Fully bisexual guy here, mature, strongly drawn to fem/shy/sub. I answered an add posted by a crossdresser. Unusually, we actually followed the convo through to a hookup. He came over in drab, a cute Indian guy, slender with delicate features and glasses. I invited him in and suggested he use the spare bedroom to change. He came out in lingerie & nylons and a really bad wig, but it was clear that he was very excited. I think I was his first actual encounter in girl mode. [EDIT: Just first time in a while.]

We sat on my couch and chatted while petting. He said his dream was to be a 50s housewife which was fine with me. His makeup was tasteful and made him look feminine despite the 5'oclock shadow and I thought he looked sexy as hell. Pretty soon my cock was in his mouth and he deep-throated my 7 inches without difficulty. Then I lay on top of him and ground for a bit. I was having fun when he pushed me off and started apologizing as he'd cum in his panties. I told him not to worry and got a towel to clean him up. Then I asked him if he wanted to fuck. He was thrilled to be asked. It took some effort but I got inside him and we fucked missionary for a while. We ended up trying different positions and I didn't cum but felt satisfied when I pulled out.

I ditched the condom and we cleaned up, then came back and this time I sucked him off. He had a cute uncut cock and came in my mouth, a small ejaculation but I loved it. Then he sucked me hard again and I put on another condom. This time I couldn't penetrate him so he had me lie on top of him face-to-face and tucked my cock between his thighs. After humping him that way I got hard again so I had him roll over and fucked him hard until I came.

We showered together and I gave him a ride to the train. Really hoping to see him again.