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I know, I know, cliché. Also, we had to black out all her windows, install a door with no peep hole and put 15 jesus in her room…. But, from the very moment she reached to undo my bra, I knew it was doomed to fail. You can get super weird and if you live in a fairly urban area, that dude is probably out there. But not as responsible as actually experiencing it. Bad hookup stories are both very interesting numbers for an online connection service. Did you go tineer a date first.
And, while we all share the sexy, thrilling parts of these stories with our friends, we so rarely talk about the emotional ramifications both good and bad and the less entertaining details that add up to reality. All of which is completely worth discussing. So, we collected stories from people to get just that. Ahead, their takes their very different experiences — orgasms, disappointments, and all. Wake up at her place in the morning, bed empty. So I get dressed, and get ready to go home. When I get the into the kitchen, her mother is sitting at the table with a kid. Greets me with, 'Hey, Emma had to go to work. She told me you were still asleep. Mother comes after and asks if I need a lift somewhere. I gave up and had a really, really strange ride back to the tram. Anyway, I end up going home with some guy, I vaguely remember mediocre sex — with a condom, thank god. But the next morning, I wake up in his bed; he's facedown on the pillow so I can't see him. I'm naked, my mouth tastes like windex or something. I frantically try to find all of my clothes, my purse, my car keys, and get out without waking him or any roommates he had. Oh, and I only had half an hour to get to campus for my test. Ended up hungover jog-of-shaming to class just in time. And that weekend, some guy I swear I never saw before slyly came up to me and handed me my keys and said 'I think these are yours, and I think you peed in our kitchen. Had drinks, danced, had fun. He asks if we can 'have a sleepover. Literally, all of it. From the fridge, from pantries, from cabinets, etc. I sleep like a log. It's a good thing I wasn't a poor college student or something. He even took dog food and milkbones. Bears, unicorns, horses, pigs... He has so many that he built shelves all the way around the walls with the smallest animals on the bottom shelf and the biggest ones on the top. No lie, there were probably 1,000 of them. I had to go outside and smoke a cigarette. Thank god he didn't smoke, because I had to collect my thoughts. He had a nice house, we sort of knew the same people in his work field, and he wasn't married. He just seemed like a decent person who was totally unashamed of his stuffed animal collection. The more I thought about it, the more I admired it because I knew he had to catch shit from his friends, so I started to find it attractive. I hate to say it, but I started thinking about a relationship. We finished up and I put my head on his shoulder and asked him what he thought about it. Don't recognize person next to me. Realize we are between some large buildings. Wake up rather attractive stranger as the night starts to de-fuzz. I thought it was yours? Paddy's in Butte is a terrible thing. Two weeks after breaking it off, the only thing I could think about was getting laid. So I convince my friends to go to a bar with me with my only intention getting smashed and picking someone up. Find someone, get to his house have great sex. Wake up the next morning he rolls over and says 'I love you so much. Then he starts talking about how he's going to pick up a puppy today and I come with him if he wants... The puppy was so fucking cute. Three years later and the dog is still freaking adorable, and I don't panic so much when he says he loves me. He called me later that afternoon freaking out because he had a 'sore' on his wiener that he was sure was a result of our liaison. He berated me about not revealing that I had an STD I didn't and calling me all sorts of horrible names and telling me I ruined his life. I told him I didn't have any diseases and I'm pretty sure even if I did, he wouldn't suddenly sprout sores that same afternoon, so, if anything, he had probably put me at risk, not the other way around. Logic was not effective. I finally got his hysterical ass off the phone but he apparently called his mother what? He went to the emergency room to have his dick checked out. It was just an ingrown hair. I did get a courtesy call with this information but no apology. After what I assume he thought was a proper waiting period of a few weeks, he tried to call me again for sex. He asks, extremely friendly-like, if I had a nice evening. I stammer that I did, thanks for asking, while wondering how long I have to live. Terrified, I say I would. It is very nice. I leave afterwards, slightly confused. The shotgun never appears. My dad wasn't supposed to come home so early! He tells me to jump in his closet I'm fully nude and my clothes are in the living room. I start to argue, but he insists, so I get in there and hear them having small talk for almost an hour. I realize I really have to pee, and they just drag on and I'm dancing around. And then the guy I slept with left for work! I can hear the dad making breakfast and just settling in. I panic, how am I gonna get my clothes.... Fuck my clothes, I'll use his clothes, so I take the stuff in the closet all I found were shirts. I fucking ran for my