"Went on a date, had a fun time. Went back to her place, asked where the bathroom was, went to the bathroom, accidentally went into the wrong room, found her parents hidden stash in the corner of the room, went home, got up in the morning, told a mate at work what happened, he told another guy at work, turns out it was his sister I went home with and his parents stuff I had caught, he wasn't happy, he approached me and threatened me, I told my boss what he did, he got fired, went home from work, found a box at my doorstep, took it inside and opened it, there's a letter (cool), open the letter, it says "we're watching you" in capital letters, looked inside the box, found a pink toy with my name carved into the side, won't be dating on Tinder for a bit."
"20 years old, hanging with this girl I knew through friends in her dorm room. I knew she was into me and she was cute but I wasn't really into her. Obviously my 20 year old self decides ahh f--- it why not. We are in the middle of it when I realize how bad of an idea this is. I'm typically a good guy and don't want her to get the wrong idea. But of course I'm 20 and can't just say "hey, lets take this slow, or sorry I'm just not really feeling it." So... I tell her I have to run to the bathroom real quick. While in the bathroom I send a text to my roommate telling him I need him to call me in 15 minutes and tell me there is an emergency back at the apartment. I get back, some light smooches and then like clockwork, roommate calls. I pick up the phone, and proceed to try my best shot at an Oscar, "What do you mean our apartment got broken into?" "Well what the f--- did they take?" "Everything?" "S---, check my desk, is my laptop gone?" "F---, alright call the cops, I'll be home soon." I turn back to the young lady and apologize that the night has to be cut short, but I promise I'll text her when I get home (Why do we always say s--- like that....) I get home and thank my buddy for helping me out of a jam and all seems good. Until a week later when our other roommate leaves the door unlocked and we are robbed and the only thing stolen is my f------ laptop...Karma..."
"This was about a decade ago and I was in my mid-twenties. I think her name was Amanda but I could be totally wrong on that. I can't remember where we met or how we started making out but like magic, we were. She was thin and had nice curly dark hair and she was unapologeticaly wearing a fur coat. We made it back to my apartment. Oh, the majesty of the chance encounter where you can embody a different life, go by a different name, work in a field different than your own, lie about every aspect of your life and feel d--- good about yourself. You are willing to go beyond your typical repertoire because there is simply no judgment. I tossed her around into all the different positions that I could imagine and we just genuinely enjoyed ourselves. When it was over, I made the mistake of trying to go again but a lot of whisky had been drank that night and I was writing checks that my body couldn't cash.
Needless to say, the spark was gone. About halfway through my attempt at a round two, she suggested that we take a break and go outside and have a cigarette. My god I was thankful. I quickly threw on a pair of pants and a jacket and by the time I got to the door, she was just wearing her fur coat (no pun intended), I liked it. Anyway, we get out to my balcony and she starts telling me that she forgot her cigarettes. I offer her one of mine and she was like "no way, those are menthols" and I was like "cool, I'll go find yours". I go back into the house for a few minutes looking for her pack but can't find them or her purse. I then go back out to ask her where she could have left them when I see it. She climbed down my fire escape to the ground level and was running across the street in just her fur coat, without shoes or anything in the middle of winter. She hails a taxi and gets the f--- out of there. I never saw her again after that. She left her clothes and shoes in my apartment. She had her purse the whole time. As I was watching her naked a-- run down the sidewalk I remember wondering if it was because I was that bad of a lay. But then it dawned on me....I don't give a s---."
"I was in a bar, having a beer and this girl starts talking to me. She seems OK, but the bar is dark. Hard to tell. She asks me if I want to go out to her truck and drink. I say "yes."
When we wander out of the bar, the bright lights outside illuminate her face in a disturbing way. I ignore what I am seeing. She says, "so where is your car?"
I say, "I thought we were going to your truck?" She says, "No, we are going to your car."
OK. I can deal with this.
We get to my car, and she says "Where is the beer?" I say, "I thought you had the beer." She says, "No. Take me home."
OK. I can deal with this.
So, I start driving her home. As I am driving, she starts rambling, "You can do anything you want to me."
OK. Maybe I can deal with this.
As we approach her apartment she says "I sure hope my boyfriend isn't home."
Oh, f---. Can I deal with this?
She points to a convenience store and says "Pull in there. And go buy me a 12 pack of beer." I say, "I'm not buying you a 12 pack." So, she gets out of the car to buy beer.
I definitely cannot deal with this, slam the car into reverse, and race off into the night.
I didn't go back to that bar for a year.
"Went out boozing big style, my friends said I was barely standing by 11pm so they told me to get a taxi home (taxi rank was directly outside the club).
Woke up next morning in a strange bed with s---loads of dollies and stuffed animals on a shelf...uh....ok.
Managed to put my trousers and jumper back on when a woman around a decade older than me came into the room carrying a fried egg sandwich, she smiled at me and said "you need to eat this then leave. Quietly," then about faced and left the room.
