Quickies!

1.Β How do youΒ tell the difference between a slow-burn connection and settling for something thatβs just okay?
Thereβs no settling down without some settling forβ¦. because no one gets everything they want where romantic partners are concerned. So, if youβve chosen someone you arenβtΒ entirelyΒ sure aboutβ¦ welcome to the worldβs most crowded club. Only time will tell whether you settled for something βjust okayβ (or worse) or if there was a slow-burn connection smoldering under the ambiguity and doubt. Good luck.
2.Β Iβm a transΒ woman. A few weeks ago, I was hanging out with friends and one of them, a gay man who is also a furry, told me that he thinks his furry identity should be granted the same level of legal and societal validation as my trans identity. My first thought was, I wasnβt aware we were getting any validation! But my second thought was to be offended at the comparison between my identity, in which I exist every second of every day, and his furry identity, which seems more like a kink. Was I right to be offended?
βThe statement this furry made is absurd and none of my friends would ever say something like that,β said a furry gay friend who agreed β somewhat reluctantly β to take a look at your letter so long as I kept his name out of my mouth/column. βMy immediate thought is what is the furry guy actually asking for? Legal recognition? Does he want hisΒ fursonaΒ name on his government ID? If he wants to make his fursona his real name, thereβs nothing stopping him from doing that; he just needs to get a legal name change. That said, while itβs certainly far harder to exist day-to-day as a trans person than it is as a furry, I donβt think boiling down being a furry to a kink is right. For some it might be βjust a kink,β but for others it is very deeply felt.β
P.S. While things have definitely gotten worse for trans AmericansΒ under the Trump administration, majorities of AmericansΒ still support the rights of trans people. Trans Americans have even gotten some legal validation β from the fucking Supreme Court, no less,Β in a decision written by Neil Fucking Gorsuch. Just as trans people shouldnβt be erased (and canβt be erased), trans wins and the progress weβve seen over the last two decades (current backslash notwithstanding) shouldnβt be erased either.
P.P.S. My gay furry friend was too polite to say it, so Iβll say it myself:Β your gay furry friend is an idiot.
3.Β I want toΒ love myself more and have the confidence to not care about other peopleβs opinion of me. Any tips for an anxious weirdo to stop caring about how the world sees me?
You can take other peopleβs opinions into consideration β you can show a decent respect for the opinions of mankind, as someone or other once said β without being paralyzed by them. But if you find yourself obsessing to the point of emotional paralysis (that βanxious weirdoβ place), a good therapist could help you strike a better balance between consideration (of others) and confidence (in your own self/choices).
4.Β I was fascinatedΒ to hear the story of the woman who traveled to Peru for an erotic massage. She expressed frustration at not finding local providers. I have been giving these massages like the one the caller described on your show for five years but just to friends and those I meet on the apps. Is there a way to monetize this service? Where to start?
Iβve heard good things aboutΒ TrystΒ β I am not endorsing the platform (βhome of the independent escortβ) but someone jumps into the comment thread to talk up Tryst whenever the subject of sex work comes up. So, just passing that along. (You also might want to listen toΒ my conversation with podcaster and βlove coachβ Shaun GelanosΒ on the Savage Lovecast. Gelanos, a straight man, successfully monetized the erotic massages he enjoyed providing to women when he lived in the SF Bay area, which we talked about on the show.)
5.Β Iβm a 30-year-oldΒ cis woman who has only really ever been intimate with cis men. Lately Iβve been chatting a lot with a trans man who has had bottom surgery. Iβm really looking forward to getting intimate with him, but since this is new territory for me, I want to do a little research beforehand. I plan to ask him about what he likes and what feels good for him when the time comes, but Iβm wondering if you have any advice or know of any good resources out there (i.e. written by a trans masc person) so that I can better understand his anatomy because most of what Iβm finding is written by doctors or people that arenβt trans masc.
βWhether youβre a trans personΒ exploring T4T sexΒ for the first time, a cis woman who has historically dated cis guys, or maybe a cis gay man whoβs never hooked up with a transmasc person, having a new sexual experience can feel daunting without guidance,βΒ Jo ValdesΒ wrote in an essay forΒ Them. Valdes, a writer and intimacy coordinator, solicited advice from trans masc people on best practices where having sex with them is concerned.Β Go read the whole thing.
6.Β Iβm activeΒ inΒ water sports during the summer β no, not that type ofΒ watersports, but the kind with surfboards and paddle boards and sand and things like that. After a few weeks, I noticed that the tip of my cock will get little red marks, small abrasion raspberries, from rubbing up against the board, and sometimes, I think because I stay in a wet bathing suit for a while. This is suboptimal because it makes it look like Iβve got an infection of some sort. Any advice on what to do here?
A foreskin might help β if you donβt have one of those, you couldΒ look into getting one. In the interim, a triathlete pal recommends slathering your cock and balls withΒ Trislide, an anti-chafing lubricant, before pulling on your wetsuit.
