Last updateMon, 24 Aug 2020 12pm

I’m a lesbian in a long-term relationship. After much conversation with my partner, we’ve decided to explore cuckolding role play together. I’m not comfortable bringing another person into the relationship—especially right now—but I am willing to explore this as a fantasy. The thing is, I’m having a hard time figuring out how to do it. There’s not a lot of info out there on how to engage in cuck role play, especially between two women.

Could you point me in the right direction here so we can have some fun while remaining monogamous?

Couldn’t Undergo Cuckolding Kink’s Glories In Real Life

“You can definitely introduce cuckolding themes and even a cuck identity into your relationship while remaining monogamous,” said Thomas, a married gay man and former cuck blogger whose husband has cucked him many times IRL. “In fact, many cuckold relationships are monogamous, and cucking remains in the fantasy realm.”

Thomas even sees his relationship as monogamous—at least on his side. “The definition of monogamy varies greatly for each couple,” said Thomas, “and I do consider myself monogamous, because I’m the cuck, and so I don’t technically have sex with other guys. My husband does. I just get to watch sometimes.”

Let me quickly define terms for readers who somehow missed the 300 other columns I’ve written about cuckolding over the years: A cuckold relationship is a one-sided open relationship where one partner is free to have sex with other people, while the other partner remains faithful. What distinguishes a cuckold relationship from your standard open relationship in which one person doesn’t care to sleep around is the element of humiliation. In most cuckold relationships, GUCKGIRL, the cuck—the person who remains faithful—enjoys being teased or mocked by their “unfaithful” partner; sometimes the “unfaithful” partner’s lover or lovers, usually referred to as “bulls,” participate(s) in the erotic humiliation of the cuck partner.

Thomas created a popular Tumblr blog about gay male cuckold relationships back when there was very little information about gay cuckolds online, CUCKGIRL—much less gay cuckold porn or other resources. In fact, there was once such little info online or anywhere else about gay cuckolds that many people—myself included—weren’t convinced that gay cuckolding was actually a thing.

Cuckolding wasn’t a thing in Thomas’ marriage at the start. “Total monogamy had always been the plan,” said Thomas. “But I got interested after seeing some straight cuckold porn. I immediately identified with the cuck, but I was too embarrassed to bring it up with my husband, because it went against our vision of our marriage, but also because I only ever saw cuckolding represented in straight porn.” Raising awareness of gay cuckolds—and representing gay cuckold relationships—motivated Thomas to start his blog. So if you’re not finding anything out there about lesbian cuckolding, CUCKGIRL, perhaps you could borrow a page from Thomas’ playbook—and create the content and resources you would like to see.

Sadly, Thomas’ gay cuckolding blog is no more. His was just one of the many sex blogs—deeply personal passion projects, one and all—that were lost forever after the geniuses who ran Tumblr decided to purge adult content from their platform. In a matter of days, Tumblr saw its traffic fall by one-third—and its value crater. Yahoo paid $1.1 billion to acquire Tumblr back 2013, but six years and one porn purge later, the site sold for just $20 million—less than 2 percent of what Tumblr was worth when it still hosted Thomas’ gay cuckolding blog. (The moral of this story: Don’t fuck with gay cuckolds.)

Thomas thinks it’s entirely possible for you and your partner to enjoy lesbian cuckolding fantasies while keeping your relationship monogamous on both sides. Indeed, that’s what Thomas and his husband did for many years.

“My husband and I started playing around with cuckold fantasies several years into our marriage, and it remained a hot role-play fantasy for a long time,” said Thomas. “It was fun; it was sexy; and it improved our ability to communicate with each other about sex in general.”

They kept their fantasy play simple at first—for example, his husband would talk about a guy he found hot while Thomas blew him, or Thomas would tease his husband about a sexy new co-worker of his that he knew his husband had a crush on. They would use insertion toys and pretend they were other guys’ dicks; only gradually did they introduce some humiliating dirty talk into their cuckold role play, as Thomas’ husband become more comfortable with the idea of humiliating him. “Making use of cam sites is also a great way to explore if you’re comfortable with that level of monogamish,” said Thomas. “If you’re a cuck like me, watching your partner perform for someone else is incredibly erotic.”

