Dear Dan: I’m a straight man and I recently got out of a relationship with a woman who would monitor my internet use to make sure I wasn’t “masturbating to the wrong things.” (My kinks are nothing too outrageous: feet and mild FemDom.) I’ve been dating a new woman for three months, and it’s time to lay my kink cards on the table. But I’m really afraid to open up, thanks to my kink-shaming ex. My new girlfriend and I read your column together — so if you publish my letter, I’ll be able to gauge her likely response if I decide to disclose.
—Help A Guy Out?
Dear HAGO: My pleasure, HAGO, but be careful: Sometimes people react negatively to any mention of a kink, not because they’re necessarily turned off or grossed out but because they assume their partner is. So don’t panic if your new girlfriend’s first reaction is negative (“Ew, gross! Feet and FemDom!”), because it may not represent her true feelings and/or openness to your kinks. To learn how she really feels, you’re probably going to have to make the disclosure you’re trying to sidestep.
Dear Dan: I’m a 24-year-old woman, and three weeks ago I got out of a long-term relationship with a guy in his mid-30s. Over the last few months of the relationship, I started falling for someone else and began dating the new guy pretty much immediately after the breakup. When should I tell my old boyfriend? We agreed to stay friends, and we still talk and see each other at least once a week. I want him to hear it from me, but I’m not sure how much time is appropriate/respectful.
—Don’t Wanna Be An Asshole
Dear DWBAA: Meeting up too soon after a breakup has a way of keeping emotional wounds open and fresh, DWBAA, particularly for the person who was dumped (I’m assuming you did the dumping here). And once-a-week meetings definitely qualifies as too much, too soon. That said, if you think your ex-boyfriend is likely to hear about your new boyfriend from mutual friends, telling him yourself (and soon) is obviously the right (and difficult) thing to do. But if your ex is going to find out about your new boyfriend from, say, your Instagram account, encouraging him to unfollow you and letting some time pass — enough so you can fudge the start date of your new relationship — would be the right (and ego-sparing) thing to do.
Dear Dan: My wife has a fantasy where she’s blindfolded and restrained on our bed. She hears the front door open, followed by footsteps coming up the stairs, and then she’s ravished by… who? She won’t know, presumably, until it’s over. My question: In fulfilling this fantasy for her, where anonymity and surprise are part of the appeal, what do I tell her in advance? Do I discuss the entire scenario with her, so she knows exactly what’s going to happen, minus the identity of the very special guest star (who would be a semi-regular we’ve played with before, but she wouldn’t necessarily know that at first)? That seems to eliminate the surprise element of the fantasy. Is it enough to tell her, without mentioning the specific scenario, that I’d like to make one of her fantasies come true, and ask her to trust me?
—Ethical Thinking In Quite Unusual, Elaborate Tied Tight Enactment
Dear ETIQUETTE: Presumably? There’s no room for “presumablies” when you’re arranging to fulfill a varsity-level fantasy. I’m guessing she’d rather not know who’s ravishing her before or during the big event, ETIQUETTE, and she may not want to know after. But you need to ask her what she wants — no presumptions — before you start making arrangements.
She might want to know everything in advance — including the identity of that stranger — or she might want you to decide everything. But you need to check in with her first: “Honey, I want to help you realize that fantasy — you’re tied to the bed, a stranger arrives, you’re ravished by said stranger — but I need to know how involved you want to be in the planning. Clear everything with you — where, when, who, how — or just make it happen?”
You may find that she wants to be surprised by who but not by when, ETIQUETTE, or by when but not by who — or by who but not by when, how, or where. Or she may want the whole thing to be a surprise. But you have to find out exactly what she wants before you make any plans.
And here’s a bonus pro tip for you: Don’t reveal the identity of your VSGS immediately afterward. Because if it goes well, and your wife wants a repeat, you may be able to get a few more encounters out of your first VSGS.
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