Back in 2004 I was living in the upstairs part of a house by the beach in San Francisco.  My landlady lived downstairs and pretty much kept to herself. But I used to go partying in San Mateo at a friend's place and there were various people who would stop by there and all.  Well a few times I'd seen this guy and he was straight and we made a good connection, conversationally.  Well, one night we ended up leaving to hang out for a bit after our friends kicked us out for the night and so me and this guy were parked in my car and were talking.  He knew about my open sexuality and felt comfortable to let me know something he'd never told anyone.  He told me he liked to dress up like a woman and masturbate, but he'd always wanted to actually dress up like a woman and be fucked by a man for the first time.  Before that time, i'd never fucked a cross-dresser, but he was hot and the thought of fucking him, as a guy or as a woman got my cock hard as hell.  

 He asked me if I'd be interested in having him dress up for me and have a good time.  I said "Sure" and we made plans for the next night for him to come over to my place and he'd bring his bag of clothes, wig, makeup, heels, etc.  And he showed up as planned the next night at around 10pm after I knew the lady I rented from would be asleep.  He and I talked for a bit and then he asked if I could wait outside on the back porch and have a smoke while he got ready in my bedroom.  I didn't mind and went outside for a smoke.  He took quite a while getting ready, nearly an hour, but I was patient.  

 Finally, he came outside but he was no longer "he".  He was "she", named "Vanessa", who looked hot in a mini-skirt and blouse, stockings and heels...wearing just the right amount of makeup and a long brunette wig and a pair of black stilettos.  I could see a black lace bra under the white blouse, too.  So, I treated Vanessa like a hot woman and took her head in my hand and started kissing her deep with my tongue.  She started rubbing my crotch and my cock got hard pretty fast.  Things got heated and then she unzipped my fly and pulled my cock out.  She then turned around and I lifted up her skirt to reveal black lace panties underneath.  I pulled them down, licked my fingers and started playing with her tight asshole, tickling and teasing it so I could feel it contracting and tightening.  After some of that, she said "Fuck me".  So, she guided my cock to her asshole and I spit on the head of my cock.  She then pushed back on my cock and I could feel the head of my cock penetrating her virgin asshole.  She started moaning and I covered her mouth out of fear my landlady would wake up. I started pushing my cock deeper and deeper and then working it in and out at a steady pace.  She was breathing heavily and I felt her asshole grip my cock over and over.  I pulled out and then led her inside into the bedroom.  Still clothed, I laid her back on my bed and held her legs up and started fucking her while I hovered over her.  I fucked her tight asshole and leaned forward to give her a wet tongue kiss.  I felt my cock swell even more at this point and she told me to cum in her ass.  I couldn't hold back any longer and I pushed deep inside her and felt my cock twitch inside her as my cum filled her asshole. 

 Things were a little awkward after and she became he again and he changed back to his guy clothes, went and washed off the makeup and took the wig off and then excused himself.  That was the last time I ever saw him or "Vanessa".  Still, I have no regrets and wouldn't mind experiencing this kind of thing again.