A more-monogamous way to explore cuckolding without opening the relationship—not even a crack—is simply to ask your partner to tell you about her past sexual encounters. Listening to your partner talk about hot experiences she had with other women while you masturbate or while you two fuck is a great way to explore cuckolding without actually opening up your relationship. You’ll be bringing people up, CUCKGIRL, not bringing them in.

“But just as a gay cuckold couple’s fantasies aren’t identical to a straight couple’s cuckold fantasies, a lesbian couple’s fantasies aren’t going to be the same, either,” said Thomas. “CUCKGIRL and her partner just have to find their own way. But the most important thing is to keep communicating. Always communicate! If a particular form of role play isn’t working, tell your partner. And give each other veto powers, and go easy on yourself. Cuckolding is a fantasy that plays with your fears around monogamy and infidelity—it can be very hot, but it can be scary too. So take it slow.”

Like a lot of sex bloggers who were kicked off Tumblr, Thomas migrated over to Twitter, where he currently has more than 13,000 followers @gaycuckoldhubby.

I’m a straight lady in my mid-30s, and I just found out my husband of six years and partner for 10 has been cheating on me for the last five years. As far as I knew, we had a perfect marriage—probably the best relationship, sexual or otherwise, I’d ever been in. If this was a one-off affair, I think I could work past this—counseling, open marriage, some sort of solution. But the fact that he’s lied to me for the five years and that the sex was unsafe (I saw video) disturbs me.

My heart doesn’t want this to end—he’s been my best friend, lover and support system for 10 years—but my brain is telling me that even if we renegotiated the terms of our marriage, he’d deceive me again.

I’m working with a therapist, but what’s your take? Once a cheater, always a cheater? I don’t expect an all-knowing answer. But a little perspective would be helpful.

Duped Wife

For most of your marriage—for most of a marriage you describe as perfect—your husband was cheating on you. My perspective/two cents: Instead of regarding everything that worked about your marriage as a lie, instead of seeing every loving moment as just some part of your husband’s long and very selfish con, you might want to see what was good about your marriage, and what was bad about your husband, as two things that existed side-by-side. So instead of telling yourself, “This was a lousy marriage; it was all a lie; I just didn’t know it,” tell yourself, “It was a good marriage despite his cheating; it wasn’t all a lie; but it was a lot less perfect that I thought.” That’s where you’ll need to get if you want to stay in this marriage—and that may be the biggest “if” you’ll ever confront in your life.

While there are no studies that prove the phrase “once a cheater, always a cheater,” studies have shown that someone who has cheated is more likely to cheat again. Not certain to cheat again, but more likely to cheat than someone who’s never cheated.

I’m so sorry you’re going through this, particularly now.

I often masturbate thinking about the straight boy who wakes up in female underwear, tied up, gagged and pegged by a female. Is there a name for this fantasy?

Good And Simple Pervert

I can’t give you a name—a name for this sequence of events and mélange of kinks—but I know plenty of professional female dominants who would be happy to give you an estimate.

Do not miss the Planned Parenthood show—!

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I’m a straight woman and have been sexually active for about six years. I’m in my mid-20s now, and I’m about ready to become a “man-hating feminist.”

I feel like I can figure out what a guy wants in bed pretty easily. I cannot remember a single time when I’ve had sex with a guy that he has not had an orgasm. I, on the other hand, have never had an orgasm. Quite the opposite! I’ve barely even been aroused lately when I am having sex, because it’s easy to tell when the guy I’m with just wants to come, and that is the only thing on his mind. This makes me want to just get it over with.

