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Sleeping With Your Friend’s Girlfriend In Front Of Him: A Cautionary Tale

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I had sex with my fraternity brother’s girlfriend, and he watched me do it.

Maybe this story needs a bit of context.

It was our fraternity’s spring formal, and no one’s livers were prepared. The weekend long trip was in Lake Havasu, which is roughly four hours from Phoenix and known as a prime spring break location. Unfortunately, I wasn’t in the most positive mood considering several potential dates backed out of the three-day commitment. Because of this, I decided to take my ex-girlfriend who I had just recently broken up with. I figured if I am going to take a girl to formal, I must as well make it a guarantee that I was getting laid, (shout out to the 0/100% rule which is a philosophy to live by).

We arrive in Havasu and immediately everyone was in their worst physical, mental, and emotional states. Afternoon drinking, jet skiing and boating is always a blast, but there was something missing. Formal is supposed to be a great time to take a new woman to join your fraternity debauchery. Taking a girl that you’ve already had sex with hundreds of times kind of ruins the thrill of the chase, and yeah the sex was still great but I’ve been there and done that. In response, I came up with a brilliant goal to accomplish for the weekend.

I was going to have a sexual experience with another brother.

Okay shit. That didn’t come off so well, either.

The goal was to have a threesome, foursome, orgy, or anything similar happen in some way, shape or form. I had never even been in the same room as another person or couple when fucking, and god dammit I needed a crazy formal story to bring home with me. Luckily, one of my brothers, let’s call him “Steve,” explained that his girlfriend, “Jill,” had wanted to hook up with another couple for quite a while. Although I had doubts that this would ever actually happen, I still maintained a little bit of hope.

On the second night, after a long day of drinking a toxic amount of cheap cherry flavored Fleischmann’s, we met with Steve and Jill and decided this was going to happen. Let’s go ahead and a paint a picture here: The four of us are sitting in a hotel room, drink in hand, and talking about quite literally anything but sex. Suddenly, Steve took initiative.

See, Steve was known for wearing a sailor’s hat at every official event our chapter had. Naturally he put on the cap and decided that he “was the the captain now.” Therefore, whoever wore the hat decided what would happen next. Steve pointed at the two girls and commanded that they start making out. They proceeded to do so, and Steve looked at me with the biggest grin on his face. Then all of a sudden, my date grabbed the hat and made her own list of demands. She demanded that everyone started getting naked. And we did.

The rest of the experience went as you would expect a group sexual encounter to go. All you need to know is that at several points, Steve and I would trade girls. Sometimes, one of us would even have two girls simultaneously while the other was completely cucked. Although this sounds bad on paper, the really comical part of the story is that Steve drank way too much. As a result, he had a severe case of whiskey dick, and because of this I would have both girls hooking up with me while Steve desperately tried to get some adequate blood flow. His girlfriend sucked him off for at least an hour and a half just trying to keep it up. Based on how sore her jaw was the next morning, she couldn’t have been happy about that. Overall though, it was an insane night that will be told in fraternity banter, and through the words of the maid that had to clean up that petri dish of unprotected sex.

So you’re probably thinking to yourself, “this guy is lying. He just wants to tell the world that he had a foursome so he can show off.” That is not my purpose for telling this story.

First off, if I was lying, I would just go ahead and say that I had a threesome and no other guy was involved. If I wanted to show off, I would go into much more intricate details of how the sex went down. To be honest, those kind of stories have been told before through graphic categorical clips on Brazzers, so I’ll leave that to the professionals.

This isn’t a story to brag about; this is a cautionary tale.

See, what people forget about having a multiple partner sexual experience with a fraternity brother and his girlfriend is that you still have to see each other afterwards. Many times. What made this especially awkward is that to this day, Steve and Jill are still dating. Now every time I see Steve, Jill, or the two together at a bar or at a party, all I can think to myself is: “I’ve been inside your girlfriend in front of you.” As hilarious as that sounds when you say it out loud, getting the death stare from a surprisingly intimidating sorority girl every time you see her on campus isn’t so pleasant.

What used to be a close bond between Steve and I quickly subsided into a more distant relationship, and we never really were the same. My advice would be not to have group sex with a couple that have been together for a long time. However, if everyone is single and just looking for a fun time, absolutely go for it. Being Eskimo brothers with a fellow fraternity member is a close knit bond that cannot be broken, but sometimes it isn’t the best idea to go through with it.

Maybe they will break up and we can laugh about this story over drinks someday, but until then, there will be more tension between us than Tom Hanks had with that Somali Pirate. I’m the captain now, and the captain would prefer that Steve doesn’t join in next time.

Image via Shutterstock

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