was going to go put on a bathrobe.
I decided to keep it simple and sexy since it was getting close to bedtime. I put on some fresh deodorant and cleaned my bottom. I decided on my white cheeky panties and no top. I put my hair up into a high bun and held it together with a pink scrunchie.
I put on my shorty bathrobe and went out on the patio to join Robert, making sure my ties were loose enough that it would "accidentally" end up partly open in the front.
"Honey, you look beautiful." he said.
"I'll bet you say that to all the boys!" I quipped.
"No, just my one and only sweetieboy!" he said with a smile.
I was feeling horny as hell.
I leaned over him for a kiss and as planned, my bathrobe opened up all the way revealing my almost pendulous boobs dangling and wiggling, and my new panties with an outline of my cute little hard on.
"I'm getting a wonderful view, honey."
"Thank you, baby." I replied melodiously.
"It's close to bed time, isn't it?" He asked.
"It is, isn't it?" I replied sweetly.
We went into the bed room and dropped our bathrobes. Robert was completely naked, but I elected to stay in my panties fir modesty as we slipped into the cold bed. He immediately wrapped me in his warmth and kissed me gently, as his hard cock touched and probed me as his ample precum left cool damp little kisses as if to remind me of it's ultimate mission.
Robert moved his lips to my nipple and rubbed my cock though my panties with his other hand as I squirmed with passion. He rolled my panties off and kissed his way down between my legs. He opened me as wide as possible, and began kissing and licking all over down there.
He pushed my legs up farther and began licking at my boy pussy. It was wonderful!
"Ohhh, baby." I moaned excitedly as I pulled my legs and hips up to help his access.
I had my legs almost up to my chest when he licked my boy pussy a bit, then took my cock in his mouth.
"Honey, I'm too close. Let me do you a bit, please?" I whined, as I guided him on top of me not wanting to cum first.
Sneakily, he pulled my legs up with him, leaving my defenseless boy pussy open to him as we kissed some more as he teased me with his cock slipping up and down near my hole until it found it's goal.
He began to push gently.
"Honey. Please, no. I'm not ready." I whispered, yet still wanting to revisit that wonderful feeling of him testing limits I had not yet set for myself.
"Just a little sweetheart, I'll be careful." he said.
As I tensed up when I felt the stretching as he pressed into me, he stopped pushing and let his cock rest where it was. When it stopped hurting I pushed back a little more before I admitted to myself that I really liked what we were doing, but I was actually being a dick teasing little bitch by leading him on.
He answered by pushing a little bit more.
"Let's stop." I said, deciding it was time to stop before it was too late.
He rolled over on his back and I started kissing him again, moving down to his cock knowing he was disappointed.
I began licking all over and around his cock and after some teasing, took him in my mouth. He was really on fire! As soon as he entered my mouth he began gently thrusting his hips to meet me, using my mouth as his personal boypussy. I kept up as much stimulation and pressure as I could, and my tongue was as busy as I could make it, as Robert worked his cock in and out of my mouth.
Sensing that he really needed to cum quickly, I reached up and rolled his nipples gently between my fingers. He was practically convulsing as I slowed down the blow job just a bit to keep him on the edge, until he couldn't hold it back any longer.
With a groan of relief, his seed gushed into my mouth in strong, manly pulses with each burst sending another surge of seed. I kept him in my mouth and swallowed every bit as he slowly softened.
After he softened, I moved up to be close to him as we both began to drift off to sleep. I rolled over with my back to him so we could spoon. I reached down and took his semi soft cock and placed it up against my hole so he could feel it. I wanted to give him hope.
He pushed playfully against my boy pussy as we both drifted off to sleep as I fantasized that his little sperms were marching five by five into me as we slept.
Chapter Five
I woke up snuggled in to him with my face nearly in his underarm. For whatever reason I didn't mind it at all. I liked it. I snuggled in closer feigning sleep and breathed carefully through my nose with my eyes closed bonding with my mate.
I was intrigued that we will be together for another five consecutive nights! I'm looking forward to being a couple and going to bed and waking up day after day, sharing each other.
I'm eager to see if my needs are simply fantasies or realty, and if I can be unselfish enough to give myself up to man who will undoubtedly change my life in unexpected ways.
It's certainly a win for me. I will get to live my fantasy of "wifing" him as much as he will let me. I want it to be my job to cook for him and serve him his food, and take care of his clothes and things, as well as his sexual needs, just as a loving wife would do. I don't know how far he will let me go just yet, but I'd really like it if he will let me get it out of my system when we are together and I can find out if he likes it.
In short order, we blissfully surrounded ourselves with a rhythm that matched our uncommon sexuality. As a bonus, he was perfectly content to let me "be myself", and be as femininely submissive as I wanted.
One night after we had been together for two months and spending five or six nights per week together, we were on the patio quaffing some wine and he said he wanted to have a "chat".
"OK." I replied, nervously.
"Honey, I want to have intercourse with you. We've been together for awhile now." he said hopefully, adding, "I promise to be slow and careful and use a condom, and make sure I don't hurt you."
