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16 Of The Most Awkward, Cringe-Inducing Sex Stories Ever Told

16 Of The Most Awkward, Cringe-Inducing Sex Stories Ever Told

Thanks to a steady diet of alcohol and bad decisions, having sex in someplace “naughty” is an activity most of us partake in after the magic of mediocre missionary wares off. Something about getting it on in a dressing room, bar bathroom, or at formal really speaks to us (and by “us” I mean our vaginas).

While bumping uglies in the handicapped stall might seem like a great idea in the moment, however, it doesn’t always go according to plan. Getting caught in the act is a painful rite of passage most of us experience, like getting our periods or dying our hair darker after getting dumped. Still, in the moment when you’re found naked, vulnerable, and with balls in your face, well, it feels pretty shitty. So, I’ve searched the deepest, dirtiest, oh-so-messy corners of the internet (also known as Reddit) to find some of the most cringe-worthy stories of people getting caught getting it on. Because you know what they say: The misery of getting caught having sex in an absolutely humiliating way loves company.

One time the wife and I are getting it on first thing in the morning. We are under the covers, and it’s a good thing because my 3-year-old son snuck into the room. We didn’t even notice until he quickly jumped onto the bed and jumps on my back. He looked over my shoulder at my wife and says “What are y’all doing?” Well that killed the mood real quick.

Reason #5,736 why I am in no way ready to have children.

A few years back my ex-gf at the time and her friend came to my place to hang out and smoke. After about an hour her friend had to leave so it was just me and my ex chilling on my bed higher than kites. Eventually, we began to get touchy feely and started going at each other hard. We ended up in the doggie style position facing my door. I’m starting to feel that familiar pressure in my groin area and pull out ready to cum on her back. Right at that second her friend opens my door (I think she forgot her phone) and in those few moments of panic, I popped a few shots over my ex and right across onto her friend. I remember her calmly freaking out, muttering “oh my God, oh my God” as she hurriedly shut the door and politely asked us to grab her phone after we cleaned up while she went to my bathroom to scrub her shirt clean.

So, you’re not even the one having sex and yet he *still* sprays it on you? Talk about a nightmare.

Mom walked in, screamed and closed the door, running away while yelling “I thought she left!”
My father could be heard laughing downstairs.

Nah, she just came. Hi-oh!

One night, my ex’s dad and ex took me home. She came into the house with me for a minute “to grab some CD’s”, and we decided to have a quickie. My grandfather walked out to the kitchen while we were going at it in the living room. He stopped, looked in at us, walked over to the counter, got some coffee, and then walked back to his bedroom. Didn’t finish due to the awkwardness. Probably for the better, because her dad got pissed she was taking too much time and was at the door when I was walking her back out to the car.

“Hey gramps! Did you want any cream for your coffee?” (Sorry, sorry! I am so sorry.)

My drunk friend was having an emotional breakdown. He told me how much I meant to him and started bawling his eyes out. Then he came over to give me a hug. My boyfriend at the time, who still had his hand down my pants, was not amused.

But like, talk about getting so much attention! That’s 10 minutes and a few awkward conversations away from being a threesome right there.

Decided to break-in my ex-gf’s new dorm bed on move in day. She said her room mate wouldn’t be back for a while. I was on top when we heard the door handle turning. I pushed myself up on my knees and turned to look at the door (I don’t know what I expected to see) and just as she saw us, my dick slipped out and started flinging back and forth like an old-fashioned metronome. It didn’t turn into the threeway that porn had led me to believe it would, but we all started communicating better after that.

And alas, sometimes no matter the setup, you still don’t get the perfect, porn-like finish.

The best story Reddit has about this is the guy who was having sneaky spoon sex with his girl under a blanket when her dad or brother came in and plopped down next to them. So he stayed there, still inside her and flaccid, for the rest of the movie until he left.

Fingers crossed it wasn’t pre-iceberg Titanic. They would have been there for the rest of their lives.

17 years old. Snuck down late at night to meet a girl who was with her family at their summer camp on a lake. We went skinny dipping and swam out to an anchored floating deck and proceeded to get it on. A few minutes later this daylight inducing spotlight was right on us followed by her dad yelling her name and telling her to “get her ass back here now.” Since he was standing by my clothes which held my wallet and keys I had no choice but to follow. He sent her inside then spoke to me through gritted teeth saying “I understand it takes two, but if I ever, ever catch you around here again…” speech. I must have stuttered the correct amount and timings of “yes sir’s” and “no sir’s” because he let me go without kicking my ass.

In case you ever feel awkward about having sex with the lights on, just imagine having sex in a literal spotlight while your dad yells at you.

