Chance Meeting

When traveling for business I often arrive the night before a meeting, I like to unwind and browse the personals. I have a thing for young crossdressers and one particular post got my attention. I emailed the contact and awaited a reply. I was getting hard imagining a young man in a wig, dress, and makeup sucking my dick when my email pinged. We clicked after two exchanges, he said he was in his mid twenties, slight build, and very submissive. I sent him my hotel room location.

He arrived undressed about a half hour later, a handsome young guy and he excused himself to change in the bathroom. A little while later I was sipping some bourbon when the door opened and he, now she, stepped into the room and twirled for me. Absolutely amazing transformation and my cock responded accordingly. She said her name was Josie and after some uninspired head I pulled her up off her knees and had she get on all fours on the bed. I get a mental rush and virile sense of power each time I penetrate a crossdresser's ass. The sensation and overwhelming lust as I pound that ass is such a turn-on for me. He-She told me i was only his third fuck and the first to bareback him. That did it, that sent me over the edge and I drained my balls deep in his ass.

He-She didn't hang around long saying something about a meeting the next morning.

I got up early the next morning and hit the gym. I got hard in my shorts reliving the events of the previous night. I grabbed a towel and covered up going back to my room. I was running a little late so I skipped the masturbation session, got dressed and went to my appointment .

The owner Joe greeted me and led me back into the offices. I met a bunch of people in his organization. His son was going to present this morning so we met him last. He introduced him as Joe Junior, he stood from his desk and smiled warmly and offered me his hand that went limp in my grasp. "Some people call me Josie"...