Yahoo chat rooms were amazing, especially when I traveled for work. This time happened in New Jersey. Mid week, I was back in my hotel after work, I got on my computer snd trolled the local chat rooms. I met a lady, we hit it off, we chatted, flirted a little and then got into sexual conversations. The anonymity that came with the internet really let your freak flag fly.
We chatted a couple days, webcammed, shared pics, and talked, it eventually turned sexual and I asked her “what’s one thing you’ve always wanted to do, that your boyfriend won’t?” She said she always wanted to peg a guy but never had anyone willing, well I quickly said, I was always willing to try something once (can’t knock it unless you try it).
So I suggested she meet me at my hotel bar, I was in an embassy suites so it wasn’t a prince of shit hotel and other people would be there. She agrees, the next day at work I was completely distracted, I get off work go back to the hotel, get ready and head downstairs at 7, we’re supposed to meet at 7:30…7:45p rolls around and I’m thinking I’m getting stood up, not unexpected, it was an internet meet. I ask for the check and she walks into the hotel bar, I recognize her from her pictures, I call her over. We get a drink and talk and I suggest we go upstairs.