“So, I dated my first girlfriend during the summer between high school and college. We got really close (for a couple of 18 year olds) so she was over at my house a lot, and my mom loved her. A few weeks into college, I decided the long distance thing wasn’t for me and broke up with her. A little while later I got a new girlfriend at the college I was attending.
Fast forward to the first day of Christmas break and I’m bringing new girlfriend (who is now my wife) home to meet the parents and she’s going to stay the night before going home to her parent’s. Well a few weeks before Christmas break my mom decides to let ex-girlfriend move into a spare room of our house because she got kicked out of hers. Words cannot express how uncomfortable of a situation it was bringing new girlfriend home (to stay the night) to meet my parents as well as the girl she replaced (who was also living there.)” – Viking042900
“My friend telling me how shitty his relationship was becoming and wanting to end it moments before his girlfriend texted me for advice on how to tell him she was pregnant…” – Lwaddlez
“When I was about 17 I went to a house party with a small group of friends. It wasn’t really a party… more of a small social gathering where everyone drinks cheap alcohol until they go to sleep. The house we were in was a decent size and had a few rooms and various places to sleep. Eventually myself and a friend (we’re both guys) end up just lying in a double bed with a beer chatting about games and life. The party had sort of fizzled out and I had been having some issues with a girl I liked so had decided to chat to him about it. After about 20 minutes, the chatting had slowed and we were both looking to fall asleep. I was facing the opposite way to him but due to the fact I had a lot on my mind I was very much awake.
All of a sudden the door creaked open and I heard a girl come in that we were both friends with. She whispered if he was awake and asked if she could get into the same bed with us as there was nowhere else to sleep. He said it was fine and then gently pushed closer up to me to allow her to get in. I wasn’t in the mood for anymore chat so figured I’d pretend to be asleep.
That’s when it started… I’m sort of lost in my thoughts when I start to hear kissing, I figure “fuck it, they’re going to make out a bit because they’re a drunk. No big deal”… then I start to hear more rustling around and am starting to work out in my head if I’m going to have to say anything… I miss my chance and then lie there accepting my fate. It gets to the point where I feel like if I say anything now, It’ll look weird… like I’ve been OK with everything prior. Then… I feel his bare ass push against my back and he’s breathing like a dog after a long walk. ‘fap fap fap’ until he eventually gives the girl her prize.
I have never ever experienced a more horribly uncomfortable thing in my entire life.” – high_snobiety
“My ex-Gf’s ultra conservative/religious sheriff father walked in us while she was going down on me at 3am.
He kicked us both out of his house and we ended up sleeping in my car.
The next day, her mom invited us to have dinner at their house and lectured us on how what we were doing was disrespectful to God and disrespectful to them, we should save it for marriage, etc. The entire time you could tell her dad was fuming. He barely said 2 words the entire meal. It was highly highly uncomfortable.
Well after dinner, her parents go to bed and we watch a movie in the living room. Gf starts getting handsy, and I’m telling her there’s no way I’m risking it. She says her parents are super heavy sleepers and their floor is super creaky, so we will hear them coming.
Well, adult things happen, and next thing I know, I’m railing her from behind in the middle of the living room. I close my eyes for 1 second and when I open them, her dad is standing there with a facial expression that is burned into my mind 10 years later. It was a look of pure hatred and murder. We end up grabbing a blanket and trying to cover up, but the damage was done.
Her dad and I both completely gave up on any sort of relationship at that point. I ended up dating her for another 2 years, and went to her house all the time. Her father never spoke another word to me after that night.” – CHUNKY_BLOODY_QUEEFS
“Hooked up with a girl from my hometown who came to visit with her grandparents. She and her brother had their own room, so while he was at the arcade we did our thing. There was a knock at the door.
We throw on clothes immediately, and in my rush I didn’t take the condom off. Open the door, it’s her grandma. She goes to get her brother because they’re going to the parks, and I’m sitting here after having just done butt stuff with her granddaughter, trying to act normal when I feel something slide down my shorts and onto the floor with a quiet splat. Without looking, I step on it immediately.
Conversation continues, awkwardly, until they come back and grandma makes her way into her room to grab something. I pick up the condom and thow it in my pocket. Kiss the girl, shake the grandpa’s hand, tell them to have fun. I’m still not sure if she saw the condom or not.” – whetsolder
“The first time a girl tried hitting on me while I was checking out a gym with my mom when 13 or 14. My mom was around the corner when the girl approached me and told me I was kind of cute. My mom overheard and came right around the corner, said she couldn’t agree more, even called me a little gentleman. The girl was obviously uncomfortable and tried to back out but my mom pulled her back in and tried to force us to have a conversation while she hovered over us. Eventually she was able to come up with an excuse to leave and bolted. It was such an uncomfortable experience that I never stepped foot in that gym again, in fear that I might run into that girl again.” – credits_equal_debits
“A neighbour with a rather interesting history gave me a lift to town one night. On the way he sees his half brother who has an even darker history than my neighbour. Half brother asks for a lift to a house a few miles away, when asked why he was going there he simply replied that he was going there to shoot someone. I was in the back seat feeling rather uncomfortable but scared to ask to get out in case he turned on me.
Something that shocked me was how nonchalantly my neighbour told him that was no problem and he’d be glad to give him a lift. I’m sitting in the back wondering how many people have gone to prison for being in the wrong place at the wrong time just like I was.
