Quickies

1. I’m an 81-year-old heterosexual woman whose husband died last May. I have found that my 56-year-old gardener of fifteen years can make me sexually happy. But now after four months he says he’s not respecting his wife by having sex with me. He relates this to going to a Catholic priest for confession. He seems to enjoy our sex. What should I tell him?

“You’re fired.”

P.S. Kidding, kidding — don’t fire your gardener. Tell him you’re grateful for the sexual happiness, you don’t want him to do anything that makes him feel uncomfortable, and then give him a raise.

P.P.S. Will no one free us from these meddlesome priests?

2. What is the most frequently asked question you get?

Hard to say — but I suspect I’ll get a lot more questions like the one above as my readership ages along with me.

3. I have a boyfriend who never asks for anything. He also never says “I love you.” Do you think this is a red flag?

It depends on how long you’ve been seeing this guy. If you’ve only been seeing him for a few weeks — especially if you haven’t had a DTR convo and your use of “boyfriend” is the relationship equivalent of grade inflation — the fact that he isn’t asking you to pick up his dry cleaning (just this once) or peg his ass (on the regular) could be seen as a green flag, e.g. he doesn’t expect you to do girlfriend grunt work before you’re BF/GF official. Same goes for saying “I love you”: if you’re still in the early stages, he may be feeling it, he may be thinking about saying it, but waiting until he’s sure before he says it? Another green flag… if the relationship is still relatively new.

But if it’s been a year and he doesn’t ask you for anything (and doesn’t offer anything) and he doesn’t say “I love you” (or stopped saying “I love you”), then we’re in red flag territory.

4. Best creative positions for pregnant people?

There aren’t good positions that work for all non-pregnant people — some positions/angles of penetration work for some people but not others — and experimentation with different positions is the best way to find the positions that work for you as an individual and/or a couple. I assume the same is true of pregnant people: some positions/angles of penetration work for some and not others, and experimentation is the best way to figure out which ones — creative or not — work best for you right now.

P.S. Congrats!

P.P.S. Full disclosure: Liberator has advertised on the show… not sure whether they’re currently advertising. So, this endorsement comes from the heart: Liberator’s collection of positioning sex pillows and wedges are truly a godsend for pregnant people. They can help you hold your favorite positions once you’re pregnant and find new ones that work for you — when you’re pregnant and after you’re pregnant. People should get gift certificates for Liberator at their baby showers.

5. Why do guys who wanna get pegged refuse to douche/prepare? What to do in those cases?

Peg a guy who doesn’t prepare once, shame on him. Peg a guy who doesn’t prepare twice, shame on you.

P.S. In fairness, some straight guys don’t know how to prepare; their girlfriends/wives/Dommes can and should direct them to one of the five million douching tutorials on YouTube. In cases where a guy has been directed to online douching tutorials and he still isn’t cleaning out properly… that guy doesn’t deserve to be pegged.

6. What amount of jealousy/insecurity in a poly relationship is okay?

“What matters most is not so much the amount of jealousy/insecurity, but the way it’s handled,” said Dr. Marie Thouin. “If someone grapples with jealousy but they’re staying on the same team with their partner(s), that’s okay; but if someone feels so disempowered that they start seeing their partner as an enemy, something needs to change.”

Dr. Marie Thouin is a dating and relationship coach who has extensively researched and written about compersion. Follow her on Instagram @drmariethouin.

7. Can lesbians please stop being so mad at me for being bi? I just want to have sex with a woman and not lie about my sexuality on my dating profile. I promise I don’t make being bi my whole personality.

You encounter two types of people on dating/hookup apps: people who are there to fuck people who wanna fuck them and people who are there to bitch about (and bitch at) people they don’t wanna fuck and/or people who don’t wanna fuck them. Yes, it sucks when a stranger goes out of their way to say something shitty to you on a hookup app; there are lots of shitty people everywhere, and some of them are lesbians. But your best move is to block shitty people and then refrain — as hard as it might be — from blaming all lesbians everywhere for the shitty behavior of a few lesbians on the apps.

P.S. You know who’s never mad at bisexual women for being bisexual women? Other bisexual women! You have options!

8. You never write about a hair fetish, let alone a fetish for completely bald heads. Because I’m a guy who’s very much turned on by women with smooth, shiny heads. And I’m not the only guy who has this fetish. What do you say about this?

I would say… you shouldn’t read anything into my not having written something about your particular fetish. I’m aware that some men like women with smooth, shiny heads, and it’s a perfectly fine fetish for a man to have. If it hasn’t come up in the column, that’s because no one has sent me a letter about it.

