My First Time AsThe time in question I was just turned 17 years of age and living with my parents and elder sister in Cornwall. I spent a lot of my spare time helping out at a small caravan site in the woods close to my house and got on well with John, the owner of the site. John was in his late 20's or early 30's and was a good-looking guy and very pleasant to work with. One day when we had finished up doing some site clearance, we returned to his apartment above the site office for a hot drink and sat on the sofa having a cup of tea and watching some TV. I had noticed John looking at me closely lately but had thought nothing about it but this was to change in a strange way on this day. John had been sitting on the opposite end of the sofa to me but suddenly he moved up to sit really close and put his arm around my shoulders and pulled me closer to him and started to stroke my thigh through my jeans. I pulled away and said that I was not dressed right for what it was he was looking for and he smiled and asked me if I would be interested if I was dressed as he wished. I should say at this point, that the previous year, Jan my sister had persuaded me to dress as a girl and go out for Halloween with her for trick or treat, and I had really enjoyed the feeling of the girl's clothes and makeup and had taken every opportunity since then to wear whatever items of her clothes that I could get my hands on and also experimented with makeup. I had been on dates with girls and even had sex with one of my girlfriends, but had never really felt entirely satisfied and I had to admit to myself that when in a dress and makeup I had often wondered what it would be like to be the female in a partnership so I hesitantly said to John that I was willing to try if he really wanted me to. He was very pleased at this and said that if I was sure, could I ask my parents if I could spend the weekend at the site as he had a big job to do and could do with my help fulltime. If I would show up on the site early on the Saturday morning, he would have everything ready for our game. Over the next few days, I thought a lot about the coming weekend and wondering what would come of the time spent with John. Did he want me to act as his girlfriend and if so, how far would he want to take the relationship, I decided that whatever he had in mind I would be happy to take in my stride as I was sure that John would never push me beyond my limits so on the Saturday morning I turned up at the site at just before 8am and went straight to the apartment where John was waiting for me with a big smile on his face. He told me to go and take a hot bath and shave all over although I did not at the time have a great deal of bodily hair and to then use the scented Talc he had left out and then go into the bedroom here he had laid out the clothing he wanted me to wear and then join him in the sitting room. I drew a deep hot bath and added plenty of sweet-smelling bath salts and climbed in to soak in the perfumed water, using a razor and shaving foam that John had left for me I proceeded to shave all the hair from my body, arms and legs until I was totally smooth and then climbed out of the bath and patted myself dry before dusting myself down with the talcum powder he had supplied. Wrapping a towel around myself I then went back into the bedroom to begin my transformation into John's girlfriend. I was so excited to see just what clothing was waiting for me and I was not to be disappointed at all. The bed was covered with an array of lingerie, and dresses that any young women would have been over the moon to own. In the centre was a cardboard box with a big C printed on it. I opened this first to find a pair

of "C" cup silicone breast forms together with adhesive and instructions to apply them and also some special makeup to cover the join when wearing them Following the instructions, I sprayed the back of the first breast with the adhesive and then lay on my back on the bed, When the adhesive was tacky I carefully placed the breast in position on my chest making sure that the edges were firmly against my own skin, when satisfied with the result I followed the same procedure with the second breast and waited a short while until I was completely satisfied that the breasts were firmly attached and then used the makeup to camouflage the area where they joined my skin. When I sat up again, I was amazed at the weight of them on my chest and reached out for the beautiful lacy black bra that was part of the garments supplied. Having often worn a bra in the past I was able to put it on easily and attach the Hooks at the back, it felt so different however to have two beautiful breasts to settle in the bra cups and to see for the first time my own cleavage, Going through the other underwear, I selected a pair of black ruffled panties and a matching suspender belt, John had supplied both Tights and also stockings but for some reason I selected the stockings as I felt that they were more sexy and would make him fancy me more. I put on the suspender belt and then took up the black