"No condom." I replied.
The look on his face was priceless.
Then I added, "I'm open to that someday, but we should get tested because it's the right thing to do given the intimacy we have. We should have done it already." I said, flatly.
"It's been awhile since I've been tested, but I'm sure I'm clean." he said.
"I want us both to get tested together, and then maybe some special day it will happen." I replied cryptically.
"There must be a testing place in Santa Rosa." I added.
Intercourse has been on my mind a lot lately and I'm glad he brought it up first.
I had been Googleing a bit and came away with the impression that generally the more manly the man the more they need this activity. It is important for them to validate their manliness in the relationship and they feel they need to constantly prove their virility to their partner.
Hell yeah! I'm so looking forward to experiencing my "manimal" at his most basic level.
"OK. Let me see what I can work out." he said.
The next Sunday when we got back together for the week we went out on the patio to catch up. He was pretty smiley. He said he found a place for couples testing. We go in together, test together, and get the results together. He said he had a couple of ideas to make it a memorable occasion.
He told me that he would like us to go as a married gay couple and he wanted me to wear his late mothers wedding rings.
He also wanted me to "fem up" a bit for the occasion so it would be obvious that I was his feminine wife.
I agreed that I sounded like a cool idea. Hell, after the trip to Victoria's Secret, this was easy!
I figured the testing places see all kinds of people, so it would be safe to "fem up" there.
With the closeness we had I felt that maybe we were almost to the point of considering marriage or something close to it someday. There was precious little I would not do for Robert if he asked.
In fact, if he asked, I'd probably say "Yes".
As our plan developed we decided that after our tests in Santa Rosa, we would plan a three day "honeymoon" of sorts at the Highlands Resort in Guerneville. The Highlands is a gay resort for fun and frolic with a suite for us overlooking the clothing optional pool .
The week before the test he produced the wedding rings. They were beautiful. He had them polished and sized for me, and wanted me to wear them when ever we were together in an appropriate situation.
"I want you to be proud to be seen with me as my feminine partner." he said.
"Honey, are you proud enough to also be my girlyboy and wear my mothers rings?" he added somewhat formally.
"Of course I am, sweetie." I said eagerly.
He got on his knees as if proposing, then asked me:
"Chris honey, will you marry me?"
"For Real" I asked excitedly.
"For real." he replied.
"Yes. Robert. I will!" My eyes began to tear up, and I couldn't get the words out fast enough.
He took my hand and slipped the rings on my finger one after the other. My eyes were watering, and I was beginning to cry with tears of joy.
"I can't wait until we get married." he said.
"I need to ease the family into it." I said. "But, exclusivity is most important to me."
"It is to me, too. How about I arrange a commitment ceremony at the resort but without the paperwork? We can save that for the actual marriage if you are OK with that."
"I like it, sweetie." I purred with my most feminine inflection, really getting into it. "But we can wait on that. Let's wait for the wedding." I added, buoyed enough by his commitment.
He was really into my feminine side, and I enjoyed playing into it. When he would buy me sexy things to wear, I enjoyed reacting with girly glee for every thing he bought me, eager to tease and tantalize him with them.
I was pleasantly aware that other than being straight at work, I was living the other 16 hours as Roberts "gender flexible" boyfriend! Now that a true, enduring relationship is on the horizon, I'm looking forward to our honeymoon and losing my virginity while letting Robert breed me proper, over and over anytime he wants it!
"We should start shopping for our engagement vacation, which I would prefer to call our first honeymoon." he said.
"That sounds like fun!"
"I'd like you to dress a little fem for me so you can get used to going out in public at the resort." he replied.
"Oh, boy. That's a little scary. I've never gone that far out in public, really." I said, hopefully.
"We'll go to San Francisco and start in the Castro. We'll just take it easy. Everything is cool there." he said.
"OK. I think I can deal with the Castro." I replied, casting my eyes downward as I caved in.
"Come on honey, the whole idea is for you to be comfortable for our testing and our honeymoon. We don't have to play it down for anyone around there." he reminded me.
When he left me alone, I began staring into my closet visualizing a "look" and putting things on the bed that might work.
I decided on my tight pair of tailored white women's jeans I bought some time ago. They fit my hips well and the back seam dives in to separate and define my butt cheeks. The high center seam helps me to tuck pretty well. Plus, it had a pretty sliver dangly metal belt to go with it.
For a top I chose a white blouse with pink horizontal stripes that was fairly tight and showed my breasts and nipples somewhat. I decided to wear my ladies leather jacket. It was a bit short so I would leave the shirt tucked. I could adjust the jacket zipper to control my jiggle if I have to.
OK. Jacket, blouse, pants.
He wanted me to wear my women's sandals and a pink toenail polish since this would be my first time dressing in public, and he thought pink wouldn't show that much.
I got out the lightest pink shade that I had, and when I was done, it was bright and obvious! I could plainly see it and was there for anyone else to see. He said it was not that obvious. He was full of it. I could see it in the mirror across the room!
