Q: I’m a 40-year-old female, cis-het. I have very discerning tastes in men, and always end up alone. Any way to be more open without sacrificing my standards?
A: You’ve either had a terrible run of bad luck—assuming you’ve dated more than ten men—or you’ve set your standards impossibly high. Some food for thought: perhaps you think you want a long-term relationship because you were told that’s what you’re supposed to want—you were told that’s what all good people want—but you actually don’t want a long-term relationship. They don’t make you happy. But instead of telling yourself that you’re a good person who prefers short-term relationships and/or being alone, you’ve set your standards so high—you’ve dialed them up to sabotage—because you want to be alone. And instead of owning that about yourself, you find fault in the men you date.
P.S. There’s no settling down without settling for.
Q: Is there any way to enjoy anal while having a hemorrhoid?
A: Nope, sorry. You need to wait for it to heal.
Q: I’m a 36-year-old man. If I get too psyched out to stay hard for (extremely rare) anal with my wife, should I just get some Viagra?
A: Well, that depends. Does your wife like long anal sex sessions? If the answer to that question is yes, then Viagra could help. Because in addition to helping you get and stay hard, Viagra and other ED meds can delay orgasm. But if your wife doesn’t like long anal sex sessions—if she generally wants you to hurry the fuck up and get the assfucking over with—lasting longer could make those already rare anal sex sessions rarer still. Maybe try a cock ring instead?
Q: Tips for helping a penis-haver last longer when penetrating other than cock rings? (Cock rings are great, but they don’t help with longevity.)
A: Cock rings are great; I recommended them to another reader five second ago. But while a snug-but-not-too-tight cock ring can help keep a penis-haver’s penis hard by gently restricting blood flow out of the penis-haver’s penis, cock rings don’t make penis-havers “last longer,” e.g., they don’t delay ejaculation. (Cock ring 101: Gentle restriction is good; trapping blood in the penis is not. Cock rings should be snug, not tight.) If you’ve already tried all the standard-issue advice to treat premature ejaculation (which I’ve covered before and don’t have the space to re-re-re-rehearse in a Quickies column), an ED med like Viagra might help (for the reasons mentioned above); a low-dose SSRI is also an effective treatment for premature ejaculation.
P.S. Whenever someone writes “penis-haver” my slightly dyslexic brain reads “penis-halver,” as in, someone who cuts a penis in half—which some people in the body modification community have done, and bon(e) appétit to anyone brave enough to do a Google image search.
Q: For those that like to fuck outside on hikes and while camping . . . should we be wary of trail cams or GoPros people are hiding in trees for whatever reason?
A: If people are doing that—if people are hiding cameras on popular hiking trails—well, then you should indeed be wary. Hike the beaten path, don’t fuck on it.
Q: An ex-boyfriend is seeing trans prostitutes. Do I tell his current wife IF an opportunity to do so should arise? And it will, as we live on a small island. I would’ve wanted to know if we were still together. Should she not be offered the same?
A: If you truly live on a small island—small enough that everyone knows everyone else’s business but large enough to have more than one trans sex worker—then your ex-boyfriend’s wife is gonna find out sooner or later. But even if it means she finds out a little later, it would be better if she found out from someone other than you. Assuming your ex’s wife doesn’t already know and approve, if the bearer of bad news is a bitter ex—or someone who can easily be cast as one—your ex-boyfriend will have a much easier time convincing his wife that it isn’t true. Better she should hear it from the vicar.
Q: I’m a gay boy in the big city and I want to start doing sex work as a side gig. But I have no idea how to start. First steps?
A: First steps: get vaccinated against monkeypox, Hep A and B, and HPV, and get on PrEP. Then talk with other people who are doing or have done sex work. There are a lot of sex workers on Twitter; most aren’t there to solicit customers, but to advocate for their rights and create community. Follow and learn.
Q: I met a guy that is very gifted at giving me multiple orgasms, but I have a hard time getting him to come at all. Any advice?
A: If he doesn’t want to come, don’t make him. No problem. But if he’s not coming because you want to make him come with your own hand, pussy, or mouth and he can’t come that way, then there is a problem here, and it’s you. Give him permission to enjoy oral and PIV and whatever else you both enjoy before finishing himself off with the same skilled hands he’s using to get you off. Problem solved.
Q: What is the best lube for anal sex with sensitive skin?
A: We’re big fans of Spunk. Full disclosure: This isn’t a paid endorsement—but the last time I mentioned Spunk in a column, they sent me a case. That was years ago . . . and we’re almost out. Cough, cough.
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