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12 Awkward, Hilarious Sex Fails That ACTUALLY Happened

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Aug 11,   12 Awkward, Hilarious Sex Fails That ACTUALLY Happened. Get ready to cringe-and then feel way better about your sex life. and I fell right off the bed-naked onto his floor. I Author: Casey Gueren.

Dude try to ack like big porn performer but totally fail with Wendy Moon. One of the worst fails in the history, funny moments.

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But when he got up, I could see that his condom wasn't there! Sex immediately stopped and we embarked on a search-and-rescue mission for the lost condom.

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After about 30 minutes, I went into the bathroom and went deep-sea diving, only to find that the condom had been smashed into a mangled ball against my cervix. This happened twice.

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Apparently I have a black hole of a vagina. It was dark, and we went to change positions when I accidentally hit him in the face, and he got a bloody nose.

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He turned on the lights and it was all over my chest and the sheets! It was definitely a mood killer. When it fell on me during sex, it left a golf ball-sized knot on the side of my head.

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The blow knocked me out for a few seconds and scared my husband to death. After finishing our 'activities' we realized I had bled quite a bit while having sex and was not on my period and was embarrassing to begin with. Of course the perfectly white duvet and sheets were a mess!

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We had to strip the whole bed and write a note to housekeeping requesting them to be cleaned since it was only the first day, they normally just make the bed and clean up.

Needless to say, we left an extra big tip for our maid.

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We obviously had to stop, and it was actually so bad that I needed to get ice. When we got there we started making out and we were just about to start having sex when he stopped and pulled away. He said very seriously"I have to play for you. We actually did end up having sex after that, but I could barely keep from laughing the entire time and obviously didn't climax.

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I told him he could come over anyway just to hang though. I didn't fully trust myself to not give in, so I put on my hugest pair of granny panties aka my chastity belt. To be clear: These babies went all the up my stomach, practically to right under my boobs, and also had lace.

Why the least sexy pair of underwear was garnished with lace trim, I will never know.

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Well, my chastity plan didn't really work, because he came over, we started making out, and before I knew it, he was feeling me up He was like, 'Anne, WTF are you wearing?! And more importantly, is this what you always wear when you are alone in your apartment?

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Don't try 'em at home. One thing led to another, and we started having sex with him behind me.

He was thrusting forward, and I was thrusting backward, and suddenly we heard a pop that brought him to his knees. We immediately iced his member, but the swelling didn't go down.

I dropped him off at the ER while I parked-I was too embarrassed to go in with him because I knew everyone would look at me.

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The doctors told us he had torn the ligament of his member but fortunately didn't need surgery; it healed on its own.

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