So rather than be difficult, I decided to go all in and put on my pair of blingy sandals to set off my pretty feet. I really had no choice now but to trust his judgment. After all, who looks at feet in the Castro? Sheeiiitttt...
I did put on some very light eyeliner and light shadow, then added some blush to my cheeks, and some light lipstick. Light, light, light... subtle all the way to help me get used to feeling comfortable being a pretty boy for Robert.
Hair was easy. I pulled my hair back with a white scrunchie, but higher than a straight guy would do and piled it up on my head and brought along my cute little newsboy hat, just in case.
I did a slow pirouette around my mirror and concluded that unless if I spoke softly, no one would know I was a guy.
Shopping in the Castro was a comfortable experience. I see why Robert brought me here. Many same sex couples were holding hands and being very touchy-feely. It really helped me to calm down. It was an area where I could be totally free to be gay and express my femininity through my clothing. Before long I turned my wedding rings around so the diamonds were facing out.
I latched onto Roberts arm and let them sparkle for the world to see!
We found a women's casual clothing and sportswear shop, and Robert suggested we look for a bathing suit for me there.
We wandered over to the bathing suits. A sales girl came up and asked Robert if he could be helpful. Robert asked her where the bathing suits were.
"They are in that room to the right."
"Honey, why don't you browse around a bit while I look for a surprise for you." he said.
While he went looking at bathing suits I browsed around looking mostly at the various ensembles they had on the manikins to get some ideas. I liked the way they mix denim and white blouses with neck scarves. Other than the scarves, I can do that.
I went to another area and tried on a pair of denim shorts that fit perfectly, and has the deep back seam that makes them look sexy. Plus, these allowed the bottom of my butt cheeks to peek out just a bit, so I decided to buy them while I had them in front of me.
"Didn't find anything, eh?" I asked.
"I did, but they have to do an alteration and will ship it to us."
"Uh, what did you buy me?"
"It's a surprise for our vacation." He said, finally.
"Honey, can we go home now? I've had enough for one day. I want to start packing. I have a lot to do." I said, too tired to wonder what he bought me since he'll be sure I wear it anyway.
Chapter Six
Today is the day! We are going to get our HIV/STD tests. I'm so tickled I can't stop grinning!
I wore some unremarkable clothes and a wide neck athletic shirt since Robert made arrangements for me to get my hair and make up done before we head off for the resort. I don't care what the stylist sees, or thinks. She is just there to do my hair, and make up, probably someone else will do my pedi and nails
Robert and I drove to a salon where he had made arrangements for them to open up early for me so I could get pretty for our appointment without a lot of people around. From our tests we were going straight to the resort.
I slipped into a quiet reverie as we drove to the salon and put some thought into my situation.
After we get cleared on our tests, I can be pretty sure my virginity will be long gone before tomorrows sun comes up!
I confess that I'm apprehensive about it hurting given Robert's size, so I've been trying to stretch a bit to avoid that. For genetic reasons, I don't express my needs the same way Robert does, but I do understand that men like Robert have a need to express their masculinity this way, and I want him to do it with me and not someone else. And the idea of us finally being joined and him filling me with his living sperm is a thought that makes me shiver with lust!
I just hope I like it as much as Google says I will, because I will probably be getting it again and again whenever the mood strikes us, all through our honeymoon and beyond!
"Honey, we also have a pedicure and a manicure booked for you before our test. I'd like them do your make up if you are OK with that." he said, waking me from my thoughtful reverie.
We arrived at the nail salon where I had my manicure and pedicure by a cute guy who I hope was gay. He didn't have a lot to say, but he got right to work. I expected a woman, but who cares?
He scrubbed my feet and make them look and feel really nice. I did a dilatatory on my feet last night so he would have less to do. He shaped and filed my toenails to get them just right. I chose to go with Barbie pink on my toes and my fingernails for our special day.
When we were done, he asked me to put on my top so it wouldn't mess up my hair when I put it on. So I went into the ladies room and quickly put on the button up blouse and my mini cami.
He combed my longish hair back and braided in some "peasant curls", then added regular curls and extensions to my longish hair. Then end result was very feminine, and sexy, yet didn't look trashy.
When it was time for make up I was a little hesitant. The guy said I had very feminine features, and that under the circumstances I should take advantage of them.
I decided given what all was going on, I might as well go all out! It certainly would be an experience.
He went to work on me and within a few minutes I was done, complete with sexy eyebrows, curled eyelashes, and tasteful make up and lipstick. Thank God, he didn't make me look like a drag queen!
When Robert returned after I was done, he stopped mid stride when he saw me in make up. He told me I was beautiful. If he only knew how it makes me purr when he says that! When I finally got to look in a mirror, I was impressed!
I noticed he used light touches of make up and made me look quite nice and not the least bit slutty.
Then Robert opened up a bag and showed me a cute pair of women's sandals he bought me that had a bit of "bling" on the straps. Given the nature of our couples testing, I had no problems putting them on right now and showing off my piggies!
He opened up another small bag and produced a toe ring that looked like a wedding set with faux diamonds. He produced another bag that had a necklace with a gold chain with a gold key on it.
