25 Awkward/Embarrassing/Weird Hookup Stories Revealed.

May 15, 2014

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When I first reached out to people asking them to share their awkward hookup stories with me, I had no idea what to expect. For those of you easily discomforted– this post is as uncensored as real life. Some of these stories will make you laugh, others will give you immense feelings of second hand embarrassment. Thank you for sharing these with me, I have to say I really enjoyed myself.


  1. I had been talking to this guy from Tinder for about a month when one (drunken) night I invited him over because we were hosting a “dorm party.” I got so shitfaced that not only did I tell him I was a bisexual (i’m not) but, I almost puked on him mid-sex. I ended up sleeping on my floor while he was on an air mattress in my kitchen. Stay Classy.
  2. We were making out, all was fine and well, and then he pulled away to try to do that whole like look-deeply-in-your-eyes-mid-hook-up thing, but when he pulled away his face went from “this is so hot” to horrified. Turns out his nose had started bleeding and I had a good amount of blood spread all over my face. He tried to keep hooking up after we cleaned it up too. Yeah, not a chance.
  3. A kid was fingering me (painfully) while we were hooking up and when he finished he had blood all over his hands and his couch from me. Guess that’s what he gets for fingering me so viciously.
  4. In college I arrived at this party at an apartment complex already prett intoxicated. When I drink, and even much more do back then, I get pretty honest and bold. I was on a deck where girls were dancing on the railing and I looked up at one and said “I wanna dance up there with you.” Dancing turned into me making out with her for what seemed to be minutes. (It was probably closer to an hour) Lots of it ended up being a blur, but I remember grabbing her ass a lot, and even putting my hands in her back jean pockets. Nothing more happened unfortunately, I think I might have asked her back to my dorm, but the next morning feeling pretty good about myself I started looking through my clothes. I noticed in my pocket was $7 and I had no clue where it came from. It was then it hit that I had gripped the cash she had in her back pocket and put it into my own. I saw her again a couple times around campus and she basically pretended to not have any clue who I was. I’m pretty sure she just thought I was a total dickhead who robbed what little cash she had while letting me make out with her.
  5. After a drunk sexcapade, the girl “finished” by puking on my lovesack (beanbag)
  6. So it’s the beginning of junior year of high school and my best friend is throwing a party at her house. I was super excited. She was inviting a bunch of her friends from her town so I was excited to meet new people. It’s was well into the party and I was definitely hitting it off with a guy that I had met there. Long story short, we ended up butt naked in the upstairs bathroom on the floor. We started making out and doing some ‘foreplay’ if you will. Twenty minutes later…..still foreplay! Apparently he just wanted to touch my boobs all night. I was getting so bored so I was finally like, “Are we gonna fuck or what?” He obviously complied and looked surprised I had asked. I was excited cause things were finally about to get interesting then it turns out he wanted me to do alllll the work (don’t get me wrong I love being on top, but I was super drunk.) I did enough to get the job done and hopped off the second I got a chance. I didn’t know what to say, I just wanted to get the hell out of the bathroom as soon as possible. The next day my friend wanted to go hangout at her boyfriend’s house with a couple of his friends there. Yup….he was there…and we didn’t talk at all. Needless to say, the entire experience was extremely awkward. I will never forget it though.
  7. After a long night at my favorite karaoke bar and one too many strong Long Island iced teas, I found myself grinding on my weed dealer. He’s pretty cute and I was pretty drunk so I just went with it and went back to his house. Once there, things started getting hot and heavy and right in the middle of sex he stops me SUPER seriously and says DONT MOVE. I freeze and he whips out a giant bag of molly. He proceeds to rack a line of molly on my bare boobs and snort it off of them, Wolf of Wallstreet style. He did that twice. Confused, I just kind of let it happen. From this day forward, my roommates and I call him The Wolf.
  8. There was the time at a party in my hometown, when my two best friends decided to walk into the room that they KNEW I WAS HAVING SEX IN…and then my friend proceeded to take the blankets off of my lover and I, and they both screamed as they saw him penetrating me, as if they didn’t know it was going on??? And they still won’t let me live it down.
