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Here is a collection of the the boldest and most shocking sexual advances stories told by Reddit users. Enjoy!


“At friend’s house, having missed the last shuttle back to my college, I was ‘forced’ to stay over. While getting comfortable on the couch, my friend asked me if I needed a blanket or anything. I said that I was good, but that if she needed a body to just let me know”

Worked.” via SekuHara


“A girl I know had just broken up with her boyfriend. I texted her saying ‘so, you’re single now?’ she said ‘yeah, time heals all wounds though.’ I responded  ‘So does casual sex.’

Then we had casual sex.”


“I was drunk at a bar. A guy I liked was there. I asked him to walk me out so I could maybe get a kiss out of him. He was being a ~gentleman~ and was like, “You’re drunk… I don’t know..” I dropped to my knees in the snow and begged. He gave me a kiss and we dated for a few months.

Boldest AND Most Pathetic. It doesn’t usually take that much” 


“Once I was making out with a girl (who didn’t want to have sex) on my bed. It was getting pretty hot and heavy and when I flipped her on top of me, I heard something go SNAP! So I got up and investigated; Turns out one of the slats holding up the box spring had broken right in half. I got back on the bed and told her “Well, we already broke the bed. People are already gonna assume the worst so wanna make it worth our while?”

She responded by taking her pants off :)” 


“I had just broken up with a girl. She had taken a dump in my heart. I was out drowning the sorrow with ungodly amounts of whiskey. Decided i may as well go to a club and see all the happy people. I was walking down the street and i bump into my ex’s little sister, just finishing work. She asks me if i want to get a drink with her and talk about the breakup. I figure, why not, i could use some company. she aks if i want to go to her house, since louise (my ex) is away. Again i figure why not i didn’t have anything better to do. So we get to her house and she pours us some wine. I’m a little drunk and i figure what the hell, so i lean in and kiss her. Next thing i know we’re on the couch ripping clothes off each other. She asks me if i want to fuck her on my ex’s bed. Fuck yes i do. we’re fucking like animals and she whispers into my ear “do me in the ass”. So i do. Turns out she fucking hates her sister and didn’t think she deserved me or something. We had an ongoing freinds with benefits situation going on for about a year after that.

fucked my ex girlfriends little sister. In the ass. In her bed. Revenge is a dish best served analy” via big80smullet