The story of how I traded my virginity for a Play Station 3. [MFF]

I made the mistake of sharing this story with a friend who turned out to not be much of a friend at all. I can look back on it now and laugh, but at the time I was a much different person, and as you may have guessed, the story got out. It was incredibly humiliating, however, I know now its really not that big of a deal for a horny teenager. I am M.

15 pounds over weight, shy, kinky as hell, masturbating twice a day just would not cut it any longer, so to craigslist I turned. I was honest, "eager, young, shy, high school kid looking to loose his virginity." I was about as bold and honest with the title as I could be. The thought of being turned away at the door was unbearable, so I wanted to be sure everything was out on the table. 2 million selfies or so later I found one or two that were acceptable and the ad went live. I was positive someone would recognise me, but to be honest, I was so desperate I didn't think twice about it.

The story of how my newly kinky girlfriend sprung sex with a guy for the first time on me as I helplessly listened to Complicated by Avril Lavigne. [FMM]

This happened a week ago. I recent started dating my best friend of 3 years. I finally got the balls to ask her out and she agreed and its been going great since. There is a bit of a story there, but I will leave that for another time. She is pretty fucking kinky, as am I. We don't share a lot of fetishes, but we have always been happy to assist each other with them, even before we started dating. I have always told her that I wanted to try sex with a guy some day, and she always tried to get me to do it, but the stars just never aligned I suppose.

Fast forward to day one of our relationship as a couple. We know each other about as well as we are ever going to, so touchy subjects are not really a big deal to discuss. I have always told her that I would want a monogamous relationship if I ever "settled down" some day, and she was always the opposite, so this is clearly an issue. Before I asked her out I decided that there is no one I trust more, so I could get past the "open relationship" this as long as I was always involved, I told her that was a must, and she agreed on that.