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When I was in high school, I was seventeen-years-old and dating an older man. He was forty-years-old and very handsome. He had taken me out to dinner and for ice cream and for walks on the beach. We had held hands and kissed but had never gone any further, but I knew he wanted to go further by the way he looked at me when we were riding in his car. I would see him looking down at my sexy, smooth tan legs and I would know, instinctively, he wanted what I had between them. Darryl had already been taking me out for six months while I was dressed as a boy when I decided to let him know I like wearing panties and bras for men to see me in. I had already been wearing sexy girl clothes for other men at the adult bookstore, but not for Darryl who lived in my apartments and made friends with me at the swimming pool last summer. I was already having sex with the handsome lifeguard every day, so I just thought of Darryl as a friend. Then in October, Darryl took me out to dinner and treated me like a guy treats his girlfriend. He opened and closed the car door for me, took to me to a nice restaurant and paid for the dinner. Then he took me for a romantic moonlit walk on the beach where he held my hand while we walked together. Finally, he took me in his arms and kissed me and he told me he was in love with me. It was magical to me to be treated like a teenage girl by such a handsome, well-built, older man. Darryl started taking me on lots of other dates. One of his favorite dates to take me on was to buy ice cream cones for me. He would buy me soft ice cream cones and I would lick them very seductively while he watched. I knew he was getting hard for me down in his pants, imagining I was licking him like he was an ice cream cone. Then we would be driving home and he would reach over and put his hand between my thighs, and rub me up and down very tenderly down there. It was all so sweet to this sexy seventeen-year-old. I had been sad when my lifeguard boyfriend had to go away to college after the summer, so it was nice to have Darryl to be my new boyfriend, now. But we had never had sex, even though he had been taking me out on dates for five months. One time, in the back of a movie theater where no one could see us, we made out for two hours during the movie. He felt my tits and reached in my jeans and played with my clitty dick. And, of course, I rubbed his big cock for him through his pants. It felt humongous compared to the cocks on the boys my age I saw in the showers at school. I knew I wanted it in my mouth as soon as I touched it. It was the kind of cock every girl wants, I thought, while playing with it. The night of making out in the back of the movie theater with lots of heavy petting changed our relationship. We both knew we were ready to take it to another level. I decided to tell Darryl that I was a cross-dresser in private and that I wanted to dress for him. To my surprise, he told me that he already knew I was a cross-dresser because he had seen me wearing sexy shorts and hot pants to the swimming pool to turn on my lifeguard boyfriend the summer before. He told me that was why he was so interested in me because he wanted me to be his first time with a cross-dresser. This made me feel so special. Not only did Darryl desire me like I was a girl, he had been willing to wait for me to bring up the subject with him first. He told me he didn’t want to treat me like I was a dirty little slut. He wanted me to be the sweet girl-next-door to him and get me to fall in love with him for real. That’s why he took me for sweet ice cream dates and to the movies and for walks on the beach. Now, he was asking me if I would take a weekend trip out of town with just him and I. He said he wanted his first time with me to be very special so I would always remember it. Of course, I wanted him, and wanted to please him, too. All the sweet things he did for me, opening doors for me, buying me treats, caressing my thighs, taking me out to dinner like real dates. He deserved to be rewarded with a weekend of sexual favors from the girl he loved. It was just a matter of setting the date, at that point. It was March then and my junior high school prom was coming up. I knew a lot of girls like to make their first time with their boyfriend on prom night to make it memorable, so that’s what I decided I would do with Darryl. Instead of going to my prom, I would go away that Friday for a whole weekend of sexy fun and pleasure with my handsome older boyfriend who loved me. The other girls wouldn’t get nearly as much sex as I would get. And my boyfriend had a much bigger one than theirs did. Ever since I had felt Darryl’s cock through his pants in the back of the movie theater, Beşevler escort Bayan I had wanted to suck it for him. And I enjoyed the way he reached down in my pants and played with me like my little five inch dick was a clit, rubbing it with his fingertips and not stroking it. This prolonged the pleasure I was feeling throughout the movie while we made out for two hours in the back of the theater like boyfriend and girlfriend. It was an innocent way to get to know each other, physically. But I knew we both wanted more. I was into dressing up in lingerie in my bedroom at night and making myself feel pretty for a man. I would put on my panties and bras and stockings and garters and teddies and high heels. Then I would put on a wig and makeup and lipstick and eyeliner and nail polish like I was getting ready for a man to have me. I started to imagine that it was Darryl, my new boyfriend, who was having me that night. I knew he was taking his time with me because he was so much older than me, so I was basically being a tease with him the whole time I waited for him to have me. That’s what high school girls do. They tease their boyfriends with flirting and kissing and holding hands to keep them interested and coming back for more. So, after six months of having his cock teased by me on dates, you can imagine how much Darryl wanted to rip off my clothes and have wild sex with me all night. And the fact that he was going to do it to me on the night of my junior prom made it even more special. I would wear a sexy cocktail dress and heels and some new lingerie and pretend I was the prom queen