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The Thursday Letter: Masturbatory Assists Are Real!

On Thursdays I share a question from a reader and try — try my hardest — to let my readers give the advice…

Early fifties straight-ish bloke living in a regional city in Australia. I’ve been with my wife for 25 years, married for sixteen. We have a wonderful relationship, and you get quite a bit of credit for that, Dan. We’ve always had a differential in our libido. She was a once-a-week orgasm girl, I have always been a once-or-twice a day orgasm guy. Since she’s hit peri-menopause though, that once-a-week has gone to more like once-a-month or less. When the mood does strike her, the sex is great — and very often it doesn’t involve any penetration, as that can be uncomfortable for her, so we’re following your guidance on defining sex very broadly and just having lots of fun together. She’s been pretty awesome at giving me masturbatory...

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...been pretty awesome at giving me masturbatory assists throughout our life together, but these days I feel reluctant to even ask for that as frequently as I’d like. Most of the time she’ll happily throw her panties to me, but sometimes even that feels like an imposition. A few months ago we discussed the situation and she said she would be comfortable with me exploring the “ish” part of my straight-ish identity with the caveats that she doesn’t want to know anything about it, and that there are no women involved. I’m happy to abide by those rules and I’m lucky in that I travel a bit for work so I get the opportunity to play away games. The other part of her not knowing anything about it is not bringing anything home. The safest thing to do that would be finding a trusted and regularly tested play partner. But I summoned up the courage to go to a sauna for the first time last week and, I’ve gotta say, I fucking loved it! I somehow lucked into being there on bear night and I don’t think I’ve ever felt as desired as I did that night. As a big hairy bloke, that hasn’t been my experience in straightland. In my younger days I never struggled to attract women but that was more to do with my charm and sense of humor. My wife has always said she finds me attractive but, my god, these men in the sauna, Dan! So many guys hitting on me, and the ones I played with just exploring and playing with my body like no woman ever has. It was intoxicating, and I can’t wait to go back! But obviously those encounters are much more high risk so I’m going to try to do everything I can to make sure nothing comes home with me except an empty scrotum, a big smile, and a pleasantly sore asshole. So how do I protect myself and, most importantly, how do I protect my wife? I’ve gotten the mpox vaccination, I’ve got scripts for PrEP and doxy-pep, and I will be testing after. I also won’t be having sex with my wife after I’ve had an encounter until I get the all-clear from the most recent test. I’ll obviously be using condoms for any penetration activities. I’ve discovered that I enjoy swallowing cum — also, got my first facial, which I loved, and I was told to be careful not to get that in my eyes and I didn’t. Is there anything else I should be doing? Are there any activities I should be avoiding? Mitigating Risks Before Enjoying Aggressive Ravishments Before inviting readers to share advice with MRBEAR in the comments — before sitting on my hands — there’s something I need to confess: I may have chosen MRBEAR’s question this week because NoCuteName declared the masturbatory assist a myth last week. Actually… Okay, okay: that’s definitely why I chose MRBEAR’s letter. (I feel better! Confession is good for the hole!) I mean, it’s kind of a tell that MRBEAR doesn’t really need advice. Unless I’m missing something — which sometimes happens — MRBEAR is already doing everything he can protect his own health, his wife’s health, and (not insignificantly) the health of the gay and bisexual men who working so hard to put a smile on his face. (PrEP, doxy, vaccinations, condoms, testing, waiting = belt, suspenders, superglue, duct tape, thumbtacks, staples.) Now, NoCuteName — as I conceded on the show last week — was absolutely right to criticize me for using “sit on his face”  as my go-to example for the masturbatory assist. MRBEAR’s letter emphasizes a point I made on last week’s show: when it comes to the masturbatory assist, lots of different things should count. Like sex, the “masturbatory assist” should be defined as broadly as possible — and for pretty much the exact same reason: Couples that define sex broadly have more and better sex. And if a couple — or the higher-libido half a couple — define the masturbatory assist broadly, e.g. if everything from your partner sitting on your face to your partner throwing you a pair of funky panties (or a sweaty jock strap) “counts,” the partner with a higher libido is a lot likelier to get an assist when he asks for one. Or she asks for one! (The caller who got the MA convo rolling was a woman in a same-sex relationship!) Okay, have some advice for MRBEAR? Thoughts about masturbatory assists or any of the other issues raised in his letter? (Differential libidos, reasonable accommodations, honoring DADT agreements, first facials, etc.) Share it in the comments!

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