Thankfully we dropped him off, he went his way and we went ours and he was arrested somehow before anything happened.
Northern Ireland was an interesting place back then.” – baconandeggsandbacon
“Got invited to a friends house for dinner. Unknown to me I was the only one invited. I was seated on the couch next to his wife, while he sat on a single chair opposite us. Wife constantly snuggled up to me, stroked my arm/face, all while making over sexual comments. He just sat there watching this. The meal was served strangely early, after which i made a quick escape. Pretty sure id been invited over so one of them could have sex with me.
I mentioned the incident to another mutual friend and he said he had a similar experience. He said the couple came into his shop, bought some stuff and asked if he wanted to stop in for drinks (they know he has a wife but she wasnt invited). Being the polite person he is he agreed and when asked for directions, the wife said not to worry because she’ll stand naked at the intersection and wave him which way to go.” – hmfiddlesworth
“Years ago, I was a delivery driver for a place that tried to bill themselves as gourmet pizza. Since they were so classy, the drivers’ uniforms were a tuxedo shirt and bow tie. I had the misfortune of delivering to two separate bachelorette parties in my time at this company, and on both occasions, the middle aged ladies refused to believe I was not the stripper. When I actually handed them the pizzas, they still tried to pay me to take my clothes off.
I know it sounds like it would be awesome, but it was beyond awkward. Mortifying. I could not get out of there fast enough.” – TheRealHIFLoClass
“I was first mate on a stunt boat full of models there for a promotion. I slipped, fell headfirst into a footwell and became stuck, splitting my boardshorts in the process and spilling my meat and two veg into the breeze for everyone to see and admire. One model was sat in a seat directly in front of where I fell, my dick was literally 6 inches in front of her face while I was upside down in the footwell.
This happened as we were pushing away from the dock, I had to spend the next half hour with these stunning women while wearing a lifejacket as improvised pants.” – MrFuxIt
” Partner from work, we’ll call him Vic, always talks about “his chick”. “My chick this, my chick that blah blah blah”. He’s a cool enough dude, so he gets a family invite along with several others for my kids’ birthday party.
He shows up with “his chick.” Beautiful girl, very sweet, her and my (now ex) hit it off. They spend all afternoon hanging, everything is awesome.
Christmastime party rolls around, my SO says “Don’t forget Vic and his chick.” At work I remind Vic Party is Saturday at 8. Saturday rolls around, and Vic shows up with a beautiful girl. It’s been a few months, a little egg nog, and anyway she looks different. Whatever, it’s his chick and I immediately don’t want to be embarrassed by forgetting her name. I call over my SO and say something like “Look who’s here” or “Look who it is” smiling like an idiot. SO looks at me like I grew antlers and I can see she’s confused. I’m used to this because I’m an idiot and do stupid things hourly.
SO finally says “Vic, is your chick coming?” The strange lady who has never been to my house begins crying as if I pepper sprayed her and shouts “You brought that bitch here too!?” and unleashes a flurry of insults that would make R. Lee Ermey blush before walking back out the door to their car. I never saw her again.
Turns out this nice lady was his wife, but the lady who brought my kid a gift and spent the day planning daycare schedules with my wife was his girlfriend. The girlfriend was no secret, but it was a ‘one-time-thing’ he seemingly got a pass on. Christmas party was awesome after that.” – fukkinmike
“I was in the room but this happened to my brother.
For his 18th birthday we took him to a strip club and a buddy got him a 2 song lap dance in the “Champagne Room”. We were all in the there and being his birthday the stripper picked the best spot in the room. The corner where she could put her leg up on the wall. When the second song started another girl began to get pissed since she wanted the corner. The two start arguing for nearly a minute and the whole time this is happening my brother has a vagina like an inch from his face while hearing them fight.” – catheterhero
“2 weeks after I got back home from my study abroad semester, I went to see my GF’s presentation at her school about her final project or something like that. (We were in LDR for the semester I’ve spent abroad).
After the presentation was over, I was talking with my GF’s family, while all of a sudden this guy shows up with like 20 roses and begs my girlfriend to take him back in front of everyone. Turns out she was cheating on me with him, he didn’t know about, her family didn’t know about, and of course I thought we were still together. You can imagine my reaction when she leaves with him, and sends me a text saying that she needs time to think about stuff. It was the most uncomfortable experience in my whole life.
Later I found out by one of her friends, that she was actually “dating” the other guy while I was away, and asked him for some time when I got back. Her plan was to break up with me without him noticing we were also “dating”.
They’re still together as far as I know, but it took me some time to get over that one.” – juanoa8
“One time in my early college days my (ex)boyfriend was throwing a party at his house. Everyone came, drank, had a good time. Afterwards we went to sleep, me and him in the bed with a couple people scattered around the floor.
A friend of ours had “back problems” aka was super whiny and wanted us to share the bed with him and the girl he’d been flirting with all night. So it’s me and my boyfriend laying the normal way in the bed, and the other two perpendicular. Well, of course half-way through the night he and that girl think the best idea ever is to just have sex. On top of our feet.
My boyfriend just whispered, “He’s a virgin, I can’t ruin this for him.” So we tucked our legs up to our chins and just… waited it out. The noises still haunt my dreams.” – fuqmook