  9. There was the typical incident in high school, after cheerleading and football practice, met up with my boyfriend to have sex in my car in the high school parking lot, got naked and before we could get it on the police showed up to make things nice and awkward. Instead of trusting that we’d leave and find our way home, he decided to follow us, so we had to fake him out by parking in a friends driveway until he left, then we went back to a parking lot to finish what we had started..OH, THE GLORY DAYS.
  10. I was hooking up with a boy that ended up being the best sex I’ve ever had, not to mention he was the hottest guy I’ve ever been with. Nothing about our sexual experience was awkward except that fact that I left his house with a limp. I THREW OUT MY BACK. I literally could not move for about 5 days and had to lie to a bunch of people as to why I was on bed rest, worth it.
  11. I had the typical drunk girl night, managed to attract a cute boy I had been eyeing, god only knows how I did it. I vaguely remember the sex, but from what I remember I enjoyed it. I met up with all of my friends the next morning for a beach day, and one of my guy friends asked me what had happened to me (seriously), asking if I had gotten beaten. People were genuinely concerned. I looked in the mirror later on to reveal a dark bruise in the shape of fingers across my neck. I thought I had a night of kinky S&M, but was he actually trying to kill me…?
  12. This was one just awkkkkkkward. I really don’t even know how to explain it. Drunken night, per usual. We had fun the night before, and we were going for a little morning sex. I decided to be nice and give him a little blowjob to get him going, but I guess he was too excited?? He pulled his penis out of my mouth fast and I was super confused, so I figured he was trying to prevent himself from ejaculating. I assumed we’d start to have sex, but nope..he came ALL OVER HIS OWN FACE..not on purpose of course. Safe to say he was not pleased.
  13. Sophomore year of highschool, I decided to sneak out of my house to go hangout with this guy I was pretty much umm *obsessed* with. We pulled onto a dead end in my neighborhood and hooked up. When it was time for him to drop me off back at my house…well, I guess we left his radio on too long…his car battery was dead. I ended up having to walk back home and promised to jump start his car in the morning. Poor thing suffered all night in his freezing car, and we couldn’t figure out how to pop my hood the next morning (think it was too rusted or something). I ended up having to leave him there because I was running late for work. He ended up having to ask some guy doing lawn work for a neighbor to jump his car. Yikes
  14. I was drunkenly giving a guy head when I went a little too far and my gag reflex (and all the alcohol in my system) couldn’t handle it. I quickly stopped but not before I got throw up all over my hair. The guy I was with luckily had his eyes closed and was pretty far gone too but I was so grossed out. I quickly grabbed him to head into the shower with me without any explination because I had no idea what to do. To this day I still don’t think he knows I almost puked right on his dick.
  15. So this guy and I had been friends for a long time and nothing had ever happened, I wasn’t even particularly attracted to him. But one night we were both drunk and I was mad at an ex, so he was being super touchy and I figured why not. So we went back to his place and we start making out, like super PG shit, literally fully clothed and out of nowhere I see his hand fly back and I’m thinking “what could he be doing” and before I know it he full on SLAPS me. Like not a light tap, like full force slaps the shit out of my face. And my jaw literally dropped. I go “Did you just….” literally his only response was “I thought you would be into it” I said “Yeah..not so much” so I put my shirt back on and peaced out. I looked in a mirror on my way out and had a legit hand print on my face. Saw him like a week later and he started to say “So I’m sorry about that whole slap situation” And we’ve never talked about it since.
  16. Peed in 5 different guy’s beds, after banging them.
  17. When I studied abroad I was regularly hooking up with a local. We met towards the end of my stay, so we weren’t together very long– but things were pretty intense for a short period of time. A few weeks after I got back to America, I had a message from him on Facebook telling me that I have Chlamydia and that I had given it to him. He explained it wasn’t common where he was from and that he had felt itchy after having sex with me and wasn’t mad– but knew I was the one who gave it to him. He told me it was common not to have symptoms, and that all I’d need to do was take a couple pills and it would be gone. So the next day I went to my schools health clinic and got checked for STIs. It takes a few days to get results back, but since I was sure that I had it they gave me the pills to take immediately, just to get rid of it. A couple days back and I still hadn’t heard, but I wanted to tell the guy I contracted it from (the guy I had sex with immediately before the one who confronted me) so that he could get checked before the weekend. I explained to this guy that he probably didn’t know he had Chlamydia but that he did and he needed to get tested immediately. He freaked out and said he’d get checked first thing in the morning. I got my test results back the next day— negative.
