Gay
2008-05-19

My name's Sam, I was 16, and had just finished my GCSEs. Ever since I could remember, I'd had a desire to sleep with an older, married man, while dressed as a girl. I knew the likelihood of it actually occuring was next to none, I especially didn't want my parents to know, because they where fairly homophobic, and the last thing I wanted was for them to look down upon me. I had however tried to fulfill my desire through mastrubating, but shoving a vibrator in my bum could only get me so far. I wanted to the real thing. It was the summer holiday of a lifetime, my parents kept telling me. To be honest, a summer at home would have been far more sufficient, but I guess if my parents where paying, then I would have been a fool to pass up a free cruise in the mediterranean. At the time, I remember summer taking longer than usual to arrive that year. What with the endless exams, and the constant revision - I needed a break. I guess this cruise was the golden oppurtunity to get just that. But, summer arrives, like does every year, and we left Britain for the small Greek island of Corfu where the ship would be setting sail. Because my parents too where 'after a break' (or so they said), they'd got themselves a suit on there own. Leaving me with a cabin of my own. I couldn't complain, a king size bed to myself seemed like heaven, especially after travelling for five hours. 'Why don't you take a look around, Sam?' My mother asked. 'Yeah, go on Sam, we'll see you at dinner later.

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  ' My Dad said. So, off I went. Keeping my eye out for any girls, or any older married men that would be willing to fulfill my desires, but of the latter, I was less hopeful. However, walking through the bar was a very sexy man that caught my eye immediately. He glanced at me and winked. Did he know what I was thinking? Did he know I was looking at his muscular chest, and thinking of only one thing? Did he know my deepest, darkest desires? Of course he didn't, he couldn't do. I looked away, embarassed, but at the same time, excited. I knew he was still looking at me. But I carried on walking, as seductively as I could, without giving too much away.

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The truth was, I wanted him to talk to me. I sat down at the opposite end of the room on a luxurious, and comfortable sofa. I glanced around - he'd followed me. 'Hey there,' He said, in a cool, calm, but very masculine voice. 'I'm David. ''Hiya', I answered, slightly stuttering, 'My name's Sam.

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  ''Sam? As in Samantha, or Samuel'? He joked, while offering a light and tantalising smile. 'Well, whatever you want it to be short for. ' I answered, trying my best to sound flirtatioucs.  He laughed, and then ansewered;'To be honest, I think you look more like a Becky. ''Sounds good to me!' I laughed. 'Do you have a cabin?' David asked, 'Or are you bunking with family?''No, I'm all alone. How about you?''Well, I'm travelling to Venice on Business, I tried to get my wife to come, but she's busy with her work. So I'm all alone too. 'Wow. Was this a set-up? It seemed too perfect to be true. This man was amazingly sexy, his light blue eyes, dark hair with a tinge of grey, and his wonderful macho figure. It really was perfect. 'So how old are you?' He asked, with what I could detect as desire in his voice. '16. ' I closed me eyes.

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   Either he wasn't going to be interested anymore, or he was. 'Lovely. I'm 48. 'I opened my eyes and gasped. He wasn't turned off, and he seemed interested. He definitely didn't look 48. 'Why don't you come to my cabin Sam? Or shall I call you Becky?'Call me Becky. But, only if I can call you Daddy. Oh, and I'd love to see your cabin. ''Sure thing Becky. I've got some clothes you might like to try on. 'He grasped my hand, and led me through several corridors before we arrived at a luxury suite. He led me in, through a sitting room, and into the master bedroom, before letting go of my hand. 'There are a few sets of clothes you might like left in the bathroom.

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I'll be here.

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   Waiting. 'I walked through the door to which he was pointing, and entered. Closing the door behind me. I looked down, and there wasn't a selection of clothes. Only one outfit, which consisted of a leather miniskirt, stockings, high heels, bra, and tank top. I stripped, I could feel my small cock growing as I put on the pieces of clothing. The thought of David taking each item off one by one running through my mind. When I finished, I opened the door, and stood with my legs apart and my arms holding onto the door frame. I looked towards David, and my eyes must have doubled in size. He was lying there on the bed, naked. His wonderful cock dangling between his toned, sexy legs. I walked over to him, as seductively as I could with high-heels on, and turned around slowly, before bending over so he could see my bare bum. 'Strip. ' He said. It was a command.

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   One that I was more than happy to fulfill. And so I did, as slowly as I could. I felt amazing, like a true woman. It was amazing watching David's eyes as he saw me sway and move to the sound of the ship setting sail. Watching his wonderful penis grow was like a drug, one that I'd definitely take. He sat up, and he didn't need to say anything, because I knew what he wanted. I climbed on the bed and crawled over to him, taking his tongue into my mouth as we kissed. The world seemed to stop, it was only me and him. What a wonderful world that would have been. We broke apart. I knew again what he wanted, and i moved south, I liked the tip of his penis, and slowly tickled his balls. I licked the shaft, rolling my tongue up and down before engulfing his cock with my mouth. After giving him oral sex for several minutes, he told me to lay down - on my back. He lay between my legs, and pushed his penis into my tight, but well trained bum, slowly revolving his hips as he entered me. Gradually getting faster, as I was gradually getting more and more comfortable.

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   My smooth legs wrapped tightly around his amazing body. After another few minutes of thrusting, he rolled over, and with him, I did too. I was on top, with his hard cock in my bum as I bounced up and down, my hands on his slightly hairy chest. 'Mmmm. . . Becky, you're so good at this. ''Hmmmm. . . you are too Daddy. . !'I started riding him harder, both of his hands carassing my bum cheeks, both of mine on his wonderful chest muscles. We came. Together.

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   It was perfect. I leaned over and kissed him. Me and David are now living together. I came out to my parents two nights after meeting David, and he came out to his wife when he arrived home. We spent the cruise making love to each other, only leaving either of our cabins for an our or two a day, before retiring to bed early. He works as a Fireman, and I work from home as web developer. We're having sex whenever we're together, and I'm currently on the waiting list for a sex change. I am to become Becky, David's wife. It truly was a holiday of a life time. .