50 Cringeworthy Sex Stories That Will Make You Die Of Secondhand Embarrassment


I was doing missionary with my ex while in high school. We were in the gym and I was so turned on I pulled out and blasted in my own eye. I turned around because my girlfriend had this terrified look of embarrassment on her face only to stare into the angry face of her gym teacher while the spooge dripped down my eye onto my lip. Yeah that was a great day….


in college, I had the best kind of roommate situation: I shared a bathroom with one other guy, and we actually had separate rooms on either side of the bathroom. With that kind of privacy, I could have a lot of loud sex. And I did.

One night I was sitting on the edge of my bed, with my girlfriend straddling me. It was that great kind of loud, dirty talking sex, and I started to spank her as she rode me. She loved it and kept asking for more, so I spanked harder as we got more and more into it. We got a lot of energy going, and I was smacking her ass pretty damn hard… Until I spanked out of sync with her movement. My hand swung down as her ass moved up, and I ended up missing her entirely and smacking myself in the balls with full force.


So it was my 18th birthday. It was about 12:30am at my house, and my girlfriend of the time and I were laying on the couch watching a movie. My family had gone to bed earlier, and my girlfriend turns her head and says to me “I’m going to give you your birthday present now”. We start going at it on the couch, and everything’s going well. We’re in the spooning position, and there is a blanket covering us up from the waist down. Not too much motion at the time just some good grinding, but I was balls deep in her.

The room suddenly got lighter, but a very natural non-electric light. My eyes look up to see my Mother, Father, and Sister with a birthday cake walking into the room. Singing happy birthday. While I am balls deep in my girlfriend.

TL;DR- My parents sang to me while I was having sex.


Sadly, i was once the foolish friend who walked in. I came into my buddies room after a night of drinking and him and his girlfriend are laying in bed watching a movie and it went like this. I walk in “yo jay, wanna smoke? ohhh shit! You guys are watching V for Vendetta!?!? i fuckin love this movie” i proceed to grab a seat and talk about how much i love that movie (I’m pretty wasted) and my buddy kinda made hints to get the fuck out that i just didnt pick up on. I eventually just left and he told me the next day… I felt like a fools fool


The first time I attempted deepthroating, boyfriend wanted me to shove his cock down my throat as he came. So like any good girlfriend I did just that when he gave the signal.

I still have no fucking clue what happened, but it turns out semen really burns when it’s gushing out your nose.

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