50 Women Reveal The Raunchy Details Of Their Biggest Hookup Mistake Ever

18. The cat watching wasn’t the worst part, but it didn’t help

I went on one date with this guy and he was really, really boring. When we texted he was so interesting and had a ton to talk about, but when we met, we had no chemistry and our conversation didn’t flow at all. I figured I’d give him another chance cause he was still kinda cute and really considerate and very well educated, so he could tell me a lot of cool stuff about plants and stuff.

Second date’s at his apartment and I show up and conversation is just plain dead despite all my efforts to keep it afloat. He’s got a cat and I’m petting it for like two hours, which is entirely uncharacteristic of me. I’m allergic to cats and the feeling of hair freaks me the fuck out.

Eventually he’s like ‘can I kiss you?’ and I figure yeah sure whatever we’ll fuck and get this over with and then I’ll go home. Unfortunately he’s legit the worst kisser I’ve ever kissed. His mouth keeps going around my mouth, like he’s just trying to eat my lips or something. I’m just like what the fuck I’ll just kiss something that’s not his face, but his entire body is like, salty? Maybe he was nervous or something I dunno.

We eventually move to his bedroom and we’re fooling around and he’s fuckin doin his darnedest to finger me but he’s got no clue what he’s doing and I’m so uninterested at this point that I’m just like whatever I’ve just gotta fake it and then we’ll fuck and then I’m out of here. His cat comes in the open door during my performance and sits on the bed next to me and he does nothing about it. It watches us.

When he’s done that he gets up to get a condom. I’ve got really bad eyesight, but I’ve taken my glasses off because this dude does not know how to keep his face off them. He comes back with a condom on and I feel like I can see that something is weird about it, but I just figure I’m imagining things. I should note now that his penis is small. Like, exceptionally small. This isn’t a problem at all for me; it’s just relevant.

He’s on top of me and the cat’s still watching and he just keeps saying my name and honestly if it was anybody else it’d be super hot but no I’m just nauseated by it. He’s taking a while so I suggest we move positions; I’m getting on top and I go to guide him back into me and something is Wrong.

The condom is missing. It’s not on the bed and it’s not on his dick. There’s only one place it could possibly be. I have to tell him twelve times to leave before he actually leaves the room. He just keeps moving slightly further away with his hands over his face knowing what’s happened and completely powerless to fix it. The cat does not respond to my instructions.

I fish the condom out of my body and tell him I’m leaving cause it’s weird. He says ‘yeah, that’s happened before…’ and what was an uncomfortable and embarrassing mistake between us turned into an egregious offense.

I ended up texting another guy I was dating who lived nearby and telling him the story and he told me to come over and I screamed a bit, cleaned up, and had a pretty nice time with the rest of my evening.

Later on I wrote the guy a long text saying pretty much ‘it’s not a problem that you need smaller condoms; it’s a problem that you use the wrong size and didn’t learn the first goddamn time. Also you need to practice kissing and I’m blocking you.’

— WooglyOogly

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