I Accidentally Fucked a Homeless Guy: Hook-Up Fook-Ups

By The Head Pro

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 [email protected]

On to this weeks fookups:


I think I fucked a homeless guy?

So it was toward the end of the night and I was a bit white girl wasted. My friend convinced me that we should get some halal food before catching the subway back to school. While waiting in line we met (what I thought) was this cute southern Heath Ledger type. Long story short I brought him home to my dorm room. However, in the stark, florescent lighting of my room I began to notice he was carrying a rather large bagpack with him and was dressed kind of shabby. But I was drunk so I slept with him anyway. The next day I woke up and he looked more like the lead singer of Nickleback than Heath. I had to go to an internship for a few hours so I left and told him he could just let himself out (Reflectively not a very smart decision). I come back to my room around 2pm expecting him to be gone, but no, he is there, naked, still sleeping.

I was kind of feeling shitty about having a one night stand with some obviously sketchy dude so I leave again and have a little panic attack about how to get this guy the fuck out of my room. Eventually I go back in and wake him up. He starts telling me all this shit about how last night was magical and he's never felt such a connection, blah blah blah. And idk exactly remember how to got to this but he told me something along the lines of how he wanted to buy me a gift and had just been given a gift certificate to the Salvation Army. It was then that I really started to figure out he might be homeless so I asked him where he lived and he kind of avoided the question giving some really vague answer. So by this point I'm really freaked out, I make up some excuse telling him he has to leave because my younger sister is coming over. He tries really hard to stay and he hangs out in my room fiddling with stuff, naked for an uncomfortably long time. Eventually I walk him out and he asks for my number and money for the subway. I gave him $20 and a fake number...

What if this guy just has some incredible game he’s working and is getting rich nailing college girls? Also, was his name Tom Jane?


My biggest hook-up fail was so ratchet and nasty I can't even.

It started out as a night out on Independence Day in NYC. My ex invites me to a big gay party and out of desperation for a messy night, I went. The moment I walk in, he approaches me looking like a crack addict. There are alcohol stains on his shirt (ew). Soon after, the party ends and he's too fucking blackout to walk. I feel bad and get a cab back to my place since he was unable to communicate. After we get to my apartment he starts attempting to make out with me and I eventually gave in since I kinda missed him (so unbetchy of me). He has the nerve to pass the fuck out while I'm giving him a bj so I do too. A few hours later, I wake up to wet sheets. Yes. Oh god. He fucking wet the bed. I slapped him awake and kicked him out. Done. End of story.

I can’t stop laughing at the image of him passed out with his ex’s dick in his mouth like an intubation tube


Back in the years of being a high school betch, the worst humiliating hookup of my hook-up history happened. While at time I was mortified, I am happy to have gotten this in the books so the rest don't seem bad in comparison. Lets go back to sophomore year on a Friday night my parents were out of town, I thought I'd invite my non committal douche bag bro over for a fun night alone. Due to the fact that he had been hooking up with the senior before we started I figured I needed to step up my game and do something super memorable, and I did a fabulous job if I do say so myself. He arrived and I went to answer the door in my best naughty schoolgirl outfit I could pull together from my old private school uniform (I had everything you could think of from the glasses to the ruler).

Being in high school and only the second or third time we had hooked up it was pretty awkward and I don't think either of us were ready for roleplaying but we figured we'd try it out anyways. After about 30 minutes of foreplay we dove into the action and were getting into it when three of my friends come barging in the door of my bedroom. The shock of my friends caused a backdoor entry that I was NOT prepared for. My friends left the room and I stood up but the shock of the surprise visit in my room and my ass hit me at once and I immediately fainted. When I finally came back to my senses I was sitting on my stairs in my full get-up with all four of them surrounding me. I walked him out and we awkwardly kissed good night and asked if we could keep this to ourselves, but I should have known that no bro in high school that is not your boyfriend would keep that a secret. I was called schoolgirl for the next two years.

Private school girls - so uptight.


A few years back I went to visit my best friend at college. When we were out that night I met one of her hot guy friends. I went back to his place that night - he wrapped it - we had sex - and then realized after that the condom had broke. The next day I went home and later that night I went over to my ex's house because we were "working on things". We started hooking up which then led to sex. When he pulled out, a piece of the condom that broke off from the college kid the night before came out. My ex looked at me and I looked at him, he immediately drove me home and said nothing. We never worked things out.

Well, at least something got worked out…

That’s all for this week. Don’t forget to email me your most outrageous hookup fookups at [email protected], and follow me on twitter at @betchesheadpro




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