A fortnight ago, we went out with friends to celebrate one of their birthdays. About half way through the night, my wife who was in a bad mood to begin with, stormed off saying I was getting far too drunk.
Ten minutes later after speaking to her outside, she apologized, but asked me if I could stay over at my friends house as she was in work early the following day, and didn't want me drunkenly waking her up when I got in.
Putting her in a taxi home, my friends and I moved onto another bar. And I soon noticed a good looking woman checking me out. Not paying her too much attention immediately I carried on having a laugh with the guys. Maybe two hours later with only one of my friends left in the same pub, he said he was going. I tried to find the other guys along the strip of pubs along the busy road, but couldn't find them. Who I did find about to enter a small park across from where I stood, was the good looking girl. She waved at me and entered the park.
Ten seconds later, I found myself following her into the park and catching up as she rounded a bend leading down to a wooded area. Taking hold of my hand she told me she knew I wanted a blow job. Moving further into the trees, he had me stop, lean back onto a tree and undid my jeans as she dropped down. Taking out my already rising cock, she instantly swallowed my cock. For a forty eight year old man to have such a good looking young girl sucking my dick, I felt myself to be so lucky and soon got into fucking her mouth. Holding her head tightly, I really began to fuck her face as she gulped down my cock, but as soon as my cock began to throb in her mouth, she moved away and said "Will you fuck me".
Producing a condom from god knows where, she handed it me, turned around and lifted her skirt. The small pair of knickers she had on, did nothing to hide the fact, the girl was indeed a boy. As I could easily see his cock from behind. Yet even knowing it was a young guy didn't stop me from feeling incredibly horny. Sliding the condom over my cock, I pushed him forwards so he was leaning onto the tree, ripping his sheer knickers off of him and rammed my cock as hard as I could up his arsehole.
Pushing further and further into his arse with each thrust, I eventually bottomed out and found myself hugging him from behind as I fucked him. I also found myself kissing him as he turned his head to ask me to fuck him harder. After a few minutes of slamming my cock into his wonderfully tight arse, plus the combination of us kissing made him judder in my arms, as a large kiss stifled groan left his lips.
I knew he'd cum as I could feel his semen flowing onto my dick, then with him telling me to cum, I shot my load deep up his bum, filling the condom. Stood still inside him, I let my cock slide out on its own as it softened and turned him around. Kissing him again, we stood kissing that way for some time.
Breaking the kiss, I asked him if I could possibly see him again. He responded by saying "Didn't your wife say you should stay out tonight". Before I could answer, he dropped down again and took my cock into his hands. Taking off the condom, he threw it away and quickly slid my cock over his tongue. sucking on my cock for some time, I'd become hard. But this time instead of carrying on, he stood up and said "My flats over there, want to spend the night".
It was nine o'clock the following morning when I walked into our home. I'd spent pretty much the whole night fucking Alison as he liked to be called. He'd swapped into another outfit at home and I could resist fucking him in it. It was a schoolgirls outfit and it fitted his small frame wonderfully. Screwing her/him was such a thrill, I actually remained rock hard for over an hour, as I fucked Alison in one position after another.
Before I left her/him to sleep off our night, I had Alison lick and suck my dick and arsehole, to one of the strongest orgasms I can remember having. Cumming all over her/his face, we then kissed and I tasted myself for the very first time.
Alison and I have met up three more times. Once for quick suck and fuck at the park. Once in his/her flat for a brief but very satisfying fuck during my lunch hour last week. And once at a golf course earlier this week where I met Andy/Alison as a guy. He works there and we took up the last available tee of the day. It was something else having my cock sucked on the ninth hole, then fucking Andy later on in my car after I gave him a lift home.
It's not cast in stone that we'll carry on seeing each other, but what I do know, is whilst I'm having so much fun fucking a genuinely horny young cross dresser, I'm going to enjoy every fuck we have as Andy or Alison.