Amy answered the door in her kimono and seemed to be very chipper. "Come on in. Would you like a drink??"
"Sure." Knowing what she keeps in the house "Anything will be fine".
She came out of the kitchen and handed me a Coke. As I took a drink, I got a pleasant surprise. Amy had made Rum & Cokes. She sat down across from me, folding her legs under herself. Oh what a view, it almost distracted me from my mission. "So, what was Christy here for?"
"Oh, nothing, I am just helping her with some things."
"She seems pretty anxious when she is leaving, I have called to her twice and she just turned and left."
"Well, it's not like you guys are real close. She is a friend of Becky's."
"Actually, we have gotten very close."
"Yah, how close."
Bashfully, I said "Well, let's just say, her aroma is as sweet as yours."
"Really?? I never would have thought that."
"Why??"
"Oh, no reason. Just never guessed it. Does she know you well too?? Know you like I know you."
Blushing, "Uhhh, yah, but she is not nearly as good as you."
"I don't imagine she would be. Does she share with you like I do??"
"No, she does not compare to you in anyway." We sat around chatting and drinking for about an hour, never really delving into how Amy was helping Christy.
"Can you come over and help me clean the gutters out on Saturday?"
"Yah, does the morning work??"
"Yes, say 8:00."
"OK. Well time for me to go." I got up to leave, feeling a little woozy from the drinks. When we got to the door, Amy gave a deep sensual kiss goodnight.
Then she said, "Oh yah, I need you to model the dress for me one more time. Can you do it after we are done with the gutters?"
"I don't know, I mean it fits her and everything, why do you need me to model it again?" Not realizing I just let the cat out of the bag concerning the pictures I saw.
Catching this, Amy said, "It is a little too long and I might want to add some bounce to it. So after we do the gutters, we will finish the dress."
"Are you sure you need me to do it?"
She grabbed my cock through my shorts and said "If you do this for me one last time, I will let you feel what it is like to have this" (giving my cock a squeeze) "inside of this" (taking my hand and putting it on her pussy) "afterwards."
Surprised and intrigued, I quickly said, "OK, absolutely, see you Saturday."
I headed home and finished cleaning up and went inside. My parents called me into the kitchen to talk. "As you know we are leaving for our cruise on Saturday. We were going to have your Uncle Bob stay, but he got sick. So we are going to let you stay here alone while we are away. You are to do your chores and keep the house up, and there will be no parties in this house. And I do not want you drinking either. We have spoken to Amy and she has agreed to keep an eye on you. No one else is to be in the house. She said the twins would be around at some point, so they can come in, but other than them, she is the only person in the house besides you. Understand?"
"Yes, I understand, it will not be a problem. I promise." And I headed off to bed.
My parents headed out real early on Saturday to catch their plane. I headed over to Amy's house around 8 to clean out the gutters and to lose my virginity. The gutters took about 2 hours to complete. When I was done, Amy invited me in for a Coke. As I walked through the door, Amy grabbed me, pushed me up against the closing door and planted a huge kiss on my lips. Her tongue forcing its way into my mouth and her hands finding their way down my pants. I had an instant hard-on. After breaking the kiss, she tore my shirt off from my body and began licking my chest. "You smell so masculine, I can just eat you up." With that she yanked my shorts to the floor. Back to kissing, she pushed me harder against the door, continuing to lick my body. As she did this, I kicked off my shoes and then my shorts from my ankles. I stood there in her foyer naked head to ankle. We continued kissing and she began giving me a handjob. Just then the doorbell rang.
Startled, I let out a little scream. Amy backed away, and reached for the doorknob, never letting go of my cock as I stood behind the door. "UPS ma'am"
Still holding onto my cock. "Oh, my overnight package, great. Just put it over there on the floor."
"OK, just sign here."
With her right hand Amy signed the electronic pad. As she signed, she stroked my cock; I let out a little whimper, hoping the UPS guy did not here me.
"What was that ma'am?"
"Oh, Nothing, Just thank you for brining it in."
"No problem ma'am. My pleasure"
"Have a good day."
"You too." Amy closed the door.
Laughing, Amy pulled me out from behind the door and smacked my bare ass.
"Owww!!"
"Hey sexy, why don't you go take a shower? Get all nice and clean for me."
Trying to hide my nakedness (not all my shyness being gone), I said, "Sure. Which one?"
