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Fantasy Gone Awry
My girlfriend and I had decided to spend the upcoming spring break weekend at her apartment for a quiet weekend alone. Her roommate was going to Daytona for the week, and we both thought it would be nice to spend it together. Besides, Sally had to work the latter half of the week and wouldn't be able to go too far anyways .
Sally and I had been dating for almost three years now, but that didn't mean she knew everything about me. We met while we were both freshman at the University we currently attended. She is a gorgeous brunette with shoulder length hair, standing 5'8" tall and having a surprisingly small waist for her large, voluptuous breasts. Her long legs and shapely body make you wonder why you don't see her modeling in lingerie catalogs. Sally is not only physically alluring, but she is intelligent, witty and charming. In light of this, she always surprised me with how soft-spoken, reserved and conservative she was. Trying to get her to try something new was always and exercise in futility. She came from a family that was quite wealthy and made sure their little girl had everything she needed....and wanted, further adding to the paradox.
In contrast, I am 5'6", and 140 pounds of minuscule man power. I did make good grades, but more than a few people wondered why she stayed with me. Included in those wondering were myself, her family and many of her closest friends. I didn't come from a family with money and had a questionable past. She was very accepting and supportive of me. Still, the question was if I would ever share my secret with her. She would undoubtedly go hysterical if I told her crossdressing was something that was a part of me. I had always come off as the macho type, or tried to anyways. It's not all that easy at 5'6". I would go to the gym regularly and make somewhat sexist comments. I would say things that people told me were typical "guy" things, just to appear more masculine or get a laugh.
We would both be graduating this coming May and she constantly inquired about our relationship. This weekend gave me an idea, and I finally got up enough courage to ask her to do something "special" with me. I picked up the phone and called her.
I didn't know what to say at first, but finally blurted, "Sally, do you wanna try something special this weekend?".
"Like what?", she asked.
"Well, I kind of wanted it to be a surprise, but will ya try it?".
She hesitated, "Okay, but what do you want me to do?".
I couldn't believe I was going to really ask her, just getting this far was fortunate. "Well, how about a little, frisky role reversal game to spice up our weekend alone?", I was trying to ease her into accepting the idea piece by piece. Anything besides the missionary position in a wham-bam type style was the only thing I had talked her into up to this point.
"Well", she began to reply.
I cut her off, "I will pretend to be you, and you can pretend to be me. That way we can show each other what we like."
"Steve, I don't know about that, it sounds kind of weird." I had to salvage this, or my plan would be blown.
"Sally, I don't think either one of us has been very honest about what we like or what we want from each other when it comes to sex. I think this will be the easiest way to know what we want from one another, since we don't seem to want to talk about it.", I held my breath. I didn't know if she would say no, get mad and think I was a freak, or if I had made her actually consider the idea.
She sighed, "Are you unhappy having sex with me?".
I had to tread carefully here. I was the first person Sally had sex with, and that meant a lot to her....and me too. I on the other hand couldn't keep a steady girlfriend, and had dated a few girls before her. She thought I was "experienced", and she always seemed to be threatened by that.
"No, baby, I Love having sex with you, but we should explore ourselves and each other so we can enjoy having sex and keep it new every time. Sally, if we never try anything new, you and I both are gonna lose interest in having sex with each other.", I was pulling out all the stops. I made a similar speech the first time I talked her into having sex. Her feeling threatened by my "experience" seemed to be a driving force leading to that accomplishment. Maybe this could work again.
"Well, alright, but as long as you let me know what to do. You know I'm not as experienced as you are."
I could hardly keep the surprise from showing while I thought of what to say next. "We need to play out the parts as realistically as possible from both of our perspectives. That means you have to act, dress and live like you want me to for this weekend.", I was talking too fast and my excitement was definitely showing now.
"That means you can buy whatever clothes you think look sexy for a man, or use some of mine."
She interrupted my rambling, "Does that mean I can wear your cologne too?". Wow, she was actually getting into this too?!?
"Sure! That would even be better!", I exclaimed, showing my rising and obvious intrigue of the idea.
"So", she asked, "you have to wear what you think I look sexy in, and live like a girl for the weekend, right?"
