My first time. AKA How I lost my virginity to a couple. [MFM]

This happened recently, last week actually, so I’ll do my best to describe in detail what happened in an entertaining way. I’ll do my best to not exaggerate but I cannot promise 100 percent the truth. It exists out there, but it’s a combination of all of our stories, not just my own, and I can’t claim to represent it.

Not too long ago, as a horny 20 year old college virgin, I discovered this wonderful, or terrible depending on your experience and/or view of such things, website called Doublelist. It essentially is an alternative to what Craigslist used to be (or at least that is what the risky online sites told me). It was on this very site, Doublelist, that I saw an ad while looking through the couple’s section that asked for a “young stud” for that evening. Being in a particularly horny mood and feeling reckless, I emailed them through an “alt” email I had previously set up with a simple description of myself and an enclosed pic of my bare chest. To my surprise, I received an email back almost immediately from the wife who had posted the ad. She told me that she enjoyed my pic and asked if I had a Kik. I responded back with my username, and soon we were texting back and forth. After a little bit, in which I had learned their names, Penny (39) and Matt (42), and had traded some pictures back and forth, Penny decided that I seemed nice enough online and decided to invite me over to their house.

[MF] How My Girlfriend Breaking Up With Me Led To My Teacher

First and foremost, before moving on, I would like to point out that this is fiction. It is not based on real life. No rules were broken, no taboos explored, no lines crossed, however much it may be a dream of many of us out there. Now, without further ado …

At the time I suppose, I was naive and moronic, not to say that I’m still not those things, but I was most certainly at that point very much so. She and I, my girlfriend I mean, had been dating since Homecoming. We were both on the cross country team, although she was an actual star while I was just average. Our relationship started as most relationships in high school did.

“Hey, uuuuuuuh … God, this is hard to say. Um, are you going with anyone to the Homecoming Dance?”

“Mmm,” Carol paused at this, she looked to me as though she were thinking about how to start a paper. (By the way, her name was Carol, still is, whatever) “Nope.”

“So umm, would you like to go with me?”

“Umm, sure.”