The salon let me change there, so we could save some time and get to the testing place.
I put on the toe ring and Robert helped me with the necklace.
I had my outfit packed on top and all ready to go, so dressing was pretty easy.
I wore my tightest white wedgie pants with my panty thong, and tucked myself into it creating a passable camel toe with my balls on each side of the seam and my little cock down the back. I put on my loose pink blouse with a thin mini cami under it so I'd still have some wiggle and jiggle.
Suddenly as an afterthought, I decided not to pretend and to let my small package show. I left my balls tucked but untucked my cock and allowing me to be seen as a guy tastefully dressed em fem with his lover.
I added my sandals and a couple of bracelets and I was good to go.
When I stepped out and took Roberts arm, the stylist smiled, and wished us well.
Next stop was the testing facility. As we walked from the parking lot, I walked slowly and let my hips undulate sexually. Robert smiled proudly at me for drawing attention to my femininity since we were here for only one reason, and that was to reach that final level of intimacy.
It was fairly crowded and everyone seemed to be sneaking glances at me, but I didn't care. I was here with Robert and we were in love, and that was all that counted.
The looks I got I felt were complimentary and admiring, and probably had nothing to do with my hard nipples pushing out my cami and denting my blouse!
Robert treated me really special and I was very excited that he held my hand as we went in together and checked in. At the counter he leaned in to me a little so I could feel his cock. I wiggled my hips to get a bit closer to it, not caring that people could see. I'll never be seeing them again.
The guy took our information and we sat down. I crossed my legs letting my sandal dangle, and leaned into Robert as we looked at "Out" magazine. I kept stealing glances at my pretty toes and my reflection in the windows as I tingled and squirmed in the chair, more conscious of my boy pussy than ever!
Suddenly the receptionist called Robert's last name and a guy led us into a room. Thankfully, Robert didnt let go of my hand. During the questionnaire part, I couldn't stop squirming, and I was getting hard, so I put my hands in my lap to cover my little dick, and Robert thoughtfully put his hand on top of mine and smiled at me.
As soon as our tests were taken, we went into a small waiting room. After many long minutes, the guy came back and we were given our happy results.
From there, we headed off to the Highlands Resort knowing we were biologically safe for each other.
We took our time getting settled in. I cleaned up my "landing strip" again and reshaved my underarms, and did an enema and lubed up my hole again. I got myself into the habit of having a clean and lubed hole and I feel dirty and incomplete now if I don't take care of it.
Robert checked and fussed with my hair so it would look nice. Together we touched up my make up, including rebending my eyelashes with the eyelash curler.
"I have a present for you, Honey. Close your eyes." he said.
I knew he bought me a swimsuit, but I hadn't seen it.
I closed my eyes and he laid it out on the bed. It was bright white and very brief!
"Whoa! That's skimpy!" I blurted.
"Will you wear it? This place is OK. I know you will be beautiful in it."
"I don't know about that. It's way skimpy."
"Come on Honey, go for it. We are at our special place! You are beautiful and I love you. Buy the way, I had a little gaff pocket sewed in it for you." he replied as he kissed me sweetly on the neck.
"Well, I admit I was afraid something might sneak out and embarrass me." I blurted shamelessly, knowing I had no choice but to wear it.
I laid it out and it had two skimpy triangles on top, but that was OK. I'm not all that big but I'll certainly show well enough in this. It had a tie at the neck and back, and both sides of the bottoms. The bottoms rode low on my butt, and just covered my crack. The front was the same as the back, only it was wide enough that I could tuck my parts into the little gaff pocket sewn in and gently cinch the retainer leaving me with a suspicious but nondescript bulge that stayed put. It should work well enough here considering. The bottoms almost didn't quite cover the top of my landing strip, so I shaved it 1/2" shorter, just to be safe.
I felt very vulnerable should something come untied. The whole affair was held together by four little string ties. Not being a Boy Scout, my knot tying is suspect, yet here are little bow ties just waiting to untie themselves!
It took me a good fifteen minutes to get the strings even and correct for my size. There wasn't a lot of swimming suit there. Finally I got it all together, and tucked my little wienie and balls into the pocket and cinched it and that pushed them back between my legs as I got into the suit. The top was confusing but easy. I tied the back part in front of me so I could see what I was doing, then spun it around so the tie was in back where it belonged. Then I lifted it up over my head then worked my boobs in.
I looked in the mirror and was surprised to see a cute little feminine bulge with a nice pair of breasts.
Being completely into my girly role, I asked Robert, "I feel naked. Do I look OK?" as I spun around slowly.
"Honey, you are absolutely, stunningly gorgeous."
Robert saying that made me feel like a runway model!
Robert took my hand and we went out to the pool for some nude sunbathing. No one was there so we both took a quick dip in the pool and got out to sunbathe. He got totally nude, and I went topless. I was wary of a tan line but I had to try to be in the shade anyway since I burned easily and got darker freckles, not that it mattered at his point in my life.
