1. I met a man whose wife was ill. Their relationship was no longer sexual, and he was in a caretaker role, and seeking release. We fell in love, and he promised to marry me when his wife passed. That was five years ago. I know he isn’t lying about his wife’s illness, but I no longer want to wait. The only leverage I have is telling his wife and children, which I would never do. It would destroy him and destroy us. But I’m drunk right now and I need you tell me I shouldn’t.
You shouldn’t — not unless you want stoned CNN viewers rooting against the detectives investigating your murder on a future episode of Forensic Files.
2. Straight boy in the big city who sometimes plays the Bull for cuck couples. Went in for a second job interview and the boss was a man whose wife I’d...
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...ll for cuck couples. Went in for a second job interview and the boss was a man whose wife I’d fucked in front of him a year ago. There was lots of verbal abuse that his wife initiated (and I played along with) but their thing was too intense and I politely declined to meet up with them again. I didn’t get the job, and I’m pretty sure why. I still have his wife’s phone number. Do I have any recourse here?
You don’t — not unless you want stoned CNN viewers rooting against the detectives investigating your murder on a future episode of Forensic Files.
3. I have some questions about pronouns. I get he/him, she/her and they/them but not he/they or she/they. This has been a discussion with friends and family. Personally, I want people to identify with their truth. But I still don’t understand he/they or she/they. Can you make it make sense?
Ours is not to reason why, ours is but to make to remember the unique and sometimes unpredictable pronoun preferences of everyone we meet. We also have the option of training ourselves to never, ever use pronouns at all, in reference to anyone, ever again (She/they, he/they: “I mostly identify with and present as my natal/biological/assigned sex BUT I CONTAIN MULTITUDES, bitches!”)
4. Sex with hubs is boring now but I have no new fantasies. How do I get into it again?
If the relationship is open, fuck some other people, alone and together. If the relationship is closed, fuck each other someplace you haven’t fucked before — at the office, at a sex club, in the ass, etc.
5. I’m a 50-year-old man. My spouse, 46, is in the process of transitioning from male to female. I want to be sensitive to this experience and don’t want to ask hurtful questions, but there are just things I don’t know. For instance, how do most people in her position feel about their male appendage? I’m hesitant to initiate any intimacy now.
Even if you knew how most MTF folks feel about their male appendages — and even if I knew how most MTF folks feel about their male appendages — neither of us knows how your particular MTF spouse feels about her male appendage. It’s entirely possible your spouse feels the way most trans women feel… or she could hold a minority opinion. So, you’re going to have to ask her. Whatever she feels about her male appendage, broaching the subject is one way of letting her know you’re still attracted to her and still wanna be intimate.
6. I am a woman who has plentiful orgasms very easily and a WAP. I prefer a larger-than average penis, which apparently is common (according to some studies) among women who orgasm a lot, because I need to have my cervix rammed to feel completely satisfied. I don’t want to be this way and I feel a little ashamed since it’s something men can’t change about themselves. What do I do if I meet someone who is otherwise a very compatible partner, however, physically through no fault of his own, can’t give me what I need sexually? I like it to be a big enough dick that it hurts a little.
Guys with big dicks are great, but guys — big or small — who are secure enough with their dicks to occasionally strap on a big dildo are even better. Find one of them.
7. What does it mean when a girl looks at you and runs her finger around her lips like in a circle with her lips open? Round the world? I wanna give you a rim job? She did it at me like three times, Dan. I want to interpret this the right way. I’m a straight guy who doesn’t get much, but I think maybe this gal is interested? Yay or nay?
If this girl was in your league (be honest), it means she wants it. If this girl was out of your league, it means she takes cash or Venmo… or she was secretly filming you for her prank YouTube channel. Proceed with caution.
8. What are tell-tale signs a relationship is doomed?
I wanna be glib and say, “Asking yourself — or asking an advice columnist — that particular question is one of the signs,” but that isn’t true. Everyone in truly long-term relationship (5+ years) has wondered at some point whether their relationship was doomed. No, the truly tell-tale signs — the Four Horsemen of Relationship Apocalypse, according to John Gottman and Julie Schwarz Gottman of the Gottman Institute — are criticism, contempt, defensiveness, and stonewalling. Learn more at their website.
