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23 Awkward Sexual Encounters That Will Make You Cringe

Oof. Sex can be awkward AF, y’all. And I’m not just talking about a little uncomfortable silence or accidentally passing gas while he does you from behind kind of awkward. I’m talking — dude is wasted and can’t find a bigger gal’s vagina so he ends up fingering her belly button for 20 minutes kind of awkward. Whoopsy daisy.

When genitals get a little slippery, and lovers get a little tipsy, sh*t is bound to go down to Awkward Town. So get your seat belts and condoms on because those wonderful awkward moments are an inevitable part of life. It doesn’t matter if you can’t find the right hole, what really matters is how you handle yourself after the fact.

I say, F*CK IT! Embrace the awkward and show your partner that you don’t have a big stick up your a** (I mean, unless that’s what you’re into) and that you can go with the flow even if he just sneezed in your vajayjay.

These are some of the most awkward and cringeworthy sexcapades from across the web:


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Written by Laura McNairy

Laura is a freelance writer for TFLN. She likes to write about what she knows best — dating, sex, and being awkward, but usually in the opposite order. She is the Assistant Editor and videographer for Peach Fuzz, a sex-positive nudie magazine in ATX.