Girls on Girls: Stories About Sex

By Playboy Staff

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What makes her sleep with you? We asked 5 women to tell us their hook-up stories.


We haven’t reached Hump Day yet, but we are one day closer to the weekend.  One day closer to the woman of your dreams or at least one day closer to a potential pick up: a no strings, no phone numbers, no expectations one night stand. But what makes her choose you? Women are nothing if not unpredictable—even to themselves. Whether it’s the nerdy best friend sequestered in the platonic zone, or the cocky player with bad news written all over his Ed Hardy shirt, sometimes a girl sleeps with a guy she never thought she’d take to bed. Sure, booze is frequently a factor, but there is often an unforeseen trigger that kicks a woman’s horny thoughts into gear. We asked girls to reveal what prompted their most unexpected hook-ups and how the sex turned out. Who knew a woman could be seduced by a drunken back-flip into a brick wall?

“I was so tired and hungover that I thought, ‘fuck it,’ and I gave in. ”

Emme; 31; Musician; Chicago A guy friend used to always flirt with me and chase me around, but I never wanted anything to do with him because he was not my type. I like skinny guys with tattoos and he kind of had a belly. He just wasn’t a guy that you look at and think, “Damn. I want to have sex with you.” I repeatedly blew him off, but one afternoon it just happened randomly. I’d been at a party all night and I was waiting for the bus so I could go home. I was hungover, felt like crap and was standing out in the morning sun just sweating and wishing I could be anywhere but outside. Out of nowhere, my friend drives up in his car and asks me what I’m doing. I told him my predicament and he said, “Why don’t you come home with me? You can chill out at my place and relax, take a nap, whatever.” I totally fell for his little invite, never imagining that I would end up in his bed. I went to his house and we hung out for a while, but it did not take him long to put the moves on me. I was so tired and hungover that I thought, “fuck it,” and I gave in. The crazy thing is that it ended up being reallygood. Basically he was a total freak in bed and I just wasn’t expecting that at all. Even though I was never very attracted to him, the actual sex ended up being super-hot and very kinky and I enjoyed every minute.

Amanda; 28; Reporter; San Francisco In college I waited tables at a restaurant and there was a guy who worked in the kitchen who always flirted with me. He would always say, “I’ll rock your world if you just give me a chance.” I ignored him because I thought he was being stupid and cheesy. We were friends but he would constantly go on about how he would knock my socks off in bed if I would only give him the opportunity, and it became an ongoing joke. One day we were meeting some friends at a bar and he had to stop by his house. I went inside with him and as I was waiting, he told me he could give me the best orgasm of my life if I would just let him go down on me. I laughed it off, but he persisted and told me to “just give him a few minutes.” I have no idea why, but I totally gave in and let him take my pants and underwear off. Then he just went to town on me and within a matter of seconds I was in heaven. It turned out he hadn’t been exaggerating. He definitely knew what he was doing and he had the strongest, most amazing tongue I have ever felt down there. He wasn’t someone I would have normally been attracted to, and he wasn’t my type in any way, but when I left his apartment that night I was happy I had given him a chance to prove himself. He gave me one of the most intense orgasms I’ve ever had. I still remember it to this day, and it’s been more than 10 years.

Read more dirty details of her hook-up, next…

Alex; 34; Architect; Washington D.C. About 10 years ago I was out at a club in New York City and there was this guy there that knew some of my friends and was hanging out with us. He was short and too much of a hippie for my taste, but as the night wore on and we partied, I noticed that shorty-pants was a really good dancer—like, really good. He was breakdancing and people were moving out of the way to watch him. The more I saw, the more attractive he became to me. I know alcohol influenced my thinking, but his confidence and dexterity on the dance floor made him suddenly hot. I started dancing with him and the next thing I know, we’re making out like horny teenagers in the middle of the club. Yes, I was that girl. Shockingly, midget-hippie-boy turned out to be a damn good kisser so I went back to his apartment. That’s where everything fell apart. He wasn’t particularly well-endowed, which isn’t the worst thing, but let’s just say that dancing and kissing were where his talents ended. We had sex at his place, but it was underwhelming. I was disappointed because I presumed a guy who could move like that on the dance floor would be able to move well in bed. Even worse, he dragged me to the Farmer’s Market at 8 a.m. and droned on endlessly about organic food and “the beauty of the early morning.” As soon as I could, I fled back to my hotel.

Amelia; 29; Historic Re-enactor; Washington D.C. When I was a junior in college, I was 25 years old and there was this guy who was only 19. For weeks he tried desperately to get my attention, but I kept turning him down. He was a big, hulking and a typical drunk, wild fraternity boy. I was so over that type, so I wasn’t interested. One evening I was sitting outside of the dorms chatting with some of my friends and I saw him heading our way. As usual, he was totally wasted and blatantly trying to get my attention. He started doing flips and crazy acrobatic moves right in front of us but because he was so drunk, he ended up catapulting himself into a bush, directly into a brick wall. After that pathetic but amusing display, I thought, “What the hell?” He had tried so damn hard to get my attention for so long, I figured I might as well give him a shot. To my utter surprise he was great in bed. To this day, he is one of the best lays I have ever had. Our bedroom romps only happened a few times and then fizzled out because there wasn’t much else to him besides his talent in the sack. But it was definitely fun while it lasted and I don’t regret my decision to throw sound judgment to the wind.

“That kiss turned into a very hot and heavy make-out session in his apartment   that lasted for hours.”

Alison; 31; Publicist; Los Angeles I used to be really close to a guy that I worked with. Although we were inseparable, I never thought of him as more than a friend. To put it bluntly, I just wasn’t attracted to my co-worker pal. He was nerdy, short, chubby, pale and losing his hair. One night I had a very vivid and realistic dream, and in it, my friend told me he had feelings for me and we shared an extremely sensual kiss. I woke up feeling like it had actually happened and couldn’t get the dream out of my head. I spent that whole day at work looking at my friend in a totally different light. Everything he said seemed extra-hilarious and I kept staring at him and wondering if I was sexually attracted to him. The next day we flirted all day long at work and then we kissed outside on the street that evening. That kiss turned into a very hot and heavy make-out session in his apartment that lasted for hours. He was a fantastic kisser—not too wet and slobbery and not too timid and light. The sex was phenomenal because we were so familiar and comfortable with one another. My short, slightly overweight, balding pal whom I’d never thought about in a sexual way ended up being one of my best bedroom experiences.


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