This is less a gone wrong moment then a "gone how the hell did that happen" moment.
Mary is on a business trip to a trade show, can't remember what city, her boss sends here and the team there a few days early, let them have a chance to relax, go over last minute details, see a few sights on the city. Anyways 2nd night, still another day before convention but things at hotel are picking up. Guys on the team decide to go to a ball game, probably a strip club after. Mary and the other woman on the team.pass. other woman decided to spend quiet night in her hotel room. Mary heads down to try and grab a bite to eat, both restaurants are packed, long wait time, she does not want to eat in her room, checks out the bar, gets a seat at the bar, finds out you can order from either restaurant at the bar. Perfect. Crowded but at least she can eat outside of her room.
Seat next to her clears, guy sits next to her, they chat, why they are in town, she answered she thinks something along the lines of working at the trade show, which might have come out as "working the trade show". Guy is nice, good looking, funny, yeah she is game to hook up with him. So when he invites her to his room, she counters with going to hers. Safety thing.
They go back, bringing some drinks from the bar. She changes into a little lacy sexy nightie. Things progress, he gets her on her knees in front of where he is sitting. She gives him a blow job, eventually ignoring his several mentions of being close to cumming...she swallows.
They finish their drinks, he gets her on the bed, playing with her. They are ready to go and he asks about condoms, she says if he wants one she has some in the top dresser drawer, but she is fine if he doesn't. He doesn't get one, they fuck, he fucks her well.
After a little resting, she goes to the bathroom, devides to shower quick. Tells him he can let himself out (polite way of saying she is done , leave now). She comes out of bathroom he is gone, he has left a note just says Thank you and has left $500.00...
Yeah he thought she was a hooker. She was mad, embarrassed, and thought it was funny all at the same time