9. I’m a cis bi female in my 40s married to a cis bi male in his 50s. He came out to me last year as bi, which was a HUGE surprise and incredibly rad. We have started to explore non-monogamy, and he has been on the apps looking for a male FWB and not having much luck. I’ve heard you mention things that were “gay coded” in the 1990s, like tribal armband tattoos. If a man my husband’s age wears earrings and has a 90s tribal armband tattoo and wears rainbow bi pride bracelets, etc., will he set off anyone’s gaydar? Is there anything else he can do?

Your husband’s earrings, tattoos, and pride bracelets may get him clocked as a cocksucker — they may set off other people’s gaydar — but they’re highly unlikely to get him laid. If a gay or bi dude sees your husband in public and thinks 1. he’s hot and 2. he must be gay or bi given those earrings, that tattoo, those bisexual bracelets, etc., that guy is more likely to open up Grindr or Sniffies or Scruff and send your husband a message — if he finds him there — than he is to approach your husband on the street and risk making a pass at him.

10. I’m a bisexual nonbinary person in my late 20s. I use gender-neutral pronouns in the workplace and on my legal documents. However, my family members don’t seem to believe me. I’ve asked my parent and my sibling to use my preferred pronouns multiple times, and they just laugh it off. I’ve tried GNC hairstyles, and I dress pretty GNC; that doesn’t seem to help. Their behavior feels dismissive, but I know they love me, which makes me hesitant to be firmer with them.

I don’t understand why you would hesitate to be rude to your family — sorry: why would you hesitate to be firm with your family — given that your family is rude to you. That said, you’re not Tinkerbell: you don’t need them to believe. I got a lot of, “Oh, you just need to meet the right girl,” from my extended family after I came out, which felt dismissive and disrespectful. My strategy was to make fun of them for being straight (“You just need to meet the right guy, Uncle Jerry”) and — if they kept it up — to describe what I loved about gay sex in graphic detail. I’m not sure what the equivalent move for a nonbinary person might be (describing your last haircut in graphic detail doesn’t have the same punch), but the general lesson applies: respect earns respect.

11. There are a million think pieces on how and why people — men and women — are obsessed with Heated Rivalry but no one has really touched on the power of a long-term, soft Dom/sub dynamic, like the one Ilya and Shane have. We need your analysis!

My analysis: it’s fucking hot when Ilya orders Shane around (“Get on your knees”) and Heated Rivalry shows us that a naturally skilled Dom like Ilya can give orders and still check in (“This okay?”) without ruining the D/s vibe.

12. How can I make sex more spontaneous?

Planning to have more spontaneous sex seems a little contradictory — like, doesn’t planning to have more unplanned sexual encounters highlight the fact that the best sex is planned? I suppose you could make a plan to spend time together in a place where you can’t or shouldn’t have sex and then go ahead and have sex in that place… but it’s still a plan, isn’t it?

13. I’m getting ready for a 1950s-themed gay speed dating party. How should I prepare?

“What a great idea for a party!,” said James Kirchick, the author of Secret City: The Hidden History of Gay Washington, the definitive book about gay life — in and out of Washington — at the height of the Lavender Scare in the 1950s. “Put aside the fear and repression that marked the decade and dress in something sexy but furtive — think Timmy from Fellow Travelers — and if you really want to stand out, accentuate your outfit with a paperback copy of Washington Confidential, a muckraking report on our capital’s seedier side. The top bestselling nonfiction book of the summer of 1951, it has an entire chapter devoted to the city’s debauched homosexual underground entitled ‘Garden of Pansies.’ Though intended to outrage hetero readers, the book became an unintentional guide to the city’s gay scene for budding gay guys and gals.”

Follow James Kirchick on Instagram and Twitter. Find out more about his work — his essays, his journalism, and his books — at jameskirchick.com.

14. Thoughts on guys saying, “I love you, bro,” or, “I love you, daddy,” during sex?

So long as no one is saying, “I love you, bro,” to their actual brother during sex or, “I love you, daddy,” to their actual father during sex — and no one is saying that to their actual brother or father — then it’s fine. Just as adults calling each other “baby” during sex doesn’t invoke, endorse, or normalize pedophilia, men calling each other “bro” and “daddy” during sex doesn’t invoke, endorse, or normalize incest.

15. Any thoughts on why and when gay men started sniffing butts before rimming? Is this a new fetish?

If there was ever something that needed to pass the smell test, it would be the ass you’re about to eat. I don’t know if this is a “new fetish,” but I sincerely hope it’s not. This is something gay men — at least the ones who eat ass — should’ve been doing all along.

16. Your thoughts on Pillion?

Haven’t seen it yet — will soon, I promise!

17. Are there “woman-friendly” glory holes in places that aren’t porn shops? And what is the glory hole etiquette?

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