- What’s the sexiest holiday food to eat off someone’s body?
While food can be sensuous, you don’t eat food off someone’s body unless you’re fucking or about to fuck… and fucking on a full stomach is uncomfortable, which is why I’m always urging people to #FuckFirst” on Valentine’s Day (and their wedding days, birthdays, anniversaries), and fucking on a slowly filling stomach really isn’t much better.
Like many people, I made the mistake of incorporating food into foreplay when I first became sexually active. Putting whipped cream on our tits made me and my first boyfriend feel like we were doing something naughty and sophisticated without either of us having to make ourselves vulnerable, e.g., without either of us having to open up about our actual kinks. And as we both quickly learned, whipped cream quickly liquifies as it rises to body temperature, and then you look and smell like an infant barfed all over you — which is not something anyone you wanna fuck could find sexy.
Anyway, everyone should enjoy holiday food and holiday sex — but not at the same time, and not in that order.
- No question here, Dan, just wanted to say we fucked first and ate later. Thanks for that great piece of advice!
You’re welcome!
- How can I come hands-free? I’m a cis male.
Like squirting or rolling the edges of your tongue to make a little tube, coming “hands-free” is not something everyone can do. And most of those “hands-free” orgasms you’ve seen in porn? They weren’t entirely “hands-free.” Most of those guys are brought to the edge of orgasmic inevitability with a hand — their own or someone else’s — before being fucked over the edge.
- Any tips for quickly preparing your butt for anal?
You could do what we used to do before douching became standard: take a dump and cross your fingers. It wasn’t a perfect system (douching caught on for a reason), but it worked reasonably well — meaning, it succeeded more often than it failed. You should also prep with lube — lots of lube — and prep with PrEP. And remember: in addition to protecting you from all the sexually transmitted infections PrEP doesn’t (PrEP only protects you from HIV), condoms also keep shit off your dick!
- How do we sneak in some quick sex while we’re staying with the whole family?
You offer to do a coffee run for the whole family, you head to the nearest “drive-through” Starbucks in the miserable suburb where you were raised, you park your car and go inside. You place your order at the counter, you head for the restroom — which is empty and clean, as very few people get out of their cars — and then you have sex (quickly!) standing up while your family’s enormous coffee order is being prepared.
- Please keep this anonymous: I’m a gay 41-year-old man. I enjoy hookups but lose sexual interest when there’s affection and a connection. Am I doomed?
If you want a committed relationship that’s romantic and sexually exclusive — or romantic and sexual but not necessarily sexually exclusive — you’re probably doomed, as it doesn’t sound like you’re wired for that. You could attempt to rewire yourself, of course, but the attempt could take years and there’s no guarantee the attempt would be “successful.” (And if you’re not broken — if this is just how you’re wired, i.e., how your sexuality functions — then there’s nothing about you that requires fixing.) But if you could be happy in a committed romantic relationship that’s intimate and loving but not sexual — because the man you’re with is wired the same way you are or he’s asexual but homoromantic — then you’re not doomed.
- What are the best Christmas-themed positions?
Christmas isn’t sexy. You can have sex on Christmas — because of course you can (and not just in the bathroom at Starbucks) — but mistletoe shouldn’t be hung over ballsacks and Santa hats shouldn’t be worn at swingers’ parties. And just as we all eventually learn that whipped cream isn’t a sex toy, we all eventually learn that mixing up “positions” isn’t adventurous or kinky. We find the positions that work for us and our partners — the ones that hit just right — and they become our go-tos. (Ideally, they become our work-up-towards after a lot of foreplay.) So, whatever positions work for you and your partner when it’s not Christmas are the same positions that will work for you and your partner when it is Christmas.
P.S. When people talk about “positions,” they mean positions for penetrative sexual intercourse (usually PIV, sometimes PIB), e.g., missionary, doggy, wheelbarrow, cowgirl/boy/hand, etc. So, if you’re the kind of person who thinks about sex as a range of possible “positions” for penetrative sex, taking PIV and PIB off the menu — doing something else for once — is the single best way to discover something new.
- My partner has a fantasy of us with a trans woman. We want to be totally respectful but it’s not a dating situation. (He wants to try it, but only as a one-time thing.) So, we thought it would be best to do this with a professional. A friend suggested we might have some luck by posting Grindr. We have no real idea how to make this happen without being jerks or getting arrested! Help!
Please don’t approach random trans women on Grindr and offer to pay for sex. There’s nothing wrong with doing sex work, of course, and there are trans women out there who do it, but trans women — even some trans sex workers — resent the assumption that all trans women are sex workers. Instead, follow trans women who are open about being sex workers on social media and then, after getting a sense for who they are as people, respectfully approach them — as people — and inquire about their availability and interest.
- A sub wants to drink allllll of my pee. And not just a little taste — he wants to drink every drop, over a few hours. I’m on an SSRI and while I assume he’d be getting a negligible dose of my meds, I don’t actually know that for sure because WebMD just isn’t cutting it this time. Can you help?
I don’t know for sure that your sub has nothing to worry about — trace amounts of SSRIs can be detected in urine samples — but I feel confident stating that if trace amounts of SSRIs in urine posed a health a risk to piss drinkers… yeah, I would’ve heard about it by now. Also, you’re not talking about that much piss — you can produce at most 24 ounces in three hours — which makes your sub about as likely to overdose as he is to drown.