People were very nice, and I returned lots of smiles. My wedding rings sparkled, and I felt pretty! I noticed through my sunglasses that people first glanced at my finger nails, then my toenails adorned with my cute toe ring, then to my crotch and boobs, and finally to my wedding rings and necklace. Then back to my crotch.
Laying in the warm sun, I took advantage of the quiet and began to drift into a half asleep twilight and began to think about my first successful relationship.
Robert is my man and I've learned when to be in the role as his boyfriend, his girlfriend, or when to simply be a submissive and feminine version of either. Or both. Neither of us wants me to try to be the alpha male in our relationship.
Tonight, it's feminine and submissive as usual. There are no more excuses. I want to get it over with. I want it hot and hard, and I want him to fuck me as if his life depended on it.
Given everything I have been immersed in the last few days, it's all like a big dream.
Jostled out of my reverie by some noise of some sort, my mind slipped back to the here and now at the pool. I suspect many guests weren't sure if I was a guy or maybe just a girl with small boobs! But I was a little jealous that a couple of guys were checking out my muscular daddy, wishing I weren't here.
It was beginning to cool, so we decided to come in and have some more wine. I put on my top, and we gathered up our things. We had brought food for the first night with us in case we decided to eat in and enjoy a romantic evening.
We soon treated ourselves to a lovely kissing and lovemaking session on the couch while still in our bathing suits.
Like a kid with a new toy Robert untied the strings on my top, one by one, letting it gradually fall away. He gently rubbed my nipples as we kissed as he untied one side of my bottoms. Robert was as hard as I have ever known him to be!
"Lets check out the bedroom, Honey." he said as he led me to bedroom.
I gasped as I saw that the bed had been turned down and sprinkled with rose petals, and little tea lights were winking everywhere!
"Oh, Robert! It's beautiful." I replied.
I noticed that our suitcases had been unpacked and things hung up or put away in the drawers, and there was champaign on ice and two glasses.
Robert untied the last string on my bathing suit and it fell away leaving me naked. I quickly slid onto the sumptuous bed.
As soon as Roberts trunks hit the floor, he joined me and kissed me deeply.
"Just remember that I love you sweetheart." he replied.
I could sense he said that to play down my fears. I knew that bearing a fire, dam break, or medical emergency, come hell or high water nothing was going to stop my studly stallion now!
As he held me, he caressed and kissed my naked body, slowly taking his time as my passion increased.
He began to shift more of his weight on top of me as we kissed. He caressed my naked body, running his fingers gently along my sides starting from my underarms, then grazing my breasts, and down to my hips and along my thighs. I never felt so naked in my life. I was mewing and twittering like a teenaged schoolgirl.
As his weight centered on me I pulled my legs up to receive him, and as he came forward, I pulled my legs up to his sides and put my arms around his neck, pulling him to my lips.
He slid down again and suckled on each of my nipples and then traveled down where he kissed and licked my cock, and took my balls in his mouth. He fondled them with his tongue, gently grinding the cords between his teeth causing me to instantly open my mouth in a quiet seductive groan. He released them from his mouth, then forced my little balls up into my body cavity. While holding them in with his thumbs, he sucked on my loose empty pouch. It was a totally surreal and sexy new feeling as I imagined they were gone!
I was in a fog of submission and tingling with lust. He moved back to my cock and took just the head in his mouth, and rubbed his tongue across the sensitive buttons below the head. I began to pant and thrust with a tingling wave of passion and had to push him away before I climaxed!
He got up on his knees and hiked my butt up on his thighs and put a pillow under me. He used his slippery shaft to rub lube on my hole before placing his stiff cock at my entrance. We both began gently rocking, pausing as the relentless pressure on my tight opening began to get uncomfortable. As he sensed the discomfort had abated, he changed to using tiny little thrusts as he applied gentle pressure again.
Each nudge went a little deeper than the last and then sensing my discomfort, he paused to let me adjust. Sensing I was ready, he began his advance again and gained a few more millimeters.
He kept up the gentle pressure until almost unexpectantly, I cried out slightly as my outer barrier yielded and his cockhead slipped in past the first sphincter and pressured the second.
He kept up his gentle and gradual in and out penetration, as I pushed back to receive him, yet trying not to give in to my discomfort. Each time I could tell he was deeper in me until I cried out as he pushed past the last rampart and his cockhead was completely in me.
He held me tightly as I adjusted to his size, then he began rocking in and out, getting me used to the bigger inches to come. He pulled out all the way and added lube, and painlessly slipped back in. I think I now know how it feels to have a baby!
He held my thighs back as he rocked in and out, ever so gently, as the wide middle part of his cock began it's impatient passage home as I threw my head back mouthing a haltingly silent scream as I was stretched even more. Finally, the pain tapered off and vanished, as the wide part passed and my boypussy enveloped his cock in a gentle embrace, and his balls rested on my butt cheeks.
Resting with his cock fully inside me, I allowed myself to appreciate the true measure of my submission to him. I felt complete knowing that we were joined, and eager for what lie ahead. I could actually feel the beat of his heart transmitted through his cock. He squeezed himself larger and I squeezed back, as if we had made a secret covenant soon to be sealed with his seed.