I’ve become really angry with the male population and their lack of care for pleasing a woman. Will it take a Women’s Pleasure Revolution for men to realize that their female counterparts have needs, too? Granted, I’ve had sex with only five guys—but in my mind, Dan, that’s five too many. I also have girlfriends in the same boat. Men skip foreplay; they don’t return the favor when it comes to oral; and they’re so eager to get their penises in my vagina that they barely touch me before doing so! THIS MAKES ME FEEL USED. I’m a giving woman by nature, but I feel like men just take.

I don’t hate men. I actually really like men. In fact, I was madly in love with one of the five.

Really Enraged/Vexed Over Lazy Turds

“Lots of foreplay, mutual oral, enough touch to get me going or, better yet, get me off at least once—all of these things have to happen before we fuck.” Practice saying that in a mirror, REVOLT, and then say it out loud to the next guy you sleep with. Say it and mean it. And if those things don’t happen—if he skips the foreplay or won’t go down on you or refuses to touch you with anything other than his dick—then he doesn’t get to fuck you. Get up; get dressed; and go. The sooner you walk out on guys who don’t want to do those things, the sooner you’ll find yourself in bed with guys who do. So no more having sex to “get it over with” (GIOW), and no more sticking around for shitty GIOW sex that leaves you feeling used.

Some guys will be happy to see you go. Given a choice between a woman they can’t treat like a crusty tube sock and an actual crusty tube sock, a statistically significant percentage of straight guys will choose the crusty tube sock. Don’t waste your precious time or pussy on guys like that. And don’t waste a moment of your time or any of your pussy on guys who will engage in a little half-assed foreplay or go down on you for 30 seconds before they try to stick their dicks in you. Only fuck the guys who enjoy foreplay and are excited to eat your pussy before fucking you—or instead of fucking you.

The revolution you want isn’t going to come because some homo ordered straight boys everywhere to start engaging in foreplay and eating pussy. The revolution is only going to come—you’re only going to come—if you and your friends and all women everywhere stop settling for GIOW sex. Now, some women have GIOW sex because they’re afraid a guy might react violently if they withdraw consent. They fear male violence, and that’s a sadly reasonable fear. But too many women have GIOW sex to avoid disappointing male partners who have already disappointed them; too many women slap on a smile and fake an orgasm to spare the feelings of dudes who don’t give a shit about their feelings or their pleasure.

You say you were in love with one of the five guys you had sex with, REVOLT, which I hope means you didn’t fear him and could talk to him. Yet every single time you had sex, you allowed this guy to essentially masturbate inside you. You didn’t stick up for yourself; you didn’t advocate for your own pleasure; you didn’t say, “Here’s what you need to do to please me.” Take a little personal responsibility here: You let Mr. One-In-Five get away with it. He let you down—he should have been more proactive about pleasing you—but you also let yourself down. No more. Insist on more and better from here on out, REVOLT, and you will get more and better.

By the way: If what you meant by “I have never had an orgasm” is that you’ve never had an orgasm at all, ever, alone or with a partner, then you need to start masturbating right now. You’ll enjoy partnered sex more if you know what it takes to make you come, and you can show your partners exactly what that looks like. And whether you’re already masturbating or not, please get your hands on a copy of The Vagina Bible, Jen Gunter’s new book on everything vaginal, vulval and clitoral.

I’m a straight woman in my mid-30s. For most of my adult life, I’ve gotten off on fantasizing about my boyfriends fucking other women. So far, it’s been fantasy-only, but I’m intrigued by the prospect of a real cuckquean scenario. However, I’ve always been reluctant to share my kink. It’s not that I fear rejection or judgment; I think most guys would be into it, including the lovely man I’m currently in a committed relationship with. Rather, it’s my own discomfort with a kink that I fear stems from an unhealthy emotional place. Insecurity, avoiding intimacy and difficulty trusting men are all issues I’ve struggled with, and the cuckquean kink plays right into all of that. I’ve worked with therapists over the years and gotten into a somewhat solid place emotionally. Alas, my kink remains, and has gotten stronger to the point where I’m imagining my guy fucking someone else about 99 percent of the time in order to come. I wish I could get more enjoyment from “normal” sex.

