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Storytime: Awkward Hookups

I have had plenty of awkward sex with boyfriends and my current SO, but there is something extra weird when it's a new or one-off hookup.

As much as I wanted to be a sleeper-arounder, I had some limited experience there, up until The Final Trampage before I met my soon-to-be husband, where I went a little berserk on the OKCupid. So what you are about to read here pretty much represented my "hookup culture" experience for a while.


You want to put what where?

There's not any background to this story. I met a guy in a bar, we went home.

At his apartment, we start making out in his bed and stripping down a bit. I was down to my undies and bra, and suddenly he is jamming his fingers into my belly button. Two fingers. I thought, wait a second, is this guy wasted? He doesn't seem wasted! That's not my vagina!


No, not wasted. Just confused. I tried to guide his hand down, and he just said, "No, no, you'll like this. This will blow your mind." And blow my mind, it did. But not how he thought it would. I could have just stopped the whole thing, but I thought maybe he would get it together. He didn't stop. He kept talking dirty: "oh you like that, oh yeah, does that feel good?" I decided the only way to end this was to fake an orgasm. Thus, because of my fake orgasm, he probably went on to do that to more women.

And that's how someone fingered my belly button.

(looking back, I realize there's a consent/boundaries issue here, because I did say no...)


Love Rollercoaster


This one's my fault, and I still hate myself about it.

I had been totally into a friend of a friend for months. I was visiting the friend, and he hosted a party where Hot Friend came. The magic happened, and oh was it magical.


Right after we finished making sweet beautiful sex at each other, I blurted out, "I love you!" Then I just burst into tears.


I escaped back to my friend's apartment. The next day, we went to an amusement park and Hot Friend was there. And I had to spend an entire day with him after this, with him in the cold light of day and all my Feelings. We didn't even make eye contact that day, we haven't spoken since, and me and that friend lost touch. I'm assuming Hot Friend told him about this, and he rightfully assumed I might be too much of a weirdo.


Give me your awkwardest, GT!

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