for Darryl, my prom king. He was taking me away for the weekend to a nice resort hotel on the ocean where we would have a big suite all to ourselves, over-looking the ocean. He would pay for everything, including my prom dress and lingerie to wear all weekend. And I was going to have fun shopping and buying the sexy things to wear for him. It felt like I was really going to the prom. I had ended up with my mother’s big ten inch dildo vibrator when she left. And I liked to use it on myself every night at bedtime and imagine it was a man. I started to imagine every night that it was Darryl’s dick that was in me and it was on my prom night after the dance at a hotel. Knowing it was really going to happen made the fantasy become so real that my clitty dick would soak the sheets after I got done fucking myself with the vibrator. So, there was a million levels of lust going on between Darryl and I by the time the big night of the junior prom arrived for me. I was just like an innocent little high school girl to him, so having sex with me for the first time on prom night was perfect for him, too. It supported his fantasy of me being a cute girl-next-door. He didn’t know the me who had been to the adult bookstore dressed and having dirty sex. He wanted sex with me to be a lovely experience I would always treasure and remember. To me, there was also the fact that he was my real boyfriend, so I wanted to make sure I really pleased him better than any other girl ever pleased him. I began to practice giving oral to him by sucking on my eight inch dildo while I fucked myself in the ass with my ten incher. I didn’t know if Darryl would still think of me as a sweet innocent girl if he knew I was doing this, every night of the week. I was a sweet innocent girl at home by myself wishing I had his cock in my mouth and in my ass, all night long. And now I was about to get that from him on prom night. It couldn’t have been more special to me. There was also the excitement for me of being with an older man. Since I always felt like a sweet teen girl every time I dressed, the thought was natural to me to make love to a man who was old enough to be my daddy — men who had stubble on their chins from their five o’clock shadows, instead of soft faces like boys my age. I knew I could handle an older man’s cock because my first boyfriend, the pool lifeguard the summer before, was a well-built college boy with a nine inch cock and I sucked it every day for him. Now, I wanted Darryl to be my new boyfriend I dressed for and sucked, every day. So, you can imagine how nervous I was and wanting everything to be perfect and wonderful and I felt just like a real seventeen-year-old girl waiting for her junior prom night with her handsome boyfriend. Would I be pretty enough? Would he like the dress I picked? Will he want to kiss me while we’re dancing? These were thoughts I was thinking waiting for the big night, the night my boyfriend would have sex with me for the first time and make me officially his girl. What a wonderful feeling it was! One evening, Çankaya escort the week before the prom, I was in Darryl’s apartment with him and we were kissing and he was reaching down in my pants and rubbing me through my lace panties and I wanted to let him take my clothes off and have me then. But I had to stop him from going any further, so we could make it more special on prom night. I had limited him to kissing me, feeling up my titties, playing with my little clitty dick and me rubbing his man-size boner through his pants. Now, with him rubbing my clitty through my lace panties, the temptation to let him finally suck me like he was dying to for the past eight months was really hard for me to resist. I don’t know how any girl can resist it. Clitties need dick. It’s that simple. There was a coming-of-age feeling all week the week before my junior prom. When a girl is young, her daddy is the most important man in her life, but when she is seventeen she has another man to replace her daddy as the most important man in her life. In my case, it was a man of forty who looked younger than that. He always had a great tan and a beautiful smile, blonde hair and a well-built, muscular body. And he wore aviator sunglasses that made him look really cool to this cute girlyboy in high school still. I was dating a man, not a boy, a man who treated me special and tender every moment we were together. How could I not want to please him the most of anyone I had ever pleased before? I had seen the way older men looked at me outside the adult bookstore and I just loved being the center of attention for an older man. Whatever I had to do to please him was fine with me because that would keep me being the center of his attention. I had been the center of attention for five months with Darryl while we dated. And I had played it well with him, playing the sweet girl-next-door who is friends with a boy and then starts dating him and then wants to “go all the way with him.” So, all week long before the prom, I looked at it as the night I was going to “go all the way” with my boyfriend. And the anticipation was killing me. I had to put ice cubes on my clitty to cool it off it was so hot for Darryl that week. I needed his lips to satisfy my clitty dick and his cock to satisfy my whole body by letting me suck it and fuck it like a dirty girl all night long. So, I knew the day after prom night Darryl would no longer look at me as a sweet girl anymore. I would become an experienced woman with men to him. He would know that my needs are the same as they are for any whore woman. I need cock to please just like they do. No matter what the motivation is, money or love, I was going to be a slutty girl who always wants more and more cock and who doesn’t care where she has to go to get it. So, I felt I was losing my innocence forever all week before prom also. The girl I was would no longer exist after I gave myself to my boyfriend like I was a dirty little slut whoreboy who loved men’s cocks. This affair with Darryl would lead to lots of other affairs with older men including one, during senior year when I turned eighteen, with my P. E. coach whose cock I had wanted to suck all through high school. I got to suck him all through my last year of high school. I didn’t know it, yet, but Darryl liked