sheer stockings. Rolling the first into a doughnut shape I rolled it up my shaved leg and ten spent some time figuring out how to attach it to the suspender tab as this was my first-time wearing stockings. Eventually I managed and the second stocking went on much faster and I loved the way tey felt on my shaved legs, Next came the ruffled panties and when these were on, I couldn't resist looking at myself in the full-length mirror on the wardrobe. I was delighted at what I was looking at as with the false breasts I looked completely feminine from the neck down,I decided that this was the time to do my makeup so sat so sat down at the vanity table where there was a huge array of makeup items laid out for me to use, Luckily My sister had already taught me all the basics for using makeup when she got me dolled up for the Halloween outing so I was able to do a good job of it without making too many mistakes. First came a foundation makeup which I used to smooth out my complexion and this I set using a powder, next was my eyes, I used two shades of blue eyeliner on my eyelids which I blended in and this I followed with a black eyeliner which I winged out past the outer edge of my eyes. John had left a set of long false eyelashes which I glued in place before adding mascara. A blusher was next on my cheek bones and some contouring to my chin and my nose. Finally came the lipstick and I chose a dark raspberry shade and added three coats, blotting between each coat. Next, I used two coats of a lip gloss to finish off my lips. There was also a set of long false nails already painted to match the lipstick so using the glue included I glued these in place over my own short nails and then attached a set of long dangly rhinestone earrings to my ears. The wig he had provided was past shoulder length and Brunette and had adhesive tabs in place to hold it better to my head. Before putting this on I went back to the bed and picked up the dress John had left for me., It was a very shot little black dress with a low neckline to show off my boobs and it had a short side zip. I slipped it on over my head being careful not to touch my makeup in the process and when it was in place, I did up the zip and the dress now fitted like a glove. I took up tye wig and going back to the vanity I put it on and then used a brush to tidy it up. Finally, I used a spritz of perfume on my wrists and behind my ears and then back to the bed to find my shoes. They were a pair of black court shoes with

at least five-inch stiletto heels. In the past the highest heel I had worn were three inches so I knew I would have to get in some practice in these before going to join John. Standing up from the bed I tottered over to the mirror feeling really off balance in the heels but after five minutes walking around the room I started to feel comfortable in them or at least as comfortable as I could be. Now was the time to meet with John. Inwardly I was terrified but looking at myself in the mirror I saw an attractive woman looking back at me so I took the plunge and went to the door and walked into the sitting room where John was waiting on the sofa with an opened bottle of wine and two glasses. As he looked at me his eyes went wide and a look of amazement went over his face, "Hey he said, you look gorgeous," "come and sit here beside me." I walked over to the sofa and holding my short skirt down I sat beside him and crossed my legs in a feminine way. He handed me a glass of wine and I took a sip, noticing the smear of lipstick it left on the rim of the glass. For some reason this made me feel a lot more feminine and I shuffled up closer to John. And put my free hand on his thigh, in return he placed his arm around my shoulders and pulled me closer until my head was resting on his shoulder. This was the closest I had ever been with a man and it felt strange but at the same time it felt so good. We sipped some more of our drinks and after a few minutes John placed his glass back on the table and leaned in towards me, He gently removed my glass from my hand and placed it on the table beside his, the next thing I knew was his lips against mine in a soft and gentle kiss, I found my own lips parting and then his tongue was entering my mouth and I found myself sucking on it as I needed so much more from John. His kisses became more passionate and I found that I was loving the taste and feeling of this man kissing me, my body seemed to take on a life of its own and all I wanted was for John to do whatever he wanted with me. We had been kissing for some time and I found my hand reaching down to stroke Johns Cock through his trousers. I was as hard as a rock and I knew that I wanted so much more from it, I suddenly knew what I had to do and slipping off the sofa, I knelt in between his legs and undid the buckle of his belt followed by the zip. John lifted himself up to enable me to pull down his trousers and underpants, and I was rewarded by the site of his long, hard cock right in front of me. I had had blow jobs from girlfriends in the past so knew what was required so moved