life, full speed through the house with sex hair and a long shirt to my car. The dad yelled, 'What the damn hell who are you?! I ended up hitting it off with a friend of a friend who was just in town on vacation. Now, my last relationship had left me feeling really sexually frustrated. I wasn't interested in any commitment so this seemed like a perfect arrangement. I could release my pent up sexual energy on him and not have to worry about attachments because he would be gone before too long. After a long night of flirting, we go back to his hotel and have another couple drinks in his hotel room. Everything is going pretty well and we have sex. At this point in the story, you should know that I have a very minor seizure disorder and that I can feel one coming on several minutes before it happens. I go out for a smoke, make it up two flights of stairs before I give up trying to make it back to the room, lay down on a landing, and have a seizure. After the seizure is done, I drag myself back to the bed and instantly pass out. When I wake up, I notice that it feels damp and sticky between my legs. My first thought is that I must have had my period all over the hotel sheets. I lift up the sheet to see that I had, in actuality, shit myself. The seizure must have loosened my bowels. I'm just laying there and silently panicking. The guy I had slept with is still fast asleep next to me. I want to hurry the sheets downstairs to housekeeping but I can't do that without waking him. I scooped all the sheets up in a bundle and rushed them downstairs to be cleaned. I got away with it. The guy never found out. That was my worst ever one night stand. It was a very small and tight knit community, and had a great party scene. So one night I was at the campus bar, and I ended up hooking up with this hot guy from one of my philosophy classes. I was extremely drunk at this point, and so was he. So we hooked up, and then immediately passed out. In the middle of the night he woke up me and said 'I'm going to throw up, where should I throw up? I told him to throw it out the window and went back to sleep. Unfortunately the pillow fell on top of a smaller building behind the campus residences. Her parents were there. I think because I had recently broken up with my girlfriend, I didn't want anyone to know. My friends were knocking on the door and trying to bust in. Without even looking how far down it was I jumped out of the second story window, slid down the metal awning and landed right next to who I think was her dad, or at least her dad's friends. I looked over at them, smiled, and then started running. Ran around the building to the front door and came up behind my friends who were still banging on the door. Felt like Jason Bourne. I was young, dumb, and ready to get some foreign strange. We were at a small gathering and ended up eating way too many special brownies, naturally followed by a trip to a bar with some of my girlfriend's new acquaintances. I naturally zeroed in on the tall, strong, Germanic boy in the bunch. From there, things got fuzzy. I recall making out in the bar — classy. Somehow, I decided that it would be OK to go back to this man's apartment with him. I don't remember much, except that it was a loft bed and I kept knocking my head against the ceiling during our gymnastic love session. After falling asleep — either from the brownies, the love-making, or the mild concussions — I awoke to harsh daylight and had to climb down a ladder, naked. As I exited the apartment, I noticed he and his roommate both had computer desks in the same room with World of WarCraft up and ready to go on their desktops. He was a gentleman and walked me to the train station. I got a lot of looks, as it was a Monday morning. The next night he picked me up at my friends dormitory and took me for a walk around the Arc de Triomphe. We made out one more time on a park bench. While we have never spoken again, we remain Facebook friends to this day. I'd heard from the grapevines this guy has been asking around about me so I knew something might go down that night since we were both going to be in the same place. The night was long but things progressed pretty fast after loads of drinks. A few bars and one club later the sun came out and I was ready to go home, at that point it was obvious he was coming with me for one reason. I mean not only everything he was doing was wrong even though I tried to help him, but he also stayed for way too long after and had weird personal life chats until I had to kick him out. It's non-existent where I come from, so this was a complete revelation. I found one of the very few, if not the only cool gay bar in the city called The Cubbyhole, located at the heart of the West Village. At first, I was really afraid of going in by myself but eventually, got the courage to go in and order a drink. It's a really small space but it was packed with beautiful women and cute boys too! After an hour wondering around and failed attempts of any interaction, a gorgeous, beautiful, boho-chic girl in her mid 30s came and sat next to me. We started talking, drinking, flirting, kissing, drinking some more, making out and eventually a couple of hours later made it out of the bar and into a taxi to her place. I don't remember all of it, but I have flashes of sex in the floor, in the bed, in the kitchen, in the sofa, in the bathroom... We never really spoke again but I've seen her twice at the Zara in Soho. I