Dear Dan: 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
Dear CUCKGIRL: “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 where 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,” participates 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 so 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’s 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’s playbook and create the content and resources you would like to see.
Sadly, Thomas’s 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% of what Tumblr was worth when it still hosted Thomas’s 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 coworker of his that he knew his husband had a crush on. They would use insertion toys and pretend they were other guys’ dicks and only gradually did they introduce some humiliating dirty talk into their cuckold role-play talk, and then only as Thomas’s 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. His handle on Twitter is @gaycuckoldhubby.
Dear Dan: 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
Dear DW: 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. And while there are no studies that “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.
Dear Dan: 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
Dear GASP: 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 that would be happy to give you an estimate.
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