I quickly scoff the sandwich in a vague attempt to stop the monstrous hangover that was starting to build as the last of the booze wore off, went into the hallway and she was standing at the front door holding my coat smiling slightly. I try to ask her what happened last night but she simply shook her head and motioned to the door.
As I get outside I realize this is a really really posh estate.
I've not got a d--- clue what happened but it left me really weirded out for a long time...."
"I was out at the bar and I was on my period. So, I had no intentions of hooking up with anyone. But, I met a cute guy, who wouldn't take no for an answer, even though I told him straight up that he didn't want to do this, that I was bleeding. But, he insisted, so we went back to his house. We had sex, then he gets up and goes to the bathroom, and when he comes back he's angry because of the blood on him. So, he starts yelling at me because he thought that I was only using my period as an excuse. So, he kicks me out of his place, cursing me out the entire way out. So then, I'm sitting in my car, and of course I left my $50 bra in his bedroom. F--- that, that's $50! I knock on his door, he doesn't answer, and I leave. Over the next 2 months every time I see this guy at the bar I'm like hey, I want my bra back. I even resorted to sending my friends over to tell him that I wanted my bra back.
Finally, one night I walk into the bar and the bartender says "I've got something for you" and hands me my nice $50 bra." Winning."
"As a server, you occasionally cross a table or two where you get hit on. I happened to serve one where this really hot girl I knew back in HS was eating with her sister and her baby in a highchair (adorable kid, too) and we did the usual back and forth conversation.
I think nothing of it but as they are paying their tab she asks me if I'm doing anything later. So we go out and grab a drink while her sis watches the baby back home. End of the night and she invites me in to watch Pitch Perfect (getting hot yet?), but by the time they have their first sing battle we are making out on the couch.
Cue the morning music. Everyone is dead asleep but I needed to get home. Only I heard the baby wake up too, so I check the crib and... It reaches out for me. I'm not afraid of babies, so I pick that sucker up and do my best to help her calm down. Feed her a bottle of formula. Change a diapy. Danced with the baby to some Harry Belafonte from my phone. I was in full blown Dad mode when she woke up.
It went so well that we would've killed to keep seeing each other but we went back to reality, I started my next semester at school and we both eventually met other people. It was a nice little precursor for the future, though!"
"Took home this huuuuge muscly guy, super alpha. He was picking me up and kinda throwing me around the place, and I was thinking, well why not! It's fun to feel a bit submissive sometimes. So it was fun, if a bit cheesy-try-hard.
But THEN... He starts purring. Actually purring like a large cat. It made me laugh SO much.
My flatmate heard it from her room underneath mine as well. I feel like it must have made the whole house vibrate..."
"He was a bigger dude, but I was ok with that until he was sweating all over me in a very not sexy way. Slobbered on my chin trying to kiss me and just plain sucked. The next morning he was very adamant about telling me he wasn't in love with me...Yeah that feeling was very f------ mutual dude. Also he thought he was clever using his mom's handicap pass to park closer to my building. Not cool, not cool. 2/10."
"Was with a girl from Russia in Orlando Florida that did not speak English. That night after drinking the language barrier was erotic and somewhat understandable but that morning it was confusing and just awkward. (She slept in my bed until noon with no polite way of saying I have to go you need to leave)."
"Took a guy home after watching some local bands play. He had tackled the male bassist of one of the bands and made out with him and then danced with me. I find bi guys to be really hot, so after all the bands were finished playing I invited him over to my place. We were having fun.
But it goes on and on and on and after awhile the fun wears off... And, man, I was tired. I had been awake for over 24 hours and needed to be somewhat coherent somewhere at 10 am (it was currently 5 am). I tell him I'm gonna need to catch a little sleep. "Can I hang out here until you're rested enough to take me home?" he asks me. I don't understand why he can't take an Uber but I say fine.
He tucks me in my bed and goes "Shhh... Rest now. You do so much for others..." and attempts to exit my bedroom but gets confused by which door to use (I have two closets and a balcony off of my bedroom). "Why does your bedroom have so many doors?!" he screamed after trying the second wrong door. I point him to the correct door and he exits.
I'm drifting off to sleep when I heard CRASH BANG CRASH followed by a sharp sound I cannot easily identify. I come out of my room and homeboy is sitting totally naked on my kitchen counter with one of my big knives, stabbing the s--- out of the cover of a Trader Joe's frozen Indian dinner while my freezer is wide open and the contents lay on the floor.
I stand there, completely exhausted, sore, and frankly a little confused. The only words that manage to escape my mouth are "My Indian food..."
He looks at me like a deer in the headlights and then starts crying. "Oh my god, this was your food! And I'm eating it! I'm sorry! I'm still really coked up from California!"
I sigh and tell him to eat the food and get dressed because I'm gonna take him home. I drop him off, never to see him again...
...except I still saw him out a few times in the following months. He got a girlfriend. I guess he found someone who doesn't place a ridiculously high value on her Trader Joe's frozen meals."
