I was on a business trip out of town a few months back, and found myself bored, lonely, and horny sitting in my hotel room. I began searching through Craigslist, and ended up posting a fairly innocuous ad looking for a female in the area. I was pretty vague, but honest, and really said I was looking for a dinner or drinks companion more than anything else.
About half an hour later, I got a response from a woman not too far away. Her name was Carrie, and she described herself as mid 30's, recently divorced, and would be up for meeting somewhere for dinner. We exchanged a few friendly emails, not ever really bringing up anything sexual, and she agreed to meet me in the restaurant in my hotel lobby. She was familiar with the area, had never eaten there, and had heard it was actually pretty good! We set up a time for later than evening. She sent me a photo so that I could recognize her, and I was reasonably happy with what I had seen: she looked to be average height, dark brown shoulder length hair, pretty brown eyes, and a great smile. She looked thin, with probably a B cup from her photo. I sent her a decent shot of me as well, and I showered, shaved, and cleaned up for the evening. I threw on a pair of charcoal dress pants and a dark button down, and headed to the lobby at the appropriate time.