"Use the one in my room, I just cleaned the other one." I started for the stairs. She continued, "I'm going to put your stinky clothes in the wash, then I will bring you some towels."
"OK."
With that I darted up stairs and got in the shower. As I stood in the shower with shampoo on my head and my eyes closed, I felt Amy's breasts against my back as she encircled my body with her arms.
"Well hello, I did not hear you come in."
"I thought I would help you get all clean." With that she picked up a bath pouf, put some raspberry smelling body gel on it and began washing my body. With my back to her, she lathered my body in soap, reaching around to pay special attention to my cock. Using the soap and her hands, Amy brought me to my first orgasm of the shower. When finished with my cock, she concentrated on my asshole, thoroughly washing me out. When she was done, I was very clean, inside and out. When she had finished my ass we began to kiss as she slid my cock between her legs. By moving back and forth, she jacked me to my second orgasm.
"Don't worry, I will still let you slide your cock into my pussy once later today."
Still recovering, I mumbled an "OK".
"Will you do something for me. Something that I find extremely sexy?"
Playfully I asked, "What would that be, besides me?"
"I want to shave your legs and chest. I love a man who is smooth to my touch when we play."
"Sure, I have done it for swim team, it is no big deal. It felt strange the first time, but I got used to it. It would be nice to have help though. Usually I end up cutting myself a lot."
"Uh baby, thank you. You know what, I got something better than a razor. Stay right here." She got out of the shower and walked over to the linen closet.
"Where would I go and why would I want to leave?? Beside you've got my clothes."
"Oh yah, you're right." She said as she stepped back into the shower. She then began to apply a cream to my legs. As she got to the top of my legs she stood up and began kissing me. With one hand she began stroking my cock and with the other, she applied the cream to my pubic area. She then proceeded up to my chest. From there, she pushed me up against the shower wall and began kissing me again. This time she pulled my hands above my head and applied the cream to my under arms. "Now we wait. Why don't you use that fantastic tongue of yours on my twat while we do?"
I got down on my knees and began to lick her pussy. After two orgasms she said "Stand up and rinse off."
As I got under the water, I saw my entire compliment of body hair slide off and into the drain. Amy rubbed her hands up and down my body, "Oh so smooth, I love it."
"Well it was a little more than I anticipated, but that is OK."
As we stepped out the shower, she grabbed a towel and patted me dry. "Go into the other room, we need to apply some moisturizing cream to keep you from itching."
"OK" and I left for her room.
Amy came out of the bathroom wearing just a towel, covering from breast to thigh. Oh what a sight. Amy thoroughly applied the cream to my body, again taking extra care of my cock and asshole. Without much trouble, she brought me to another orgasm with just her hands.
"OK, all done. Stand there and let the cream soak in while I get dressed." I stood the as she went into her closet. When she came out she had on a nylon tracksuit and her camera, with which she began taking pictures of me naked.
"Hey, no pictures."
"Why, your just naked, not like you are wearing panties or anything."
"Well... I guess your right, but still I don't want them getting out."
"I would think you would, a body and cock like that, you would have girls all over you."
"That is ok, I don't need them. I've got you."
"Aww how cute, now off to the sewing room."
Off we headed down the hall to the hobby room. Amy dressed in her nylon suit and me, naked as the day I was born, my cock bouncing to the rhythm of my steps.
When we reached the hobby room, laid out on the bed was the dress. Next to the dress were the panties, bra, garter belt, stockings, heels and the wig I wore the last time. As she handed me the panties, she said, "Let's get started." I pulled the pink panties up my legs and adjusted my cock so that they fit comfortably.
"Can I take your picture?"
"No".
"Why not?"
"Cause now I am wearing panties, I don't want anyone to see me in them."
"I see you in them."
"You're different, you put me in them, you know why I am wearing them."
She smiled and teasingly said, "If I let you have sex with me, not just slide your dick in once, will you let me take pictures of you?"
My eyes lit up, she is going to let me fuck her. Unable to hide my grin, I said, "Yes, but nobody gets to see them but us."
"OK, just for our viewing." she delighted replied. She grabbed her camera and began taking pictures. From all the stimulation, I was sporting a good woody, making it impossible to hide the fact I was a guy wearing panties. After about ten pictures she said, "Your little dicky is ruining the lines of your panties. We have to do something about that." She stepped over to me, dropped to her knees and gave me a no non-sense quickie blowjob. When she was finished, she pulled my panties back up and adjusted my cock to hide it between my legs. She grabbed her camera again, and shot about 10 more pictures with my "new" outline.
