Welcome once again to Hookup Fookups, where we all revel in your most hilarious hookup failure stories. Remember, we’re laughing with you, not at you (but also at you, a little). Email me yours at firstname.lastname@example.org, and wish me a happy birthday (tomorrow) on twitter at @betchesheadpro
Ugh. So this is my worst hookup story and also my most embarrassing story to date. So rewind to my sophomore year of college Halloween. That year my roommate and I were Mario and Luigi ( but no not sexy Mario and Luigi, full on men costumes with mustaches and all. So unbetchy of us but we were young and thought it would be funny) So anyways, being a betchy sophomore already sick of the boys in my grade, I went after so freshman boys that night. Upon meeting two, I liked my options. Although, one was a commuter and was inviting me back to his friends dorm where he had a blow up mattress. I knew no way in hell I would do that, so i decided on the other cute freshman bro telling the commuter my friend had thrown up on me and had to go back to my room (poor excuse I know)
So back in cute bros room sans luigi costume, we started hooking up. He left to get a condom from his friends room and when he came back he started to jerk himself off. I was like UM HELLO?! he said that when he got up to get the condom he lost his boner so had to jerk himself off, but isnt that the point of having a girl in your bed?! so you wouldnt have to jerk yourself off!? Either way I stayed and still hooked up with this bro which lasted for 30 seconds and ended with the question “How was I?” Which then led to him telling me I took his virginity. I was horrified but still stayed cause it was late and didnt want to walk back.
On top of all that it was snowing the next morning and I had to walk back to my dorm in the snow past all the monks on their way to morning prayer in my luigi costume.
“Already sick of the boys in my grade, I went after freshman boys that night.” All you need to read, really.
Last summer I was at a house party with a guy I had a brief hook up with months before. We hadn’t really spoken since the previous hookup but eventually gravitated towards each other at the party. Approximately 3000 shots of tequila later I find myself in a room with said Pro and things are heating up. Belligerently drunk and about to go down on him I suddenly felt warm stream of what I believed to be pee coming from his boxers. I was wearing my favorite pair of Jcrew shorts at the time and hoping for the best I said “are you peeing?!” He replied” what, you can’t handle it?” I ceremoniously burned the shorts.
I guess you couldn’t!
I was in cabo last summer with my best friend. i’m 5’8 and proportionate (excluding my large fake boobs), so i had zero hopes of hooking up with anyone (I feel like everyone on vacation is short), until we met this guy with “bottle service” (lol) at one of the clubs, who was tall and handsome and VERY spanish. He takes a liking to me, we hang out a couple of days, he invites us to move out of our hotel into his penthouse at a much nicer hotel, and we decline but continue to hang out with him as he’s very generous and he and his “best friend”/assistant aren’t actually bad company. we’d drink at the pool all morning, so one afternoon i went in to take a nap.
I wake up to his head buried between my butt cheeks. literally, cheeks spread, nose in, just inhaling. i played possum for a while, cause I was a little curious what was going on, but he literally just rested in between them and inhaled. once he realized i was awake, he started tossing my salad, but more importantly, started fingering my butthole. He then proceeded to PUT. HIS FINGER. IN. HIS MOUTH. I literally rolled over and said wtf? you like poop. you LIKE. poop. he shrugged and said, “i like poop”. factor that made this story more interesting: he is a mexican (publishing, although he was from mexico city so let’s make our own presumptions here) billionaire. i googled him. -_- rich people get freaky i guess.
Um, I think he’s more creepy/quasi-rapey than he is “freaky,” but Christ: [shrugs] “I like poop.” Also – being 5’8” and having big fake jugs has never equaled “finding someone to hook up with is hard.”
This isn’t exactly a hookup but I would’ve hooked up with the guy if he wasn’t so crazy. I was going to a party with a big group of people and one guy (friend of a friend, never met him before) was cute and we started flirting, drinking, and eventually making out at the party. Then the alcohol suddenly hit him and he got ridiculously drunk (or whatever else he may have been on). At first he started calling me Maggie which is not even close to my name. His friends told me later that Maggie is his ex girlfriend. Then he started holding onto me and would NOT let go and his friends had to pry him off of me. Then he started yelling passionately in my face saying “Maggie! Look at me Maggie! Look at me! I love you! LOOK AT ME MAGGIE.” over and over again until I would look at him and be like “ok yeah I get it you love me whatever.” It was like he had PTSD from his last break up and was having a flashback and literally could not wake up from it. He even made me tell him I loved him too. At this point I obviously did not want to hook up with the guy but he kept holding onto me and telling me he loved me and that I’m beautiful while his friends were trying to hold him back and contain him. Eventually he tried to grab me again and I ducked and he tripped over an entire couch and landed on the floor and I’m pretty sure he just called it a night and went to sleep right there. The party got better after that.
“The party got better after that.”
Coming from a JAB
(Note this story is only funny if you are familiar with the Jewish prayer, the Sheheckianu)
I worked at a Jewish sleepaway camp one summer going into senior year of high school. Anyone who goes to sleepaway camp after about 6th grade knows that shit goes down after dark. The counselors get drunk and high and the campers sneak off into the woods to kiss before curfew. I had been hooking up with another counselor and we decided to have sex for the first time. We were both virgins. Things were going great in the shed that holds the hockey sticks and basketballs. The minute he came, he made us both pause and say the shehechianu prayer to bless his first time.
In case youre not jewish its a prayer you say the first time you do something like visit Israel or the first night of a holiday like Hannukah.
Wait, but what about your first time?