Straight Male / 51
Crossdresser Fuck
A few years ago, talking on Whisper, i got into a long conversation with a guy in his early twenties who had a crossdresser fantasy. He wanted to dress as a woman, wait in a hotel room, for an older man who comes in, lifts his skirt and fucks him cumming inside him.
He had taken steps. He was totally smooth having no body hair, he had a wig and with make-up he looked like a thin girl. He sent me a bunch of pictures in which he looked pretty hot.
Then he asked me if i would fuck him, help him live out his fantasy and he was hot, I said yes. We made plans and the day before I popped a Cialis knowing I'd be able to get and stay hard forever and I met him the next day. My dick was hard and throbbing all day. He was waiting at a shithole motel.
I walked in, he was on the bed, on all fours, butt up wearing a skirt. He looked hot as fuck from behind. I walked over, lifted the skirt, he was naked underneath, his asshole smooth and waiting. There was a bottle of lube on the bed, I used it on my hard dick and his hole, then made myself rock hard, and pressed my head against his hole. He'd never been fucked. he went instantly ridged as I pushed against his yielding asshole. I pushed firmly, slowly spreading his hole, he was re-adjusting trying to make it more comfortable but I was ready, I grabbed his hip and forced my cock in hard. I felt his hole give way and I slid in then pushed all the way in balls deep.
After some slow fucking I pounded his ass. I long fucked him. I was glad I'd taken a pill as I was surprised that there wasn't much friction except right at the hole itself. I figured it would be like fucking a sleeve but not really I could just fuck him hard but to really feel good I had to fuck the hole with my cock head which is what I did when I wanted to cum. I used his hole to get to the edge then slammed it deep when I came.
After I pulled out, he rolled onto his back panting and happy. And he was so pretty he really was hot all made up. I cleaned up, re-joined him and he started playing with my dick. He got me hard again with his mouth and he slid right down my dick and rode me while stroking himself. I shot my load in his ass, he sprayed cum on my stomach.
A quick showed and off I went. We never spoke again but I'd fuck another crossdresser if they looked as hot as he did without question.
He had taken steps. He was totally smooth having no body hair, he had a wig and with make-up he looked like a thin girl. He sent me a bunch of pictures in which he looked pretty hot.
Then he asked me if i would fuck him, help him live out his fantasy and he was hot, I said yes. We made plans and the day before I popped a Cialis knowing I'd be able to get and stay hard forever and I met him the next day. My dick was hard and throbbing all day. He was waiting at a shithole motel.
I walked in, he was on the bed, on all fours, butt up wearing a skirt. He looked hot as fuck from behind. I walked over, lifted the skirt, he was naked underneath, his asshole smooth and waiting. There was a bottle of lube on the bed, I used it on my hard dick and his hole, then made myself rock hard, and pressed my head against his hole. He'd never been fucked. he went instantly ridged as I pushed against his yielding asshole. I pushed firmly, slowly spreading his hole, he was re-adjusting trying to make it more comfortable but I was ready, I grabbed his hip and forced my cock in hard. I felt his hole give way and I slid in then pushed all the way in balls deep.
After some slow fucking I pounded his ass. I long fucked him. I was glad I'd taken a pill as I was surprised that there wasn't much friction except right at the hole itself. I figured it would be like fucking a sleeve but not really I could just fuck him hard but to really feel good I had to fuck the hole with my cock head which is what I did when I wanted to cum. I used his hole to get to the edge then slammed it deep when I came.
After I pulled out, he rolled onto his back panting and happy. And he was so pretty he really was hot all made up. I cleaned up, re-joined him and he started playing with my dick. He got me hard again with his mouth and he slid right down my dick and rode me while stroking himself. I shot my load in his ass, he sprayed cum on my stomach.
A quick showed and off I went. We never spoke again but I'd fuck another crossdresser if they looked as hot as he did without question.
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