I was at a trans friendly bar last night, actually didn't know that's what it was as I'm not from this city. It was early, I had time and nothing to do, so I just stopped by a little side street bar to get a couple of drinks. I noticed a young "girl" in the back sitting at a table. I bought her a drink and she and I sat together, out of hearing range of the 2 people I suspected were post op trannies as women behind the bar. I realized what the place was and what this girl was, even though with the makeup, lipstick, and what I found out was naturally long hair, HE was very pretty. Tiny tits, in a blue dress, great legs though. After a couple of drinks, I asked how close his apartment was, though I referred to her as feminine. She was only 3 blocks away, and with it now just dark outside, I took her out for a walk to her place. My arm around her waist, hers around mine, and my hand deliberately and embarrassingly sliding down to her ass for a good squeeze now and then.

When we got to her place, I took her to the dark bedroom, reached under her dress, and pulled her panties down, leaving them on one ankle. I took off my pants and shirt, and bent her over rubbing my hard cock in the crack of her ass. She handed me lube and I spun her around laying her on her back with her legs up over my shoulders, I continued to rub my cock on her thighs as I lubed by cocks new home in her ass. Then I laid on top of her, made her wrap her legs around my waist and kissed her and I pushed into her jelly-like ass cheeks. There was a slight gasp, the same kind a woman makes when you push your cock into her all of a sudden. Then I fucked her until I splashed my cum all over her insides. I pulled out, looked at that gaping ass, and that 6" of flaccid cock she had, and told her I hoped I'd see her again sometime and left.