closer until the end of his cock was right in front of my lips, There was a small drop of precum glistening on the tip and I found my tongue reaching out to lick it up, I found that I liked the taste and holding the base of his cock in my hand I took the head in between my lips and started to lick and suck on the head and shaft. Seeing my long-painted finger nails around his hard shaft made me feel really sexy and more feminine and I removed the head from my lips and started to kiss and lick right down the shaft until I reached his full ball sack. I took one of his balls in my mouth and sucked and licked on it. Johns' soft moans told me that I was doing the right thing so I carried on and then kissing all the way back up to the tip, I took it between my lips again and then licking and sucking I took the hard shaft deeper into my mouth and throat until I could feel his balls against my chin, I was amazed that I had been able to deep throat him as I had felt no gag reflex but it felt so good to have taken my man's full length right into my mouth. I continued to move up and down his hard cock licking and sucking until suddenly he shouted that he was coming and his cock seemed to enlarge and suddenly I felt a long jet of his cum hit the back of my throat and start to fill my mouth, it was

followed by several more jets and I tried to swallow it all but my mouth filled and some of the thick cream managed to get out between his cock and my lips. He pulled his shrinking member from my lips and I tried to lick off any cum that was around my mouth and on his cock. I looked up at him from my submissive position on the ground with my lipstick all smeared and mostly gone, and he smiled and said I should maybe go and touch up my makeup again.

I got to my feet and made my way to the bathroom again, my killer heels giving my hips a sexy sway and looking back over my shoulder I could see John appreciating the sight, I had a quick pee and then cleaned off my ruined makeup and went back to the vanity table to repair the damage. After re-applying the lipstick, I had ruined I made my way back to john and again sat beside him as before, He pulled me onto his lap and started to kiss me again as before but after about ten minutes I felt his erection under my ass and knew what we both wanted. He looked into my eyes and must have seen the desire in them so he lifted me up and carried me in his arms into the bedroom where he gently laid me on the bed and undressing himself, he laid down beside me. Unzipping my dress, he helped me remove it leaving me in my underwear and heels. He then opened a bedside draw and removed a tube of KY gel and slipping my panties aside he liberally coated his fingers with the lubricant as well as my ass, I felt him insert a finger inside me and this he followed by another and then a third He moved them around and I felt the muscles of my ass relax and start to enjoy the feeling. He then slipped my panties off having some trouble getting them past my heels and he then took a pillow and placed it beneath my ass to raise it from the bed., He then opened my legs and lathered some more of the gel on his hard Cock he climbed on top of me and moved my legs until they were over his shoulders, I could feel the tip of his cock against my opening and was suddenly terrified, would it hurt or what would it feel like. He asked me if I was ready and I said yes but please be easy on me as it was my first time He smiled and said that he would be gentle with me. I felt his tip as it moved further into my opening and suddenly there was a sharp pain and he was inside me, the pain soon went away and I could feel every vein and part of his cock as it slipped deeper into my body, until I could feel his balls slapping against my bum cheeks. He slowly started to move in and out of me and the sensation was wonderful. Every now and then he hit my prostate and each time this happened it was like an electric shock going through my whole body I found myself pushing to meet his thrusts and he was kissing my breasts as he had taken my bra cups down to give him access to my nipples. I was groaning with each thrust inside me and I suddenly found myself shouting, "For god's sake John, fuck me as hard as you can and make me pregnant" At that point all I could think of was having his cum deep inside me and making a baby with him. I was in love with this man even though I was only a pretend woman but at the time I felt 100% a full woman and wanted everything a woman would have from her man. He took me at my word and increased his thrusts into me until I could feel his cock start to throb and I felt the first of many jets of his hot cum shoot deep inside me, I held his butt cheeks with my hands and pulled him further inside me until he was empty and as he started to pull out of me, I used my muscles in my butt to milk every bit of his juice from him. When his cock had fully left me, I felt empty and wanted it back deep inside me again. I don't know what had happened to me but I suddenly knew that I would never be satisfied with a relationship with a girl now I had experienced the hard cock of a man

