Indeed he is a mess. Yet she wrote him as "really cool" despite all the dizzying details that follow.

PINK: A man with respect wouldn't make you go though such contorted role playing. Don't worry about seeming judgmental or choosey - dump him.
PINK- before you proceed you need to ask yourself what is it that YOU want out of this relationship, and how committed you are to each other.
If it’s a short term full of play sessions you’re looking for then it seems like you already have it. I think Dan may have been a bit too cautious about guy’s guy potential danger to you. You didn’t mention how he behaves once a play session is over and that’s a good sign. Some people feel a deep remorse once the act is over, break down, cry, blame others, get violent, etc. (as my opinion this is probably one of the main reasons sex workers are being attacked.)

That said, guy’s guy certainly has some self-accepting issues he needs to work on. If that helps, try and take his misogynist and homophobic comments as an inner struggle of someone who hates himself for what he feels and does. I’m not saying you should accept it, but it will give you a perspective to work with.

If you’re in it for the long haul then it is my impression that he is likely to have sex with men sooner or later, something you can incorporate in your life in case you’re interested.
As for his femme side, there can also be some developments in this arena once he is finally at peace with his female self. This can be anywhere from dressing up at home just because, going out en femme, hair removal, hormones, and more.

And be aware that some people may never change, raindrop @ 1 is still an idiot.

I agree the guy is a minefield of contradictions, but he is consistent with:

Sissy play is humiliating because of the culture's misogyny. For the cock sucking to be humiliating, he has to run down gays because society doesn't demonize enough anymore (and a 26-y-o, kinky switch who reads Savage Love certainly doesn't).

Is the cock-sucking a turn-on for him because he can construe it as humiliating and demeaning in his mind if it's "gay"? Or is the bigger attraction some same-sex attraction that he's buried very deep? (because, yeah, he could easily be a gay closet-case).
Great answer Dan, and kudos to PINK for demonstrating great sexual ethics in asking for clarification on the campsite rule in this scenario. She is the more experienced partner when it comes to kink, although younger in chronological age, and she appears to fully understand the responsibility as well as the fun of being a good Mistress to her sissy-boy. Until this guy can acknowledge and own whatever he is currently repressing about his sexual identity and desires, ordering him to explore gay sex within their subspace is fraught with potential for disaster. Also, as things currently stand, I pity the unsuspecting GGG gay man who gets goat-roped into being the third for their play party. Yeeesh!

PS Dan something is going wrong with the post-100 commentary on the Big Dicks letter - same problem as before, where comments do not show up unless you click on the number of the last visible post. I hope the Stranger tech crew can fix it.
PINK, if I were you I'd start up a conversation about including some other members of your local kink community into this roleplay. Group events, even (especially) where there is no sex involved, could be a gentle way to explore this without hitting the issue head-on. Being a sissy in front of other people, in a place where he knows he won't be judged for it and could even wear a disguising mask if he's uncomfortable, could be both humiliatingly hot and helpful for him. I'd have thorough discussions ahead of time about what is and isn't on the table for events like that, and if he seems to want to go beyond those lines 'in the moment' (ie: being forced to suck cock or other humiliatingly 'gay' things) then don't let him (in an in-character, domineering way) but revisit the possibilities when you're out of the scene and coming up with new boundaries for your next group event.

I don't know what you're classifying as 'distressingly homophobic', whether it's genuinely his thoughts and feelings or just him parroting cultural garbage that got wrapped up into his macho persona. Either way, being around men way more comfortable with their sexuality could help him get rid of that toxic residue. Get him on fetlife, take him to munches, start with a few toes in the water instead of diving in head first. It could be good for him and add new dimensions to your sex life for you to enjoy too!
What was I saying on the weekly thread about adults not communicating their desires through a system of hints and winks?

Guy is probably bisexual if not biromantic. It seems like he is trying to come out and using the medium of kink to do it. As always, the answer is to communicate. Not when in scene, but when fully clothed and able to have a private conversation. "You've been making a lot of comments about being gay. Is there something you want me to know about your sexual orientation? Are you attracted to men, or are you just interested in cock as a way of being humiliated?" She should lead with "are you bi" rather than "are you gay" since that is a much stronger possibility, due to his obvious sexual interest in at least one woman.

