1. My boyfriend swears he’s cut. I say he’s totally uncut. He insists he was circumcised as an infant. How do I convince him?

Some circumcisions are “tight” (all of the foreskin removed) and others are “loose” (most of the foreskin left intact). The looser the circumcision, the more “uncut” a man’s cock might appear. So, it’s entirely possible your boyfriend was circumcised as an infant but that his cock — if his circumcision was loose — more closely resembles uncut cocks you’ve admired in porn and encountered IRL.

P.S. For the record: Your boyfriend should not have been circumcised in infancy. No infant should be.

2. What’s the best song about cheating? I nominate “One Way Out” by the Allman Brothers.

There are so many greats — “Heard It Through the Grapevine,” “The Piña Colada Song,” “Don’t Hurt Yourself” — but in the category of “Best Song About Cheating,” my vote would go to “Torn Between Two Lovers” by Peter Yarrow and Phillip Jarrell as performed by Mary MacGregor. Readers are invited to offer their own nominations in the comments! (The tech-savvy, at-risk youth made me include one of the above songs — can you guess which it was?)

3. I’m interested in exploring a D/s sexual dynamic, but I have no experience and I don’t know where to start. How do I explore?

“The best thing you can do now is to identify the tone of D/s that excites you most,” said Lina Dune, host of the “Ask a Sub” podcast. “D/s is a big umbrella, but if you can tell someone that as a sub you want to feel like someone’s secretary or like a raccoon they’ve trapped on their back porch or like their most prized houseplant, then you’re that much closer to living out the fantasy — and if you need any additional help on either side of the slash, the Ask A Sub podcast is here to enable your highest filth.”

Follow Lina Dune on Instagram @askasub2.0.

4. If you post X-rated stuff to “close friends” on your Instagram, do you need to ask your friends before you add them?

Yes.

5. Can one person be the primary partner of two different people?

No.

6. Tips for a first foursome?

Clean sheets on the bed, hand towels and lube on the nightstand, four pints of ice cream in the freezer.

7. Getting an AI boyfriend
 is that cheating?

I’m allowed to have an actual boyfriend because my marriage is open and we’re (zzzzz) poly, so it wouldn’t be cheating if I got an AI boyfriend. Pathetic? Yes. Cheating? No. While someone in a monogamous relationship might be tempted to argue that the non-existence of their AI boyfriend — at least in corporeal form — means it’s not cheating to get one, their monogamous partner would probably disagree.

8. How do I ward off the opinions of friends who disapprove of the age gap in my current relationship? (I’m a 33-year-old man, my partner is a 23-year-old woman.)

A romantic relationship between two people who did not experience gestational concurrency — a romantic relationship between two people who were not in utero at the same time — is inherently problematic. To be truly egalitarian, there must be a period of significant fetal overlap. And while I would argue that your current relationship (and my current relationships) should be grandfathered in, no relationship with an age gap greater than eight months should be allowed going forward.

P.S. Just kidding. Tell your friends to google “consenting adults” and “fuck off” in that order.

P.P.S. For the record: relationships with significant age gaps should come in for a higher degree of scrutiny from family and friends and the older partner should welcome that scrutiny. If the older partner is defensive about this scrutiny, that’s a red flag. Also: you should google “Dan Savage” and “campsite rule.”

9. As a gay/neurodivergent man, how do I get on the apps and meet other men IRL?

The same way neurotypicals do: you post some recent pictures on dating/hookup apps and put what you’re looking for in your bio. You send messages to guys you might be interested in and respond to messages from guys express interest in you. To meet guys IRL, you go places and do things: join clubs, volunteer for community groups, find a few good “third places” where you feel comfortable — cafĂ©s, gyms, libraries — and frequent them. You should also seek out services and social groups serving the neurodivergent community in the city where you live.

10. If you accidentally used silicone lube on a silicone sex toy just once, should you toss the toy to be safe?

“Most silicone toy manufacturers and reputable retailers advise against combining silicone lube with silicone toys, as the lube can bond with the toy and degrade its surface,” said Searah Deysach, the owner of Chicago’s beloved sex-toy shop Early to Bed. “But we have found that silicone lube does not always damage silicone toys. So, if you accidentally combine the two and your toy shows no visible marring or sticky spots, you should be fine. No need to toss your toy out! But if you are still concerned, you can throw an unlubricated condom on the toy — most lubricated condoms use silicone lube — to be extra safe.”