"Absolutely!", I replied. "I will wear what I think looks sexy, along with some enticing perfume." I was shocked at how well this was going.
"Steve, your gonna look kind of silly with a bra on and chest hair!", she giggled through the phone.
"Then I will have to shave, just like I always ask you to do", I suggested.
"Does that mean I shouldn't shave for the rest of the week?"
"I think if we're going to try and keep this as realistic as possible you shouldn't."
Throughout the next week I couldn't stop thinking about the upcoming fun. I had pulled it off!! I lathered my body every morning with lotion, so that when I shaved I would be as smooth as possible. Sally seemed to forgot about it, but made mention of how great a mood I had been in all week.
When Friday finally rolled around, I asked her if she had gone shopping, or if she would be coming by for some of my clothes for the weekend.
"I went to the mall today and picked up some studly clothes," I sensed she was actually having fun with this so far. "You know, things you don't like wearing....some khaki's from Eddie Bauer, a nice belt, dress shoes, a pair of flannel boxers and a navy blue dress shirt." "Oh, and I almost forgot, the hunk cologne that I like so much and you never wear!"
"Your right", I replied, "I never where that stuff." "But hey, if that's what turns you on," I jeered.
"Well, Steve, did you get anything?"
"As a matter of fact I did, and it will be a surprise," I teased. This was turning out to be everything I was hoping, mainly that she was going to relax and enjoy herself.
"Fine, what time will you be dropping by?"
"I'll come over after work, with my new wardrobe, okay?"
"Sounds good, see ya tonight, sexy", Sally teased.
I had purchased new lingerie, shoes, make-up and perfume just for this occasion. I was so excited I felt I was going to burst!! Finally, I will be able to transform in Stephanie in front of someone.
I left work early, and had my bag packed with everything I needed for the weekend; two matching panty and bra sets, two pairs of regular nylons, my make-up and shaving case, two slinky dresses and some hot lingerie.
She wasn't home when I got there, but she had given me a key to her apartment. I let myself inside and tried to relax and wait for her to come home. The "wait" probably lasted two minutes before I started to draw a bubble bath to prepare for the evening. I stripped down, climbed into the tub and shaved everything the way I liked. Legs, arms, underarms and everything else was shaved bare. The only exceptions were my head and the cute little triangle patch I left at my groin. This felt great, my skin was so smooth and sensitive.
I heard Sally come into the apartment. "Steve, are you here", she called out.
"Yes dear, but I am in the tub and you can't come in here yet", I didn't want her to see me until I was all "dolled" up.
"Why don't you change and get ready for tonight?"
"Okay, but how long are you going to be, because my sister wants me to go over to her house before she leaves for spring break."
"Go ahead and change, then go see her and come back as soon as you can, okay?"
"Whatever you say Steve", she replied sarcastically.
"Sally, how about if we change names so we can complete the mood", I didn't want to be called by my male name when I was dressed as Stephanie. I wanted to feel completely feminine.
"And just what do you want me to call you then", she asked, annoyed.
"How about Stephanie since it's the female equivalent of my name and I'll call you Sal", I didn't want to seem like I had this name thing planned out, so I was offering her a name too.
"I don't think so, STEPHANIE", amusement in her voice, "too close to my real name, and since you picked yours, I will pick mine." "Let's see, I have always liked the name Anthony." "So, Stephanie, you can call me Tony."
I hadn't known she "always" liked that name, but if she was actually playing along I couldn't ask for more.
"Okay, Tony, when will you be back", I asked in the feminine voice I had worked on for years.
"I don't know, I might have a few beers before I come home", she replied in a husky voice.
I heard her walk toward the bedroom. Immediately I began indulging in my feminine fantasies again. A few minutes later I heard her walk back down the hall.
"Alright, I am changed and off to see my sister, be back later", came her husky voice through the door. I heard the door close, and decided to get out of the tub.