7.Β Iβm a young 65-year-oldΒ straight woman and my ten-year relationship with my (narcissistic) guy ended abruptly without a reason. Prior to the end of this relationship, this guy successfully isolated me from all of my old friends. Now I am on my own. Dating apps are a wasteland and my day job has me in bed by 11 PM, even on weekends, and night life doesnβt get started where I live until after midnight. What can I do?
Reach out to your old friends and throw yourself on their mercy: βIβm so sorry for disappearing on account of my shitty ex and I would love to apologize in person and reconnect β if you have the time β and I promise I wonβt spend the whole time complaining to you about my shitty ex.β
8.Β Have you readΒ The Great Believers? It made me think of you.
I have not β but it sounds amazing. Thanks for the recommendation, and I will add it to the pile on my nightstand.
9.Β Does having aΒ threesome with two people who are siblings constitute incest?
Interesting question.
Iβve always said thereβs nothingΒ necessarilyΒ gay about two straight guys having a threesome with a womanβ¦ so long as neither is quietly hoping something gay happens. So, by the same logic, one could argue there isnβt anythingΒ necessarilyΒ incesty about two siblings having a threesome with a non-siblingβ¦ so long as neither sibling is quietly hopingΒ that sceneΒ from season three ofΒ White LotusΒ happens. But just as MFM threesomes will always be haunted by the specter of homosexual desire, SNS (sib-nonsib-sib) threesomes will always be haunted by the specter of incest.
P.S. There was definitely something gay about the threesome I had with another man and a woman when I was a closeted teenager β it was me, I was the gay thing about it.
10.Β If you couldΒ fuck any guy in history β theyβre all gay in this scenario β whoβs catching a facial?
My top three:Β BagoasΒ (as brought to life by Mary Renault inΒ The Persian Boy),Β AntinousΒ (prior to his deification byΒ Emperor Hadrian), andΒ Leopold IIΒ (at the time he was painted byΒ Pietro Leopoldo).
11.Β Iβm a gayΒ man. My boyfriend says all gay guys watch porn and Iβm lying when I say I donβt. But I honestly donβt.
I curate and host theΒ HUMP! Film FestivalΒ β tickets for the fall season areΒ on sale now! β so I watch a ton of porn (mostly straight) when the HUMP! Jury meets in December to select the films that make it into the festival. But Iβm an erotica and imagination guy otherwise, perhaps because I came of age before online porn became a thing. That said, men like us β gay or otherwise β who donβt watch porn are rare, and shame does lead some people to lie about their porn consumption, and the lie is always βI donβtβ and never βI do.β So, your boyfriendβs skepticism is understandable.
P.S. Tickets are on sale now for the HUMP! 2026 fall tour β watch the trailer and get tickets to a screening near youΒ here!
12.Β My wife wantsΒ to go to a sex club βjust to watch.β Is that a thing?
Lots of people go to sex clubs just to watch. And while watchers sometimes frustrate doers, smart sex clubbers goers β goers and doers β know that most couples come βjust to watchβ the first few times. So, making a couple thatβs just came to watch feel welcome on their first visit (being friendly and respectful, not pressuring them to do anything theyβre not ready for) could pay dividends on that coupleβs third or fourth visit.
13.Β My (straight) husbandΒ and I have been monogamous for ten years. His go-to fantasy when weβre fucking is always β always, always, always β me sleeping with other men. Do I keep treating this like dirty talk or does listening to this over and over and over again (and helping him spin his the fantasy out) mean I have a hall pass at this point?
Keep treating it like dirty talkΒ if youβre not interested in actually sleeping with other men. If you are interested in sleeping with other men, initiate a conversation with your husband about this fantasy when you arenβt having sex. (βIs me sleeping with another man something you want to keep a fantasy or is it something you actually want to happen? Because I am down.β) If he gets mad because youβre actually thinking about doing the thing heβs been encouraging you to fantasize about doing for more than a decadeβ¦ yeah, then he never gets to bring it up during sex ever again.
14.Β My new exΒ isΒ running aroundΒ telling all of our mutuals that I was βemotionally abusiveβ basically because I broke up with him. No one has said anything to me about it. What the fuck do I do?
At least one of your mutuals said something to you β I mean, you wouldnβt know your ex running around talking shit if one of your mutuals hadnβt told you about it, right? As for why your other mutuals havenβt said anything, my hunch is that they know itβs bullshit. If mutuals suddenly start cutting you out of their lives, youβll have to raise the subject yourself. If they arenβt cutting you out of their lives β if your mutuals are refusing to take sides (or, even better, if theyβre easing your ex out of their lives) β continue to maintain a dignified silence.
15.Β My controlling exΒ had a huge problem with me posting thirst traps while we were together β not allowing me to show off was just one of the many ways he didnβt allow me to be myself β but now that weβre exes he likes every single one my thirst traps. Why is he doing this? I would ask him, Dan, but we had a bad breakup, and we are not speaking. (Weβre straight.)
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