How I Gambled Away My Butt Stuff Virginity


In the game of life, there are some things that are just not worth gambling on. One of them, as I have come to learn, is anal.

Some back story. I had fallen in love with my best friend and it turned out I suckered him into liking me too. As it turns out, my best friend turned boyfriend and I had always been very honest with each other about what we wanted sexually both before and while we were dating. We both liked some weird shit (like candle wax level weird), but there was one thing that he wanted that I had sworn up and down I would never do. He always had his eyes set on the booty.

We were living in different cities over the summer, and he had come to visit me. His visits were usually filled with copious amounts of alcohol, mediocre non-anal sex and Chipotle. This visit was going to be a little bit different though, because he would be meeting my best friend and her boyfriend. I had no concerns that my best friend and boyfriend would get along great, but her boyfriend and my boyfriend was another story. My friend’s boyfriend is the type of person who your parents would want you to come home with — doesn’t drink even though he is twenty-one, doesn’t have sex before marriage. Just an all-around good guy. Much different than my butthole-seeking boyfriend. So naturally I was very worried about their meeting and was trying to prep my then boyfriend on how to act. When he suggested giving him some alcohol to loosen him up I made a horrible mistake.

I bet he wouldn’t be able to get her boyfriend to drink with him.

Mistake #1: Never underestimate a fraternity brother’s ability to make someone drink.

He smirked, and asked what I would be willing to bet and I being extremely overconfident in my ability to predict her GDI boyfriend’s actions said anything. I swear to God my boyfriend’s eyes lit up like a kid on Christmas. “Anything? Are you sure about that?” He prodded again, and I realized what he was implying.

Mistake #2: If someone gives you an out to a bet where they can do anything they want, especially to a part of your body that is strictly supposed to be an exit door, TAKE THE OUT.

“Anything.” I said confidently. This kid had been of legal drinking age for months and I had never seen him take a sip of beer. We shook on it and waited for them to arrive. When they knocked on the door I let them in, and the night was progressing as I expected it to. My boyfriend and I in a drunken heap with my friend’s boyfriend looking down with a hint of disgust and annoyance. I was fine with that, because that meant my B-card would not be getting swiped.

Mistake #3: If you decide to bet on someone’s actions, it is best not to tell them about said bet.

In my semi-drunken state I made some joke about how I was incredibly confident and was willing to bet my friend’s boyfriend not having a single sip of beer that night. Her boyfriend looked at my boyfriend, who confirmed what I said. He asked what was on the line, and I refused to tell him but texted my friend the peach emoji so she knew what was at stake.

Mistake #4: If you do decide to gamble with your anal virginity, I suggest making it clear that there cannot be any bribes involved.

My best friend got the text, and her reaction made it extremely clear that whatever was on the line was a big deal. My friend’s boyfriend then looked at mine and said, “How much would you give me to take a drink?” My boyfriend jumped to his feet and whipped out his wallet and offered him five bucks.

Mistake #5: If a bidding war begins over your anal virginity, flee to Mexico.

In a panic I ran to find my wallet, offering ten. My boyfriend offered fifteen. I offered twenty. This is the point when I started to cry. My best friend, realizing her boyfriend was unintentionally auctioning off my ass told him it was time to go and dragged him from the apartment before any money could be handed over. When they stepped outside I was incredibly relieved, and as I walked towards the door to lock It, my friend’s boyfriend pops his head in the door, grabs a beer, raises to my boyfriend, takes a huge swig and tells him to have a fun night.

In my drunken stupor I began to cry again, and locked myself in my room for a while.

Mistake #6: If he wants anal, find a new boyfriend.

Eventually I came back out, and ultimately fulfilled my end of the bet. However, that relationship much like my butt, would never be able to recover fully. The moral of this story is do not ever gamble away your anal virginity because you will lose both your anal virginity and your dignity.

Email this to a friend


Sophomore Alpha Phi Go blue and white

For More Photos and Videos

Latest podcasts

New Stories

Load More