If PINK hasn't already, she should incorporate strap-ons into their sessions, as a precursor to bringing in another guy. If this ends up being an opportunity for kinky threesomes, well, I don't think it matters so much whether his cock-lust is a kink or an orientation, so long as they both get to enjoy the hell out of it!
Raindrop sweety... nobody is making anyone go thru anything, ok. The LW is choosing to play. Perhaps you could go troll elsewhere.
I would agree except that a gay man would likely not be involved as the third. A bi man who is closer to straight would be ideal for this.

I do agree there are two types: a humiliation lover, and a closet gay.

I have a knee-jerk reaction to the idea of forcing anyone to do anything, even if requested.
What @6 said - strap-ons as a first step, see what happens... (I like being lazy but still feeling like part of the community!)
So... naive question here, but if this guy really does feel that there are things that are humiliating about being a gay man or being a sissy man, or even if he has homophobic or misogynistic feelings about being gay or being a woman, AND he gets off on humiliation, then why would his kink be an indication that he is really gay or wants to explore his female side? Like, wouldn't the point be that he's into the humiliation, and these stereotypes of being gay or being female are the things he thinks are humiliating?

I also don't see what evidence there is that he's such a masculine man's man. I mean, she just said he wears black, drinks beer, and smokes and that he comes off as masculine. Great, but I don't see how that's evidence of any sort of over-compensation- like she doesn't say anything about how he's going out of his way to be manly when he's not in kink mode.

So the reason I'm asking is, sure some people like to be treated like dogs. Some people like to be treated like babies. Apparently there are a variety of ways to be a sub- we had a column last week from someone that wanted to clean house as a slave, etc. We aren't speculating that those people really and truly deep down want to be their kink- no one suggested the foot fetish dom talked to her house cleaning slave about maybe really becoming a butler. So why this?

Also second naive question. Let's say he wants to suck cock because he thinks that's humiliating and he wants to be forced to do humiliating things. Would that mean he's bi? I mean, to hear her describe it, he wants to be forced BY HIS MISTRESS to suck cock right? I don't think it's way too uncommon thing with straight couples that are into pegging that the straight guy wants to suck his female partner's "cock". Seems a bit more extreme with a real cock, but I can't see that this would make a guy bi any more than it makes someone bi if they get physical with the same gender during a threesome with their partner, right?

I'm just wondering what all these red flags are that are making you all think he's got a lot more to unpack here. Dan's response was pretty sure that the guy's got a lot going on. You all have way more experience with these sorts of kinks than I do since I'm not into humiliation AT ALL and have a very limited repertoire for role play. So maybe you can explain it to my mostly vanilla self because I'd just assume the guy likes to be humiliated and his socially/personally problematic feelings about gay people and masculinity explain why he thinks being gay or being a sissy is the ultimate humiliation.
PINK, in my view, you have to tread carefully. Humiliation scenes can spiral out of control fast, and there are enough warning signs to suggest that is a distinct possibility. In the past, I believe Dan has quoted from sex workers who engage in humiliation play scenes with outwardly dominant men, who remarked on safety concerns in such scenes. In short, humiliated men can act out violently and with little warning.

In part, your question is what is your obligation to your boyfriend in assisting him address his issues. I think he needs to take primary responsibility for unpacking his masculinity and homosexual attraction. Often times, people eroticize certain insecurities or fears into kinks, and so long as they are generally well adjusted, their kinks can be a healthy way to interact with their issues. But you seem to sense boyfriend is not well adjusted. If that is your view, I would suggest he talk with a therapist about this feelings, before exploring his kinks in the direction that he has been discussing with you in scene.

As an aside, you suggested that you're concerned that he may not be playing within bounds that you are comfortable with, in particular when and where scenes begin. That is absolutely something you need to address. While it can be very exciting to segue from vanilla to kink when you are out together and are on the same page, it sounds like that is not what is happening, and you should communicate your feelings about that to him. In that same vein, it sounds like he's communicating his desires in scene, but you two may not be discussing them out of scene. However you proceed, I think some out of scene conversations are in order.
None of the sex play going on is weird or indicative of anything else but hot, steamy sex. The off-hand, possibly homophobic comments... That's weird. It comes across to me as a way of talking-about-his-sexuality-but-not-really-talking-about-it. I'd say you two need to have a serious negotiation conversation. Or re-negotiation session, and discuss his fears: of being actually gay simply because he craves some cock.

