Category: Hookup Stories

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Hookup Horrors Hookup Stories

Another Hook up Horror Story

I had so much fun talking about my worst hook up that it seems a lot of people really enjoyed laughing at me. That’s fine. One of my friends liked it so much that she asked me to relay her worst hook up experience. It’s a pretty good one, so I’ll tell it the same way that she told it to me. If she still enjoys it after other people find out about it, maybe I’ll make it a regular things. There’s nothing wrong with sharing our most humiliating experiences and they’re always a good laugh.

She knew the guy

So this was a guy that she had hooked up with in the past. They had done it enough times that they were both able to start getting a little weird with the sex and that’s always a good thing. Anyway, she was horny one night, so she called him up. He didn’t have anything going on, so he invited her over. She showed up and, just like in my story, the guy was hammered. The two of them drinking together was nothing new, but she stone cold sober and he was about ready for a nap. They decided to just get into bed and go at it.

He went first

She says that the mistake she made was not paying attention to how close he was in his state. She was lying next to him and just jerking him off. It was all she could do to keep him hard in her hand. She was so focused on getting him stiff enough to fuck her that she lost all track of just how much stroking she was doing. He was in so state to tell her to stop, so she says that he just came in her hand. That was it for any hope of sex, plus she learned that men don’t have to be fully erect to ejaculate.

He tried to make it up to her

Even I his drunken haze, he felt a little bad about shooting his load off like that. He decided he could at least do the same for her and reached over to give her a handy. It would have been a nice gesture if he didn’t start snoring as soon as he touched her clit. So, basically she just went over to a drunk guy’s house, jerked him off, and now she just lying in bed next to his snoring self.

She still got a hand job

She says that now that he was passed out and she was still worked up, she just had to make the best of it. She just grabbed his hand and used it like a sex toy. She flicked her bean with a sleeping man’s hand and came all over it. Then she just rolled over, pulled his arm over her shoulder and fell asleep for the night. Hey, it’s still sex, even if you have to do all of the work yourself!

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Hookup Horrors Hookup Stories

My Worst Hook up Ever

There are good hook ups and then there are bad hook ups. No one wants them, but they come anyway. There isn’t a whole lot that we can do about it. If you spend your time doing anything, it’s going to come with its own problems. I once had a hook up that was so bad I started to question whether or not I could go on. I had to question who the people I was hooking up with actually were. If it wasn’t my worst hook up ever, then it was certainly very close to it.

I met her online

This was a girl that I met online on a hook up. She had an ad looking for someone with a fair amount of oral talent to head over to her place and trade a little mouth action. I happen to be pretty good in that department, so I volunteered my services. A few messages later and I was on my way over to her place. It wasn’t terribly far away, but it was the end of the night, so I had no other options if she turned out to be catfisher. I wasn’t prepared for what she actually was.

She was well-sauced

She answered the door and I could immediately smell the alcohol on her. I’m never one to turn down a good drunk fuck, but this girl was over the line. She was stumbling and slurring her words, and practically fell to the floor when she turned around to lead me inside. I hate to say it, but even I have my limits. She was clearly losing control of herself and I had to tell her that I wasn’t comfortable having sex with her in that condition. I mean, who knows how she’s going to feel about it after she sobers up?

She begged me

I tried to leave but she wouldn’t let me. She actually got down on her knees and begged me to eat her pussy for her. She had this whole story about having a few drinks to loosen her to the point where she was able to look for a hook up. I guess I’m a softy underneath because I agreed to go downtown for her. I even said I’d do it without any reciprocation. I could see her being okay with a pussy eating after she sobered up, but remembering that she blew some random dude might be too much for her.

It didn’t last long

Anyway, she stumbled and fell onto her bed and spread her legs for me. I assumed the position and it smelled like someone has poured a whole fifth of vodka down there. Still, I’m there to do a job, so I go to work. I’m eating her pussy like it’s the last let of lips on the planet when I hear it. She was snoring! I look up and she’s passed out cold on the damn bed! Well, that was enough. I wasn’t about to wake her just to lick her pussy for her. I just got up, through the blanket over her, and left. That was literally the worst hook up I’ve ever had. I couldn’t even give the other person an orgasm, let alone have one myself.

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Hookup Stories

My Strangest Hook up

I’ve had a lot of hook ups in my day and some of them have been pretty damned odd and interesting. I’d say my strangest one took place about a year ago. I’m not against what went down at all. I just really wasn’t expecting it. I wouldn’t be against doing it again, either. I’d just prefer to know what was going on ahead of time. I would have had time to process what was going on before it all happened. Still, it was a fun experience and I know that she had a good time with me.

