Q: I am an 18-year-old pansexual girl. I’m currently in a relationship with a guy. He is a bit younger, though mature for his age. We get along great, our friends like us together, yada yada yada. He wants to do the waiting until marriage thing for sex. I’m cool with that, less pressure in the relationship. He wants to do this for religious reasons, which I mostly agree with. We met in youth group, after all. Here is the real kink. I lost the big V about a year ago. He knows about that, isn’t happy about it (’cause he hasn’t), but is willing to date me anyway.
What hasn’t really come up is the subject of porn and masturbation. Back to the religious reasons: He doesn’t do either and doesn’t approve. I, however, do both. Especially since my breakup (and thus no more sex) last year, I’ve come to rely on masturbating to take care of my sexual needs. The porn I am willing to forgo, but I don’t want to give up pleasuring myself. This guy knows nothing. He has talked about how we ought to “keep ourselves pure.” Is there any good way to communicate to him that I’m not going to give up masturbating without him going crazy? It took long enough just to show him I wasn’t the spawn of Satan because I like girls as much as I like guys.
Mismatched On Sex
A: The best way to communicate to this boy that you aren’t gonna give up masturbation is to break the fuck up with him, MOS. Your boyfriend is essentially forcing you to pick between him or masturbation, and the choice is obvious: Masturbation is a pleasurable friend that doesn’t judge you or shame you, and your boyfriend is an unpleasant, sex-negative, controlling, judgmental scold.
Then, after you’ve enjoyed a few dozen celebratory guilt-free orgasms, MOS, ask yourself why you wasted even two minutes of your precious pansexual time on a guy like him, i.e., someone with whom you’re clearly not sexually compatible. You’re pansexual! Somewhat sexually experienced! You masturbate! You enjoy porn! I could understand you dating a guy who was a virgin and wanted to remain sexually inactive for now — for religious reasons or otherwise — but dating someone you had to talk out of seeing you as the spawn of Satan? Dating someone you have to lie to about something as common and healthy as masturbation? Not worth it — not in the short run, not in the long run. You want to be with someone who likes you and wants to be with you, and this boy doesn’t like you. Why on earth do you like him?
Q: I’m a 24-year-old straight male and I’m unattractive. Physically I’m not bad (not hot, but not ugly), but sadly, I’ve suffered from extreme depression all my life. I’ve gotten help, and it’s made me a little better, to the point where I’m functional. Now here’s my issue: Low self-esteem and lethargy aren’t exactly the best things for attracting the opposite sex. My sex life is poor, and my love life is nonexistent. I’ve never felt romantic chemistry with a woman ever, and I’m honestly losing any faith that it will ever happen. I’ve always tried to respect women, but my inability to attract them sometimes leaves me feeling resentful. I don’t want to become a bitter men’s rights activist, so I’m wondering if you have any advice.
Unattractive Guy Longingly Yearns
A: Did you see Louis C.K.’s most recent comedy special? He does this bit about schlumpy guys — guys like him — who don’t have much luck with women when they’re young. “I like getting older,” he says, “because for me, the kind of guy I am, getting older makes my life better. My sex life? Way better at 45 … I’d like to make one of those ‘It Gets Better’ ads for dumpy young guys. We could use a little help, a little encouragement.”
Louis C.K.’s advice for you: “Stay relatively employed and washed; you’re going to be amazing in your 40s. You’re going to be the branch she can grab before she hits the ground. It’s going to be so great. It just takes time for her circumstances to match your looks. When real shit matters, you’re going to be the sexiest motherfucker in the world.”
My advice for you: Keep working on your depression, throw yourself into nonsexual pursuits that you enjoy, find a job you like and build a career, locate and patronize (and overtip) an independent sex worker (which can help you learn to interact with women), and don’t allow bitterness to ruin you for all those women you’re gonna get with in your 40s.