The Most Embarrassing Person You've Ever Had Sex With


In a life full of sexual misadventures, not everyone you choose to have sex with is going to be a total winner. In some cases, your sexual partner might even be a complete embarrassment who you can’t even tell your friends about, but you go through with it anyway because they’re hot, you’re horny or, hey, maybe there’s just nothing better to do. And now it’s time for you to confess.

But first, the winners of last week’s Pissing Contest, where you divulged your most stupidly acquired injuries.

Betty shooting birds gets an honorable mention for her story, which I enjoyed for its sheer simple stupidity:

Bloody nose and lip pulling up my own bra strap. My hand slipped and I punched myself.

Gnomi Malone also kept it painful and simple:

Dislocated my jaw by yawning.
I yawned my face off.

But the hands-down winner is nadaforgretchenwieners, whose afternoon went very quickly from awesome (pizza!) to nightmarish (having to poor milk into your own junk):

Well, my now husband and were having pizza one afternoon. After we were done eating, one thing lead to another and I starting giving him a good ol BJ. I was horny, so was he, so I got on top and started riding away, enjoying ourselves. Then I felt a slight burning sensation. I was like, oh whatever, it’ll go away. But it didn’t, it got worse and worse. I said “Uh, I’m starting to burn” and apparently he was burning too. I climbed off of him, and oh dear lord,the gates of hell opened up on my vagina. The burning intensified to the point where I almost started crying. We run into the restroom, and he tells me to hold on. He ran and got milk. There we were, ass naked in the tub. He’s standing and me laying on my back and he’s pouring milk on his dick and all over my vagina. The sweet sweet relief !!
That’ll teach me to not eat pizza with peppers in it THEN give a blow job.

Congrats to the winners, who will soon be relocated into Jezebel’s victory village.

And now let’s spill the dirt. Who is the most humiliating sexual partner? Dean of admissions at a clown college? A fedora wearer at a nightclub whose name you can’t remember? John Mayer? SPILL.

Image via Universal.

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