Next came the bra, with the falsies again, and about ten more pictures. As I added each item of clothing from the garter belt to the stockings, and finally the heels, she took about ten pictures at each stage. Once again, it did not occur to me that I had seen this same type of pictures before, but they were of Becky.
Finally we got to the dress. Amy helped me step into the dress and zipped it up for me. Once again she took a few more pictures. With a whistle, she said, "You are so cute, I could eat you up." She leaned forward and kissed me. I just smiled. She had me pose for a few more pictures.
When she was done with the pictures, she turned me toward the mirror. Once again, I stood there amazed to know it was me, but yet there was my face on the body of a teenage girl. I was speechless. Amy just smiled, giggled and cooed over how pretty I was. "Can we do your make- up and hair again?"
Still not thinking straight, I absentmindedly said, "Sure" giving no fight at all about it.
Amy grabbed a make-up bib to cover the dress and proceeded to do my make up. First a base, then some blush, next came eye shadow, liner and mascara and finally the lipstick. Without any argument from me (I was still off in my own world), she took my hand and applied nail polish to my nails. Then she added a necklace, bracelet and clip on earrings. With my back to the mirror, she brushed out the wig and placed it on my head. Amy covered my eyes and turned me toward the mirror. When I opened them, I stood staring at a very cute 18 year-old girl. As I stared at the mirror, Amy took up the picture taking again, continually carrying on about how cute, adorable, and beautiful I was. At her suggestion, we went to various rooms of her house to take pictures of me in different poses and with different settings. She had me walk around a lot and sit down and stand up a lot. Little did I know as she had me parade through out the house; I was quickly learning to walk in heels and present myself as a young lady. Over the course of two hours, I was in every room of the house, sat in every chair, went up and down the stairs, picked up things, moved things, and added props or other clothing items (fur coat, purse and a few other items). Being in my own world, I never noticed that Christy had been watching the scene several times through various windows.
"Let's take a few outside."
"What?"
"Outside on the deck, with the trees as a back drop."
"I don't think so, Tim" mimicking Home Improvement.
"Oh, come on, no one will see you."
"So, I don't want to risk it. Why do you want to go outside anyway?"
"Well two reasons. First, I think the setting would be great in the pictures. Secondly, the sensation of being outside in a dress is incredible, and I want you to feel what it like to be outside in a dress."
"I don't care what it feels like."
"Oh, come on, I promise to let you take and print some naked pictures of me to keep."
"Really??"
"Yes, really."
"Well, OK, this one time." We headed out the backdoor to the deck. Amy posed me in several different ways, taking a few shots of each pose. Then she had me do a few `free flow' shots where I tried to duplicate poses/looks I have seen in magazines or on TV. During this time, Christy walked around the corner and on to the deck. I recoiled in surprise as she said "Hi."
Amy turned to her and said, "Hi! Christy. What's up?"
"Not much. I just wanted to drop off the information you asked for." She handed Amy an envelope.
"Christy, this is...Kaitlyn. Kaitlyn, Christy. Kaitlyn is one of my waitresses. Christy is a neighbor girl I am helping with a problem."
"Hi, Kaitlyn," She stuck her hand out for a handshake.
Trying to disguise my voice, I said, "Hi, Christy, nice to meet you." To Amy, "I am going to go inside, leave you two to talk."
"No need, we'll only be a minute."
"Really, just come get me when you are done." It took all my strength not to run into the house.
Once inside the house, I stumbled into the kitchen. Outside, Christy said something and I heard Amy laughing. I thought for sure she recognized me. I waited in the kitchen for about five minutes, calming my nerves. When Amy came in, she called out, "John?!?!"
"What?"
"Where are you?"
"In the kitchen."
"She's gone, you can come out here now." I left the kitchen and enter the family room.
"I knew this would happen. I knew some one would see me in this dress. How did I let you talk me into this and going outside, how could I have been so easy about it. And what were you laughing about, she knew it was me and said something, didn't she?"
"First off what is the big deal that some one saw you? Secondly, she did not recognize you; I doubt your parents would recognize you the way you look. Thirdly, we were laughing over how she had gotten the information she brought. And finally, didn't you get all hot standing there, her not knowing?? I did."