I met her at a Bar

I was hanging out at a bar when this girl caught my eye. She was sitting by herself and it was clear that she was looking for some action. She had that short skirt and big cleavage thing going on that’s always a dead giveaway. The place was a well-known hook up spot and I was in the market for some fun, so I made my move. I bought her a drink and plopped down on the stool next to her to share a few words. I could barely get anything out before her hand made its way to my knee and I knew that it was game on.

She started opening up in the Car

It was the drive to her place where things started to get interesting. She had invited me to her place and she was all over me. I think her hand was actively on my crotch when she whispered in my ear that she was married and hoping I was okay with it. Once again, I would have liked to know before we got into the car, but whatever. I was ready to go and I wasn’t going to let a detail like that get in the way. If she wanted to cheat then it was her decision. I was just there to get laid.

She stopped in Front of the Bedroom

We were just about to open the door to the bedroom when she stopped again. She had a really naughty smile on her face and a look in her eyes that made me want her more than anything. Then she really let me know what was going on. It turned out that she loved to cuckold her husband. She made it clear that he could never satisfy her and she always had to remind him of that. Then she hit me with the bombshell. She caught her cuck of a husband jerking off to another woman and she needed to punish him. That was why she was at the bar that night. She was looking for a man to help her out in the punishment department. Then she opened the door to the bedroom and I found out just how deep this whole thing went for them. I wasn’t expecting it at all, but there I was.

Kink was the Name of their Game

I was standing in the doorway of the bedroom as she danced across the floor and hopped up onto the bed. She had the sweetest smile I could ever want to see as she invited me by tapping on the mattress. My focus was on the floor, though. It was right there, at the foot of the bed. Her husband was completely naked except for a leather harness. He was also locked up in a dog kennel. I couldn’t see any expression on his face because it was totally covered by a gimp mask. This was certainly something that I had never experienced before. This woman wanted me to have sex with her while her husband watched from the crate. I can’t say that I wasn’t intrigued. I was also ready to go and I made my decision quickly. It was the first time that someone actively watched me have sex. I loved it. I was taking this man’s wife and giving her what he never could. She even asked me open up the kennel after we finished up so he could clean the mess I left on her face. It was the weirdest sexual experience of my life and I still meet up with them for the occasional dinner and night of cuckolding.

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Hookup Stories

The Best Hookup I’ve ever had

We’ve all had that one hookup that we wish we could relive over and over again. It doesn’t matter if it was because it was with a really fun person or if the sex was just amazing. It was so impressive that it settled deep in our brains to sit there until we want to replay it all on a lonely night. I thought that I would share my personal favorite hookup. You may have had hookup that were better for you, but this one just did it for me. It’s the best I’ve ever had and I hope to have a lot more just like it.

It was with a Booty Call

This wasn’t just some random hookup that night. I suppose it might be possible for it to happen with a total stranger, but it’s much less likely. This was a girl that I had hooked up with in the past and was hoping to hook up with on that night. I was texting her when she brought up her friend who lived right down the street from me. They were apparently talking about hanging out and she asked me if I could pick up the friend and head over to her place. I figured it was worth playing a taxi driver if it meant hooking up with my booty call at the end of the night, so I agreed to it.

The Friend was Crazy

Her friend was out of her mind and I mean that in the very best way. As soon as she got into my car, she started bitching about catching her boyfriend cheating on her. She kept saying that she was going to get revenge and wouldn’t shut up about it. I was just about to resign myself to an awful night of complaining and boredom when she reached over and grabbed my dick over my pants. It was certainly a shock, but I wasn’t going to complain about it. I certainly didn’t complain when she leaned over, took it out, and blew me all of the way to the booty call’s house. She was still wiping me off of her lips when we got out and went inside.

It was All Planned Out

It turned out that the entire night had already been planned by the two girls. They had both been scheming about helping her get revenge on her cheating boyfriend, and what better revenge than a threeway with her friend and her friend’s booty call? These two girls went at each other like they had been flirting and horny for each other for years. Then they turned their attentions toward me. They wanted to do it all and they really wanted me inside every single hole that the cheated on girl had to offer. I guess it made the revenge all the more delicious. It went on for hours and let’s just say that it was the very first time that I found out what it meant to be fully and completely emptied out.

I’m always looking for My Next Best

It was an amazing hookup and I always look back on it with a smile. It gives me hope that hooking up will just keep leading to crazier and more satisfying scenarios. It’s part of the reason that I still hook up as much as I do. If you’re on the fence about hooking for your first time, just take the plunge. You never know what kind of fun that you’re going to be getting yourself into and you never know how crazy the girls are going to be getting.