to be a voyeur and watch me have sex with other men while he hid in the closet and watched. So, after our wild weekend we had after prom night, he let me use his place to bring older men I met at the adult bookstore. One thing led to another and the men started paying me and Darryl became like my pimp who got to fuck me and suck me after the men left. So, I really was losing a lot of my innocence on prom night, a feeling I’m sure every girl has. It made it really special to me to know that he really did love me and want me like a girl, too. I had had lots of experience dressing as a girl in my bedroom and I had been to the adult bookstore dressed a few times and met men for sex, but I had never spent a whole weekend dressed in sexy lingerie for a man. So, my clitty stayed hard all week just from me thinking about my cum-loving weekend to come. On Thursday night, I packed my bag full of all my sexy lingerie I was going to wear for Daryl. We were planning to leave right after school on Friday. We would drive two hours to a resort hotel on the ocean and then I would get dressed as a girl for her prom in her dress and sexy lingerie and be a complete girl for my boyfriend all weekend, never acting like a boy for him again. I didn’t know it, yet, but Darryl was my Svengali, the charmer who takes an innocent girl and makes her into the kind of girl Cebeci Escort he likes, sexy, dirty and wild. He said he loved me but he passed me around to other men so he could watch me suck their cocks and fuck them for his pleasure. Then he started having group sex with me and the other men. I became his ticket to get lots of other men to suck and fuck, since most of the men from the adult bookstore didn’t care if they were being sucked by a man or a woman or tranny. They just wanted blow jobs. Darryl was a gay male who had his first experiences with men while in the army. And he loved sucking men’s cocks as much as I did. But being an older male now, he wasn’t getting as much. So, I was the lure who he could use to get lots of naked horny men to suck on. So, I thought it was only fair for him to let me use his house for free to turn my tricks for money. I was the star attraction. Without me, there would be no dick for him since it was my hot young lips and ass that men wanted. But Darryl enjoyed getting sloppy seconds after I was with one of my clients. I used his spare bedroom for my tricks and then Darryl took any in his bedroom who wanted more head. It became a great arrangement. So, driving to the resort with Darryl for the weekend in the car, I felt the past leaving me and I was leaving it. Whatever would have happened in my life if I had gone to the prom with a girl would no longer exist after this night of hot and wonderful passion. Because I knew after this night that I am a tranny girl who needs men with all her heart and being with them would never seem wrong again after Darryl made me his sexy little girlfriend. In hindsight, I think I stopped growing emotionally after that night, so I still have the seventeen-year-old-girl inside of me. That’s why I still like sucking and fucking men, but I also like it when they buy me ice cream and hold hands with me, too. I’m a teenage girl at heart and have that same spirit now. When we arrived at the hotel, I waited in the car while Darryl checked into our room. Then we pulled down and used a side entrance to the hotel so we could be discreet about our weekend in paradise together. When Darryl came back and got into the car, I felt is was time to tell him about my past. He pulled down to the end of the parking lot where had some privacy. “Darryl, “I said. “I’m not really the sweet girl you think I am. I had a boyfriend last summer whose cock I sucked, every day. And now, I want you to be my boyfriend and let me suck your cock , every day.” “That’s okay, Courtney,” he said. “I was willing to wait as long as you wanted just the same.” “There’s something else,” I said. “I haven’t been true to you. Since we’ve been dating, I’ve gone to the adult bookstore dressed as a girl and had sex with a few different men in their cars and I even spent the night with one in his house.” “So, you’re really a slutty little girl who likes lots of cock from different men, but you wanted me to be your sweet boyfriend who takes you for ice cream.” I laughed. “Well, you did like to watch me lick the cones,” I said. “I sure did. I could tell by the way you licked those cones that you were an experienced cocksucker, Courtney. My cock was so hard watching you do it. That’s why I always took you for ice cream so you could turn me on.” I smiled. “So, that did turn you on?” “Every time, my dear.” “And you knew I was experienced with other men?” “Yes, doll,” said Darryl. “You shake your ass just like a girl when you walk. Any guy experienced with gay boys knows when one likes cock in his ass.” I was shocked. “You mean, you know I like cock in my ass?” Now, he laughed. “Of course, doll.” “Do you know that I put a big dildo in my ass every night and I wish it was your cock instead?” “I didn’t know that. But I’ve been wanting to give you the best blow job you ever had ever since we met?” “Really?’ “Yes. That’s what I’m into. I like to give blow jobs to young men for hours. I like looking at their sweet faces and knowing they love my mouth on their cocks.” I suddenly smiled widely. “Well, I’m going to be happy to let you do that.” It felt good to be honest with Darryl about my past. I didn’t want him to be shocked to learn that I am an experienced tranny girl when I showed him I knew everything a man likes, tonight. I figured it would help avoid having to explain later. This way, he knew I had been honest with him. We got out of the car and carried our bags to the hotel side elevator. We went to our penthouse suite where I would learn how to be a tranny whore for men, this weekend. After Darryl learned what a dirty slut I was, he set me up with other men who paid me to have sex with them. It turned out that the resort where Darryl took me was a gay hotel where there were lots and lots of men who loved being with a sexy teenage girlyboy. It started out with Darryl complimenting me, telling me I was beautiful and sexy. He said, I should be flattered to be with lots of men because it meant I was a hot chick that many men wanted.