7. Craigslist threesomes
“Am a bi male (that’s simplified but will do) in a hetero relationship with a straight girl for the last 3 years. Mostly on vacations, but sometimes locally we will use Craigslist to find a guy for a three-way.
I’d honestly say we are average looking, but usually get dozens to hundreds of responses, (80% or more are immediately discarded). We’ve had 2 what I would call successful one-night events, a couple of kinda awkward encounters, and one ongoing FWB that got a little weird at the end.
Cheaters do abound, and we won’t help someone cheat, that we know of. It’s actually kind of interesting how many people are upfront about it.
Occasionally we have posted an ad and just go “well, haven’t gotten anything in a hundred responses that sounds good” so we just go on our way and take it down.
We do get some of the kinda creepy “well, I’m not bi or gay, but I guess I can do guy on guy stuff so I can play with the girl.” That to me is pretty sad and desperate and not what we want.
So, long story short, usually works out, some hiccups, some meets that have started in public and end up with no connection, some last minute cancellations, but never had a no show.”
8. Lost my virginity on Craigslist
“Last summer I had just reached a point where I was in the best shape of my life, really had been working on my looks and appearance and I was about as tired as you can get about still being a virgin. I’d put some posts up on Craigslist a few times in the past but they weren’t very serious and didn’t have much on them so there’s no real surprise that I didn’t get any responses.
This time I was very straightforward on what I was looking for, had a good picture of myself and made it a point to refresh my ad every 3 days. After a couple refreshes I got a got a reply from a woman who basically said I was a fake and demanded we swap proof pictures. (She had a huge thing for redheads.) She was a very fit, mid-thirties but still had a really cute geeky kind of look to her. We met for coffee about a week after she messaged me and spent an hour talking about Game of Thrones and The Walking Dead since I’d mentioned it in my post on Craigslist (Put a favorite show in your subject line). If I was reading this I’d probably be like, “yeah that happened.” I got extremely lucky.
One thing I remember vividly was how there was this stuck up, snobby looking woman sitting with her husband in the cafe at the table next to us the entire time we were talking. The tables were situated so the woman I met had her back to the snobby old woman’s back, I thought for a second the snobby lady’s neck was literally going to snap the way she spun around to look at us when we finally talked for a little bit about sex and what our expectations were from each other.
I met up with her another week later at her place and the rest is history, people talk about how awkward their first time was but honestly it felt very natural and relaxed for me, no nerves at all. Her attitude towards sex and the whole situation made it really easy to just enjoy myself and focus on the experience. I’m not saying I was amazing in bed but she liked me enough to bring me back almost every weekend for the rest of the summer so I learned a lot, turns out I got a skill for giving head and that probably helped with the repeat invites. As far as first times go I honestly don’t think I could have asked for a better time or person to experience that with and I’m really grateful to her, we still text each other occasionally about Game of Thrones and The Walking Dead.”