A Tale of One Head and Four Titties

By Mandy Assets

So this threesome started with a twosome. I can honestly say that I am one of the lucky few that had a beautiful and healthy friends-with-benefits relationship with one of my close guy friends. Now, the secret to having a functioning and successful friends-with-benefits relationship is to start as benefactors, then become friends. It is also key that you do something mildly unappealing in front of each other to fend off potential mushy feelings—like burp or blow your nose aggressively.

Anyways, after a late night romp with my “friend,” who we will refer to as Sid for storytelling purposes, we were ferociously attacking some spicy wings (see, mildly unappealing) and landed on the idea that we should have a threesome. Now, it can be tricky finding a third party—you can’t just go around a party asking people, right? Wrong. People in college seem to be quite open to the idea.

I left it up to Sid to find a willing, attractive girl to bounce around in bed with us. We were at a party and he was flirting with a cute blonde with huge boobs. I can’t say I really had a preference—I mean, the idea was to have sex with another woman, so I guess go big or go home, right? I digress, so from across the room I make eye contact with Sid, who not so inconspicuously mouths the word “Threesome” to me as he points at the girl. I shrug, nod, and grab a bag of wine. If this was going to happen I’d need it.

I began to chug as I watched them out of the corner of my eye. Suddenly as Sid pointed directly at me she spun around and yelled, “YA!” Well shit, that was easy. The in-between was blurry, and the blonde, who we will call Lily, seemed very excited to get down to business as we went upstairs to Sid’s room. I hid a few beers under the bed—just in case I began to sober up at any point during this adventure.

In hindsight, how this threesome was actually initiated is cringe worthy. We were jumping on Sid’s bed, we “fell,” then suddenly everyone was naked and making out. It was not graceful or sexy; in fact, if a pornographer were there, he probably wouldn’t have even bothered wasting his film. Once things started heating up, I realized how much machinery was actually involved in a threesome and began to feel slightly overwhelmed.

Sid began to penetrate Lily cowgirl style and frankly, I felt a little left out. After assessing the situation I decided that my best plan of attack was to awkwardly kneel next to them and smooch Lily. She must have been into it, because next thing I know I’m suddenly the horse and Lily is riding my imaginary saddle and fingering me.

Seeing as I had never found myself in this position before, literally and figuratively, I instinctively did what I thought a male in my position would do: grab her tig old bitties. She continued to grind against my pelvis for a little while longer, and Sid awkwardly lay next to us, trying to decide if he should participate or enjoy the show. He chose the latter, leaving me to my own devices with Lily.

Then I realized I was approaching the whole situation wrong—I shouldn't think about what a guy would do, I should think about what I would want a guy to do to me. So, I boldly began to rub her clit. Now, not to toot my own horn, but I think I did a really good job because she came in about ten minutes, or at least faked it like a champion—which I appreciated.

At this point I had really worked up an appetite, and decided I didn’t want to stick around in the morning. I figured there was a good chance that when she woke up and saw herself sandwiched between Sid and me, she might have a panic attack. So I said my goodbyes, which involved two smooches and a slap on the ass, and made the trek home. When I got back I made myself a quesadilla and watched It’s Always Sunny in Philadelphia in all my glory.

So what now? Well, Sid and I are still best friends. Lily has also casually entered our group of friends, which was far less awkward than one might think. Moral of the story? There isn’t one really—but good times. #college.