Sex With My Friend Story

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"It works better if something about them annoys you."
Friends with benefits is a concept many of us have attempted to get right (and if you're me, failed at miserably - I always end up dating them for YEARS). Yet still it remains something we seem fascinated with. And we're talking about the close friends you sleep with, not the fuck buddy situs some people get themselves into.
So, how does sleeping with your mate actually work, like logistically? Does it always end in tears? Here, people who've done the deed with their close friends explain what happened.
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"I actually tend to sleep with many of my friends, and we are all still very close. I hang out with them, some of their significant others, and a lot of the times their girlfriends want me to join. But when I am dating someone, I tend to stay away from any single friends I have slept with. I think it depends on the personality." [via]
"I’ve only slept with one of my friends so far. We met back in high school and we were friends for a few months before we did the deed. We’ve been friends for a decade now and I consider her a very close friend, nay, a sister. I wouldn’t be sleeping with every friend all willy-nilly just because that can get very messy, specially when feelings are involved." [via]

"I slept with a few we are all tight bunch. However we had ground rules to follow. Which overall helped. What happens when friends get a partner, [they might] not be comfy with the fact you guys slept together and [that] may be the demise of friendship. We will have a specific place to discuss and engage in sex (no sex can be discussed or engaged in outside of this space). If someone starts dating, we cease our sex space and solely continue with our friendship and respect our friend's new [partner]. [via]
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"I have a very similar setup with my best guy friend right now - after 3+ years of being close, we finally hooked up and decided it could be a continuing thing unless one of us started monogamously dating someone else (he's in an on and off open relationship ATM). I started casually dating a guy shortly after, but on our first date made sure to mention the arrangement so he could decide if that would be an issue upfront. It's only been a few months, but so far I'd say our friendship hasn't changed, and it's nice to have someone who cares about you but can have their own life without either party feeling ignored or like they're more emotionally invested." [via]
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"In my experience, after we had sex we would never acknowledge what we did outside of the bedroom. Like, it never came up in conversation while hanging out, watching a movie, playing video games, listening to records, talking about dating prospects, etc. Not talking about it wasn't something that was previously discussed or planned out, it just happened that way. It's a fun thing to do with your buddy, but when you're not drinking it's not like you sit around talking about all the times you've had beers together." [via]
"After a couple times I realised we clearly were not compatible"
"I've had sex with quite a few of my friends. I have yet to lose a single friendship because of it. For me at least, it has everything to do with being 100% comfortable with sex/sexuality, so there's never any embarrassment/awkwardness. We talk everything out so we know exactly where each of us stands, and what each of us wants. We also know the importance of being honest about if we only want something casual, or if we want to give an actual relationship a go." [via]

"The first one I had feelings for after a while, which sucked cause he clearly didn't. Now I hate him. The second was with a coworker that I had a lot of sexual tension with, but after a couple times I realised we clearly were not compatible with each other and we are just friends again. Not really awkward and we still talk just fine and joke around. So it really can go either way. Almost works out best if you find someone you can be attracted to physically, but something in their personality annoys you. It helps keep the feels at bay." [via]
"I used to do this with my best friend. It lasted about four years, nothing changed for a while, but he once mentioned if I wanted to be with him. I thought he was joking when he told me it was for real. I said no, because that wasn't part our agreement of just casual sex. After that, he started treating me differently and we just grew apart. It really depends on the person." [via]

"After 15 years from the first time we fucked, I'm still good friends with a woman. She's married with children, and she's happy and I'm happy for her. Another friend wasn't so easy. After fucking, she grew attached. We even talked about conceiving a child together. Which was fine. We were THAT close." [via]
"Didn't work for me... I fell for him after a while and we dated some. Just saying, as much as guys and girls both like sex, the brain is weird and dating is what tends to happen. It also permanently changed the friendship and we were less close after. I've never been keen to keep former male friends around who I've previously had sex with. Not going to say all people end up in that shitty situation, but a sizeable amount do." [via]
"When I was in my early 20s (35 now) one of my best friends and I were 'friends with benefits'. Neither of us wanted a relationship but we both wanted casual sex whenever. This lasted about two years before I [started working out of the country] for an extended period. In that time she fell in love with, and married, a great guy. We're all still the best of friends today. There was never any problems or jealousy. No... we have not so much as even seen each other naked since then. Yes... her husband and my wife know about the prior arrangement. It's a running gag these days."
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Sex With My Friend Story