And no, he doesn't sound gay. He sounds bisexual. It's understandable the confusion, because bisexuality is far more complicated than either hetero- or homosexual attractions. For myself, I don't see it as sitting "somewhere between" the other two, but as a distinct orientation itself.
Renewing my call: We need a term for people's whose... uh... sociosexual(?) position (ie, dom, sub, etc) matches or mismatches their public persona. In control dom guy actually likes to be a sissy. Captain of Industry CEO wants to poop in a diaper. Mild mannered file clerk keeps a dungeon and has mastered the cat-o-nine-tails. GirlBoss wants to be used and abused like a $5 street whore. You get the picture.

A few questions:
1 - are most people "matching" or "mismatched"? We certainly notice when people are mismatched, but are we surprised? Would you describe yourself as mismatched?

2 - Are men more or less likely to be mismatched than women? It sure seems like it - but then again, we mostly hear about this stuff when it's a powerful man who's had their submissive fantasies revealed.

Does this stuff matter at all?
@7: Okay.
Re my own PS @4, problem appears fixed now - thanks!

Vab @8, I was picturing PINK as the Mistress running the entire scene and ordering her sissy-boy to suck Third's cock, with little if any sexual contact between her and either of the men. But she did identify as a switch and their games are probably more complex than someone with my naivete in all things kink can even imagine, so yeah - more likely a bi man than a gay one as their best choice for a third. But still - YEESH on inviting in an unfortunate and unsuspecting third partner, until her guy gets his wannabe-gay issues at least semi-resolved. (Loved Dan's line, "...who amongst us can claim to have fully resolved their issues?" -YES, so true!)
EL @ 9
“Why would his kink be an indication that he is really gay or wants to explore his female side?”
Last week’s issue was a foot fetishist who may agree to clean as a way to get some toes. His main issue is assumingly feet, not cleaning, which led some commenters question the quality and sincerity of that side of the deal. (The “mistress” authenticity was also questioned as she may only lend a foot in order to have her share of the cleaning done by someone else.)

I think in this particular situation submission may have kicked in as a result of struggling with shameful feminine and/or homosexual urges.
Submissive tendencies can sometimes manifest as a need to let go from otherwise seemingly secured and love to be in-control folks. They can also come from guilt and shame, and can also serve as an excuse to do certain things you may be reluctant to do otherwise for whatever reason. “Hey, I didn’t really suck on that dick, Mistress made me do it.”

My own experience/journey and observations lead me to this assumption, based on what PINK was writing. The process as described and the guilt that can be associated with it do ring a bell.
Admittedly I may be wrong, only people like raindrop are always right.

Around the time I began dipping a toe into kink, I was involved with somebody who was into crossdressing and forced fem and I was the first person he had ever talked to about it. I like to think I followed the campsite rule, although it might not be true. I was impatient with his inability to articulate what he wanted. I was frustrated when he didn't acknowledge differences between play ("oh no don't make me wear that I'm so weak and I can't stop you from laying that sweet lace on me like an innocent 18 year girl this is so humiliating and my traitor dick is so hard about it") and not play (18 year old girls wear a lot of things, there's a range of weakness and strength across all people, being a woman isn't the same as being submissive, etc.). I was bored when it became the only thing we talked about. I hope he found somebody more compatible, in general, and they have mutually satisfying times together.
Ankylosaurus @ 16
I don't know if that helps, but I think you were in full observance of the campsite rule regardless of how things ended. For many of us who are into cross-dressing of any shade it’s hard- well, semi intended- to concentrate on anything else when first accepted to whatever degree.

It is also my experience that the more you are out and about in your female-self persona the easier it is to gauge what is it that you really want and able to get in a particular situation without being too much of a nuisance to others.

Vab @8: "I do agree there are two types: a humiliation lover, and a closet gay."

And the bi erasure award goes to...

Pedantic note to EmmaLiz and CMD: We did not "have a column last week from someone that wanted to clean house as a slave." We had a column from a woman who theorised that she might be able to find someone to clean her house by offering him foot worship in return. This person, so far as she or we know, may or may not exist.