unconsciously still look around in case I see her. They're a cool family and we're from the same town, so she ended up inviting a bunch of our friends. Anyway, we all got pretty rowdy and I ended up making out with her hot older cousin on the dance floor. We went back to his place to continue the steamy evening. It was actually great. When I arrived, I realized half of her family was there — including her cousin's mom! They're a tight-knit Greek family, so everyone basically knew I slept with him and kept asking me all kinds of questions. It was pretty humiliating. As an active, sexual person, I went out on a mission the weekend before my surgery: Have the hottest sex possible. I guess you can say I 'settled' but it worked out for the best because I really couldn't get on top, so I just made him do all the work, and I never saw him again. When we went back inside, there STILL wasn't room for us to sleep, so he brought me to my house in a cab. I never heard from him again but that porch sex was damn hot. I know, I know, cliché. But while I was at that party, learning the finer points of Beirut ping pong balls are for wusses , I started to eye the cute guy playing against me. Competition brings out my flirty side, so I started talking shit. Then, I promptly lost. I walked away with my head held in shame. I ended up leaving the party with him, mildly tipsy and annoying his neighbors with my vocal aerobics. I woke up in the wee hours and snuck out, paranoid his roommate was going to come back. After crashing and sleeping off my hangover, my roommate and I wandered to the dining hall. On the way back, I noticed a guy in a hoodie kept turning around to stare at me. I mentioned something to my roommate about a total creeper giving me the eye. To which she responded, 'Um, you hooked up with him last night. Ten years later, I married him. All I remember is waking up from a dream about my ex-boyfriend to find myself in a strange place with a cute, albeit relatively unknown, guy. I gathered my things and realized I couldn't find my jacket from the night before. He was no help. I'd last seen him over 15 years ago. He had been my first love and our relationship consisted mainly of awkward teenage fumblings in awkward locations. We skirted each other like matador and bull until alcohol and slow music led us to stumble against each other in a clumsy reunion. We lay there and reminisced about those awkward teenage fumblings until we partook of some very awkward 30-something fumblings. I knew he never would. Nights spent stalking the phone as a 15-year-old had at least taught me he wasn't the type to phone. But, it didn't matter. This one-night stand had given me closure. My first love was no longer the boy who made my heart race like no other man had, ever since. He was just a man who slept way too close to the floor, surrounded by nylon. Heart vacated, it was now available for new occupier. We went on one date, didn't have sex, but continued to text when we were both drunk. So, obviously, I gave him a call, and he told me to meet him at a bar nearby. We had a few drinks, and then decided to go back to his apartment to smoke a joint on his roof. Things progressed pretty rapidly from there, and before I knew it, we were both naked from the waist down, and he was pulling a condom out of his pants. We had sex in the middle of the roof, in the middle of the night, in clear view of anyone and everyone who was in the apartment buildings around us. I haven't seen him again. Not coincidentally, I also haven't fucked on a roof since. We'd been looking at each other all night and then she introduced herself to me before getting swept up by a crowd of moshing people who smelled like they didn't believe in deodorant. I thought it was really cool that she didn't mind being tossed around like that. She was wearing a red bandana low on her forehead and lots of black eyeliner. She looked like an andro Natalie Portman and she'd been staring at me as though she already knew we were going to sleep together. But, she left without saying anything more and so I found myself posting about it on CL the next morning. Not because of any sort of Cinderella fantasy; I thought she was hot and seemed really cool — way cooler than me, at least, which is always appealing. I figured she was the kind of girl who had been dating girls since she was 12, who would be assertive in her interest, who could read a map, and who could maybe fix my sink. She said she thought it was romantic. We were both under 21, so we met at a cafe and had tea. She talked the whole time, which was fine because I was too nervous, and then she followed me back to my apartment. To be fair, at the time, I had a nearly-shaved head and mainly wore ripped jeans and tank tops. I was still my fairy-princess femme self on the inside, but was enjoying the experience of being visible to other queer women, through pretty standard visual signifiers. So, the fact that she didn't realize I would turn out to be 'such a girl' wasn't exactly her fault. Plus, I had said so little during our date — while I knew the basic outline of her life story, all she knew was that I was a good listener. It seemed that we each expected the other person to take charge. It also came to light that, despite her initial swagger, this was actually her first time. I found this to be extremely disappointing — but also feeling guilty about it. But it felt too late to turn back. When I woke up alone the next