  18. One time i was about to have sex with a guy and realized i forgot to shave a spot on my vajayjay, so i ran into his bathroom and “borrowed” his razor just for a few min, popped a squat on the toilet to do the damn thing and as he walked in i dropped it into the toilet because i was so frazzled. Needless to say he thought the plop sound was me taking a huge dump until he later realized it was me actually using his razor to shave the rest of my vagina.
  19. Freshman year I lived in a suite in miller hall, I had my boyfriend over one day when my roommate was out and I was giving him head… We were both completely naked and suddenly I hear my suitemate and her family go into her room and I thought nothing of it because I didn’t think she’d come into my room…. I was very wrong(thankfully her alone and not with her family). So she saw me mid act and then we all screamed and she ran out. And then later she told him that he should trim his pubes and I was very thankful.
  20. I think this is more embarrassing on the guys part but one time mid hookup this guy turned on Bobby Valentino “tell me” (seriously… he legit searched it on YouTube on his iPhone like does he use Bobby Valentino often?) and then tried to eat me out to the song.. After I refused he put on Bob Marley as we fell asleep.. My own personal sexual DJ! 
  21. When I studied abroad I hooked up with this Australian guy named Brad. Brad was a hot surfer babe, but an elitist jerk. Anyways,  while he was using my bathroom I took a little “trophy”– his USC school ID from when he studied abroad. He was hot and I wanted to show my friends, no shame. I never saw Brad again and wasn’t overly upset about it. A few months go by and a rumor was spread about me hooking up with this guy Tim. I was pretty offended because I had never hooked up with a guy named Tim and didn’t know why people had that idea. My friends and I denied the rumors and went about our lives. A couple months ago I was going through my desk and came across Brad’s student ID………. his name isn’t Brad, its Tim.
  22. So casual saturday night celebrating my friends 22nd birthday, she decides she wants to see male stripers so we all bought tickets to the show. We all pitched in for my friend to get a lap dance on stage from one of the stripers. well worth the money! while she was on stage getting a lap dance another on the the stripers came down from the stage shimmed alittle bit for all the girls to get afew tips, got to me, threw me over his shoulder and brought me up on stage. Next thing I know im on stage getting a lap dance and for the rest of the night this particular striper was dancing with my friend and I. At the end of the show we spoke to him about going to a bar or coming over, my birthday present to my friend….he was so sexy and very sweet. He agreed and offered to drive us back to my apartment, I politely declined and said we could meet him back at my place, it took some thorough convincing to get my friend away from thier car and into ours. Our DD drove us back [friend] fell asleep on the ride and decided to go home. I agreed that was a good idea since we didnt think the striper would show up anyway. I got home called my boyfriend and next thing i know the striper is calling me saying hes in my driveway with his friend. I ran downstairs and told them my friend had gone home. They came up anyway and we akwardly all sat in my living room. Thankfully my roommate came home, confused why i was in our living room with two random guys. I told her they were stripers and said she cshould get a lap dance since she had recently been dump. it happened and it was wierd to watch. Next thing i know im cuddling with a striper on my couch and hes asking to see my room. Naive me shows him leaving his friend on the couch. He picked me up threw me on the bed and i had hot sex with a striper.
  23. My friend and I banged these two blonde surfer boys the same night and my friend woke up with the word “localized” on her tummy. The next day I asked the guy I hooked up with if he was in high school, becaues he looked like he was 12… ever since then he never says hi to me and we literally see him everytime we leave the house. He’s practically our neighbor.
  24. One guy I was hooking up with took eating me out a little too literally… there was blood.
  25. Banged a legit thai guy in bangkok who didnt speak a lick of english. In the morning when I asked for water…he didn’t understand and gave me a warm coca cola.
More about Mackenzie

Retired scene queen living in Astoria, New York with my boyfriend Ben. Accidentally started blogging in 2011, haven't stopped since. Lover of Nutella, hater of white jeans after labor day. Graduate of Suffolk University with a degree in Sociology. During the day I work for Petrossian Caviar, the world's largest caviar supplier and buyer. I have a wonderful life, and I'm excited to share it with you. Also, I have seen every episode of Law & Order: SVU.