The journey of Tim to Jennifer

Introduction:
I would never have believed that a stop at a rest area would have had the effects on my life that happened just a few short years ago.
I had done this a few times knowing that many times the rest areas would have other men looking for a young man who wanted to have his cock sucked quickly. This time I met a man by the name of Bud. Bud was a friendly guy and instead asked me if I would like to have a quick drink with him at his home nearby. There was nowhere I had to be and I was just beginning a two week vacation. I was a little tentative but his friendly ways and knowing he was quite a bit older than me I allowed him to talk me into it.
I followed him to his rather large home in the way back in a wooded. It was fairly well hidden with a long driveway and I noted it was an big expensive looking home. He pulled into his garage and I left my car in the driveway near the door. His house was beautiful and I could tell immediately that Bud was very well off. We went into the living room and I commented on how beautiful his home was and how nicely it was decorated. Bud told me that he was an interior decorator and his business did fairly well. He asked my name and I was tempted to make one up but decided to use my real name, Tim.
Bud complemented me on how beautiful I was. I was not sure what to say but thanked him very much for the compliment. I had never been called that before. After a little small talk, he asked if I had family in the area. I explained that I was on my own and my family was pretty much on the other side of the country. I did not talk with them very much. Bud smiled and said he understood and that he was an only child and his parents had passed on several years ago. He offered me a drink and I asked if he had any scotch. If so I could sure use a scotch and water. It was pretty strong but I could tell it was a very good brand. After a few sips, Bud started asking some more pointed questions. I could not resist and answered every question without thinking. He asked about my sexual habits and I told him that I had been with a couple of other men, but only to have my cock sucked and my ass eaten. I had never sucked cock. He asked if I had any interest in cross dressing. I could not resist and told him that I really liked wearing silk and satin panties and garters with thigh highs. He smiled at that and asked if I would like to dress up for him. I giggled and said maybe sometime. he asked about any fantasies that I might have and I could not resist telling him I had always wondered why it would be like to be made to have sex while dressed up as a little slut.I was beginning to feel even more light headed and I think whatever drug he had put in my drink made me pass out completely.
I awoke in a big beautiful bedroom with mirrors on the walls and ceiling. I tried to move my arms but found they had soft handcuffs on them. I tried to move my legs and they were cuffed t the bed as well. I looked at the mirror on the ceiling and saw a beautiful hot girl laying where I was. A tight blouse with smaller tits, short skirt hiked up slightly showing the tops of nylons and garter snaps. I felt the shoes on my feet and the mirror showed they were sexy black heels. Hearing me stir, the door opened and Bud walked in with a robe tied about the waist. I demanded to know what was going on, what had he done to me. Bud sat down on the bed next to me and put his hand on my leg. It felt electric. Bud told me he had given me a sedative because I looked nervous and I had fallen asleep. I had told him some of my deeper secrets including that I liked being dressed as a woman and sometimes wished I were a woman. I was a little embarrassed but he told me not to be as he rubbed his hands up and down my stocking leg. He began to tell me what he did to help make a dream come true for me. When I passed out, he had taken my clothes off and completely shaved my arms, chest, pubic area and legs. He had carried me up to this guest room and dressed me in a garter belt, black silk stockings, a short hot little skirt. A bra with large silicon breasts built in and this tight blouse. He had applied light makeup and this wig. He knew I had never been treated as a woman and wanted to grant my wish but did not know how I would react when I woke up, so he had used these soft bondage handcuffs to see if I would cooperate. I was upset and told him so. As he stood up he removed the tie around his waist and removed his robe. He was a tall man, probably 6’2″ and his hard cock must have been at least 8 inches. He climbed onto the bed and his cock was about three inches from my face. I will start you out by teaching you to suck a man’s cock. I protested and turned my head but he grabbed my head and pushed his cock against my soft lips. You have nowhere to go and you will suck my cock before I let you go, he said. I knew I had always wanted to try it and relented. With a smile on his face I opened my mouth and took in the smooth head of his beautiful cock. I was surprised, it tasted good. He slowly began to fuck my mouth, pushing in a litle more each time until he was pressing against the back of my throat. I started to gag and he explained that if I breathe through my nose it will make it easier. He kept pulling his cock part way out and pushing it all the way in. I was beginning to really like it and started sucking hard. He was running his hands all over my body and I was really