Gradually, he began to work his cock in and out a little at a time. I held on tightly and bravely returned his kisses each time I needed to stretch a bit as he withdrew. Soon, my boy pussy seemed to be at peace with it's new role, and I felt wonderfully loose down there as my pussy dilated and contracted to match the contours of his cock as he slowly moved in and out.
Sensing I was ready, he made several complete, slow, deliberate in and out cycles. His oversized cock's upward slope augmented my it's substantial bulge in the middle, filled me completely as my hole dilated fully and then contracted again, ready to dilate again as each penetration cycle created tingling spasms of delight inside me as he began to find our rhythm.
His wonderful lovemaking skills were sending me over the edge as I began experiencing a wonderful tingling all over that gradually increased to where I felt as if I was suspended in an orgasm that kept increasing in intensity, but wouldn't quite go over the top! I squeezed my hole more tightly trying to cultivate this new and overwhelming sensation! My toes were flexing open and closed and my hands made little fists. I began panting lustily, lost in the search for relief as his balls slapped audibly on me with each thrust.
Instinctively, I squeezed him tighter and pulled myself closer to him as I squeezed my pussy as tightly as I could, desperately trying to ride his thrusts over the waterfall to my climax! I breathlessly panted and mewed like a teenage virgin as he methodically plunged his rigid cock in and out of me as I tried with every fiber to reach my elusive climax.
He began to push harder and faster until suddenly, he froze and held himself tightly in side of me and let out a loud triumphant groan as I felt his cock pulse as jets of his seed spewed deep inside me. As he began to thrust and hold again, I felt him pulsing as he delivered more and more surges of seed in side me. I pulled him as tightly to me as I could to bring him in as deep as possible.
As he began another series of thrusts, I clung to him with all my might. I froze in ecstasy as my skin began tingling and tickling, and my body became rigid in pursuit of my orgasm.
I held him tightly like a teenage virgin as he plunged in and out, forcing girly little high pitched "oohs" and "ahhs" in time with his thrusts. I cared not one bit that people could probably hear us all the way to the office. I am not going to be denied my climax!
Finally, the tingling could go no higher and I began quivering inside and began to shiver with electric pulses as the ecstasy of my orgasm washed over me!
It was wonderful. We've finally mated and I'm seeded and fertilized and had a special orgasm to boot! I had a climax better I have ever imagined possible. I even started giggling as spasms of pleasure coursed through my body!
He continued to kiss me as he told me how much he loves me as he rocked gently in and out of my wet and gushy hole until be began to soften.
We rolled on our sides and he made remained in me for as long as he could.
I rolled over on my stomach and faced him, hoping I only oozed a tiny little mess. He rubbed my butt gently with his hand.
Teasingly he asked me, "Are we going to have a baby?" he asked in his kindest voice.
"I hope so, honey." I replied in the most sweet and feminine voice I could muster.
"Good girl. It could happen, you know. I want my sperm in you all the time." he replied with loving finality.
"I love that idea."
"How about I give you a little kiss." he said as he got upright and lay between my legs.
I spread my legs to make room for him, and he began licking my hole. I was a wonderful act of love, and was a most calming and sexual experience ever. I'd been worrying about my hole after this experience, but now in my mind, all was well and good!
I felt wonderful. When he was done, we took a nap.
After a bit, it was time to get up and dress for hor d' oeurves tonight with other guests. As I began to think about dressing for the occasion, Robert came up to me and gave me a big hug and a kiss.
I was so lost in the moment during his sudden embrace, I neglected to intercept a little rivulet of semen that escaped and slowly made it's way down my leg, tickling every inch of the way. It felt very sexy!
"Oops. I should take a shower." I said, noticing my dribble.
"No, you're just fine. I think it's cute that you had a little dribble."
"But I smell like sex, too." I answered.
"I know. I like it. I'm proud of you, Honey."
And that was that, so I began to lay out my clothes for the community happy hour.
I decided to wear my black, below the belly leggings and a my black panty thongs. The leggings are nice and tight but ride fairly low. For a top I put on a thin white fluffy blouse with a mini cami under it, giving me some modesty in case I take off my spa jacket. I plan to wear it unzipped so I can show some jiggle under my blouse. I combed my hair back and held it with a rainbow scrunchie, then slipped into my pink flip flops with plastic flowers so I could show my pretty toes.
I lightly retouched my make up and realized how happy I felt being able to dress for Robert, especially knowing Robert's seed was inside me.
We joined the people milling about sampling hors d' oeuvres and wine.
As we stood around and made chit chat, I noticed that the more manly partners seemed to wander away and separate from us less manly partners. Robert gave me a nudge, so I stayed with "my" group.
This separation I learned was the custom here and soon we eight guys were all in a gaggle. One guy started acting out and talking with a very gay and girly inflection. After a couple of glasses of wine, we were all doing it and making feminine gestures and carrying on. We were soon all hinting about sexual things our partners liked, and how much we loved to do this and that.
