He was too young, I was too horny so I fucked him

I am 34, in good shape, decent looking. I have a 7 inch cock that isn't too thick. I did jack off with a guy when I was 15, he wanted me to fuck him, but I just rubbed against him in the crack of his ass with some baby oil as lube. I came, spurted all over his back. He turned around quick, some got on the bed, and he got the rest on his belly. He scooped it up and then licked up the bit on the bed. He had me wash the rest off his back. I confess I did it three times, when I'd get horned up but girls were for me. I've been fucking women ever since, never looked back. I have not been laid now in 3 months, my girl left me, and I was out of town in another city for a couple of months now. Dean (dee) is next door to the temp apartment I have here. He lives with his mom and sister. He is 14 and very thin, with a femme body, indented waist, great legs and ass, and looks very femme in his face too.

He has hung out with me a bit, his mom who is pretty damn hot at 43 lets him come over. I didn't think much of it. Dee came over dressed in a plaid skirt, white blouse, frilly socks and black short heels. I could tell he had what I guess was a training bra I could see under the blouse. It couldn't have been his 15 year old sisters or his mothers they had probably C and DD cup tits. He was made up, his hair down to his shoulders was fluffed up and I honestly didn't recognize him. I asked if his mother knew he was like this and he said she did. I asked if she knew he was coming over here and she did. Then Dee asked me if I didn't like him this way, if I only wanted him here as a boy. I guess I didn't care, he started coming over more and more as a girl. He was actually very attractive.

Then one night sitting on the couch he asked me to rub his shoulders and neck. As I was doing it he laid down on my lap, his head on my crotch. He reached back and as he shuffled around his skirt came up. This fine fine fine looking ass staring at me. I looked up his great legs and at those two perfect globes at the top. I was hard, and I reached to his ass putting my hand on it. "mmmmm, " he moaned as he wiggled that cute ass under my hand. He reached to my hard cock rubbing it in my shorts. Then he reached up under the leg hole of my workout shorts and into my underpants. "it's big" he said. I started rubbing his cheeks, he pulled my cock out of my shorts and started sucking on it. "You shouldn't be doing this, I shouldn't be doing this Dee" I told him. "I want to" he told me. "I want to also but we can't, you're too young. Have you done this before with anyone?" I asked him and he said he hadn't. He went back down on my cock and I spread his cheeks looking at his tiny asshole. At that I was rubbing my finger on his asshole, that tiniest of little puckers, I knew I wanted to fuck that hole but didn't see how it would be possible it was so tiny. Then I came in his mouth. He was a good little one, and took as much as he could. He looked at me and swallowed, then licked the rest up. He moved up so his crotch was up against my lap and his ass my primary focus.

I was soon hard already. "I want you to do it to me" he said. I told him again he was too young. "I wasn't too young to suck you, you enjoyed it didn't you?" he asked. Yes, I enjoyed it I told him but this was something different. He got up, took off his skirt picked up some lotion I keep on the end table and walked to my bedroom. "I want to do it in bed my first time" was what he said as he sashayed off. When I got there, I was already hard, he pulled down my shorts and underpants, and started using the lotion on my cock. He pulled off his blouse, leaving his trainer bra on. He put a lot of lube on his ass and pushed some inside. "I've used my moms vibrator in my butt before but that's all". Then he laid down on his stomach. I rolled him over, got between his legs. I positioned to enter him, and asked if he was sure. I pulled down his bra and sucked on his flat chest, pulling at his nipples, he loved it. "That feels good, I didn't know that would feel so good" he said. Then I kissed him and pushed my cock into his hole. I stopped with my pubes up against his fabulous ass. I paused, asked if he was OK. I got the nod, and kissed him and started fucking. It took me about 30 minutes to cum since he'd given me a BJ already but he took it all. The whole time.

I was horny, he was underage and looking hot, I fucked the tightest hole I've ever fucked. It just happened to belong to a 14 year old boy dressed as a girl.