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I've been hooking up with a guy for awhile now who will only meet up with me if he can wear a ski mask. We live in a rural area with very few options for sexual partners so I begrudgingly went along with this at first. I have asked him so many times for him not to wear the mask but he refuses to as he wants to be discreet and ultiately being horny I usually give in and meet up with him. Once when he was in a vulnerable position I pulled his mask off but he immediately bolted out the door before I could see his face. A month later he messages me asking if I'm "over that." I replied NO and told him I wouldn't be meeting up with him anymore if he's going to continue wearing a mask. After eight months of persistence requests to meet back up with him, I decided I would do it.

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Some of his original emails sent to me showed his real name as the sender. So I knew his name all along but I wasn't able to match up his name during a search through social media that would show a picture of his face. Until recently. Finally there he was on Instagram showing his cute face to the world while hunting, fishing, and doing lots of boating. He looks like a great friend to have. I thought, great, I'll meet up with him and show him I found his Instagram account and he will surely see how ridiculous he's being and take his mask off. Nope! He didn't care that I knew what he looked like and he wanted to keep wearing his face mask and keep meeting up with me on the regular while pretending I didn't actually know what he looked like! I can't seem to break him of this habit no matter what I do or say and it drives me nuts and I struggle to understand it.

I can't find anything online that addresses this topic but I do like mask boy a lot even though I strangely have never seen his face in person so I am hoping you have some suggestions to get him to ditch the mask and be more open with me and perhaps even be friends.

Hookup's Oddly Obsessive Demand Isn't Erotic

Let's do the math, shall we?

He told you he wanted to wear the mask to preserve his anonymity + he sent you his real name + you found him on Instagram + he now knows you know who he is and what he looks like + he insists on wearing the ski mask when you fuck regardless = HE LIKES TO WEAR THAT FUCKING SKI MASK.

I hope you're not operating a table saw or anything, but... it sounds to me like the guy has a kink. It could be a lifelong kink, HOODIE, or he may have worn the mask to preserve his anonymity when he first started hooking up with men and the mask/subterfuge/anonymity carved such a deep groove in his erotic imagination—he forged such powerful associations between ski masks, facelessness, and arousal—that he can't have gay sex without wearing one. So if it wasn't a kink to start, it functions as one now. (My money's on lifelong kink, for the record; this guy has probably always gotten off on the idea of being the Masked Cocksucker.)

So what to do?

Well, he's made it clear that he's not going to stop wearing that ski mask during sex. So if the mask bothers you and/or isn't something you find sexy and/or makes you feel like someone/something he's ashamed of and you don't like feeling that way, then you'll have stop hooking up with him. He clearly isn't interested in (or capable of) integrating a friend with benefits, much less a boyfriend, into the hunting, fishing, and boating sides of his life right now, HOODIE, and he may never get there. And he's under no obligation to get there.

And a day comes when he's ready to have a FWB or a BF, it's unlikely that FWB/BF will be you. He's placed you in a box, e.g., you're a quasi-anonymous sex partner, and you're probably going to stay in that box even if he outgrows the need to keep guys in that box.

So... my advice would be to fuck someone else. But I get it: you live in a rural area and the pickings are slim. (Still, I hear things are looking up for queers in rural areas—which is amazing since things seem to be going to hell everywhere else.) As slim as the pickings are, HOODIE, they can't be so slim you have no choice but to put up with this guy. In the pre-hookup-ap dark ages, horny rural homos had to risk outing themselves slipping into gay bars that looked like fortified bunkers or risk arrest at truck stops. Grindr, Scruff, Jack'd, Manhunt, et al, have made it easier for geographically isolated homos (and bimos!) to find each other.

P.S. Hail Mary pass: tell him you're happy to hook up with him on the condition that he only wears the ski mask during sex. He arrives without it on, he put it on when you start messing around, he takes it off after the sex is over and hangs out for a bit. He knows you're only pretending not to know what he looks like... which means he's pretending too. Perhaps you can get him to compromise on when the pretense begins and when it ends. You do have some leverage here—he's pursued you pretty relentlessly—but you can only use that leverage if you're willing to cut him off.


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