My boyfriend and I in HS would usually bang it out on Sunday’s because the parents had a pretty consistent schedule at that time. We were in the middle when we heard the door slam. I kid you not, we hear my mother, sprinting down the hallway towards my room. My bf is butt naked and runs into my closet, which maybe has a foot of room. I luckily had my top on and my mother screams “Where is he”! In shock, all I can do is point toward my closet. She opens it to see him standing there just covering his junk, and proceeding to awkward shuffle to the bathroom.

This is why you hook up in your car in the middle of the night like a normal horny teenager.

Deputy sheriff opened the door of my truck mid coitus with my gf. Told me to “find somewhere else to bone,” and promptly slammed the door.

I stand corrected. Still, I need to know — was it a volunteer deputy sheriff? Was it Dwight Schrute? These are the questions people need answers to!

Her mom walked in on us. Made me change my gf’s 2-year-old sisters diapers for the next week when I was over in order to not tell my parents.

Hey, a dirty punishment for a dirty crime. Seems like a fair trade.

First girlfriend I ever slept with. I had been sneaking out at night and riding my bike to her house for a couple weeks with no issue, snuck in real quiet and left around 4 or 5 before her parents woke up. She slept a floor lower than her parents we kept it quiet, it was exciting and felt dangerous plus we were young and horny. One time after a night of vigorous love making we both accidentally fell asleep. I woke up in a panic around 7 and immediately got dressed and thought I could still hustle into the basement and out the back door. I had the dash through the kitchen to get to the door and low and behold there were her parents sitting down for a nice breakfast oblivious to the fact I had just plowed their daughter. Her mom’s face of disbelief and her dad screaming WHAT THE FUCK will forever be embedded in my memory. Needless to say, that day didn’t go very well for me after I dashed out the front door and attempted to escape on my bike and her dad promptly drove up next to me and demanded I “take a ride with him.” We didn’t last very long after this debacle.

You know what’s worse than having to sit in the car with the parent of the person you were just caught having sex with? Literally nothing in the whole world.

My girlfriend came home from school for the weekend. Dropped her new puppy off at her parents’ house and came over to my place for sexy time.

In the middle of going at it, my bedroom door flys open and in comes her mom screaming about not watching the dog while she’s on her back.

Ugh, moms these days are such bitches.

Virgin me had gotten to 3rd base quite a bit but never had a chance to close the deal, until one night…
Her mom was a nurse and worked nights. Her dad left to do some night fishing. She and I proceeded to get naked and do the deed… for some reason, in her parents’ bed.

I lasted about the typical 90 seconds for my first time. She’s giving me head to get me ready for round two when suddenly the bedroom light flicks on. Her dad walks in… Looks at us…. picks up my pants, hands them to me and asks me to go to her room.

I was scared out of my wits, but I remember hearing as I walked out, her saying “Daddy, hand me my clothes too! Give me some dignity!”

His response: Dignity, hell girl, I think you done lost that by now!

I don’t know what’s worse, getting caught fucking in your parents’ bed, or having a father who says things like “you done lost that by now.”

First times are always awkward — mine was no exception.

It’s the middle of winter many years ago and my then-boyfriend and I had decided it was time.

To start off with he didn’t know where to put in — that’s okay. I’m the youngest of 5 children so I had a fair idea of what to do. After some absolutely devastating embarrassment on both sides, the ball was rolling and it was happening.

About half way through his mother walks in with a tray of hot chocolate and biscuits. She stands in the doorway dumbfounded and demands an explanation of what her son was doing to me.

Then my boyfriend pretends to be asleep. On top of me. While my vag was in a considerable amount of pain.

She then just put the tray down and left.

Honestly, total cool mom points for leaving the tray of biscuits.

We thought our mom had gone to work, but she came back in a few minutes later. She opened the bedroom door and looked inside, and she was as pale as a ghost. She just closed the door, got what she needed and went back to work. She never mentioned anything she saw.

I thought this was just another “mom caught me” story but then I read it again. See that third word? Our? Is this just a disturbing typo? Was someone adopted? Is their last name Lannister?

So, don’t even worry about the time your little sister walked in on you and started crying. Things could be so, so much worse.

[via Reddit]

Image via Shutterstock

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Rachel Varina

(yeahokaywhat) Aspiring to be the next Tina Fey, Rachel spends her free time doing nothing to reach that goal. While judging people based on how they use "they're" vs. "there" on social media, she likes eating buffalo chicken dip, watching other people's Netflix, and wearing sweatpants way more than is socially acceptable.

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