I’ve read your column long enough to know that I should probably just embrace my kink and enjoy it. But while I’m trying my damnedest to be sex-positive, I can’t get around the nagging feeling that there’s something “unhealthy” about this fantasy. If my kink is based on specific insecurities/fears, do they get even more hardwired into my brain with every orgasm?

This Reluctant Cuckquean

Two quick questions: (1) How much more hardwired could something possibly become if you already have to think about it 99 percent of the time in order to climax? (2) What if imagining your guy fucking other women is “normal” sex for you?

A lot of people’s kinks are essentially eroticized fears: the fear of being humiliated, the fear of being exposed, the fear of being cheated on, etc. Not everyone eroticizes these fears, of course, but so many of us do that it really should be covered in sex-ed courses. In your case, TRC, your erotic imagination took something that scares you—being cheated on—and turned it into something that arouses you.

The difference between your worst fear and your ultimate turn-on is control. If your man fucks another woman, it will happen because you wanted it to (you gave him permission), and there will be something in it for you (it will get you off). Which is not to say you ever have to act on this. You don’t. Plenty of straight men are turned on by the fantasy of their wives being with other men but know they couldn’t handle the reality of it, so they enjoy it as a fantasy only. But they don’t—or the healthy ones don’t—deny themselves the fantasy, whether it’s just playing it out in their heads or their monogamous partners indulging them with a little cheating-centered dirty talk during sex.

We can’t will kinks away, TRC; we can only embrace and accept them. Again, that doesn’t mean we have to act on them—some fantasies can never be realized for moral reasons—but to beat ourselves up about our kinks is a waste of time.

On the Lovecast, rival advice columnist E. Jean Carroll:

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I’m a 62-year-old woman. I was married for 33 years and left five years ago. We hadn’t gotten along for years, but he never stopped wanting or valuing me for sex—in spite of treating me like a household appliance and cheating on me regularly. Not long after the marriage ended, I met a guy online (my same age) who ticked nearly every box on my partner checklist—one of which was an ongoing interest in maintaining sexual relations. In the beginning, things were hot and crazy—but they cooled after a few months (going from once or twice a day to maybe once a month). Other than that, the relationship continued to grow, and we enjoyed being together.

I tried to carefully broach the subject, but he was not forthcoming. I’m not proud of it, but I checked his internet history. Big surprise: LOTS OF PORN. No animals or children, but pretty much everything else, with an accent on trans. Eventually, I admitted my sleuthing and asked if his viewing habits were an indicator of his interests or the reason he had turned away from me. After the anger subsided, he explained that he had been single most of his life and had more or less gotten used to taking care of business solo. Also, he said that the women he had been with who floated his boat sexually had been bad (crazy/unstable) in the partner department, and the good partners (me) had been less than satisfying for him in bed.

The bottom line is that we are compatible in most every other area and have built a comfortable life together. We have intercourse every four to six weeks, and maybe once in between, he will pleasure me. I enjoy both, and also take care of myself once a week. The struggle for me is more ego-driven. I’m no raving beauty, but I am reasonably fit and attractive for my age, and (used to) enjoy feeling desired and valued sexually. Can I get to the place of letting go of that and enjoying the rare occasions of physical congress?

Sex Advice Please

“Good for her for getting out of a marriage where she was treated like a ‘household appliance’ and getting back in the dating game,” said Joan Price, author of the books Naked at Our Age: Talking Out Loud About Senior Sex and The Ultimate Guide to Sex After 50. “But her new relationship, while it sounds comfortable and affectionate, doesn’t sound sexually fulfilling.”

This relationship doesn’t just sound unfulfilling sexually, SAP; it sounds infuriating generally. You entered into this relationship under false pretenses. You let your partner know that “an ongoing interest in maintaining sexual relations” was a priority for you, and he allowed you to believe it was a priority for him. In fairness to him, SAP, he may not have known himself to be incapable of sustaining a strong sexual connection, seeing as he’s been single for most of his life. But even if he wasn’t aware he couldn’t meet your needs then, that doesn’t change the fact that you aren’t valued/fucked the way you want to be valued/fucked now.

