1. I’m a 57-year-old guy, married but separated, in reasonable shape. I usually masturbate at night as a “sleeping pill.” Over the past few years, it’s gotten more difficult to orgasm. I get hard, I vary my technique, but I just can’t come. Sometimes I’m up for hours jerking it before trying to fall asleep. Toys like sleeves sometimes help, but they’re messy since they need lube, so that’s not my first choice. Any magic suggestions for things to try?
Fire on all cylinders — use sleeves and lube (keep a small stack of hand towels on your nightstand), put clothespins on your tits (whether they’re wired or not), get a powerful vibrator with a sleeve attachment, slip a plug in your ass (flared base!), read some erotica and/or watch some porn and/or think some thoughts. Past a certain age, you may need to crank things up to meet production...
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...ughts. Past a certain age, you may need to crank things up to meet production goals.
2. Best lube for anal sex?
Adrenochrome when available, ivermectin if adrenochrome is in short supply, and the blood of Christian babies in a pinch.
3. What is the most common cause of bickering in long-term relationships?
There are four: the unbelievably stupid shit your partner insists on doing (despite being asked not to do that shit), the bleedingly obvious shit your partner refuses to do (despite being asked to do that shit), the stupid shit your partner likes (despite it being explained to them how stupid that shit is), and the amazing shit your partner doesn’t like (despite it being explained to them how amazing that shit is). Basically, it’s them.
4. Is sexual compatibility in a relationship a prerequisite or an achievement?
Establishing some basic/bedrock/baseline sexual compatibility at the start is a prerequisite; sustaining sexual compatibility over time is an achievement.
5. What’s the best threesome position? (Do not say “The Eiffel Tower.”)
The Three Gorges Dam.
6. My rent went way up and I’m thinking about starting an OnlyFans account for extra cash. Thoughts?
You submitted your question via Instagram DM, so I took the liberty of scrolling through your feed… and the answer is yes. Yes, you should. Yes, please. Yesterday.
7. Online romance novels help me get off. Lately, I’ve been reading about BDSM, as some of the lighter versions of that practice are featured in novels I’ve recently read. I searched for photos using Google. Nothing I’ve found looks anywhere near as pleasurable as what I read. How do guys keep an erection while enduring things that appear to be painful? Do they take a drug?
Lots of male porn performers take drugs — ingestible or injectable ED medications — to stay hard during porn shoots; while some may take boner drugs to keep an erection while enduring something they may not enjoy (although lots of porn performers, like lots of regular people, enjoy BDSM), most take boner drugs so they don’t lose their erection during the tedious parts, e.g., lining up shots, repositioning cameras, actually getting into complicated bondage, etc.
8. How does one re-train their dick to stay hard for another person during partnered sex after decades of self-pleasure?
One incorporates self-pleasure into the partnered sex one is fortunate enough to be having with another person — one might also wanna lay one’s hands on some boner pills.
9. Former fat girl here. How do I not hate my body compared to the cute girl my boyfriend and I play with?
“Comparison is the thief of joy,” as someone or other once said. “Stop comparing your body to others” is a lot easier said than done, I realize, but if I could learn to do it — I’m a former fat kid myself — so can you. Look, in every same-sex encounter someone is always the “cuter” girl or “hotter” boy. If you’re with another girl and you think she’s cuter, you can choose to feel terrible about yourself or you can choose to believe you must be pretty cute yourself. The facts in evidence point toward “must be pretty cute yourself,” seeing as you pulled that cute girl in the first place. Taking “yes” for an answer — from the universe, from cute girls, from hot boys, etc. — isn’t always easy either (again, speaking from personal experience here), but with time and practice you can learn to do that, too.
10. Thoughts on the person who went to the Folsom Street Fair in San Francisco covered with his own feces?
11. What is the etiquette when you puke on a sex partner during a deep-throating session?
Shower off, towel off, get off — perhaps in a more reliable orifice.
12. Someone I met on Biggercity moved across the country to my city. He then changed his Biggercity name to one that includes my BC name. It’s hot as fuck. But I just realized he might be a stalker. Within the last hour I left him a bunch of flirty texts. Stupid and horny. TBH, now I’m a bit scared. Any suggestions?
