Dear Dan: My ex-three-exes-ago was a cuckold. I swore I would never date another cuckold after he blew up at me for not cheating on him juuuuuust right. I was just a prop, and I came to hate him. I also hated you, Dan, because he raised the subject by giving me some of your columns to read. Fast-forward five years, and my brand-new boyfriend tells me being cuckolded is his ultimate fantasy. I literally started to cry. He held me, he apologized on behalf of all cuckolds everywhere, we laughed, and then he dropped it. He didn’t pressure me, and about a year later, we gave it a try on his birthday. It turns out my boyfriend — fiancé now — is much better at this kink than my ex was. He’s open and honest, he communicates constructively, and he was willing to step outside his comfort zone to accommodate my needs. (He wanted the other guys to be strangers, but I need to know someone before letting him in my body.) I have a regular thing with an ex-FWB, and sex with my cuck is frequent and hot. Things couldn’t be better. So I’m not mad at you anymore, Dan! All is forgiven!
— Cheating Happily Ever After, Thanks!
Dear CHEAT: Congrats on your upcoming wedding, CHEAT!
Dear Dan: I’m a straight woman who’s about to cuck my man. We’re trying to figure out if my first sexual encounter with another guy should be in front of him or not. He says he doesn’t care; he’s excited either way. I am so nervous, but it’s a good nervous. We have been monogamous until now. I know you say to take it slow. But when it comes to cuckolding, does slow mean “Only kiss the other guy in front of him the first time” or “Tell him about the other guy I kissed”?
— On Him Watching Or Waiting
P.S. It’ll be more than kissing either way!
Dear OHWOW: “Everybody’s different,” says FleeMarket (u/fee_market), one of the moderators of r/cuckold on Reddit. “There are guys who love being left at home while she goes out on a ‘date,’ there are guys who love being in the house/hotel but not in the room, there are guys who want to be in the room watching or participating. But as far as whether you should dip your toe in or jump in with both feet, there is no ‘right way,’ only what’s right for you two.”
That said, OHWOW, the reality of a partner sleeping with someone else for the first time — in front of you or not — can be a lot more intense than the fantasy, and you should definitely take things slow the first time.
“There’s the ‘baby steps approach,’ i.e., just flirting with or kissing the other guy (whether in front of him or not) and then seeing how he reacts,” FleeMarket says. “Or telling him that you slept with the other guy, when you really didn’t — just to see how he takes it. Then there’s jumping in with both feet and getting a hotel room and a few drinks with this other guy before taking both men up to your room.”
Whatever you decide, OHWOW, FleeMarket recommends having a plan in place in case things/feels/dicks go wrong.
“Use the traffic-light system,” FleeMarket says. “Things getting too intense? Say ‘yellow’ to slow the play down. Someone getting upset? Say ‘red’ to stop the play and all three of you can talk. It’s always better if everyone understands it’s okay to call a stop to play if you need to.”
Dear Dan: I just came across the word “wittol.” It means “a man who knows, condones, and even encourages his wife’s enjoyment of coitus with another man or men; a contented cuckold.” Considering the frequency with which cuckolding comes up and your influence on language, I thought you might want to know.
— He’s Expanding Lexicon Perpetually
Dear HELP: Discontent is a big part of the cuckolding kink, HELP, as cuckolds get off on feeling humiliated and jealous. So I’m not sure “wittol” quite works. But if the alt-right white supremacists succeed in making “cuck” synonymous with “race traitor,” maybe cucks will switch to “wittol.” But don’t give up without a fight, cucks!
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