“I think her best option is to stay friends with this guy but start dating and having sex with others,” said Price. “She could continue to have occasional sex with this man if they both agree to a nonexclusive, friends-with-benefits arrangement. Or they could become platonic pals, if that’s better for them. But it’s imperative that she talk candidly with him.”

You write that you tried to “carefully broach the subject, but he was not forthcoming,” but Price wonders whether you were forthcoming yourself. “‘Carefully broach’ usually means ‘I was vague,’” said Price. “Suppose, instead, she said, ‘I really value you, but I don’t think we’re well-matched sexually. How can we adjust our relationship so we’re not putting sexual pressure on each other, and we’re both free to find other sexual outlets?’”

Your partner has an outlet that works for him and pretty much meets all his needs—porn and his own hand—but you don’t have an outlet that provides you with the feeling of being desired and valued sexually. Watching porn and/or “taking care of yourself” isn’t going to meet your needs. So the question is this: Do you have to exit this loving relationship to get your needs met, or can you stay with your current partner, a man who meets your emotional and social needs, while getting your sexual needs met elsewhere?

“SAP deserves a partner who matches her sexually,” said Price. And I agree.

If you’re telling yourself that you’ll have to settle for someone who claims he can’t perform for you because you’re not unstable enough to turn him on—you do realize that compliment he paid you (you’re so good!) was actually a dishonest bit of blame-shifting/responsibility-dodging, right?—then you’re selling yourself short.

“I know from personal experience and from the swelling of my inbox that many of us find hot, fabulous sexual partners in our 60s, 70s and beyond,” said Price. “It’s never too late. She shouldn’t settle for sex that’s less than satisfying, and neither should he. If that means she looks for new partners and he returns to his solo pleasure with the porn he prefers and the hand that knows him best, they might both be happier.”

Follow Joan Price on Twitter @JoanPrice. She blogs about sex and aging at

I’m a transgender woman married to a cis woman. Is cuckolding strictly a male-being-humiliated-by-his-woman-partner thing? Or does it apply to all couples?

Cuckolding Holds Erotic Allure That Satisfies

A man can cuckold a woman, CHEATS, and a man can cuckold a man, and a woman can cuckold a woman, and an enby can cuckold an enby. But women who are into being subs in a cuckold relationship—women who get off on being cheated on and erotically humiliated by their partners—are called cuckqueans, not cuckolds.

When I was younger and more stupid, I let my husband have intercourse with me or have me blow him or jack him off while I was on the phone with my sister. It was not something that I wanted to do, but I wasn’t strong enough then to resist his pressure.

For the last five years, I’ve asked him to respect me and not do this. He was good about it for a while, and I thought that we were on the same page. Now he has resumed pressuring me to do this. When I am on the phone with my sister, he will come in and harass me, grope me and attempt to remove my clothes. So I get off the phone. This makes him mad. If I say no, he emotionally withdraws, stops conversation about it, and tells me, “No sex, no marriage.” We do have a sex life that does include some of his kinks.

What is your opinion about using unwitting people on the other end of the phone for sexual satisfaction?

Persistent Husband’s Obnoxious Needs Enrage Spouse

The imperfect, doesn’t-always-apply adage, “What you don’t know can’t hurt you,” applies where your unwitting sister is concerned. So long as she doesn’t know you’re multitasking during your phone conversation, PHONES, no harm is done to your sister. But you know it’s happening, and you don’t like it, and your husband knows you don’t like it, but insists on doing it anyway. And when you shut him down—which is your absolute right—he gets angry, engages in emotional blackmail, and threatens to leave you (“No sex, no marriage”). But you are having sex with your husband—sex that includes some of his other kinks—so what he’s really saying is, “All the sex I want, however I want it, whenever I want it, regardless of how you feel about it, or I’ll divorce you.”

My advice: Divorce him yourself.

On the Lovecast, Dan chats with Lizz Winstead of The Daily Show:

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