15 People Tell Their Most Cringeworthy Experience Ever

Tuesday, Aug 25, 2020, 4:00 pm

Sex itself can be awkward! What if some really weird things happen during sex or sexual acts? People who have sex sometimes land themselves into some bizarre and embarrassing situations. Now, it's time to read some of those craziest and awkward things that have happened during sex. We have fifteen people here who shared their most embarrassing sex stories with us.

1.This Wet Dream

I had a wet dream on an overnight bus once where I called out the name of the girl I was dreaming about when I came. The girl was sitting next to me.

I spent the next 9 hours pretending/hoping to be dead.

This Wet Dream-15 People Tell Their Most Cringeworthy Experience Ever

2.When Girlfriend's Little Brother Walked in

Had girlfriend's little brother walk in while I was cumming in his sister's mouth. He waved at me because he didn't realize what was happening at first. All I could think to do was wave back.... while cumming.

When Girlfriend's Little Brother Walked in-15 People Tell Their Most Cringeworthy Experience Ever

3.This Girl and Her Curiosity

When I was a kid and first discovered that I could put things into my vagina, and it felt good, I experimented. A lot. One memorable time I shoved a bunch of Barbie clothes inside me. They obviously sopped up any natural lubricant I had and were incredibly hard to remove. I lost a dress up there for a day.

This Girl and Her Curiosity-15 People Tell Their Most Cringeworthy Experience Ever

4.A Guy's Unsuccessful Attempt at Creating an Artificial Vagina

When I was a novice masturbator, I attempted to synthesize a vagina using household products - plastic wrap, a paper towel roll, some rubber gloves, and vaseline. It didn't work.

A Guy's Unsuccessful Attempt at Creating an Artificial Vagina-15 People Tell Their Most Cringeworthy Experience Ever

5.Ouch That Must Hurt

When asking about what she liked, I misheard gentle as genital. Soooo genital hair pulling doesn't seem to be appreciated as foreplay.

Ouch That Must Hurt-15 People Tell Their Most Cringeworthy Experience Ever

6.This Porn-inspired Act

My ex and I had a pretty nice BDSM relationship and always tried new things that we heard about or watched in porn. Anyway, there was one video where a guy came in a glass and made her drink it all. I was not really into it, but she thought it was kind of hot, so I agreed to it. So when it came to o-time, I started to cum in the glass that was just above her head by a few inches. I guess cumming and holding a glass was too difficult for me, and I dropped the glass on her face. I just looked at the glass fall, and some of the cum slide down her face... I never did that one again.

This Porn-inspired Act-15 People Tell Their Most Cringeworthy Experience Ever

7.This is Really Weird

I once pretended to be my brother for my girlfriend, who had a massive crush on him, while we had sex. Responding to her in character like him and saying, "It's (name), I love you" and stuff when she asked who I was.

Yeah, that shit was fucking weird.

This is Really Weird-15 People Tell Their Most Cringeworthy Experience Ever

8.This Unfortunate Accident

After a night of heavy new year's eve drinking, I took a girl home which isn't really like me. Sexy time commences, she starts blowing me when I hear a funny sound and she stops. I ask her why she stopped, but she doesn't answer just gets up and casually walks out of my room. I'm confused as duck at this point, so I go to get up and realize she puked all over me. It was chunky.

This Unfortunate Accident-15 People Tell Their Most Cringeworthy Experience Ever

9.This Unforgettable Sex Act

In high school, I wrapped a fruit rollup around my boyfriend's cock and blew him in an apartment stairway. I still can't walk through the snack aisle at the grocery store without thinking about dick.

This Unforgettable Sex Act-15 People Tell Their Most Cringeworthy Experience Ever

10.This Girl Who Lost Virginity in School's Prayer Room

17 years old, just started school at this very religious college. There was absolutely no coed dorms. The opposite sex was only allowed in your room with the door wide open. Oh, and if you were sitting on the bed, both feet HAD to touch the ground. We were only allowed in the opposite sex's dorm between the hours of 5 to 10 on week days and 1 to 10 on weekends.

Well, the first week of school I met this guy. We hit it off well and would hang out on campus at 10 pm till about 3 am. 2nd night we hung out we were getting a little frisky, kissing and stuff. Few more nights of that and little virgin me decided to go all the way.

So we sneak off into the only place on campus where no one can question you if the door was closed: The Prayer Room. This room was filled with bible quotes, praises of Jesus, and religious pictures all over the wall. There was a cross and a huge bible in the center of the room, with a little pew. That is where I lost my virginity and continued to sneak off to have sex for the rest of the semester.

This Girl Who Lost Virginity in School's Prayer Room-15 People Tell Their Most Cringeworthy Experience Ever

11.Another Deeply Embarrassing Sex Act

We were at a party and we "snuck" into the bathroom (I think everyone at the party knew about it eventually), and had sex, I was on top. When we were finished, we turned on the lights, and there was blood everywhere. It was my period. He was wearing a white t-shirt which was now blood stained, there was blood all over the floor, it was just great. He was pretty cool about it, though...

Another Deeply Embarrassing Sex Act-15 People Tell Their Most Cringeworthy Experience Ever

12.This Inexplicable Sex Moment

On our wedding night, my husband made me stick my finger up his ass then smell it and taste it. He said "just stick your finger in there like you're sticking it into a cherry pie." I was a virgin at the time.

This Inexplicable Sex Moment-15 People Tell Their Most Cringeworthy Experience Ever

13.This Crazy Kid

A kid did this in my middle school math class, but it was because he hated the teacher. Played some pocket, came on his hand, walks up to our teacher and goes "High-Five Mrs. Teacherlady!" She gives him a high five and gets jizz all over her hand, realizes what it is and actually played it pretty cool. Sent him out, washed her hand, and he got suspended for two weeks.

This Crazy Kid-15 People Tell Their Most Cringeworthy Experience Ever

14.The Youngman Who Kept Things Going

I was once fucking a guy, and he came, and we fell asleep. All of the sudden, hours later, he woke up and started plowing me. He thought he fell asleep during the middle of sex and thought he had to continue haha.

The Youngman Who Kept Things Going-15 People Tell Their Most Cringeworthy Experience Ever

15.This Bizarre, Scary and Painful Situation

I was giving head to a guy with his dick pierced. It wouldn't have been a big deal, but his piercing was gauged. As I was deep throating his cock, his jewelry got stuck behind my tonsils. I freaked out and for a solid 5 seconds thought I was going to die. I eventually just jerked my head back causing both his piercing and my tonsil to rip. He was OK but sore. I had to go to the doctor for my throat and explain why half of my tonsil was missing. Two weeks later, I got my tonsils removed.