Advice

Sex Advice From Friends With Benefits

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In honor of Hollywood's new favorite relationship, we sat down with some real-life FWBs.

Taylor, 29 & Winston, 29

How did you guys meet? How long did you know each other before the “benefits” began?
T: On OkCupid. One month. We started with the intention of being friends with benefits. 
 
So, in the movies, here’s how this goes: you’re both "over love" because you’ve been dumped or you’re just bad-asses. And then one of you, usually the girl, falls in love and the whole thing falls apart. What makes you guys different?  
W:
Feelings will always develop beyond the initial boundaries set in a FWB situation. Let’s be honest: what’s a true friend you enjoy having sex with? A girlfriend. But, to make a relationship really work, you need that little something extra, the spark, and we don’t have that. The real difference for us is that we know that.
T: Winston and I became very close friends, so naturally I did begin to have feelings for him. I value his friendship and would much rather keep him in my life as a friend than mess it up with a failed attempt at a relationship. 

Which one of you is more likely to get jealous? Secretly jealous?
W: Well, Taylor but, since it’s a secret: [whispers] Tay — lor.
T: I fully admit it, me. 
 
I tell my Aunt Martha that my two friends are sleeping with each other, but that they don’t date. She says, “The poor dears! Their parents must have raised them to have some terrible commitment issues." What do you say back?  
W: "Maybe they just want to get their fuck on, Aunt M. Don't be such a cunt." In reality, I would nod and smile. I know there's nothing wrong with how I live, but the older generations look down on it. But hey, remember slavery? Old people are rarely right when ethics come into question. 
T: My parents didn't give me commitment issues — shitty boyfriends did — but really, I don't agree that participating in a friends-with-benefits relationship means you have commitment issues. My parents have a great marriage and instilled good values in me, but I don't necessarily want a boyfriend until someone who is worth it comes along. In the meantime, this is fun. 

I’m a guy, and I’ve been sleeping with this guy on and off for about a year. The sex is great and casual, but I’m nervous — the more I learn about this guy (it’s a small town), the more I realize he really sleeps around. No judgment; I’m just worried about my safety. Is it okay to ask him about the other guys he sleeps with and if he’s safe with them?  
W: Yes. If you're comfortable enough with another person to give or receive some hot hot lovin' then you should be comfortable enough asking if that hot hot lovin' is going to give you a hot hot rash. And, if you're not comfortable enough to ask a question, then you should keep your parts apart.

Is it reasonable to break up with a girl who won’t even discuss letting me try anal sex?  
T: She wont even discuss it? You need to be able to talk have an open dialogue with the person you're getting naked with, even if she's just going to say, "No, I don't want to do that and here is why."
W: I asked a girl that very question back in college. She simply responded, "Sure, let me try it on you first." That put things in perspective. But really, if a girl doesn't want to have anal, it's likely because she knows it will hurt or be uncomfortable. At least that’s the consensus. Why would you want to make someone you care about uncomfortable? Asshole.

I’m a straight woman who got married too young, and my husband and I don’t really click sexually any more. We have a three-year-old. What’s a bigger sin — cheating discreetly and keeping things together, or getting divorced?  
W: Get divorced, you nut-job. Yeah, I'm sure random people sneaking in and out of your house at all hours of the night followed by blank stares and awkward dinner conversations that eventually lead to blow-out fights are much better than double Christmas presents and rad weekends with Dad. You moron.

My girlfriend and I like to have a threesome or so a month, usually with another girl. If we meet someone out, bring her home, and sleep with her, does she spend the night? I think it’s weird to have some stranger sleep cuddled up with us, but my girlfriend always says it’s rude to throw someone out at 3 a.m., and I agree… if it’s pouring rain. Who’s right?  
T: Threesomes are about sex and only sex. Not emotional support. You don't have to be rude and kick them out but you can ask them politely to go. I can't imagine they would want to stay and cuddle. Awkward. 
W: Thank them for coming and offer to get them a car service. Sex is sex; cuddling is for cats. You wouldn't fuck your cat would you? 

Period sex — a right or a privilege?  
W: That's what blowjobs are for.
T: Copy that, Winston.

My boyfriend wants me to shave my pubic hair. I don’t. I know he’s grown up watching porn and thinks it’s normal, but it’s not, and I hate that misconception. I don’t want to sacrifice something that I believe in for him, but I also want him to turn him on. What’s a girl to do?  
W: Is that a real question? First off, it's hair — it'll grow back. Second, are you really fighting for normality by protecting your pubic hair? Third, fine, don't shave. Also, don't get oral sex. There's your sacrifice. No one wants to eat Jelly Bellys off of Don King’s dome piece.