Follow Early to Bed on Instagram @Early2Bed.shop.

11. I just went to a cabin for a friend’s birthday. We all got super drunk and put on lingerie and we all made out. I can’t stop thinking about my best friend’s boyfriend
 who I pegged in the bathroom while everyone was partying. I’ve been fucking him in the bathroom of his job every day since and I would like to steal him for myself. Bide my time or go for it?

At this party where everyone got drunk, put on lingerie, and made out
 were other people slipping away from the group to hook up in bathrooms and bedrooms? Or were you and your best friend’s boyfriend the only ones who spent time alone? Another possibly relevant detail you omitted: Are your best friend and her boyfriend in an open relationship? Is he allowed to get pegged by other women? And has this boy — your best friend’s boyfriend — expressed any interest in being stolen from his girlfriend?

P.S. Unless your best friend is a cuckquean who gets off on her boyfriend hooking up with her friends — unless she was on the other side of that bathroom door masturbating — you’re a lousy best friend.

12. I’m having trouble staying fully hard while waiting for the bottom to “open up” before penetration. Advice?

If opening up the bottom doesn’t make and keep your dick hard
 and if a few self-administered strokes once the bottom is open don’t you hard enough to penetrate him
 you could ask the bottom to do a little advance work, e.g. lube himself up and have a plug in before you get there. Personally, I think opening up the bottom is a top’s responsibility — you should regard it as privilege and a pleasure — but if all you wanna do is walk and dump your load in some gaped dude, there’s no shortage of bottoms looking for tops like you on the apps.

13. After hearing so many stories about people who didn’t discover their kinks until they got a kinky partner and something clicked, I figured that would be how I discovered mine, if I have any. But my partner is vanilla. Can two vanilla people just randomly try kinks to see if something clicks? How would that work? Could it work? Vanilla sex is great but I find myself wondering if that’s all there is, my friend.

“I’ve spoken to countless clients who were able to explore new kinks — things they had never even considered before — with established partners; many found they love D/S dynamics or foot play or tying someone up,” said Certified Sex Therapist Claire Perelman. “But it can be daunting to figure out where to start with exploring kink and BDSM. Finding kinks that might turn you on — especially starting from vanilla sex — can feel overwhelming, but it can also be a surprisingly hot exploration. To help people on that journey, I created ‘Un-Vanilla Your Sex Life,’ a consent-centered guide full of therapist-backed reflections, questions, and activities that can help you explore kinks on your own or with a partner.”

Follow Claire Perelman on Instagram @SexClarified.

14. Where do I find the sapphic orgies?

They’re in Berlin and they’re in porn and they’re in porn made in Berlin.

15. Rape/SA made me asexual. But I’m 39 now and want a partner ASAP. I don’t know if that will change. What do I do?

If you want a romantic partner but not a sexual one (some asexual people are sex averse, some are happy to have sex to please a partner), you should be upfront about not wanting to have a sexual relationship, just a romantic/intimate/committed one — basically, you should disclose. And if you don’t wanna fuck your partner and you’re not okay with your partner fucking other people, you should look for a partner who is also asexual.

16. I know you’ve answered this before, but is there a book/influencer you recommend for seniors entering the dating pool safely and with solid, sex-positive advice? Just sorting through the many options online for a friend. Much appreciation!

The great Joan Price is the senior sex author/influencer I’ve recommended most — she’s been on my show many times — and her book, Naked at Our Age: Talking Out Loud About Senior Sex, is packed with great advice for seniors who fuck, wanna fuck, or wanna keep fucking. Naked at Our Age was just reissued to mark the fifteenth anniversary of its publication and you can oder a copy for your friend here!

17. My 18-year-old son has told me that, ideally, he’s only willing to date virgins because he would be jealous. Also, he would be opposed to dating anyone that had sex outside of a long-term committed relationship because he doesn’t think you should just “give” sex away. I told him he needs to get over this, but he seems unwilling/unable. Is there anything I can tell him?

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