My asshole is so sore at the moment, that's because out with a friend I lost a bet. The bet involved the winner taking a good looking woman back to the hotel rooms we'd booked. The loser had to entertain her friend. I lost the pool game and my friend really enjoyed himself fucking the good looking woman. What I didn't tell my friend the next morning, was I'd had the sexual experience of my life.
You see the person I took back to my room was dressed as a woman, looked like a woman and had real tits like a woman. But she/he also had a cock. If it wasn't for the drink I genuinely would have said no, but I had been drinking and I allowed the transexual called Karen to suck my cock. Then because I'd gotten so turned on, wearing a condom, I fucked Karen. Busting my nut up her tight sweet ass filling the condom, should have had my cock going soft, if anything my dick got harder. (Later I found out I'd been given a cock boost). Still extremely horny I wanted to fuck Karen again, but she had other ideas. Sucking my cock at first, she moved around to my asshole and then began to tongue it. It felt awesome as she stuck her tongue up my butt, but felt even better when she slipped a finger in there. Telling me she going to fuck me, I just said "Yeah baby".
Rolling a condom down her cock, and finally taking off her bra, Karen put her cock to my asshole and pushed in. Not anything I'd ever been through got me ready for the pain, but it wasn't a pain that had me telling her to stop. It was different and I found myself asking her to fuck me deeper. I don't know how long Karen fucked me for, but we did change into three different positions. Firstly I was on my back, then I was knelt up as she fucked me from behind and finally I was on my left side aas Karen fucked me, spooning me and wanking my cock at the same time. I came first all over the duvet and then as Karen built up speed I heard her telling me she loved my ass. Moments later she came in a long shuddering orgasm.
We all met again over breakfast, and just as I'd asked Karen told them I'd fallen asleep before anything could happen. That night isn't why my asshole is sore right now though. No it's sore because over the past two months karen and I have been meeting up to have sex at a motel close to where I live with my fiancee. Only two hours ago, she fucked me for over an hour and had my asshole leaking with her cum dripping from it. It might be sore just now, but I can assure you, the next time we meet (Saturday afternoon) I'll want more of the same.