inside me, I wanted John to kiss me, suck my nipples and fuck me every waking moment of my life. We lay side by side on the bed and I could feel his cum as it slowly ran out of my body and so wished that I could keep it all inside me to make me pregnant. John kissed me gently and said that I should take a shower and redo my makeup as it was in a mess after our lovemaking and I knew that I would need to get rid of the cum which was all over my inner leg. Climbing off the bed I found that it was harder to walk as it felt as if I still had John's cock inside me and I guess it must have showed as well when anybody saw me, I went into the bathroom and took off my stockings and underwear and climbed into the shower, After steaming in the hot water for five minutes I dried off and returned to the bedroom. While I had been showering John had laid out a new outfit for me, this time with red underwear and a red minidress that was really sexy

I got into the new underwear after repairing the makeup around my breasts and then sat at my vanity and redid my full makeup and as it was later in the day, I went for an evening style with a darker shade of everything. I then slipped into the dress and the matching pair of five inch heeled strappy sandals that were waiting for me. I also replaced my perfume with another one and went back to join John, I found that he too had changed and was wearing a pair if smart trousers and a nice jacket over a smart button-down shirt. He looked great and I told him so, He replied that I was looking fantastic and he just had to show me off. I asked what he meant and he said that he had reserved a table for us at a nice restaurant and we should be going soon. I had never been outside like this before apart from the Halloween night and that was different, This time I was to be seen as a guys date and would I even pass in a public place. John told me to go and look at myself in the mirror, and if I saw anything like a boy, then he would cancel. I did as he requested and when I saw myself up close with my cleavage, well made-up face and sexy dress and heels I knew that he was right so I went back to him and with a quick kiss on the cheek told him I was ready to go. He handed me a light coat and a handbag which he said had all the necessary items in it for the evening so I looked inside to see what he meant and was delighted to see a condom prominent in the bag. I laughed and showed it back to John who said you never know when the urge may come upon us. I kissed him on the lips gently so I would not smear my lipstick and we went outside to the car. He held oen the passenger's door for me until I was settled and then closed the door behind me. I had never realised just how difficult it would be to get into a car when wearing a tight skirt and high heels. I guessed that I would need to practice some more if this was to ever happen again The Restaurant, he had chosen was in a town several miles away so we drove there and parked in the restaurant's private car park He opened my door and helped me out and when I was ready on my heels, he took my hand and led me into the premises. It was a really nice place with low lighting and a really special ambiance. Maitre d' took my coat and led us to a quiet table and helped me to get seated and handed us the menu's While we chose, he gave John the wine list and he selected a suitable wine and placed his order, while we waited for our meal we chatted and he held my hand over the table. He kept looking at my breasts and I found myself getting very warm and I started to use one of my feet to rub his crutch area and he looked as though he was about to cum there and then, We received our meal and after we had finished, we went outside and

took a short walk in the park beside the restaurant, He hooked my arm in his and we walked close together for a while before he led me to a park bench under a tree and we sat down together. It was not long before his lips were against mine again and I was sucking his tongue as though I couldn't get enough of it which is actually the truth, He was feeling my breasts and my hand strayed down to his crotch and unzipped his trousers and soon I had his hard cock in my hand again. There was nobody else around in the park so I bent towards him and took his cock into my mouth again and loved the feeling of the hard satiny feel against my tongue and lips. I sucked and played with him until he again ejaculated in my mouth but this time, I was able to swallow every drop, feeling very proud of myself I looked up and suddenly his lips were on mine and his tongue was in my mouth licking at the remains of his cum that was still there, we walked back to the car hand in hand and when we were inside, I used the mirror to repair my lipstick that I had lost on his lips and around his cock. We drove back to the site and went back to his room where we had a glass of wine before he asked me if I was ready for bed. I kissed him and said that I was always ready and with that we headed into the bedroom and he