People Share Their Most Horrible and Hilarious Sexual Mistakes

Trying to Forget

Mistakes happen. No matter who you are, you’re bound to make some pretty big mistakes at some point in your life. Unfortunately for these people, the mistakes happened in bed. You’re getting it on with your “new boo,” but, all of a sudden, everything goes south; you make a boneheaded mistake that has you cringing just thinking about it. Check out these Reddit users sharing the worst bedroom experiences they’ve ever been a part of.

Whoops!

It was dark and I put her nipple in my mouth. She asks me what I’m doing after a bit. Turns out it was a sideboob mole. (AdditivePackage)

Starfish

I never thought ‘Starfishing’ was real until I experienced it. She just laid there, and did nothing. Imagine someone laying like a starfish, and thats exactly what happened. There was not much room to do anything. I tried to make it work and to suggest some things here and there, but nothing changed, worst one night stand ever.
I then tried to help her to completion, but nope, like a furby with dead batteries. All the buttons pressed but nothing else than a cold dead stare in return. (Stotakoya)

Too Confident

This one gal bragged about her amazing blowjob skills for weeks. We get together for the first time and it’s all teeth, dry sandpaper mouth, and she’s just going at it really fast with no buildup and barely any warning, just hyperspeed. It felt like my d**k was caught in a toothy fingertrap.
I suggest I go down on her instead and she gets excited. The minute she leans back the entire room smells awful, but I don’t notice until my face is closer that she, apparently, hasn’t changed her tampon in quite awhile. Things are bloody and clotted. As disgusted as I was, my first thought was “did…she not know I was coming over today?!? no wait she invited me whattheF**K” (WhoaMilkerson)

…What?

Dated a guy once who, for reasons unbeknownst to me, did not have the head of his penis.

I didn’t find this out til the first time we had sex. I still insist that I deserve an Oscar or something for managing to hide my shock. (BirthdayCookie)

Gagging

I fooled around with my first girlfriend when I was 14
she had a yeast infection since I had no idea what a vagina was supposed to smell or taste like I went with it
after I fingered her I had to go home & wash my fingers with soap & lemon juice to get the smell off. It lingered there for over a day if I didn’t.
the first time I went down on her was awful. I literally came up gagging & doing that sour facial expression. it was so nasty
after we broke up she had a STD check & found out then. she explained it to me (pauljohn408)

“That’s why we have the paper!”

One time I got a prostate check. The doctor stuck her fingers in my butt and I ejaculated instantly on the table. She laughed and said,” Thats why we have the paper!” I was so embarrassed. (Messaloia96)

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Original by Emily Hingle