Flying across the country to meet someone you’ve been chatting with on a dating app is understandable. (Please have somewhere to stay, let people know where you are, tell someone what and who you’re doing, etc.) Moving across the country to be closer to someone you met on a dating app and taking his name… that does seem a little stalky. It also screams “I don’t have a job or friends” (broke and won’t be missed back home) or “I don’t need a job or friends” (wealthy and is an asshole). If your gut is telling you to block him, you should block him. But if your dick is telling you to fuck him… we both know your dick is going to win. So, be prepared to move across the country and change your name.
13. Straight cuck here. I did the one thing a cuck should never do and blew up at my girlfriend for doing what I’d asked her to do. I found a kink-positive therapist, did the work, and now I am ready to try this again. But I’m single now. Advice?
Um, this seems kind of obvious that I’m sure your therapist covered it but if you need to hear it from me, too, here it is: find a new girlfriend and don’t fuck it up this time.
14. This is too off-topic for a regular column, but perhaps you could treat it in one of your Quickies columns, or turn it over to your readers? Which currently active English-language advice columnists would you recommend to someone who has a question that doesn’t have enough to do with sex or relationships?
My short list: Carolyn Hax, Miss Manners, Lizzie Post and Dan Post Senning, Lori Gottlieb, Meredith Goldstein, and Alison Green.
15. Is it possible to learn to squirt or is it either you’ve got it or you don’t?
I’ve spoken to women who’ve tried to learn and couldn’t — they unsurprisingly believed woman either got it or they don’t. I’ve also spoken to women who’ve tried to learn and succeeded — they unsurprisingly believe it can be got.
16. Any advice for a burgeoning masochist?
Don’t let anyone do anything to you that they haven’t let someone else do to them — also, masochists make the best sadists.
17. Are “gynosexual” and “androsexual” real sexual identities or are they like “sapiosexual”?
A gynosexual is someone who is attracted to women and/or femme traits and/or people and an androsexual is someone who’s attracted to men and/or masc traits and/or people. Seeing as there are lots of people out there who fit those descriptions, and seeing as there’s smaller number of (often insufferable) people who use those terms, we will have to concede that those are real sexual identities… unlike “sapiosexual,” which is some made up bullshit.
18. Is it unethical to attribute the lack of any wish for romantic and sexual intimacy to menopause when it’s quite a bit more complicated? It’s a partial truth. Should I feel guilty about this?
Sparing someone is one way of loving someone.
19. Boxers or briefs?
I don’t care what my Christmas presents come wrapped in, so long as my Christmas presents keep coming.
20. Ever since we built our dungeon, my parents have been trying to bust their way into it. We are out of excuses as to why they can’t see our “recent room renovation.” They are both very religious and probably don’t know what the word “kink” means. Part of me just wants to say “FUCK IT” and let them see it.
Tell your parents they can see your room renovation after they watch every episode — every single one — of How To Build a Sex Room on Netflix and send you an episode summary about each episode. Trust me: if your parents watch every single episode of How To Build a Sex Room on Netflix… your parents will not want to see your “recent room renovation.” (But I do! Send pics!)
21. I want to pull your pants down and lay you over my knee and spank your bare butt so hard with my hand on your bottom over my knee that your bottom is red from the spanking you get from me. I live in Concord, New Hampshire, and I am serious about doing this.
Unless you’re willing to move across the country to be near me and take my name, I won’t ever think you’re serious about laying me over your knee and spanking my bare butt. (Me taking you seriously ≠ me letting you spank me. It equals me getting a restraining order against you.)
Dan is answering your Qs LIVE on Zoom this Thursday! If you’re a Magnum Sub, you’ve already scored your invite. (If you’re not a sub, what’re you waiting for??) So mark your calendars — this Thursday, October 12 at 12:00n Pacific / 3:00pm Eastern — and plumb the depths of your sex lives for that burning Q you need Dan to answer for you. Our phone lines are open below!
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