My Shitty Hookups #1: Buddy and Adam

My life is filled with good sex, bad sex, and moments where I lose my sanity. Here are some of the most awkward moments in my sex life.

I decided that it's time to air some horror stories from my absolutely appalling dating life. Why? Well, because they make good stories, because I'm burnt out from trying to find love conventionally, and because honestly, I think we've all been in shitty hookups before. 

My dating life has helped me develop a drinking problem. In this series, you'll understand why I have a drinking problem — and why everyone has been telling me to discuss my dating life. 

So, we're going to talk about a guy we're going to call Adam, for the sake of his dignity and this series. Adam had a crush on me for several years, to be precise. Adam, at this point, lived directly underneath Buddy. 

This will come in very valuable today, and in the rest of the series, because Adam is a recurring person in my life. We're friends now, but there was a while where it was just not happening. 

Back when I didn't know Adam had a crush on me, I met his roommate, a guy we're going to call Buddy. This story is about Buddy, and what happened on our first date together. 

The Stage for Disaster is Set

I had recently been dumped by my long-time partner, and asked out Adam for a quick rebound one-night stand. Adam accepted, but never really gave me a day to meet with him. After a month or so of trying to hook up with him to no avail, I gave up and decided that he's not interested. Normal enough, right? 

Well, Buddy, one of his ten-ish roommates, decided to confess that he's had a crush on me. By confessing, I mean that a conversation that went like this happened...

Me: Hi. My friends told me to come here and talk to you about something?
Buddy: Yep. 
Me: Yes. 
Buddy: You have a large ass. I like your feet. 
Me: Yes. 
Buddy: Turn around so I can grab your ass. (I turn around.) Can I grab your ass? 
Me: Yes. 
Buddy: Mmkay, now I'm going to masturbate to your ass later on. That was nice. 
Me: Yes. Can I go now? 
Buddy: Oh, I see, I must have been a bit creepy about that. Well, I see that now, I'm sorry. You're like, "Okay, I'm creeped out and Imma go, Buddy." 
Me: Yes. (Leaves.)

Yes, drugs may have been involved. Don't judge me. 

I Wanted to Hook Up

That being said, I asked him if he was down to hook up and help chase away the blues. Buddy, who lived in the room on top of Adam's, agreed.

We had a wonderful date, and he even bought me my favorite violet mints for us to share. He's a legitimately fun, wonderful date when he's on his best (non-party) behavior. 

We then headed upstairs to his room, all the while Buddy was sneaking me in with a hushed voice. I, being an idiot, didn't think Adam would mind. Heck, I didn't think he was even there. All's fair, right? I already gave him the option to hook up...

So, I might've been a bit louder getting up the stairs. 

Then we had sex. 

Loud sex. For at least an hour or so.

Surprise...

Buddy and I had pretty explosive orgasms, and yes, we were loud about it. We kept going on and on, until I heard sniffling and rustling outside the door. 

"Buddy, what's that?" 

"Oh, that's Adam."

Record scratch. Adam was here? Below us? The entire time?  

Well, shit. 

On one hand, I realized that this was not my fault. I had already told Adam that I was assuming he wasn't interested, and I'd been barking up that tree for a while without any success. 

I also just then realized how bad this looked — and really, if I were honest, was. Adam and Buddy were both sweet guys, both of which I found extremely attractive. And, right now, I looked like either a total skank or the psycho stalker who has sex with a roommate of the person they like. 

This was not my proudest moment. This is one of many, many moments where my trainwreck of a dating career careens off the tracks via a shitty hookup and maybe one too many joints in my system. It is also one of many moments that has turned my mind into an unglued mess. 

Due to the sheer level of awkward, Buddy and I broke up a week later. Adam switched rooms with Buddy, too. 

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My Shitty Hookups #1: Buddy and Adam