I dried off and the sensations from my newly shaved body were intense. My member was as hard as it had ever been and I had to use all my resolve not to spill my load. I lathered my body down with some vanilla body lotion to prevent irritation from shaving and for the feminine scent. I got the red lingerie I had purchased just for this occasion out of my bag. Putting on the thong panties and garter belt got blood pumping to my crotch again. Trying to restrain myself was too much to ask, but I had to try. I pulled on the stockings and attached the garters, this felt so erotic! I put on my bra and rubbing my nipples, they responded by poking out. I was way too aroused, and had to pull the panties down as quickly as possible before I made a mess of my brand new outfit. Without even touching myself I spilled my seed on the rug.
After cleaning up, my cock was tucked so that it was unable to be detected. I proceeded to put on make-up and do my hair. My hair was almost shoulder length, and I had practiced styling it more than just a few times. The bangs and edges of my hair were curled for a playful feminine appearance. With the perfect placement of some red lipstick, base, blush, eyeliner and eyeshadow from techniques long since practiced, all that was left to do were my nails. A bright red to match my lipstick. The shoes purchased for this occasion took a little getting used to. They were 5 inch heels, and were a bit higher than the three inch heels I was accustomed to wearing.
I couldn't wait for Sally, ...I mean Tony to get home. I knew just what I was going to do when she came through the door. I had rehearsed it time and time again during the week. I waited and let my nail polish dry, like the "perfect" girl would.
Finally, I heard the door open. I came out of the bedroom and went straight to Tony. The look on her face was one of shock. I hid my face from her eyes as I knelt down in front of her to undo her pants. I pulled down Tony's pants and boxers and began licking and sucking on her love hole. She began moaning and grabbing my head. Her fragrant juices running down my chin. I didn't stop until told to do so. The look on Tony's face was that of desire. I kissed her, and could taste beer on her breath. I led Tony down the hall to the bedroom and slowly undressed her. Licking and sucking on her nipples and toes as each was exposed. She hadn't shaved her legs in at least a week and that made me even more hot. I unsnapped the buttons holding the thong in place and my cock snapped out. I spread my legs and straddled Tony. She pulled me into her and I gasped. The orgasms that followed were unreal. This was the best sex she and I have ever had. We both fell asleep, exhausted. Tony held me in her arms and I curled up to her breast.
I awoke the next day to find myself alone in bed, and still wearing lingerie. Tony was in the kitchen cooking breakfast when I found her. "Good morning, princess". she said to me.
I smiled and said, "Thank you, stud", in the most gracious way I could.
"So, that is what you want me to do when you come over?"
"Well, it would be kind of nice", I giggled femininely.
She just looked at me in awe. "What's the matter", I asked.
"Nothing", she replied. Very short, and a hint that I better leave that alone.
After breakfast I told Tony I was going to take a shower and get dressed in a slinky dress for her. She stared at me for a moment and then smiled. "Stephanie, I am going to go out and get a present for you while you make yourself pretty for me."
I couldn't hide my surprise, "Really? Oh, that would be so sweet, Tony!" I hurried off to shower and change with anticipation of my present!
After showering, and dressing in a tight black dress with stockings, crotchless panties, shoes and a bra to match, I was getting excited again. I sat down and decided to watch some Soap Operas while I waited for Tony, and to calm myself down.
When Tony came home, he had a bag, but told me to stay where I was until she called for me. I was more than a little excited and intrigued. I had to squirm around on the couch just to keep myself under control.
"Stephanie, would you come in here, princess?"
She was in the bedroom. I quickly jumped up and pulled down my high skirt hem. Smoothed out my dress and walked into the bedroom flagrantly swaying my hips from side to side with each step. I was feeling sexy and seductive. I saw my girlfriend sitting on the bed, and she waved me over. As I got closer I finally saw a large dildo sticking out of her pants.
"Stephanie, you don't have to do it if you don't want to, sweetie."
I was stunned, but thought if she played along for me, I could do this for Tony.
"No, it's okay, I want to, baby." I got down on my knees and opened my lips up to take this six inch dildo into my mouth. Six inches was significantly more than me at full erection, and was kind of intimidating for me. As I worked my way around the head, and tried to see how much I could fit in my throat, Tony began squirming and moving rhythmically to my touch. I then realized the dildo was a double and the other part was inside her. She grabbed my head and pulled me onto her cock, shoving the dildo down my throat. She screamed and moaned, while I tried not to choke on every thrust of her pelvis. She finally let out a scream of ecstasy and fell back onto the bed. I was so hot, and was hoping she wasn't through. I was going to have to whack off or explode.