Taylor is one half of The Urban Dater. Check out her writing here

Patty, 51 & Kyle, 40   

How did you guys meet? How long did you know each other before the “benefits” began?
P: We actually met on Facebook, and started chatting right away and soon after, meeting up to hang out. I don't think we actually hooked up until about a month after. I seem to recall that right up front we both said we weren't looking for anything serious. He was just dipping his toes in the whole scene anyway and wanted to explore. I think we both knew right off we weren't supposed to be anything more than good friends. I'm heavy into helping people explore their sexual capabilities and he is a very good student!

Can you tell us a little about your relationship? How does it work? Are there rules?
P: We chat almost every day on the phone, and try to meet up when convenient. So many people are so fricking busy these days! We usually make plans to meet at least once every two weeks or so for some slap and tickle. 
K: I don't have a clue how it works, but we can talk about anything. I don't think we have any rules. But what’s really important is communication; otherwise someone’s going to get chased with a butcher knife.

So, in the movies, here’s how this goes: you’re both are  "over love" because you’ve been dumped or you’re just bad-asses. And then one of you, usually the girl, falls in love and the whole thing falls apart. What makes you guys different? 
P: Everything was right on the table, pretty much from the get-go. I think I got into this with him because, while he's really cute and funny and great to hang around, he's not "the one." I think we are different because we can read each other pretty well, he's pretty calm and funny, and he can put up with my stoned rants when we hang out.
K: Well, the first part’s still right! I think the real thing is we don't have any expectations; I don't really have time or interest in a real relationship right now, but I'm a giving and generous friend. With benefits.

Which one of you is more likely to get jealous?
P: We haven’t had any jealousy, save for one incident early on, when he was really dating someone and I became verboten! (I think I got upset less from the fact that we couldn't play anymore, and more from how controlled his time was — he had none for me for a while.) If he gets jealous, it’s only because he hasn't gotten a chance to play with me in a while and he's a bit pent-up.
K: I don't get jealous — I can wait my turn. (Oh, wait, does that make you sound slutty? She’s not, I promise!)

I tell my Aunt Martha that my two friends are sleeping with each other, but that they don’t date. She says, “The poor dears! Their parents must have raised them to have some terrible commitment issues." What do you say back?
P: "Well, Aunt Martha, seeing as you've been married and divorced three times, I don't see where you can say that. Can you?"

I just broke up with someone after six years together. I feel like I need a while — a long while — by myself. But I’m also horny as hell. What’s the best way to find a friend for regular casual sex, without giving off the wrong signal?
P: If there isn't a willing partner in your immediate circle you think might work, I'd explore the online sex/dating /swinger sites for hook-ups. (Not Craigslist though, it's gotten very good for hosting the creepiest of creeps lately.) As far as wrong signals, make sure you approach your friend when you're both sober, and can discuss what it is you're looking for. If you see puppy-dog eyes, run!
K: Oh God. I'm the wrong one to ask. If not for word of mouth and good reviews, I'd be as celibate as a priest.

Is it reasonable to break up with a girl who won’t even discuss letting me try anal sex? 
P:
If it's the only thing that's going to rock your world, then yes. If after your presentation of numerous charts, graphs, tons of lube, training videos, and testimonials, she is still reluctant, then only you can decide if it's worth staying in the relationship. See, this is where a FWB can come in handy. You can get them in all kinds of models, from straight-sex-only all the way to orgy-ready.
K: That’s what your other friend is for, silly.

My girlfriend and I like to have a threesome or so a month, usually with another girl. If we meet someone out, bring her home, and sleep with her, does she spend the night? I think it’s weird to have some stranger sleep cuddled up with us, but my girlfriend always says it’s rude to throw someone out at 3 a.m., and I agree… if it’s pouring rain. Who’s right?
P: I'm a bad one to ask, since I've been hating sleepovers lately. (Unless it’s George Clooney. George, are you reading this?) That lovely white lie, "We have to get up really early for a family wake," always works. But think of safety — if she's riding the subway home that late, I'd say let her stay.
K: I don't know. I've never had a threesome before. Patty, got any friends?

Period sex — a right or a privilege?
P: You say period sex. I say sex. Period. (This is where towels and rubber sheets come in handy.)
K: Is her mouth broken? Just kidding! This is why I didn't have anything going on last night. But what's another week? I’ve got two hands!