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. 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. 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.
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.
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? 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.