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Sex Advice From Friends With Benefits
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.