Tony grabbed my arm and pulled me to her. We kissed passionately, with our active tongues probing each other. I reached down to her sopping wet crotch. The dildo was still there. I grabbed it and started moving it back and forth. Tony's moans let me know it was the right thing to do. The throbbing in my crotch intensified, I had to do something. With my other hand I pulled up my dress and straddled Tony. Her eyes opened and she saw my crotchless panties.
"You don't have to do this", she moaned.
"It's okay, I WANT to!!", I screeched in erotic passion. I slid down onto the dildo, working it up and down to meet her thrusts. It rubbed against my anus, the back and forth motion eased it into me. I let out a little squeal of pleasure and pain as the dildo slid into me. Our moans were intermingled, as I met Tony's every thrust. The rhythm was the same as always, just reversed. I grabbed and pulled Tony to me, as the dildo rubbed against my prostate. I confessed my love to her over and over again, moaning and wailing in pleasure. I couldn't contain myself anymore and lost my seed all over myself and Tony. I fell back exhausted, and rolled over. I needed to sleep.
As I drifted off I heard Tony crying and rolled over. She was sitting up in bed. I laid my head on her lap, and purred "What's wrong, Tony?" The euphoria I was still feeling was definitely showing.
"I don't know", she replied. "I have never seen you so turned on." "You had the biggest orgasm I have ever seen you have, and you just confessed your love to me more times during sex than during the past three years." She was beginning to regain control of herself. Good, this might still work out then.
"I'm sorry, Tony, I really do love you", I was groping for some eloquence, but too tired to think of anything. "It was just the most fantastic sex though....wasn't it?", I was trying too hard, and not thinking well enough.
"See!! Your still calling me Tony", she cried in frustration. "I just have to think for a minute", she said as she got up.
At least she stopped crying, I thought. I wanted to follow her, but with the lack of encouragement, exhaustion and sheer euphoria I was feeling, all I could do was roll back over.
"Stephanie, sweetheart?" I was awakened by Tony calling my name. I opened my eyes and searched for my girlfriend. She was leaning against the doorframe with her arms crossed.
"There, there, princess. Are we awake?" I couldn't tell right off if it was sarcasm or sincerity in her voice. I decided to play toward the sincerity card.
"Hey, baby." "Yeah, I'm getting up", I said sweetly as I smiled at her. She smiled back. Good, played the right one.
"I have an idea", she said perkily. I smiled and stretched as a reply. She returned my smile and said, "I am going to go out for a few minutes, so why don't you put on that outfit you wore last night and lets try that again." "It was more fun."
She had definitely seemed to enjoy last night more than what happened today. Even though the reverse was true for me. I decided to play along in hopes this would smooth things out before she had to go to work tomorrow and our weekend alone would be over. I wanted her to do this again, so I had to make sure she enjoyed this and would allow us to do it again.
"Anything you want, stud", I said as seductively as I could. She smirked.
"Thank you, princess." "I'll be back in about a half hour", she said, still in her husky voice. When she left, I thought how lucky I was that she would still be playing along.
I hurried off to the shower to perform the same ritual as the night before. I was out of the shower quicker this time, anticipating Tony's return. I didn't want her to be waiting on me. I waited in the bedroom just as the previous night. After an hour of waiting and with the accomplishments of last night and especially today, I fell asleep.
The opening of the door to the apartment woke me. I quickly checked my face and hair in the mirror before I went out to the living room. I came out of the bedroom swaying my hips with every step to convey the fuck me now attitude that my lingerie was intended to do.
I was shocked, Tony was there with a tall man standing at the door. She was smiling, and didn't say anything. I ran back into the bedroom and closed the door. My mind was racing a mile a minute. What was she doing??
"Stephanie, what's wrong", she inquired as she came through the door. I backed away and asked, "What are you doing, Sally?"
"So, now I'm Sally again, eh Stephanie?" "I want you to know more about yourself and I think this is what you REALLY want!" She was talking with an authority that took me by surprise. "If you don't do exactly what you did with me today for this guy, your major professor, boss, and entire family will know about you extracurricular activities!"
