The best hookup of my life was also the most messed up.
I dated an abusive guy for about 2 years. After everything had ended, I developed a kink for hooking up (never sex, just teasing) with people he knew. It was a way of showing him, hey, I can get anyone I want. And look at all this stuff I did for you. I can do that for other people too.
So the hottest guy from my high school messages me and just happens to be the brother of the ex’s best friend. Which is exactly my type. Let’s call him H.
We match on a dating site and talk constantly. He’s really fun to talk to. I’m hooked. We talk about everything from hobbies to jobs to future plans. When he started talking to me though, I knew he would snap my heart in half.
He’s also over 6 ft tall, bigger guy, (the exact opposite of my ex), nice face, really hot. Stimulating in both ways.
He eventually leads the conversation to watching Game of Thrones at his place and tells me to watch an episode. So, I get really stoned and do just that.
At the same time, my male friend Dale happened to hit on me because I messaged his friend back on Instagram and he just assumed I would go for anything.
That’s when it hits me. How much guys gossip about me. As I watch this episode and see how much sex is in it, I turn away and literally start laughing my ass off for 20 minutes. I can’t stop.
The thought of them gossiping and trying to figure out what I would do like some sort of game is fucking hilarious to me. And the fact that they gossip more than most girls I know. The thought makes me laugh and laugh and laugh.
The next day, I’m distant from H. He can tell I’ve figured it out. But I also don’t give a fuck what any of those people think anymore. So I lead him on and pretend it’s fine and I’m still down to watch Game of Thrones. Which is exactly what this little screwed up mind game is.
A part of me knows this is a terrible idea. But a bigger part of me didn’t care.
So the part of me that knows it’s bad resists. I distract myself with friends while he tries to get me to come over. But the one night, he caught me on the right one. I was alone, everyone was with their significant others, and I thought fuck it. Let’s settle this once and for all.
So I head over to his place , which I’ve been to many times before having dated the 2 year guy.
I was a little late, about 15 minutes, which I think made all the difference.
I walked up to the door, he greeted me, everything was good. We talked for a bit about the obvious fact that I’d been there before and I joked about talking to his mom but never seeing him.
He lead me upstairs to his room. We had casual talk about his trip to Europe and all of the cute little souvenirs in his room. He gets me a drink. Eventually we start watching Game of Thrones on his laptop. I try to pay attention but I honestly couldn’t give a shit about that show. It reminds me too much of my ex.
Then he says he has to go to the washroom. This is where it gets interesting and our little conflict arises.
He leaves to the washroom, and suspiciously tried to get me to keep watching the show without him. I check, and it looks like he’s brought his phone, which is also quite suspicious. I sit there, wondering what the fuck is up.
Then, I get a text on the laptop. It was from his brother, B. The one that’s connected to my ex.
It says “Can I go to the washroom?”
That’s when my suspicions are now valid. He’s trying to do some recon to see how far I will go with him. Not only that, but his brother and God knows who else are in the house and can hear literally everything.
He comes back right away because he realized he screwed up. We continue to watch the movie and pretend that everything is fine. I say to one of the characters on the show “You little bitch.”
But I’m not talking about the character on the show.
He starts to get super nervous. He can tell I’ve figured it out and gulped. This is when my fight or flight response kicks in. I am going to fight with everything I have not to let this guy fuck me. Everyone in his life has already fucked me enough.
So I cuddle up and get really close to him and pretend that everything is fine. One of the characters on the show says “She still loves you.” And he rubs my arm because he thinks that’s the case and doesn’t realize how bad I’m going to mess with him back. I mentally shut down to that ridiculous show.
He notices I don’t really care about it anymore and asks what id rather do. I play coy and play up my sexuality times 10000. I act like a silly little sexy girl until he tries to hook up with me.
It gets super heated. But I do nothing major. I don’t let him see my boobs, touch anything of mine, nothing like that. I tease tf out of him and then randomly cut it short, claiming I’m just such a good girl.
That’s when he figures out what I’m doing.
So he talks me down out of this little anxiety attack I was having, as I was acting pretty aggressive. He’s so smooth and so good at it. He uncovers my mental state and figured out why I’m even at this house still. It’s because my ex has hurt me so bad. I did so much for him and he did barely anything for me.
So it gets really sweet and cute and we start cuddling. He puts his body on top of mine and dares me to squirm away. He’s so big and I’m so small that I literally could not get away. He overpowered me times 100. Which was super hot.
Then I tried it to him. I put my body on top of his and said “Can you get away now?”
He said “I don’t know if I’d want to.”
So we cuddled like that for a while. It was so nice. I felt a real connection with him in that moment, so I kissed him. I told him sorry, the urge just came over me so I did it. He told me I could do it again.
So I did. And it got super fucking hot. Insanely hot.
He knew exactly what buttons to push. He knew exactly how to turn me on with just his fingers. That’s all he needed.
He does everything to turn me on. Grabs my tits, tell me they look amazing tells me “you’re so hot.” Chokes me while fingering me. I lose my fucking mind and I’m pretty sure I came twice. It’s the most intense hookup of my life. So much buildup leading up to it.
But there’s one issue still. He wants to actually fuck Me. In the shower. But after he lied, there’s no way in hell im getting in that shower for his brother to listen to me get fucked.
Or letting him fuck me at all.
So I resist as much as I possibly can with everything in me. If he gets to fuck me, and he wants to do it doggy style, then he wins this messed up little game. Just that I’m taking it like a little bitch. Like I did that entire relationship.
So I resisted. He tries every trick in the book to get me in that shower. He makes a pros and cons list. He tries to force my hand by leaving the room. He tries to convince me saying “You’ll feel so much better.”
But none of it works. Because I know he’s full of shit. And a little gossip. So I’m going to win this game, to some extent.
So I finished. Twice. It was mindblowingly good. After all of that, he still wants to get off too, obviously. So I tell him, let’s compromise.
Now I see why he wanted to do it doggy. For such a big guy, his size isn’t particularly impressive. But he doesn’t need it to drive me wild, and I prefer medium ish sizes anyways.
I give him a handjob. It lasts maybe a minute at the most. Probably even less than that.
He said “I like compromises” after we’re done.
So I sleep over and fuck with him a little more by keeping him up longer than I needed to. I left at 7 in the morning and We had a very brief discussion the next day before I blocked his number. I sent him a text a few days later explaining that I knew and was upset, but hoped we could be on good terms with no weirdness. I got no response.
But that’s not too important because it’s a fun memory to look back on. Thanks for reading!!