So, I’m seriously shook up about this. About 6 months ago I was involved with an older guy. He was about 10 years older than my 24 year-old self. It was purely sexual, not really a relationship.
One night I wanted him to come over, but he was having poker night with a few of his friends. I made a joke saying “I wish I could be the prize”, to which he didn’t respond and I quickly forgot about it.
The next time he came over he asked me point blank if I was serious about being a “prize”. I told him I was joking, but that it was always a fantasy of mine to be with multiple guys at once. A few hours later, we’re in bed and he brings it up again, joking that I would have 6X the fun if I came to poker night. The comment and the look he gave me really turned me on and I responded, “Okay, set it up, but only if you think you can handle watching me fuck your friends.” That made it real and for the next couple of hours we talked about how we would do it. Then we fucked again, and afterwards decided we were both sort of uncomfortable with it for different reasons. For me it was the size of the group. Six guys is a lot of fun to fantasize about, but in reality I think it might be too many. For him it was insecurity. I guess he was worried about me being more attracted to his friends.