morning, she had left a note in careful script on a crumpled receipt that read, 'It was beautiful. What had been beautiful about our anxious fumbling? If anything, it seemed to me that maybe she had gone into it expecting to have a beautiful experience from the moment she declared my CL ad romantic, and was determined to name it that regardless of what happened. We had both projected different things onto each other, and somehow our night together hadn't ruined her vision of me. I guess she was more committed to the fantasy of me than I was to the fantasy of her. She called me a few times and I didn't pick up, because I was young and didn't know how to politely turn someone down. It's been over five years, but I still see her every now and then at queer parties. We usually nod at each other, but that's it. We've both grown our hair out and are dating butches. I had never had a one-night stand. I was out with a few guy friends that I barely knew. The club was full of overeager young financial types, but I was lucky to be around a few 'nice' guys. My friend introduced me to a colleague of his. Apparently, we knew some of the same people from back home. Having mutual friends made us way too comfortable... His eyes opened wide. He grabbed my hands and we were in a cab in what felt like 30 seconds. He lived in a barely furnished apartment on the UES. We started fooling around and it was okay, but a little bit awkward. Something felt off that I couldn't quite pinpoint. In a wave of panic, I realized that I was probably his first one-night stand as well, and that he probably had pretty limited sexual experience. When I wasn't going down on him before sex, he was genuinely surprised and said, 'You're not going to go down on me?! I really couldn't see how anyone could just expect another person to give them head. He wanted to try all these things he'd heard about somewhere.... He spit out different poses and tried to position my legs all crazy. And, I remember thinking that if I was actually in a relationship with this guy, it would have been okay for him to ask me to try new things with him. But, I didn't trust him and I felt like his weird science experiment, which is what turned me off. Looking back, he was kind of my own experiment as well, so maybe we're even? It was just something I wanted to experience, and I knew NYC was the place where it needed to happen. Afterward, I felt pretty stupid. I literally told people this was the stupidest thing I had ever done. Plus, having sex with someone I didn't actually like was boring. I haven't had a one-stand stand since. It was in the park, in the middle of the day, in a planned meet-up during a run. I had a crush. And so I gave it to him. And it never happened again. In some ways, that day set the precedent for my many sexual flings that have since ensued. Do I really like this guy? Can I see myself telling him my deepest secrets? Putting my heart, body, mind, and soul in their hands? I genuinely believe that after a good first date or night out with someone, I know what my intention is for them. I'm in for a one night stand. I manage my expectations for that person on the spot. It's okay if I never see him again, or if he doesn't call. I only sleep with someone on the first night if I don't particularly care whether or not I see them again. I know he won't be my forever prince, and therefore, will make him my knight for a night. We spoke for 30 minutes after the showing — it was flirty, fun. We met a week later for drinks in a charming, dimly lit corner bar. We talked about life, our families, and aspirations. There was a strong commonality and connection. We went back to his place. In the moment that we were moving from the couch to the bed, I judged the situation —whether or not I would go all the way with him. As charming as he was, my gut told me: He is not the one. And not because there was anything wrong with him. He was just missing something intangible that would reserve a place for him in my future. So, we had a one-night stand. The weirdest thing about it, though, was that throughout the entire sexual experience, his face kept changing. Every time I looked at him, he looked like someone different. Like he was wearing a camouflage image-changing suit, to hide his true identity. It was trippy and distracting. I figure it's because I didn't really know him. I wasn't used to his face. They are an easy way to satisfy my desire for interpersonal connection. A way to protect myself from being vulnerable and susceptible to someone else's influence and power. A way to keep my emotions separate from my experience. I've taken v-cards and stolen hearts. Mine has only been broken once. And since then, I see that how you give yourself to someone is just as important as who you give it to. Sex has two different roles — hedonist pleasure or intimate love. Don't expect longterm intimate love from a one-night stand if you want to avoid disappointment. And hold back if you want to hold on. I didn't feel ready, and I definitely harbored fairy-tale fantasies about my first time being with someone who felt like a soul mate. In college, I carried that with me, so I hooked up and went almost all the way, but never quite there. And by my early 20s, the weight of my inexperience held me back in relationships — out of fear of being discovered for this thing I was missing, this knowledge that I didn't have. So, when I started seeing my next boyfriend, my experience was