went to a drawer and gave me a beautiful baby doll pyjama set, While he was getting ready, I went into the bathroom to clean my teeth before repairing my lipstick again I then slipped into the baby doll set and climbed into bed. It felt so sexy to be lying in a mans bed wearing nothing but flimsy panties and a light top but to me it felt wonderful. John arrived back and climbed into bed beside me and his lips were at once on mine and my hands were on his cock. I couldn't wait and just rolled onto my back and opened my legs and ordered John to hurry up and fuck me again. I have never needed anything as much as I wanted that hard cock inside me and to feel his hot cum fill me I had never in my life wanted and needed anything as much as I wanted to be filled again with Johns hard meat, and to be filled with the hot cum. He wasted no time before climbing on top of me and I felt his cock against my waiting hole. I was open and needed no lubrication this time as he inserted his cock in me and soon, he was as deep inside my body as was possible, he rested there for a few moments before starting to pump me as hard as possible, the sound of his hips as they slapped against my bottom was like music to my ears and I felt myself screaming out loud to John to go deeper. All too soon I felt the throbbing start in his cock and the first of the cum jets were soon exploding deep inside me. He slipped out and again I felt empty and wanted him inside me once again, He rolled off me and kissed me and then cuddled up beside me and soon we were asleep. I awoke in the morning with a strange feeling between my legs and soon realised that it was Johns cum having dried in my panties and around my ass crack. John woke soon after and soon he was ready to go again and I had to take his hard cock into my now rather sore ass once again but It felt so good when he was deep inside me that the pain soon went leaving me with nothing but deep pleasure. That day we spent most of the time snuggled up on the sofa in the sitting room. I had dressed simply in bra and panties, Black fishnet stockings and black ruffled panties with a tartan mini skirt and a white lacy top with long sleeves and a very low neckline that showed my boobs really well. I also wore sandals with four-inch stiletto heels and was now feeling really at home in heels. I had done my full makeup as usual but I have to say that with John , my lipstick didn't last very long so he often requested me to go and repair the damage, Twice in the day he caught me bending down and took advantage of the very

short skirt that I was wearing to bend me over and slipping my panties to the side he released his seemingly permanent hard on to slip inside me again, It seemed that I no longer required any extra lubrication as I felt that there was enough of his previous donations of cum into my body that it was sufficient to keep my passage way sufficiently lubricated so he could have sex with me at any time. I so wanted to have his hard cock deep inside me whenever possible and when we were not making love, I felt empty and wanting to be filled over and over again. By the time the weekend was over I have to admit that my ass was feeling as though it was on fire as it had been penetrated so many times. I was also now completely at home wearing women's clothing and makeup full time and the feelings associated with it and having a male companion was making me feel as though it was my natural way of living. I had had several sexual encounters with girls in the past but never had I experienced the feelings that I felt when kissing John and feeling him inside me. It was about 8 pm that Sunday evening and I was preparing to change back to my male self when John came up to me. I was undressing and only wearing my bra and panties and had yet to remove my false breasts, nails and makeup and he kissed me and said how he had loved having me as a girlfriend. He asked if I would be prepared to carry on as his girl and if so, he would make sure that he stocked the wardrobe in our bedroom with many more feminine outfits and shoes and much more makeup and so at any time I could turn up and become his girl. At that moment it was the only thing that I wanted in the world, The thought of being Johs full time girlfriend and being able to have his gorgeous cock deep inside me whenever I wanted was a dream come true so naturally, I replied with a passionate kiss and accepted him as my boyfriend and lover. This relationship continued for almost two years by the end of which time I had lost all interest in women apart from the clothing and makeup and felt myself to be a woman in every way. It was on my 19th birthday and John had arranged a celebration meal for me with a bottle of Champagne when he got down on his knees and asked me to marry him. He said that if I agreed he would pay for me to go to Thailand and get full SRS so we could live together as man and wife, I agreed at once and now I am the proud owner of two beautiful breasts and a very well used vagina. We are now considering adopting a child to make our family complete.