Dear Dan: 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
Dear BBB: Nope.
Dear Dan: 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 by squeeze as if I’m coming. Any suggestions?
Wants Real Orgasms
Dear WRO: 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 during intercourse — 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.
Dear Dan: My fiancé is 35 years old.
Between 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 [porn genre]. 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
Dear FLATWH: 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.
Dear Dan: I’m a married straight man. My wife and I have been married for five years. I thought my wife was GGG and open to new things, so six months ago I brought up my desire to wear lingerie — she did not react well. We struggled a bit but gradually got back to normal, with me just not mentioning it again. My birthday is in May, so I proposed a weekend of indulgence of my fetish as a birthday present. I thought that would be easy enough to accommodate. I was wrong and got totally and uncomfortably denied. I’m at a loss for what to do. I don’t want to destroy a marriage over a small sexual interest, but I don’t want to be locked into vanilla sex forever. Any advice?
Partner Against Nighties That Intrigue Eager Spouse
Dear PANTIES: Someone can be “open to new things” without being “open to everything.” So your wife might be up for exploring other sexual kinks, positions, and circumstances — hubby-in-lingerie isn’t the only form of non-vanilla sex out there — but seeing you in panties could be a “libido killer,” a term coined by Emily “Dear Prudence” Yoffe. If that’s the case, PANTIES, she may never come around. But if it’s not a libido killer, if it’s just something she hasn’t had time to wrap her head around, your best course of action is to drop the subject for now. Let the wife see that your interest isn’t all-consuming and you still enjoy vanilla sex in genderconforming underpants, and indulging this particular kink may come to seem less threatening.
Dear Dan: Where can straight women find men who won’t make odd sexual requests?
Dumped One Again
Dear DOA: Graveyards.
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