Now Reading
10 Embarrassing Sex Stories That Will Make You Cringe

10 Embarrassing Sex Stories That Will Make You Cringe

Embarrassing sex stories are some of the funniest stories people have. Sex is usually one of the most magnificent things a person can experience. Unfortunately, though, sex can be host to some of life’s most embarrassing moments. That’s why we compiled these 10 real sex stories that will make you cringe! Make sure to take notes so you do not have to go through the same embarrassment these people did.

Black Out At My Graduation Party 

“It’s my college graduation party and me, my WHOLE family, and a bunch of my friends are celebrating it in my backyard. We are having a good time drinking a few beers throughout the day and the later it gets, the crazier it gets..” “I’m near blackout at this point and all I can remember is being behind my pool with this girl I was friends with, eating her out. Now in my drunken state, I coulda swore that it was dark enough behind there but when I awoke the next day, my father assured me it wasn’t. Not only could he assure that but about 60% of my family could…”

10 Embarrassing Sex Stories That Will Make You Cringe

Always Clean Yourself Before Sex

“I was dating this girl for a few months when I was a senior in high school. We were both virgins at the time, and after months of sexual frustration from both of us, we decided to finally have sex. I was excited at first. We both wanted to try 69ing, so we began… This is when my problems began. I don’t want to get really graphic, but all I will say is that you should make sure your backside is clean before 69ing…”

You Get What You Ask For

“I was seeing this girl who would play up the fact that she was into weird things. The vagueness of how she said it both turned me on but ended up being my downfall. She was [performing oral] on me one night when she said something sassy to me. I responded jokingly saying something along the lines of “If you don’t stop I’m gonna have to smack you.” She stopped and said “Do it”, and with the way she said it, I thought she was being serious. So I smacked her lightly. Not threatening or hard, but what I felt was a kinky turn on for her. She stopped, looked at me blankly, and asked “did you just smack me?” All I could think to say was “Well, you told me to…” She started laughing so hard and we didn’t even finish.”

10 Embarrassing Sex Stories That Will Make You Cringe

You Mess With The Bull

“The one that instantly comes to mind is when my boyfriend and I had sex for the first time after I started using the NuvaRing. He pulled out after a while only to find my NuvaRing caught under his foreskin. For some reason, it reminded me of those hoops that hang out of a bull’s nose and I lost it. He’s standing there with my birth control dangling from his peen and I’m just laughing my ass off.

 

10 Embarrassing Sex Stories That Will Make You Cringe

The Worst Thing You Could’ve Said

My friend told me the key factor to make a woman feel good is being funny. So I came home with a girl in the middle of the night, on the way to my bedroom I told her “You’re going to walk funny tomorrow”… She’s giggling and asks me the obvious “why? are you so big?” .. after which I locked the door and said the sarcastic “No, I’m going to cut off your legs”. She started crying – kind of ruined the moment”

Hydration is Important

“She was on top and riding like a champ. When I came, my toes curled and everything in my body flexed and I must have been dehydrated because both of my calves cramped like crazy. I yelled and had to get her to roll off me. I walked with a limp for a couple of days.”

10 Embarrassing Sex Stories That Will Make You Cringe

The Heart Wants What The Heart Wants

“So I and my boyfriend were having sex one night. We were both really drunk, and I remembered I had leftover Olive Garden in the fridge that I could not stop thinking about. My boyfriend was really into sex though, so I had to still act like I was too. He kept moaning and building, but all I could think about was my leftover garlic bread. When he finished, I told him I needed to go to the bathroom but the second I was out that door I ran to the fridge, and retrieved my food.”

10 Embarrassing Sex Stories That Will Make You Cringe

Meeting My Gay Roommates Boyfriend

“This wasn’t embarrassing for me, but I used to share an apartment with another gay friend who hooked up a lot. One day, I had just come home when my roommate’s door flew open and a younger guy in his underwear burst out of my roommate’s room and headed into the bathroom. I remember the look of surprise and terror on the kid’s face when he saw me, and then I saw my roommate, lying on his bed, on his back, still with a raging hard-on. I walked into the kitchen and pretended to do something until I heard the bedroom door shut again.

See Also
A sex toy party is certainly an interesting experience. Here is what my first time going to a sex toy party was like for me!

It turned out that the guy [went down] on my roommate who [ejaculated] in his mouth. The guy freaked out and wanted to spit it out, and his first impulse was to run to the bathroom to do this. So, yes, he met me for the first time half-naked with a mouth full of my roommate’s [ejaculate]. I will never forget the look on his face.”

10 Embarrassing Sex Stories That Will Make You Cringe

Mom Caught Me Sleeping With Her Friends Wife

“I was sneaking around with this married woman for a year. She was an older family friend and I knew her husband pretty well. He was really good friends with my mom through work. It is also important to know we live in one of those closed in neighborhoods where everyone has backyard space, but there are no fences. One day I was in bed with her at her house, when he showed up unexpectedly at the house. I tried to sneak out the back window and assumed I got out without being seen. The next day my mom called me at work and told me our neighbor asked her why I was in my underwear running around the backyard. I told my mom I was just jogging but my mom was smarter than that and called me out as soon as she got home. She chewed my ass out pretty good and lost a lot of respect for me, but she never told him. He still doesn’t know, and when they come around for family stuff I am not allowed to talk to her. Worth it.”

When Bottoms Meet 

“Had plans to hook up with this cute guy I was chatting with for a while who was tall and jacked. I kinda wanted to try bottoming for the first time and his appearance made me think he would want to top… Jokes on me, he was a total power bottom. Kissed the hell out of me before pushing me onto my back and started riding me. He was kinda heavy so I had to awkwardly ask him to switch positions.”

These stories are cringe for sure, but sometimes the moment you connect with someone is through a weird sex thing that happens to you. Like it or not it happened, and you two now have a little secret. Do you want to share your weirdest sex story for some reason? If so, do it in the comments below!