I was the only one dressed this fem, but the guys appreciated that and remarked positively about what I was wearing. We all made little jokes and some shared that they often wore feminine things underneath, or to parties and, of course to bed.
We all got to giggling stupidly as we kept our wine glasses full. It was really fun being one of them and for the first time in my life, enjoying "coming out" into a different sexual identity. I really did feel like a blushing bride!
With more wine we began to get more silly, all of us at least hinting that we just came from an afternoon of having powerful sex with our alpha males!
After my second glass of wine, I noticed Robert looking in my direction. That meant it was time for me to leave my new friends. As I left the gaggle, I couldn't help but notice "My" group did act like a bunch of silly girls! I smiled proudly to myself.
We went to the restaurant and had two nice steaks and more wine. I felt completely different. I felt comfortable dressed the way I was, I enjoyed being with the other "boys" tonight, and I feel really great that I've crossed the Rubicon and am carrying Robert's seed. I felt happy, loved, and complete.
But, I was about done in and ready to go back to the room.
We got back to the room and poured a glass of wine.
"I'm beat. I can't wait to get to bed." I said.
"Me too."
We went in the bathroom and maneuvered around each other until he got done and left. I lubed my tender hole again just in case and put on my sheer baby doll nighty with the frilly panties and got into bed with Robert, who was nude.
I snuggled up to him and gave him a kiss, then turned my back to him to spoon with him. He put his arm over me to comfort me, then moved it under my nighty and gently rubbed my breasts and nipples before coming to rest on my stomach.
"That's my sweetieboy. Do you feel OK, honey?" he asked me, kissing my neck.
"Will it always hurt?" I asked.
"Not really. After this vacation, you should be used to it. The more we do it, the easier it becomes. Are you hurting?"
"It hurt at first, but it's not bad now."
"It a matter of me being careful, and you getting used to it."
"How do you know that?" I asked, too quickly.
"Google, honey."
"I think I'm looking forward to that." I said, careful to not give the wrong impression.
He reached under my nighty and began playing with my nipples again. I could feel him poking me with his cock, so I reached back and lowered my panties and kicked them off. Then I put his cock up to my lubed hole. I was hoping we could do it again! Get that baby in shape!
With very little discomfort, he was balls deep inside me.
He pulled out and rolled me over and lifted me so I would be on my knees. I widened my legs, pushing back to present my boy pussy to him as he painlessly reentered me. He began working in and out, holding my hips to him, as I enjoyed each thrust.
"Oh, honey. You are wonderful. You make me feel so good. I love you." he whispered to me.
I was fascinated my the slapping of his butt and balls on me as he grasped my hips and pounded deeply in me.
I squeezed my pussy tightly as my skin began to tingle and my cock began twitching and oozing as he plunged in and out of me. He grunted and I felt him twitching gently as he gave me another measure of his feminizing liquid for me to absorb.
We gradually sunk into the bed with Robert on top of me.
In a few minutes of gentle kisses, he rolled off of me and kissed me gently.
"That was wonderful. Good night, honey." he said.
"Good night, sweetie." I replied.
I was thinking, "Wow. My first quickie!"
We quickly dozed off after that. I was beat. But, boy howdy, the dreams I had.
Chapter Seven
I woke up early and did my thing. There was no semen that I could see in the toilet so happily it all soaked in and I didn't jettison any of Robert's sperm. I went ahead and did a douche and shot a bit of silicone lube up me. I took a shower and felt around a little back there. I was only slightly sore but I was definitely looser down there than before. Other than that I was I was pleased to find myself in a very happy mood.
There wasn't much to do in Guerneville, so we had a leisurely breakfast at a local bar/restaurant. I really had a case of the grins. I don't know what got into me, but I felt as if I was the happiest person in the world. I couldn't help but wonder, "What is in that stuff besides sperm? Tranquilizers?"
Finally, we each got the same idea and decided to head back to the resort. Robert decided to call to have the room made up so we could go to the pool again and not get in the way of housekeeping. Since I got a bit of sunburn on my nipples yesterday, this time I had little choice but to wear my top, and accept my tan lines as being part of who I am.
As we began undressing we took our time and when we were both naked, he gathered me up in his arms and maneuvered me onto a sitting position on the bed.
"Did you think I forgot about my sweetieboy?" he said as he moved my legs out of the way and knelt down on the carpet and began to kiss and lick my little cock.
He slowly licked along the side and the bottom and around the head, then licked all around my crotch. I began to breathe heavily as he took my cock in his mouth. He slowly sucked on me and massaged all around the head with this tongue, causing me to feel as if I was getting tickled by a thousand butterflies as I crept close to a climax. As I writhed with passion, he knowingly licked the head as if it were a clitoris until I had the most wonderful slow motion climax imaginable, as my thin semen dribbled into this mouth.
"Oh, baby. That was wonderful." I said, breathlessly.
"Hummm.... I love you, honey." he replied.
I climbed back on the bed and rested for a bit waiting for the tingling of my orgasm to subside while he softly rubbed my sides and my stomach.
We kissed deeply for a few moments, and then he scooted down between my legs. He lubed up his cock and wiped some on my hole and pushed my legs up. I widened my legs more and reached down to guide him to my opening.