"No, I did not, I was too scared. And it is a big deal; I don't want it getting out that I have worn a dress and got all `dolled' up. Kids at school will think I'm a sissy."
"Well I know you are not a sissy. In fact I know you are a stud under that dress and panties. Now sit down and relax, it has been an eventful morning. Would like a drink?? Coke, Beer?"
"Sure, how about a beer?"
Amy walked into the kitchen and said, "Actually I have something better." She brought out two glasses and a bottle of wine. "This is more lady like." I laughed. "Have a seat. Those heels are probably killing you."
"Yah, they are, how do girls wear these all day." I sat down.
I jumped out of my skin when Amy screamed, "Stop, you can't sit like that!!"
"Why not?"
"You'll wrinkle the dress. Now stand up! Stand up!" I stood up almost spilling my wine on the dress.
"This is how you sit when wearing a dress or skirt." She showed me how. "Now you try it." I did as she showed me. "Again" I did it again. "Another time." So I did it again. "One more time."
Sitting down, I asked, "Why, do I need to know how to sit in a dress."
"Oh, yah, I almost forgot, you're not a girl. You are just so convincing all made up like that. I remember teaching Becky how to properly sit and stand and so forth."
I laughed it off, but she had accomplished her goal, because when I sat down, I did it in a lady like manor. After finishing the bottle of wine and a small snack for lunch, Amy announced "Time to take the dress off."
A short look of disappointed crossed my face, (barely noticeable, but caught by Amy), and I said, "OK."
As we headed up to the hobby room, Amy commented, "Nice ass, want some fries with that shake?"
"Stop it, I am not shaking my ass."
"Oh, yes you are sexy. And it is really turning me on."
As Amy unzipped the dress, I began to get aroused. But with my dick tucked in its silky confines, I was unable to get hard. As Amy hung the dress in the closet, I reached into my panties and repositioned my cock to get more comfortable. When Amy returned, she saw my now fully erect cock pushing at the confines of the panties. Her eyes lit up and she licked her lips, "Well you held up your end, now I need to hold up my end of the deal. Come on `Big Boy', we're going to my room to pop your cherry." She reached out, grabbed my panty-covered cock and pulled me to her room.
When we got to her room, she released my cock and pulled my head to her lips. We kissed passionately, sliding our tongues in and out of each other's mouths. Our hands explored each other's bodies as she led me toward the bed. As the back of my legs bumped the bed, she said, "I want you to just lay back and enjoy your first fuck, I will do all the work and it will be the most memorable time in your life. Now scoot up on the bed and put your head on the pillow. Right now is all about you." I shifted myself up on the bed as she turned on some music and began a strip tease. As she danced, she slowly unzipped her jacket and tossed it aside. Then with one big pull, her break away bottoms came off. She stood there, a sexual goddess, in a red and black, silk and lace teddy. She posed for me and asked, "Do you like?"
"I love. You're the most beautiful woman in the world!" She came toward the bed and proceeded to crawl up to my panty-covered cock, rubbing her hands up my stocking covered legs the whole way (send electricity through my body.)
With her hands stroking my cock through the panties, she exclaimed in mock surprised voice, "What's this, it is so big, how will I ever take it all." She then licked my cock through the panties. With her teeth she pulled the front of the pink panties down to release my 7" of manhood. It sprung free, right into her waiting mouth. She began to lick my cock and balls like they were a lollipop. The morning's build up and the sensations on my naked balls put me over the edge and I came, spurting semen all over her face and onto my panties. With cum dripping from her face, in a mommy tone, Amy said, "Awww, wittle Johnny is all excited. She spurt her crème all over her panties." Amy licked my cum from the panties while her hair tickled my balls. I never got soft.
She then proceeded to clean up my cock and balls, licking the cum right off. When she stopped licking, my rod glistened with her saliva. She began kissing her way up my body, fondling my fake tits like they were real. As she smothered my body with kisses, I reached out to heaven and played with her beautiful boobs through the silky material of her teddy. After a several minutes of boob play, she asked, "Will you release my love canal??" I reached between her legs and unsnapped the teddy, quickly sliding a finger in her pussy. "Not right now big guy, I want something bigger inside of my love canal."