- Can you get hemorrhoids from rough vaginal sex?
“Hemorrhoids are a natural part of our anatomy and it’s only when they become inflamed or start to protrude that they become noticeable,” said Dr. Rachel Gelman. “Typically, things like constipation or anything else that places a lot of downward pressure on the pelvic floor is associated with hemorrhoid dysfunction. And while linking vaginal sex with hemorrhoids is a bit of a stretch — pun intended — if someone had underlying pelvic floor dysfunction and penetrative sex was aggressive enough, that could over time result in rectal issues or bowel dysfunction and lead to hemorrhoids.”
Dr. Rachel Gelman is a pelvic floor specialist and a sexuality counselor. You can follow her on Instagram and Threads @pelvichealthsf and learn more about her work — and pelvic health in general — at her website pelvicwellpt.com.
- Being around family is a turn-off for me. Any suggestions?
Don’t move back in with mom and dad, if you can help it, and head to the nearest drive-through Starbucks when you’re feeling desperate.
- How do I get my boyfriend to eat out another girl in front of me? He says he doesn’t think he can do it unless we do it together. But that’s not exactly what I’m looking for. (It’s what I want for Christmas.)
I’m guessing you’re a straight woman — you wanna watch your boyfriend go down on “another woman” but you don’t wanna go down on that woman yourself — which means there’s a chance your boyfriend doesn’t wanna go down on another woman and setting “after you” as a condition allowed him to say no without seeming like an unadventurous prude. There’s also a possibility he thinks this is a trap — he might worry you’ll be angry if he seems too eager to take you up on this offer — and he’ll modify his position if you keep asking.
- How do you navigate dating exes of friends or friends of exes in a healthy and respectful way?
You owe a friend the courtesy of a heads up after you start dating one of their exes. If you’re friends with an ex, you owe your ex — as a friend — that same courtesy. But that’s all you owe them.
- Ball punching and squeezing: At what point does it get dangerous?
When a guy says he wants you to punch him in his balls as “hard as you can,” what he means is, “I want you to punch me in the balls as hard as my balls can take it while we both pretend you’re punching me in the balls as hard as you can.” So, ball punches are always pulled punches. As for squeezing, increase pressure gradually and ease up when he really starts to squirm. That said, there’s always a risk of a testicular rupture when you get rough with someone’s balls.
- Are we still coming out at Thanksgiving?
Gay people who wanted to come out to the whole family at once — to get it all over with — often came out at Thanksgiving, even at the risk of “ruining” the holiday. Also, gay people who worried that a family member reacting violently often came out at Thanksgiving because there was a certain safety in numbers, e.g., your violently homophobic dad was less likely to beat the shit out of you in front of your grandmother and aunts and cousins. Nowadays, you can come out to the whole family on a group text and dads are a whole lot less likely to beat the shit of their gay kids, which means coming out on Thanksgiving — while still a thing some gay people do — isn’t really a thing as many gay people do.
- How do you dispose of used poppers? What am I supposed to do with all these little bottles?
You’re supposed to take your used and/or expired poppers to a waste disposal site that processes household chemicals that shouldn’t be poured down the sink or leach into a landfill. Or you can do what most gay men do and let those little brown bottles accumulate in your nightstand until you die and stick whoever has the sad task of emptying your apartment with figuring out how to dispose of them.
- How do I explain being poly to my rural Kansas (but Midwestern nice!) extended family?
Matter-of-factly — and if any of your relatives have divorced or been widowed and remarried (or even gone steady more than once), they already understand that a person can have more than one committed romantic partner over the course of their life. You’re doing it concurrently instead of sequentially, but you’re not doing anything most of them haven’t done. In other words: serial monogamy is a form of polyamory.
- I recently did molly and watched a female friend masturbate while my wife slept. Are we okay to memory hole this?
The memory hole — like the turkey — isn’t going to stuff itself.
- When was the last time you were in a bathhouse?
I’m curious why you’re curious — were you hoping to run into/through me in a bathhouse? — but I’m happy to answer the question: I’ve only been in a bathhouse once or twice in my life and only when I was doing outreach for a gay man’s sexual health organization. Now, I’ve been to some sex parties that didn’t take place in bathhouses, but I brought a date because, while I’m no prude, I am a lady.
- What’s your opinion on displaying sex toys or BDSM gear in your bedroom vs. having a “toy chest” that blends in with the décor? Obviously, it’s better to have a secret and separate sex room altogether, but not everyone can afford extra space.
Having a toy chest is better than leaving your gear on display and/or strewn around your bedroom — not because owning BDSM gear is shameful (and your toy chest doesn’t have to blend in!), but because you want the sight of your gear to mean something.
- What’s a piece of advice you regret giving?
I can think of a few things — but I’m more interested in how my readers would answer this question. So, gang, what have I gotten wrong, when did I get it wrong, and am I still wrong or did I come around?
- Having sex in your partner’s childhood bed in their childhood bedroom while their parents sleep in the next room? Yay or nay?
Yay — so long as you can keep it quiet. (Just as there are things a mother has a right not to know, there are things a mother has a right not to hear.) If you can’t keep it quiet, having sex in your partner’s childhood rec room — or dining room or living room or garage (whatever is farthest from their sleeping parents) — feels every bit as naughty as having sex in their childhood bedroom. You also have the option of fucking your partner in their childhood bedroom when alone in the house and/or everyone else is busy making food and/or entertaining guests.
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