"Careful, baby, she's still a little tender down there.".
"I'll be gentle, my love." he replied.
I was in worried disbelief that he went in so easy with just a few gentle thrusts, and almost no pain. I felt his heavy balls bouncing off my buttocks, as he began to work himself in and out slowly and purposefully.
As he began to pick up the pace of his thrusts, he lay fully down on top of me. We began kissing as I got my hips in motion to match his thrusts and held him tightly, buffeted by his earnest pounding. I squeezed as tightly as I could in time to his thrusts in the hope of achieving a climax. The harder I squeezed the better it felt and the closer I came.
As I worked my hips and my tired sphincter began to slacken, I strived to hurry my climax by pleading in his ear. Since we have been having a lot of sex lately, our sessions have become longer and less frantic until right at the end when he really goes for it. If I climax, that's when it happens.
"Oh, baby. I am so close!"
He started thrusting more powerfully, and I held on tightly as I changed my angle a bit, greedy for my pleasure! My little cock oozed and quivered gently in sync with the slow rolling waves of pleasure sweeping over me as Robert thrust expertly to bring me to my special climax, realizing now that my orgasm was born of a different process than his.
"Arrrgh!" came out of his mouth as he began pulsing inside me just as my climax came and waves of pleasure wracked through my body. I held him tightly, feeling every twitch of his cock as I tingled from every pore and nerve ending in my body as if each had it's own personal climax.
He rested on top of me thrusting gently as I greedily took every iota of pleasure I could. When we regained our composure and rolled over, I felt loose, wet, and messy, and very loved as I rolled face down to keep from leaking.
"How are feeling, honey." he asked.
"Absolutely wonderful." I replied.
"Ready to go to the pool?" he asked as he gently rubbed my butt.
"Sure, in a bit." I lied. I was still foggy headed and buzzing from my climax.
After we rested a bit, we put on our suits and headed for the pool. The shady chairs were taken, so I had to take the sun until it moved.
I smiled and nodded to guys I met the other night when we "boys" all got together for a giggle. We all had secrets to share.
After two hours, it was time to go in. I was getting cooked!
We went back to the room and I took off my clothes and we took a nice cool shower together. Robert was getting frisky again, and I was wondering if maybe I could give him head and give my boy pussy a break.
We got out of the shower and the first thing out of my mouth, was "Oh, wow!". I had a serious and obvious top and bottom tan line, if you consider darkened freckles a tan. I didn't know how to feel about that, except that it was obvious I have been wearing a two piece womans bathing suit. Oh well.
We both lay on the cool sheets, naked and spent.
We went to dinner in a nice up scale restruant, then went back to the resort and began packing and went to bed. I missed getting the dick. I know he probably thinks I don't want it all the time, but I do. And besides that, his semen seems like a drug. Really. I feel better than I have ever felt and different in a positive way.
We woke up early, and I got in the shower and douched and lubed. I got my travel mirror and positioned it so I could look at my boy pussy. It looked like a coin slot. It was not a round, tight little sphincter anymore. Not that it matters, I guess. All in all, it's fair to say, I've changed.
So I slipped back into bed. Robert was stirring, and gave me several sweet "morning breath" kisses which I gladly accepted.
And with that, he began kissing me again, and for the first time in my life I mouthed the words:
"Please fuck me, honey!"
It seems so dirty and unlike me, but today and the last few days have been really special!
I turned my back to him and put his rigid cock up against my hole and pushed toward him. He was inside me in a second.
He rolled me face down, and began pounding his cock into me.
"Let's turn around, honey." he said as he withdrew and rolled my on my back.
He pushed my legs up all they way to where I could rest them on his shoulders and entered me again. I pushed my hips up to help him go as deeply as possible, as he put his arms outside my legs pinning me, allowing my boy pussy to be pummeled.
I began to cry out in my most uninhibited and feminine of voices, and egged him on by panting and huffing like a dime store harlot.
"Oh baby, please." I cried as the tingling began to take over and I began to come close to my orgasm.
"That's my girl. Daddy knows you what you need." he said as he pounded into me, constantly changing positions so as to hit the places inside me that got me over the edge.
"Oh, baby!" I cried out, seconds away from my orgasm.
"Oh!" I almost screamed as my orgasm washed over me with a the force of a Tsunami!
"Oh honey, that's a good girl, let it come." he said as he kept on thrusting into me. I clamped my arms and legs around him so tightly, we became one. He finally let out a roar for all to hear as I felt his familiar pulsing as he released another flood of his feminizing potion deep within me.
"Oh, honey. That was really special." he replied.
"That was wonderful." I said as I rolled over to let his juice soak in.
He began rubbing my butt again, then moved down to play with my little balls and asked me,
"Do you really need to keep these, honey? The hormones would work better." he said.
I replied, "I should probably keep them for now, honey. I don't know if there is much demand for a story about that!"
And after that, we checked out and on the drive back to the hotel we began to talk seriously about matrimony, and agreed to come back again as soon as we had time.