"This wasn't awkward or hilarious more depressing. After going to a girls place we're in the middle of playing pelvic pinochle and suddenly she has her climax. Before I could bask in my achievement she shoves me off her and starts throwing my clothes at me. Apparently once she had finished she wanted me gone...so that was a really s---- moment. So now I really don't do one night stands. That moment kinda soured the entire idea of those encounters."
"What was going to be a one night stand ending up being me comforting the guy while he cried about missing his ex. Awkwardly held him in my chest while he told me about how his high school sweetheart left him. Yes that sucks, but it wasn't exactly the right moment for a heart to heart."
"About 4am on New Years Day I decided to hook up with a guy who I met over tinder. He'd been sending me messages and really talking up his prowess. On the way to his place I decided to buy an ice cream sandwich. I only took one bite and left of it in my car. Keep in mind this is NYE in Australia so it was about 25 degrees C outside and even warmer in my car.
So I get to his place, start kissing. After the minute passed he says, "no it's not going to happen. You can go." He starts pushing me out the door before I even have time to put my dress on. So I leave and walk back to my car wondering what the f--- just happened. The whole thing was so quick that by the time I got back to my car my ice cream sandwich was still frozen. So I spent New Years morning watching the sunrise and eating my ice cream sandwich.
And that is my most awkward one night stand ever."
"Slept with an old friend one time. She'd been sleeping with women for a long time but we hooked up one night. We had a good time but she was weird in the morning, wouldn't stay for breakfast etc and on the way out she shook my hand and said "well, well done then" then she left for her taxi. Was unnerving at the time but we stayed in contact and all was explained."
"Was on a night out with a few friends, got completely f----- up. Met a guy outside McDonalds who I took a liking to, Australian, pretty hot, long hair got a bit of a beards. Took him back to my flat.
Then the next day I found loads of fries in my bed??!! Was pretty confused as despite meeting him outside McDonalds, I didn't have anything nor did he?
Asked my friends and turns out when I was talking to him they had been throwing fries in his hair, which had obviously fallen out during..."
"A friend of mine brought her friend over, we will call her Nikki, one night I believe ~4-5 summers ago. I had a gathering at my house, some of us were smoking, drinking and just shooting the s--- for most of the night. That night ended and Nikki and I proceeded to talk via social media then by text. She informs me that her younger sister is having friends over her house to swim, go in the jacuzzi, drink, etc. She wanted me to bring some alcohol, I was living at my parents house at the time, so I brought a good ol' box of Franzia. Show up. Start having fun with her and flirting as much as possible, making her smile, I was on a d--- mission that night. We proceed to drink more, she's wasted and I'm pretty wasted... I drank a lot back then so I still kept my cool. At this time it was around 12:45am/1:30am and we were all in the jacuzzi, people started filing out to sleep but she had been sitting next to me giving me a nice old fashioned...
And I proceeded to touch her leg, whisper cute s--- in her ear, mission finale was closing in and I had my sites dialed in...
Everyone leaves the jacuzzi, we are the only ones left...
She proceeds to take her tops and bottoms and chucks them, not very sexy like, into the yard, some ~20 feet away.
She climbs on top and mission successful, she got the D but boy she was pretty annoying the entire time we are doing the deed she keeps on...
"Are you going to be my boyfriend after this?!"
"Are you going to call me after this?!"
"Will we be together?!?!?"
F---, that was annoying and to be honest I would have definitely called her to date her because she was really cool and really attractive, just obviously drunk. So I comforted her and told her what she wanted to hear...
Oh, but there's always a but...
BUT mission compromised...
The lights on the back deck turn on, she is full on riding me in this jacuzzi and I ask her "Why did the lights come on?"
"Don't worry about it, it might just be my sister..."
Back door slides open, enemy spotted at my 5 o'clock.
"NIKKI WHERE THE H--- ARE YOU?!?!?"
It was her EXTREMELY hot milf of a mother wondering why she had not come in OR her b---- of a little sister ratted her out.
Milf proceeds to walk over to jacuzzi because she saw us, Nikki tries to find her bikini, sorry you chucked those things bye bye.
I'm sitting there with a s--- eating grin on my face and her mother goes "Nikki what the f--- are you doing?! Get over here..."
Nikki proceeds to be dragged and yanked out of the jacuzzi by her mother naked as all can be, SLIPS on the edge of the jacuzzi falling ~3" straight on her face to the deck and rushed inside... I couldn't stop laughing...
I find my suit, get out, dry off then I did what any gentleman would do... I cleaned their entire deck of all the party s---, got to my car, packed my bowl (back when I smoked), drove home and called my buddy about the story because his family were good friends with them.
Next day she texts me to apologize, we don't hang out after that. Sucks because I wanted it.
Fast forward a month, I'm doing walking leg lunges at the YMCA I was personal training at and as I complete a set for a certain distance, guess who is directly next to me on the recumbent bicycles? You guessed it, Nikki and her mother... I proceed with a smile, Nikki was embarrassed and the mother glared, grabbed my weights and lunged back to the free weight area grinning the whole way."