getting excited. Suddenly he pushed his cock all the way into my mouth and I felt it grow even larger as he moaned and I felt his hot cum splashing against the back of my throat. I tasted it only as he gradually began to pull it out and I kept sucking it, wanting more. I was panting as he kept running his hands over me and they settled between my legs. His finger pushed aside my panties and I felt it enter my tight little back pussy. I gasped as his finger entered me up to the knuckle. Bud smiled down at me and told me I really was a bit of a slut. “can you untie me know?”, I asked. “Not yet”, he said, ” I want to show you more of the pleasures of being a woman.” He told me I was so hot and I could see his soft cock stirring again. “Oh no”, I pleaded, “Not that!” Without a word, Bud pulled out a bottle of lube and smeared it all over his cock. He positioned himself between my legs and lifted my ass up as he put a pillow under my hips. He moved my panties aside so he could access my little girl pussy, as he called it and I felt the tip of his hard cock at my tight little back pussy entrance. “They say that you always remember the man that took your cherry”, he said as he pushed the large smooth head of his hard cock gradually into me. It hurt at first and I begged him to stop. When the smooth head popped into me I screamed in pain. He stopped for a minute and then pushed in a little more. He withdrew slightly then pushed in a couple more inches. The pain was subsiding and it was beginning to feel really good. He smiled as he pushed all the way in and I could feel his balls against my ass. He was buried all the way to the hilt impaling me on his hard cock. “How does daddy’s little girl like daddy’s hard cock in her little girl pussy?”, he asked. I couldn’t answer but I started moaning with the extreme pleasure I felt building up. It started feeling so good I found myself pushing my hips up to meet his every thrust. I had never felt anything like this and my own little cock was ready to explode. He leaned over me and planted his mouth on mine. Kissing me hard and thrusting his tongue into my mouth. I began sucking on his tongue and returning his hot kisses. One more hard thrust, deep in my little girl pussy and I felt his cock grow even larger. As I felt his big cock become larger, he grunted and I could feel his throbbing cock begin pumping hot cum deep inside of me. I climaxed extremely hard and felt myself soaking my panties with my own cum. I screamed with delight and decided to play his game. “Oh daddy, I am cumminnnggggg! You are fantastic daddy, I want you to fuck me again!”, I yelled. He smiled as he collapsed on top of me with his huge cock still buried in me. He had cum so hard in me that I could feel his hot juices leaking out of my ‘little girl pussy’ around his cock. I threw my arms around him as he planted another hot deep kiss on my soft lips. I looked in the mirror on the side wall and felt that Bud had indeed done me a great service by making me his woman. I felt so hot and spent. I had never orgasmed like that before. I felt his spent cock gradually soften and begin to pull out of my used back pussy and finally pulled out with a pop. Bud got up and asked me if I still needed the cuffs. I told jim that I thought they were really kinky and added to the experience but he would not need them any more to use his ‘little girl’. He told me to get up and clean myself up a bit. In the bathroom I would find a change of clothes and to come back out when down. He wanted to talk to me about something important. Walking not the bathroom in heels was a bit awkward but I managed. He told me to change but to leave on my heels, hose, garter and bra. In the bathroom I looked in the mirror and had to admit the look was really hot. I had to stare at my sexy self in the mirror not believing it was my reflection. Bud called out to me, teasing me not to play with that hot little girl in there but to hurry and come back out to him. I removed my blouse and skirt. I removed the sticky panties and using a washcloth cleaned myself up. I could not help marveling at how hot my shaved legs and pubic area looked. I noticed he had even shaved me under my arms. On the counter was a hot little red nightie with red silk panties. I put them on and my cock immediately stood at attention. Looking back at me from the mirror was a girl that I would have loved to have been with. Beginning to get the hang of walking in these heels, I walked back into the bedroom to see Bud laying on his side completely naked. When he saw me he smiled and I could see his large thick cock liked what it saw. He asked me to sit on the bed next to him. “I want to call you Jennifer if you don’t mind”, he smiled. “You can call me anything you want”, I said. “You have shown me pleasures that I never believed were possible”, I smiled. “I have a proposition for you. I would like to offer you the opportunity to live as Jennifer full time.”, he said. “I will make it worth your while by offering you a contract that will guarantee you 1 million dollars over 3 years if you will think agree to do as I ask”, he said with a wicked smile on his face. I was so surprised that I just sat there with my mouth open. “If you keep that mouth open without answering me, I have something here that I will be happy to fill it with” he teased.
Daddy was not anywhere near finished with me.
end of part 1

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