Q: I'm a 41-year-old male who looks like the tall, strong, professional, alpha-male type on the outside. On the inside, though, I would like to find a strong, confident woman who wants a cuckolding relationship—she sleeps with other men, while I am faithful and submissive to her. There must be women out there who would love to have a loving, doting boyfriend or husband waiting at home while they go out with other men, but I tend to attract women who want the alpha-male type. What can I do to find—or attract—the kind of woman I'm interested in? Or should I go in for vanilla dating and then have a discussion about cuckolding after we've started having sex? —Another Lad Pursuing Humiliating Action
A: "Most women, even dominant women, are still looking for guys who look like they 'kick ass and take names' in every other aspect of their lives," said FleeMarket (u/flee_market), one of the moderators of r/cuckold on Reddit. "As for how to find dominant women, I see a lot of submissive guys on various websites—OkCupid, Reddit, Tinder, FetLife—and something they don't understand is that women looking for sex or love online tend to get buried in unsolicited PMs from thirsty guys. That makes it hard to find that one respectful PM from a guy like our letter writer here. The signal gets lost in the noise."
Before we get to some practical advice for ALPHA, a quick word about the term "cuck." While it has long been an affectionate/horny term embraced by self-identified cuckold fetishists, the alt-right has attempted to turn "cuck" into a term of abuse, hurling it at any straight white man who gives a shit about racial justice, police brutality, and the plight of undocumented immigrants. In an effort to wrest "cuck" back from the bigots, and to mark the waning days of the Trump campaign, I'm dedicating this week's column to "cuck" as properly understood: a guy who wants his partner to sleep with other men.
So, ALPHA, how can you attract a woman who wants a cuck?
"What's worked for me is using the Internet not to find people but to find kinky events where dominant women gather in real life," said FleeMarket. "I'm on my second openly dominant female partner in four years, both of whom I met at kinky parties. The events are usually listed on FetLife, and you usually have to attend a munch first to demonstrate that you're not a dingus who can't follow the rules or a psycho who doesn't care about them."
You will find a lot of advice for wannabe cucks on r/cuckold, most offered in response to men trying to talk their vanilla wives or girlfriends into cuckolding them. But you're as likely to read stories of failure (she said no, absolutely not, never) as you are to read success stories (she's fucking other guys, and here, with her OK, is the video).
"As much effort and time as getting into the kinky community takes, it's still easier than trying to turn a vanilla woman kinky," said FleeMarket. "He shouldn't 'lead with his kink.' If a woman asks him what his interests are, mention it, but dial down the excitement level. These ladies deal with a lot of creeps, and it's easy to scare them off. Basically: Be in the right place, treat the women there with respect, and get to know them as people first."
Q: 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—fiance 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!
A: Congrats on your upcoming wedding, CHEAT! And ALPHA? It would appear some vanilla women can be turned.
Q: 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
PS: It'll be more than kissing either way!
A: "Everybody's different," said FleeMarket. "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," said FleeMarket. "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," said FleeMarket. "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 OK to call a stop to play if you need to."
Q: 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
A: 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. 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! v
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