My first Shemale

“Not bad,” she said as she took her first sip of the martini and I again inhaled her perfume. “It’s the money. You can make a lot but have to travel a lot to do it–more than I’d like to.”

We fell into easy conversation and discovered we both lived in Key West. “No kidding?” she said, interested in what part I lived in. I told her and found out she lived a ten minute drive from me. We wondered if we’d ever passed each other.

Two more drinks and our tongues were loosened, and to my surprise my cock behaved itself. As for Jamie, she wasn’t dumb; she caught me taking in her breasts, manicured nails, makeup, false eyelashes, everything. I’m sure she knew she had me on the line and maybe all she needed to do was reel me in.

I was still trying to puzzle out whether she was the real deal, a female. In spite of the absence of facial hair and no sign of an Adam’s apple everything said she wasn’t female. She broke into my thoughts. “You’re looking at me like a horse at an auction.”

Caught! I tried to recover but only managed to look embarrassed. I blame it on the drink but before I knew it I said, “Can I ask you a question?” She arched an eyebrow and moved over the table to peer into my face. “And that is. . .?”

“I hope you won’t feel offended,” I said and dropped my voice, “but are you, you know, what do they call it–transgendered?” She took the question in stride, giggled, put her small fingers over my hand and said, “How diplomatic of you to say it like that. Why: do you have something against ‘transgendered'”?

“No, not at all,” I replied, maybe too fast. “Besides, as they say, ‘different strokes.'” She licked her red lips and seductively said, “Would you like to be stroked?”

I had no time to answer because the PA system came on again and announced that our flight was cancelled. We were told we’d be on a flight in the morning. Everyone was given a room for the night at a nearby hotel. I had no further time to engage Jamie as the next half hour was taken up with getting our restaurant vouchers and new boarding passes for the following morning. As a result I was on a different bus when we arrived at the hotel.