I pulled my hand out from between her thighs and Amy straddled my body, positioning pussy right in front of my cock. "Are you ready my little one?? Time for me to pop Johnny's cherry. I am going to fuck you like...well, like you will never be fucked again. I am going to ride you so hard, you'll do anything to get some more." Amy slowly lowered herself onto my cock. As I entered her pussy, I moaned in ecstasy; she cooed in pleasure. The lower she went the better it felt. As with the picture taking, Amy kept the chatter going, continually, telling me how much she wanted me, how my cock was so big and just how sexy she found me right now. As she rode me, even I, a virgin, could tell she was an expert and loved to have a cock in her twat. She would fuck me fast, slowing only when I got close, then accelerating to a fevered pitch when she knew I was not. Sometime pulling completely free of my cock, other times, barely moving up an inch. She pumped my rod with her vaginal muscles, providing me a sensation that drove me right to the edge, and then she would stop before I went over. For nary one second, was she not in control, complete command and charge. Even when she orgasmed (which was at least a dozen times), she would not let me. We went on this way for over an hour (I still can not believe I lasted that long, but she had complete control). As the time progressed, her words began to take on a different undertone. An undertone my consciences mind did not comprehend.
She began by extolling my masculinity and my sexiness. Next came words tenderness and love. Then she began referring more to my body and how it feels, smooth, silky, soft. These led to affirmations of the present, my hair, my panties, my stocking, how hot I made her, and how pretty I was. Then she mixed in thoughts of love, tenderness, and feminine ideas. All this led to how I looked beautiful and sexy in pink. As she moved into the final stretch toward my ultimate climax, her words became more commanding and controlling. Things like "I love you my darling, you are so pretty, I love the way your body feels, you know how to hold me, your clothes are so sexy, I love you in pink, your legs turn me on, I want you, I love making sweet love to your body" led to "Come on bitch, cum! You're mine you little whore! You know you love it, slut! Come on, your mine and I am going to fuck you! You're here for me, slut! Cum now you, Bitch!!!" As I exploded with my biggest orgasm ever, she screamed "'Bout time you came, you little whore!" I shuddered in ecstasy. Collapsing onto the bed completely spent. Amy climbed off my now limp cock and body and lay down next to me. As she kissed me and nibble on my ear and neck, her fingers played with my nipples (both my real and fake ones). As I laid there in my euphoria, it never connected that my first full sexual experience with woman, had me dressed in lingerie and had her treating me as the female partner in the activity.
After snuggling and playing a little more, Amy sat up in bed and said, "I'm hungry, let's eat."
"Me too"
"Let's go to Applebee's for a late lunch, early dinner thing."
"OK, sounds good."
As she slid out of bed, she said, "I'll go get your clothes out of the laundry." She slipped on her robe and headed downstairs. I laid there luxuriating in the sensations and memories of what I had just been through. I never gave one thought to what I was wearing, other than to pull my panties back up. When Amy came back into the room, my eyes were closed and I was caressing my cock with one hand and my tits with another.
As she came back she said, "Well I see you like the feel of your clothes."
Startled, I opened my eyes and said. "What?"
"You look wonderful laying there and I have problem with your clothes."
"What kind of problem?"
"I goofed and forgot to move your clothes to the drier. They are still wet." She held up a pair of jeans (a pair of girls jeans as it turned out) and said, "But I did find these, I think you left them here after we put up the Christmas lights and got all wet."
I sat up and she tossed me the jeans. Laughing, I said, "Oh yah, I remember that, ended up going home in a blanket and boots."
Amy went over to a drawer and dug out a light blue Nike t-shirt and tossed it to me. "You can wear this and the jeans and you will be fine."
"What about underwear and socks?'
"Don't be silly, just wear your panties and leave on the stockings, no one will be able to tell what you are wearing under your jeans."
"I don't know, going outside wearing this?" Pointing to myself.
"No one will see it under your clothes."
"I'm not wearing the bra."
"I didn't expect you to wear the bra, people might see the straps to that. Now get dressed, I'm hungry."
I watched Amy get dressed. She put on black panties and a matching bra, then pulled on a pair of shorts and a t-shirt. I took off the wig and Amy helped my clean up and get dressed. In doing this, she did not remove all the make-up and brushed my hair a little more feminine (plus I forgot about the nail polish). We headed to Applebee's. I did not notice it, but I got few looks from some guys, but no one said anything. Amy got us a couple of Rum & Cokes and began rubbing her foot up and down my stocking leg. I relaxed and forgot anyone else was there.