pretty limited. When that relationship, which had consisted of a lot of missionary sex and limited orgasms, ended six months later, I still didn't feel like I was where I was supposed to be, as an adult in charge of her own sexuality. I didn't really know how to ask for what I wanted, or really, how to figure out what I wanted, when I wasn't on my own. I laid low for a while, emailing guys and going on some dates, but never feeling comfortable enough to go home with any of those men. And then I heard from a professor who was a few years older than me, and emailed him back just once before asking if he wanted to meet for a drink. We went out on a Sunday night and hit it off. I didn't feel a real connection — or in all honesty, real chemistry — but I did feel pretty comfortable with him, having easy conversation and laughing a lot. Three drinks later, we left, made out in the street, and headed in the general direction of both our conveniently neighboring places. When he offhandedly was like, 'I don't supposed you want to come up, just for a drink,' I surprised him with a yes. We went up to his place, started making out, and things easily escalated. And for the first time, maybe because I didn't feel any real pressure or expectations, I was able to be more vocal about what I did and didn't like. I put his hands where I wanted them. I stopped worrying about whether the jiggle around my middle was going to be unattractive if I got on top. And ultimately, I still didn't orgasm that night, but I did change some of my own ideas and inhibitions around sex and intimacy. I didn't want to be there. So, I lied about an early meeting, left, and never called him again. And he didn't call me, either. The only problem: Despite the fact that I didn't want to see this guy again, the fact that he clearly felt the same, and was on the same page as me, felt like tacit rejection. That's why I never did it again, but in a weird way, it's one of the most important things I've ever done for myself. As in body shakes, hesitant hands, and overall timidity. But, let me back up and give a little back story. I've found with lesbians at least the ones I hang around that the 'typical' one-night stand where two drunk strangers meet at a bar and go home together at 3 a. I guess reasonably sober conversation is needed first? I knew right off the bat that we had a connection. We had many mutual interests — art history, weird families, and a distrust of social norms, to start. So, I decided to do what a recently single girl does after three Heinekens — invite her back to my place. She rode on the back of my bike and we made it to my apartment around 2:30 a. I knew she was inexperienced, so I opted to take things slow. Instead of ripping off her clothes the moment we got in the door, I made her a drink and showed her around the apartment until we got to the bedroom. After some light making out, I noticed she was shaking and a bit unsure with her hands. I said to her, 'I don't want to pressure you, we can absolutely just go to bed if you want. She was funny, intelligent, attractive, reasonably sane. All the things I'm usually a sucker for. But, from the very moment she reached to undo my bra, I knew it was doomed to fail. We should hang out some time this week. I know what you're thinking; I am a complete douche. And no, it was not one of my finer moments but I have also never been good with disappointment. I just had no idea how to tell her that we were not ever going to see each other again because she was horrible in bed. My friends all said, 'But you could teach her right? But what happens when something you think is a one night stand, is someone else losing their v-card? To clarify, I only found out much after the fact that she was in fact a virgin. Is it your responsibility to let them down gently? Because chances are they are not going to be orgasm-inducing in bed. But then again, isn't that counter to the purpose of one-night stands? I have never had an orgasm from a one-night stand, yet I still continually have them. I'd like to think its because I can. I'm young, single, reasonably attractive, and live in NYC, which means I could essentially have someone new every night of the week if I wanted to. It is a good story to tell over brunch. Do they ever amount to much? In my experience, no. But do I regret any of them? Not even with the virgin. This particular evening I was drinking with a friend and my sister, who were both visiting from out of town. We started talking to Jeremy and his friend about the basketball game and proceeded to verbally spar for the remainder of the evening. He was about my height, which as shallow as it may seem, is usually a deal breaker. There was a certain ease to conversing with him. And, at around 1:30 a. There was no mistaking what this was and I was surprisingly more okay with that than I thought I would be. When we got back to his place, we shared a joint, which coupled with the amount of drinks we had had meant that I remember very little of the main event. But, when I woke in the morning, Jeremy was just as jovial as he had been the night before. We laid in bed for two hours and talked about our lives before I got dressed to leave. There was no exchange of numbers, although that wasn't the last time I saw him. We live in a small city and we have bumped into each other and sort of smiled but never spoken. And I am okay with that, too.
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