Once on vacation I found myself seriously attracted to a man I definitely wasn’t supposed to be—a friend of my dad’s, whom he’d invited along. (Hey, I was 24. And he was only 30. OK, maybe 35.) After a day of sailing and a night of hotel bar karaoke, we ended up hooking up on the beach, and spent the rest of the week having a super-secret fling.
Why? Precisely because he was the one person I shouldn’t have gone anywhere near. At some point every girl has had a thing for someone in the “do not touch” category—her best friend’s brother, her sorority sister’s ex—and has, per the rules of polite society, done her best to stay away. But if you think there’s no way she’d cross that line, you’re probably wrong—I’m living proof. Thanks to their illicit nature, off-limits hookups are usually off-the-charts hot. And when played correctly, the reward can be worth the risk.
The girl: your roommateI know four couples who started out as roommates—which shows this challenge can be met, but also stands as a warning: Things can go from zero to husband-and-wife-like very quickly. Still, if it’s easy sex you’re after, a coed roomie can be a jackpot.
When Margaret,* 33, got a new roommate, she said it was only a month before they were fucking on the couch. “One minute we were laughing at Modern Family, the next we had our hands in each other’s pants.” Even hotter: They had to keep things secret from a third roommate. “While we were all hanging out, he’d give me a look, and I’d count the minutes before I could sneak into his room.”
Why? Precisely because he was the one person I shouldn’t have gone anywhere near. At some point every girl has had a thing for someone in the “do not touch” category—her best friend’s brother, her sorority sister’s ex—and has, per the rules of polite society, done her best to stay away. But if you think there’s no way she’d cross that line, you’re probably wrong—I’m living proof. Thanks to their illicit nature, off-limits hookups are usually off-the-charts hot. And when played correctly, the reward can be worth the risk.
The girl: your roommateI know four couples who started out as roommates—which shows this challenge can be met, but also stands as a warning: Things can go from zero to husband-and-wife-like very quickly. Still, if it’s easy sex you’re after, a coed roomie can be a jackpot.
When Margaret,* 33, got a new roommate, she said it was only a month before they were fucking on the couch. “One minute we were laughing at Modern Family, the next we had our hands in each other’s pants.” Even hotter: They had to keep things secret from a third roommate. “While we were all hanging out, he’d give me a look, and I’d count the minutes before I could sneak into his room.”
If you’re not social with your roommate, it’s still easy to get cozy after a night out. “The first time my roommate and I hooked up, we’d gotten in late around the same time,” says Erin, 25. “He asked if I wanted a nightcap, so we cracked some whiskey and stayed up talking, and one thing led to another. Now we do it every few weeks.”
The move: Adjust to her schedule so you can bond. Does she wake up at seven to do yoga? Get up to make coffee. She likes to watch American Idol? Make it your new show.
Danger factor: Any resulting awkwardness only lasts as long as your lease.
The girl: your GF’s sisterThe guilt factor in destroying a blood bond could be major. The good news is, it’s tough to do. “I had sex with a guy my sister dated, only because she and I had a rivalry that made him seem like a prize,” says Stephanie, 30. “It was a few years after they’d gone out, so she was pissed when she found out, but not enough to stop talking to me.”
Younger siblings tend to have a chip on their shoulder from years of being compared to big sis, so tell her how smart, pretty, or funny she is and she might reward you. Or she just might be a psycho, in which case you won’t have much work to do at all. “My little sister boned my college boyfriend right under my nose,” says Kelly, 32. “He was visiting me on our winter break, and my parents made him sleep in the basement. She was still in high school and going through some party phase—pills, booze. Part of her ‘cry for help’ was to crawl on top of him in the middle of the night. The best part was that he fucked her but told me about it as though he’d been taken advantage of somehow. I dumped him immediately.”
The move: Siblings are notoriously competitive. Prey on that—and hope it’s worth the pure hell that may follow!
Danger factor: Upset the sisters and you might have to deal with the dad. Just sayin’.
The girl: your intern
Hooking up with a colleague isn’t that unusual these days, but it’s much riskier when she’s your subordinate. Still, in a way you’re in luck: Women are seriously attracted to men in a position of power.
“I had sex with my boss when I was a 20-year-old intern at a newspaper,” says Kat, 27. “He’d take me out for lunch and help me with my résumé. I made the first move, but the fact that he was willing to risk his job to do it with me made me feel irresistible.”
The potential for scandal is actually a turn-on for a lot of women. One girl said she wanted people to find out about her affair because it made her feel superior over other colleagues—that her boss had chosen her almost felt like approval for a job well done.
“I’ve hooked up with several superiors,” says Melissa, 28. “One was my HR director, so it was beyond wrong. Another guy was my direct boss, and he’d give me crappy tasks, like walking his dog at lunch. When I got
to his place, he’d be waiting for me. People at work had no idea we were fucking.”
The move: Make her feel like one of the gang: Invite her out with more established colleagues, and give her legit work to do. But look into company policy first—no one wants to be ID’d as a harassing sleazebag.
Danger factor: Smokin’ assistant versus ongoing employment. Hmm.
The girl: the out-of-your-league crush
She’s not strictly off-limits, but society still deems you can’t sleep with her. Why? Because, frankly, she’s a lot hotter than you. However, that doesn’t mean she won’t give you the goods.
“I hooked up with my nerdy lab partner in college,” says Colleen, 28, who was president of her sorority. “He was pock-marked, with an orange ’fro. But we spent long hours working together, and he was super-supportive when I’d get frustrated. One night I needed a stress reliever, and he suggested we blow off work. We snuck into an empty room, and he made a move. I was shocked—he was a great lay!”
The move: Give her the right kind of attention. When other dudes dote, be casual. If they treat her like a trophy, act like you’re on the same level. She’ll find it refreshing.
Danger factor: You may be embarrassed when people wonder why she’s with you. But who cares?
The girl: your best friend’s ex
Assuming you spent a lot of time with her, it was probably hard not to imagine her naked. The good news is, she likely had the same thought. And if she’s upset about being newly single, nothing says “screw you” to her ex like screwing his buddy.
“My current boyfriend used to be good friends with my ex,” says Alicia, 29. “After the breakup, we’d talk about what went wrong, and he’d say things like, ‘He’s crazy to let you go.’ Soon we were making out, half because he made me feel good and half because I just wanted to burn my ex. Eventually, we fell for each other for real—and they stayed friends.”
Not all endings are that tidy, but who cares when the sex is so good? “Once when my boyfriend and I were in a huge fight, I fucked his best friend,” says Diana, 23. “I ran into him at a bar right after the blowout and was so furious I pulled him into the bathroom and rode him like crazy. We kept it on the DL when my guy and I worked things out. But I still smile thinking about how hot it was.”
The move: When women are going through a breakup, they love nothing more than talking about it. So be her shoulder to cry on. He was selfish? You love giving foot rubs! Play his opposite and you’ll be the new boy in her bed in no time.
Danger factor: This is a terrible idea that will never, ever end well. Trust us.
