...masculine man, to only have him become my sissy in private.

What is starting to give me pause is that his requests regarding humiliation during our scenes have started to center around calling him gay and "forcing" him to do gay things. This has ranged from watching sissy hypno and gay porn to writing a fictional "coming out as gay" letter to his friends and family. Don't get me wrong, the power exchange is hot and intense. However, as a sissy he'll say he dreams about cock, that he wants to suck a guy off, he begs Mistress to train him to take cock. As a guy, he's made some upsettingly homophobic comments that I've called him out on. Recently, when we're not in a scene he'll quietly say, "I'm gay... just kidding!" These frequent small comments, leave me feeling like it's not a joke and that he actually might be closeted AF. It also makes me uneasy because it makes me feel like it blurs the line of when a scene begins and ends.

My question is, is this more than just role play and wanting to be humiliated? If not, how do I get him to explore the possibility that he really might be gay (or bi)? I love your campsite rule and live by it, so is this on me to help him unpack?

Person Into Nuanced Kink

I'm glad the power exchange is hot and intense, PINK, but you need to proceed with caution before you "force" a dick into this dude's mouth.

Because this absolutely, positively sounds like more than just role play and a desire to be erotically humiliated. This is a man with issues—excuse me, a guy's guy with some hot, intense, sexy issues. His persona and public presentation seem to have been carefully constructed to cover for his deep, dark, thoroughly eroticized secret(s): the sissy thing, the hunger for cock thing. I worry that if you go there, PINK, and do what he's asking you to do—if you force a cock down his throat—your guy's guy might have a major melt down.

And who knows how he'll over compensate then?

Now there are certainly guy's guys out there who get off on forced feminization and even forced bi who are healthy about it—they don't go to pieces when "forced" to suck a cock—because they understand who they are, they can calmly and clearly articulate why these things turn them on, and they're capable of compartmentalizing this shit. They know this is a sexy game—one informed by all sorts of icky cultural messaging about women and gay men—and they're capable of playing this game without being a misogynist, a homophobe, or unstable and potentially violent basket case.

Ask yourself: Which one do you think this guy is? Stable and cool and able to communicate and compartmentalize—and able to enjoy a kink informed by toxic cultural messaging without succumbing to that messaging—or is he a mess? If I had to bet, PINK, I would put my money on "mess." All I have to go on is the details you've included in your letter, of course, but the fact that this guy gets off on the idea of being gay—or being forced to do gay shit—and then turns around and says upsettingly homophobic shit (and presumably believes that upsettingly homophobic shit), well, that's a bad sign. (Does he say/believe equally upsetting misogynistic shit? He may not have said anything misogynistic in front of you, PINK, but that doesn't mean he hasn't said and doesn't believe that shit too.)

As much as I'd like to sign off on forcing this guy to suck a cock, PINK, I didn't come away from your letter thinking, "He'll be fine! This experience won't shatter him! PINK won't be in any physical danger if this dude has a melt down after this experience!" I came away thinking, "This dude has unexamined and consequently unresolved issues about his desires—issues he needs to get a handle on before he asks anyone else to help him realize these fantasies." (I wanted to say, "he needs to fully resolve before he asks anyone else to help him realize these fantasies," but who amongst us can claim to have fully resolved their issues? Full resolution may be setting the bar too high. But he needs to get a grip.)

Finally, PINK, could your sissy be gay? Maybe. Sure, PINK, of course. He could also be bi. I think you should talk to him about the possibility he's bisexual—not 50/50 bi, not someone who could fall in love with a man or a woman, not someone doesn't only sees people and never gender, blah blah blah. But a guy who, under a very specific sort of circumstance, is capable of being sexual with another man. Bisexual activist Robyn Ochs's reality-friendly definition of bisexual might surprise and comfort him...

“I call myself bisexual because I acknowledge that I have in myself the potential to be attracted—romantically and/or sexually—to people of more than one sex and/or gender, not necessarily at the same time, not necessarily in the same way and not necessarily to the same degree.”

And he might benefit from reading this old SLLOTD where we discussed it. He can still get off on being called a fag (lord knows lots of gay men do) and fantasize about being forced to come out not as bi but as gay. But, again, before you do any of this gay shit with and to him, PIN, he's got to demonstrate that he understand who he is, what he wants, and what he's asking you to do. He hasn't done that yet.