I was stunned. I didn't know what to do. Standing there in the clothes bought just to illicit sex and looking like the whore I was. I decided to call her bluff, "Nobody would ever believe you, Sally." This was my last hope.
"Really?", she replied with a smirk. She reached into her purse and pulled out a camera and snapped off some pictures. I froze, I didn't know what to do. "Stephanie, were you sleeping with your dress pulled up and crotchless panties today?" She had a huge grin on her face. "Well, I have pictures of you in your slutty clothes, and looking like a prostitute after a hard night's work."
"Come here, princess", she said sarcastically. She stepped over to me and took my hand. Just then the tall stranger walked into the bedroom with a smile on his face. I just looked down at the floor, knowing there was nothing I could say or do to resist my fate.
Sally introduced us, "Stephanie this is Rick, and Rick this is Steve my boyfriend. Although he prefers to be called Stephanie."
"Your were right, babe", Rick said with a large grin. "I didn't have anything to worry about with your girlfriend here." "He actually looks like a real girl and he's kind of cute," he said while he looked down at me.
"Stephanie, tell Rick how happy you are to meet him and how handsome he is."
I couldn't say anything, and just stared at the floor.
"She's so shy it's cute", Rick chuckled.
Sally grabbed me by the chin and forced me to look at Rick. It was the first time I had really looked at him. He was a little over six feet tall, dark hair and seemed to be quite muscular beneath his sweater. I had thought about trying to take the camera and pictures by force, but for me it would be a challenge with just Sally. With Rick, I didn't stand a chance, he would just crush me.
"Don't embarrass me, Stephanie", Sally snapped. This was not something I was accustomed to from Sally.
"Tell Rick what you think, you little slut", Sally was getting extremely agitated and I thought I had better submit.
"Rick, it's a pleasure to meet you. You truly are an attractive man", I said as sweetly as I could in my feminine voice.
"Thank you, Stephanie." "You truly look like you want to give an attractive man head", Rick firmly stated with a smirk on his face.
Sally knelt down, and pulled me down with her. Still having my hand, she smiled at me and pressed it against Rick's crotch. I fondled the lump, and gave a gentle squeeze. Sally retreated from my side. I rubbed back and forth and felt his cock grow larger and larger, but never got extremely hard. I was amazed. I undid his pants and his huge cock flopped out at my face. I grabbed a hold of it and gently stroked back and forth. This cock had to be ten inches long. Staring at Rick's gorgeous tool, I realized I had no business calling myself a man. At rock hard I am only four inches long, that is about the width of the cock I was fondling. This cock was a masterpiece. I leaned forward and kissed the head.
"Go ahead, bitch", Rick said, "be a good girl." I took the head of his cock into my mouth. I could barely fit my lips around it! I slid down as far as I could, like I practiced with the dildos I had.
"That's right, you are a faggot slut aren't you?", Rick moaned.
I started sucking on his tool more fervently, sliding as much as I could done my throat while I massaged his balls and jacked him off into my mouth.
"Look!", Sally exclaimed. "He's as hard as I've ever seen him!!" She pointed at my poor excuse for a dick.
"All four inches, standing to salute you, Rick", she laughed.
I was embarrassed, sucking on a another man's cock in front of my girlfriend while I was dressed like a whore. With all this going on, all I could think was this is the most gorgeous cock I had ever laid eyes on. I had it all to myself, and I loved it.
I could not help myself from getting as hard and as excited as ever. I moaned with every thrust Rick gave me. I couldn't hear anything except he and I in our chorus of ecstasy. From his increased speed and as he got louder I guessed he was near an orgasm. I wanted every drop. His tool sent his seed deep into my throat, and I greedily swallowed all I could, and lapped up whatever was remaining on his cock
"Man, this is the best head I've ever gotten, your pretty good you little faggot", Rick half moaned as I slurped on his prick.
Rick picked me up, and spun me around with ease. He bent down and kissed me on the back of my neck. He walked me over to the bed, picked me up and set me on the bed.
He rubbed my panty covered ass and could not help but moan at his touch.
"Get on all fours', he commanded.
