City Paper is not for tourists.
I’m a cis woman in my mid-40s, and my significant other has a cuckolding fetish. My first response was “Oh, hell no!” But if I’m willing to have a threesome, how much further of a stretch is it, really? He does have some experience with this varsity-level kink, so he knows what to expect. I’ve asked him some questions, but some things I prefer to research on my own. My questions for you: (1) I don’t get cuckolding. I’ve read all about it, but nothing about it resonates with me. My SO really wants me to be into his fetish if I am going to act on it, but what if I’m just into being GGG? Can’t that be enough? (2) How should I go about finding appropriate candidates who would be into sharing this experience with us? I’m not really sure that I’d want someone with experience as a bull, because I don’t feel good about this playing out the way I’ve seen it in porn. (3) We enjoy cross-dressing and chastity play. How do I find someone who will be cool about my SO sitting in the room in a cock lock and lingerie? (4) I kind of have a “type” (don’t we all), and I’m not certain my type plays into this kink. I prefer someone who is very dominant in public but submissive to me in the bedroom. This doesn’t seem to align with your typical bull behavior. However, I do not enjoy being dominated. Do you think this matters? —Can’t Understand Cuckold Kink
1. Cuckolding isn’t that hard to understand: A cuckold gets off on their partner fucking other people and being humiliated or degraded by their partner and/or their partner’s playmates. Seeing as you already enjoy dominating guys and threesomes, CUCK, what’s not to enjoy about a cuckolding scenario?
2. Vanilla PIV intercourse rarely plays out in real life the way it does in porn. So whether you go with an experienced bull or find someone who’s unfamiliar with cuckold play but game, you don’t have to reenact whatever cuckold porn you’ve watched or read. Write your own script!
3. By using your words, CUCK. Tell any guy who’s interested in being your very special guest star (VSGS) that your SO is a cuckold and he’ll be there in lingerie with his cock locked up. If that turns a VSGS candidate off, then he’s not the right VSGS for you.
4. In most cuckold porn, the bull—the man who fucks the cuck’s wife or girlfriend (or boyfriend or husband) in front of him—is the dominant partner. But, again, you get to write your own script, and if you want your bull to be submissive, make that clear to your potential bulls. —Dan Savage
I’m a 54-year-old gay guy living in New York City. I’m into bondage, and I have a profile on Recon with plenty of pictures showing what I’m into. A guy visiting from San Francisco cruised me. He asked me to send a face pic, and I did. He invited me to his hotel. He didn’t have any gear with him, so I stopped at a hardware store and picked up $40 worth of rope and duct tape on my way to meet him. But after 30 seconds of small talk, he said he just wasn’t feeling it. I said OK, that happens, and I left. I’m totally confused. I’m a decent looking guy, and the photo I sent is recent. I was freshly showered, so no hygiene or BO issues. Obviously, you can’t force yourself to be into someone, but could he have handled it better? Should he have followed up with a message apologizing? Should I reach out and ask him what happened, or is that just pathetic? —Bondage Offer Not Delivered After Getting Evicted
Typically when this happens—photos exchanged, hookup arranged, mind changed—it’s because the photos were out of date or were not representative. Since we aren’t always the best judge of our own photos, BONDAGE, you should ask a friend who won’t bullshit you to look at your photos and give it to you straight.
If your no-bullshit friend clears your photos, then reach out to Mr. San Francisco. He had to make a snap decision when you arrived with that bag of rope and duct tape: Did he feel comfortable letting this stranger render him helpless? In a vanilla hookup, he could give it a little time and back out after some foreplay—it’s a lot harder to back out when the foreplay involves rope and duct tape. So send him a message via Recon. Open by telling him you aren’t buttsore or angry, and he had every right to change his mind, even at the last minute—which means he has nothing to apologize for, so you aren’t owed an apology and you shouldn’t message him if you’re seeking one.
Then ask if you said or did something that made him feel unsafe. If you did, BONDAGE, accept his feedback graciously—don’t argue with him or attempt to litigate what went down. Just listen. It may not have been your intention to freak him out by making, say, a few serial-killer jokes, but his impression is what matters, not your intention. And who knows? A sincere effort to get a little constructive feedback may leave him feeling better about you and up for playing the next time he’s in town. —DS
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
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. —DS