I’m a 26-year-old lesbian 18 months out of an eight-year relationship. I do not want to be in another monogamous relationship. I want to have a couple of sex buddies or, preferably, a couple of friends with benefits. In the last 18 months, I have had three FWB “arrangements” with different girls. The problem is, about two or three months in, each girl developed serious like/love feelings. Each time, I had to reiterate my feelings about not getting into a relationship and wound up feeling like an asshole. I care about these women and don’t want to hurt their feelings. Am I a bad person? Or are FWB impossible? —Fears Wilting Boundaries
Friends-with-benefits arrangements may not be committed relationships, but they are relationships. They’re ongoing sexual relationships, and—you might want to sit down for this—people have been known to develop like/love feelings for folks they’re fucking on a regular basis. So if “getting into a relationship” is something you want to avoid, and you don’t want anyone developing feelings, you should have one-night stands and/or NSA sex instead. (Those are also relationships, in my opinion, but they’re extremely short-term ones, and people rarely develop serious like/love feelings in a single sex session.) On to your questions: You are not a bad person. FWB are not impossible—there are a lot of successful FWB arrangements—and a desire for exclusivity or a future together is not proof someone entered into a FWB arrangement under false pretenses. And reiterating your disinterest in a committed relationship isn’t assholery.
The sitch: Tend bar with a hot girl who has a boyfriend. Hit on her anyway because I’m that guy. She says I can fuck her but only if her boyfriend gets to watch and eat her out after. I don’t want anything to do with that scene. I was down for some traditional cheating, not this kinky shit. But I’d still like to fuck this girl. Any advice for me? —Blue-Balled Baller
I’m a 28-year-old straight female. I’ve only ever been able to orgasm if I self-induce while alone or if I’m on top during sex with a guy and my clit is being rubbed on the guy’s abdomen. (This works best with bigger guys.) When there is no abdomen rubbing my clit, I fake it. I can squeeze so it feels as if I’m coming, but I’m not. Do you have any suggestions? —Wants Real Orgasms
You’re having real orgasms, WRO. When your clit is fully engaged—using your hands or toys when alone, rubbing against the abdomen of a big guy—you get off. Some women’s clits are fully engaged during intercourse without any extra effort (they can come “just” from fucking), but they’re in the minority. If climaxing during intercourse is important to you, WRO, you’ll have to sleep with big guys exclusively, rub your own clit during sex, or instruct skinny dudes to rub your clit for you.
My boyfriend and I have been together for two years. We were long-distance for the first year and a half. When we were long-distance, he complained that it was hard to have a relationship over the phone. Now that we are in the same city, he says he feels like our relationship has gone “stale” and he feels “trapped.” I’m sick of his complaining. What is he really trying to say? —Confusing Lad Is Nagging Girl
“I’m intolerable and you should break up with me.”
My question concerns my fiancé. He is 35 years old. Between the ages of 20 and 30, he was in and out of jail. He has admitted to me that while in prison, he had sex with a [trans woman]. I know he loves having sex with [cis] women, but I found out that he watches [a porn genre that features trans women who have penises]. He says he is just looking, but I know he masturbates to this. To be fair, he watches tons of porn featuring [cis] women. A lot. He loves watching [cis] women and having sex with [cis] women. My worry is that he wants to have sex with [trans women]. Is this a legitimate worry? He doesn’t watch gay porn. I just want to make sure of everything if we are going to be married. —Fiancé Lusts After [Trans Women] Hottie
You would be foolish to waste your time wondering whether your fiancé wants to have sex with trans women, FLATWH, as it’s clear that your fiancé wants to have sex with trans women. The question you should concern yourself with is this: Can your fiancé be trusted to honor the monogamous commitment he’s (presumably) about to make to you, or is he going to cheat on you with other trans and/or cis women? If you trust that he’ll honor the commitment he makes to you, then his taste in porn and his fantasies about other partners—trans or not—is irrelevant.
Election Day 2014: Tues., Nov. 4