I eagerly did as directed, my cock throbbing and aching as never before. He unbuttoned the crotch to my panties and spread a lubricant on my anus. He started working his finger in and out. I thrust back onto his hand, wanting it in me. I looked back at him and he smirked at me.
"What do you want, Stephanie, my little slut whore?", he asked continuing to smirk.
I couldn't contain myself anymore, I NEEDED to have him inside me.
"PLEASE FUCK ME, Rick", I begged. He made me beg over and over for his gorgeous cock.
"You've been a good girl", he said as he pulled his finger out of me.
I felt him place his hands on my hips as I waited for what I NEEDED, and had been made to beg for in front of my girlfriend. I felt the head of his tool at the door to my love hole. He gently rubbed and prodded his way around trying to get in. He was too big, I couldn't be teased any longer. I thrust myself back onto his massive cock. I let out a loud squeal from the sheer pain of being opened up by a real man.
"Oh, God YES!!", I screamed as he thrust his cock into me. The pain began to subside as Rick stretched me into his well worked lovetoy. I met his every thrust with my own. Screaming and moaning every time his tool worked against my prostate. As Rick began picking up his pace, I knew he would soon plant his seed deep within my bowels. I followed his lead as the pace increased. I had never screamed so much in my life. I felt Rick's seed warm my insides and had the most intense orgasm ever. Spilling every bit of energy into meeting his thrusts, I knew I was his bitch and he was my master. Whose cock I wanted whenever I could get it. I collapsed on the bed, unable to move and covered in sweat.
When I awoke the next morning I was still in bed and dressed in my cock catching clothes. My butt was sore, and I smiled. It felt like a good kind of sore, one I wanted to wake up to again. Sally walked in while I was smiling to myself about last night's interlude with Rick.
"Good, your up", she said matter of factly. "Alright, I now know why our sex wasn't any good, you have a dick half the size it's supposed to be, and your more of a girl than I am. You shocked me walking out in that outfit the first time. I could never be that feminine. I had an idea that you were a little faggot, especially after you cummed all over and screamed so much with my dildo. I don't even scream that much when I use it.
"Sally, I'm sorry, please", I tried to interject.
"Shutup you little bitch, before I kick your ass." I knew I had better just stay quiet, unless I wanted to get into more trouble than I was already in.
"Rick told me you were one of the best fucks he has ever had, and gave head better than anybody else. I guess that shouldn't surprise me."
I surprised myself by actually taking pride in that, and almost smiled.
"So, I don't want you anywhere around me, you little, sissy faggot", she screamed. "I can't get any pleasure out of that worthless little pecker of yours, and you've already started to steal my real men." "You just suck cock too well and do it too willingly, and fuck better than a real girl!" "I can't believe I thought you had all those other girls and were more experienced. One time around with that cock and they were outta there, right?"
I knew she was, but couldn't say anything. She knew all my secrets now, some I had just discovered. She just glared at me. I had nothing to say, she was right.
"Here, take your bags and if I see you near me or anyone I know, those pictures of you will be hanging in frames at your boss's office, understood?" She handed me my bags that I brought over.
I just nodded and stood up. I tried to get a dress out to wear over my lingerie, but a quick punch to my face sent me to the floor. I cowered on the floor and covered my head as Sally through a series of punches again.
"You little bitch, you lied to me for three years and then fucked the cutest guy at my work!!" I just started sobbing.
"You are such a little sissy", she screamed as she stormed out of the bedroom. I dried my eyes and quickly slipped on the teal dress I had saved to wear on the last day of our weekend alone.
As I walked down the steps to her apartment, a handsome man a little over six feet and very muscular approached me.
"Does a gorgeous young lady need help with her bags?"
Rick gently took the bags from my hand and placed his arm around me. He pulled me close to him and I buried my face into his chest and started to cry.
"There, there, princess, everything will be alright."
He didn't lie either. After a few weeks of dating and a few months of hormone therapy, he is a great husband to me. Rick told me he doesn't want me to lose my last vestige of being male so that he will know I will always be his.
I feel safe in his arms and the sex is still the best I have ever had! We both look forward to a happy life and many years together as man and wife.
The End
Any comments or questions are welcome, please e-mail me at hotstacey@hotmail.com