Dear Dan: I’m a 30-year-old straight woman, and I’ve been with my male partner for four years. Here’s the thing that’s been bugging me: After four years, the sex has gotten predictable. But it’s also gotten better in the sense that I orgasm a much greater percentage of the time, now that he knows my body and what I like. More orgasms for me are great, but in the service of that, we’ve fallen into a “tried-and-true” rut, which I don’t think is good. I try to switch it up sometimes, and I surprised him with some sexy lingerie last night… and I got self-conscious, started to worry about whether I’d get off, and then didn’t come. I know he really likes it when I get off, but I don’t want for us to have such a limited repertoire. My feeling is that I should not worry about my orgasms and focus on spice and variety, but I think that if we go too many times without me coming, it might be a downer for his boner, too. So which do we give preference to: variety or orgasms?
Rutting Or Undertaking Totally Interesting New Experiences?
Dear ROUTINE: Your “tried-andtrue” repertoire may feel like a bit of a rut, ROUTINE, but it’s a successful rut.
You have two competing and conflicting interests: You want to come regularly (because of course you do) and you get off consistently when you stick to your routine, but you also want to shake up your routine and try new things. But trying new things — even something as low-stakes as fucking in frillier underpants — makes it difficult for you to come. My advice would be to relax and give yourself permission to not come when you’re trying something new. To stave off frustration and/or selfconsciousness, ROUTINE, constantly remind yourself that new things you both enjoy will be incorporated into your routine. And when things that work for you both join the ranks of the tried-and-true, you’ll be able to come while you’re doing them. This problem solves itself.
And remember: You don’t have to stop doing the shit that works now. Let’s say you try something new on Wednesday night — new kink, new locale, new hole — and you enjoy yourself but you don’t come. So the next time you have sex, ROUTINE, stick to the already “tried-and-true” stuff that gets you there consistently.
Dear Dan: My best friend has a girlfriend of two years. They break up a lot, and he has slept with plenty of other girls over the last two years. I’ve had a crush on him for about three years, but I never made any advances. We did have a threesome with a girl in March — he was broken up with his girlfriend at the time — but it was all about the girl and nothing happened between us guys. He got back with his girlfriend after that. Then last month, he and I had sex with each other. We had been drinking, he initiated it, and neither of us came.
It was awkward, and we didn’t talk for a week. Then we bumped into each other, and he came home with me and we had sex again. I came this time, but he drank too much and couldn’t. Then three weeks ago, I initiated it and we did it again. This time he came. The next day, he said that the “gay sex stuff ” had to stop. He said he felt like he was cheating on his girlfriend. I agreed. But later that same night, he started getting flirty with me and seemed to be on the verge of initiating again. The issue is, I still want to sleep with him. Do you think that he may have freaked out about liking it too much? Could he be developing feelings? I rarely see him now, due to him hanging with his girlfriend all the time. I can tell that he has had sex with a guy before — it slid in pretty easy and he kept saying how good it felt. I’m so confused on what to do!
Boys Easing Sex Tension Secretly
Dear BESTS: Maybe it would help if you told your friend that you’re not having gay sex — you’re having hot, sweaty bi sex. As for what to do… You might wanna look around for some other guy — maybe even a gay one — who you can have a crush on and slide into. But I’m not going to push you to do that, because it’s clear that you’ve got feelings for this guy and at the very least he’s got Feelings While Drunk for you. And while I should probably scold you both for fucking around behind his girlfriend’s back, I have a hunch that you’re very young adults. So you’re getting a pass because this kind of bullshit is often a necessary rite of passage for kids who are still figuring out who they are, and who they can and cannot trust. But I predict that this will end badly, and you will one day look back on the way you once believed that “breaking up a lot” was evidence of a passion that could not be denied (when in actual fact it’s evidence of a couple of twats who cannot be endured) and be deeply, deeply embarrassed. But in the meantime, BESTS, enjoy sliding in.