9. I’m wanting to get into fisting, but my boyfriend isn’t into it. We are open. How do I go about it? How do I even get started?
“Open and honest communication about your needs and your partner’s needs is always the most important thing, whatever you’re into,” said Jazzmatazz, the fisting blogger who cohosts the Such FFun podcast. “Two fisting-specific tips: train with toys first, solo and with partners. And find some experienced fisters in your area — guys you feel you can trust — who are up for showing you the ropes. Then explore and have fun!”
10. Is it safe to mix X-Lube with piss?
Since X-Lube is powdered lubricant (just add water) that’s popular with fist fuckers and I already had Jazzmatazz on the line, I passed your question to him: “Your large intestine has one job: absorbing water,” said Jazzmatazz. “Piss in your butt will get absorbed, with or without X-Lube. If you trust the quality of the piss, go for it.”
You can find Jazzmatazz on Twitter @jazzmatazzoz and the Such FFun podcast — now in its fourth year — on all podcasting platforms and Twitter @SuchFFun.
11. Is it normal during a foursome (FMFM) for one couple to forbid any kissing?
It’s not unheard of for a couple in an open relationship — even a couple who swings together — to hold something back. Some couples only “soft swap,” meaning they only engage in oral and mutual masturbation when they play with others; some couples don’t play with others in the bed they share or in the time zone where they live. For this couple, it’s kissing they’re holding back. People are allowed to rule anything in and anything out, and what may seem trivial to you — you’re fucking so why not kiss? — could have deep emotional significance for the couple you played with.
12. How to deal with tears, fissures, and inflamed bowels as a tight gay bottom?
Use lots of lube, take things slowly, stop at any sign of pain or discomfort, play solo (no pressure not to bail), and make sure your sex partners know — in advance — that they’re not guaranteed anal to completion (no one is) and that you won’t tolerate pouting if you have to bail. Also remind them that oral or mutual masturbation — the acts you’ll be pivoting to if you need to bail on anal — are great sex, not sad consolation prizes!
13. Best BJ trick?
A gentle bite — a little pressure applied with the teeth at a moment when the dick isn’t sliding in or out — paired with sustained eye contact. It’s a great way to remind the person fucking your face that they don’t actually have all the power, since you could literally rip their cock off with your teeth at any moment. So, best behavior.
14. What other kink-minded dating apps are out there besides Fetlife and Feeld?
Any dating app is a kink-minded dating app so long as you’re prepared to be open and honest about your kinks. But no one — not even other kinky people — wants to see a list of fetishes or kinks on a non-kinky dating app. Just drop a hint: “GGG seeking GGG.”
15. Can you fuck university faculty after you’ve graduated?
So far as I’m concerned, yes — but I write filthy sex-advice columns, not uni conduct codes.
16. I’m a 50+ male. In the past five to ten years, it seems like the skin on my penis has gotten more fragile. Where I used to be able to masturbate for as long as I liked, I have started getting an abrasion where my thumb rubs if I do it too long. I don’t think I have changed anything and have never been a “death grip” guy. I’m sure you are going to suggest lube, but I just don’t like the clean-up afterwards. Is this just an unavoidable byproduct of aging or is there something to be done to toughen it up?
As we age, our skin becomes thinner, and our orgasms take a little longer to achieve. So, even if you’re not stroking your aging dick any harder, you are stroking that aging/thinning dickskin longer than you used to. Pick your poison: beating holes in your dick until you bleed out or using some lube and having to do a little clean up. The choice seems obvious to me.
17. Why do I want to keep sending dirty videos to a guy I know is bad news?
Because bad news means great sex — not always, but often enough that we sometimes can’t resist sending videos and following up with ass.
18. How does your expert gaydar react to Speaker of the House Mike Johnson? When I heard that his wife is a conversion therapist and that he has a phone app to try and keep him accountable for his porn use, I immediately thought, yeah, gay porn for sure. Given his toxic homophobia, I automatically suspect a self-loathing closet case. Is he pinging on your gaydar?
Is he ever! With apologies to Little Richard: a ping pong a ling ping a lop pang poom!
19. Does the refractory period get longer as you get older?
Indeed, it does.
20. You suck.
Indeed, I do.
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