Sportlandia @12: So you mean, would this guy be a trans sis or a cis sis? :)
I do think match vs mismatch matters. Using myself as an example, I've had some partners who were kinky in the bedroom, but egalitarian out of the bedroom, and that's exactly the way I like it. I currently have a partner who wants to be my slave 24/7. I don't like it. Being dominant outside of a sexual setting feels abusive to me, and in retrospect I might have avoided this person if I'd known that her desire to be bound, pegged and flogged was inseparable from a compulsion to buy me presents (when she has no income), be late to events due to cleaning my kitchen (unasked), follow me around constantly, and even let me win at games. I suppose if I'd met her via her Fetlife profile rather than OKCupid, I might have had a better idea of what I was in for. I'm aware that I'm in a campsite situation, and I'm hoping a balance can be struck.

And I think my own kinks are in evidence here, as I'm thinking not only how lucky PINK herself but any potential third in the situation would be!

CMD @17: Kudos to your second, possibly inadvertent, genius innuendo there: "semi intended." :-D
I know this one! I date crossdressers. It's been my experience that bisexuality goes along with crossdressing, particularly if the crossdresser is submissive. The CD is only interested in being with men when dressed as a woman. It's part of the whole idea of the turn-on of passing, the men fantasized about being "straight". In a weird way it's a confirmation of the basic hetero orientation of the CD. I used to worry about my partners being gay gay, but it's not that at all. In fact a lot of the turn on for them is me "forcing" them to do it. If I wasn't in the picture it wouldn't be the same. For sure it's bisexuality, but a particular flavor.

Therapy is a good idea, but it's also fun to tie them up and force confessions. Videotaping the confessions and posting them on FetLife is fun too. And also severe punishment administered during dressed kink sessions for any previous homophobic utterances while male.

I can understand Dan's reservations, but "gay panic" violence is less of a worry if the Domme is good with rope and the submissive remains completely tied up and immobilized during initial MM exploration, especially if that comes after warming up with a good long period of kinky confessions, talking it out with the Domme, and seeing a therapist.
@7: PINK says "My question is, is this more than just role play and wanting to be humiliated?"

It certainly sounds like he's exerting some pressure on her that she is unsure about.
@18: "We had a column from a woman who theorised that she might be able to find someone to clean her house by offering him foot worship in return. This person, so far as she or we know, may or may not exist."

I've witnessed persons offer such services (with no stated expectations) to a friend at a nightclub, she politely declined so I can't attest to the one-sidedness or commonality of the transaction.
@20: "It certainly sounds like he's exerting some pressure on her that she is unsure about."

I don't know if "pressure" is the right word, but the interest seems real and not very well compartmentalized within the bounds of whatever scene, bleeding out into the "just kidding!" (not just kidding!) attempts to blur reality and fantasy.

She would be better off having a nonsexy but still comfortable/trusted conversation with him about these desires before things get weird for her.

His performance of gross and casual homophobia does suggest that "gay panic" doesn't sound an illegitimate concern if he's ever going to perform his preferences in front of others.
@22: And such services are typically pitched with a drink in hand.
23 refers to 21
@22: You're right. Pressure isn't the right word. Perhaps 'feeling obliged' is more accurate.
Undead @21: Oh, no doubt there are people out there who are into both foot worship and forced cleaning. My point was that the LW had not yet met one, she was only thinking about looking for someone with these interests. So the letter/discussion was not from or about the desires of a hypothetical slave, it was from and about the desires of an actual Domme. Told you I was being pedantic.
PINK asks Dan what she should do if her sissy lover turns out to be gay. What's the implication of her question? That, if so, he would have to leave her for men? That the campsite rule would oblige her to kiss him on his way? I'm not sure I see this. What he enjoys at the moment is being humiliatingly made to act gay--to bottom or be a gay sub--by her. This is a specific orientation that might be lasting.

Certainly, she should try having a conversation with him--'do you think you might be bi?'. But it seems this is hard to put into practice --because his avowing, then retracting, his homosexuality is so erratic or unpredictable. Or he shuts down any further consideration of it. Could he even stand the prospect of munches? I think everything Capricornius said at @4 was measured and properly considered.
I'd also think the threat of 'gay panic' violence, as warned about by SublimeAfterglow, is something PINK has to be concerned about--maybe primarily.
@9/EmmaLiz: Humiliation play isn't about humiliating someone in a conventional sense, and people being "forced" to do "humiliating" acts, aren't actually being forced to so these things. Dominants aren't actually exercising any real world powers, that compel the their submissive to behave in a certain manner.

Humiliation play is about the eroticization of certain fears. While on one level engaging with these fears cause intense feelings of shame, the submissive seeking humiliation play is simultaneously aroused by these same acts. And as is readily apparent from PINK's letter, dominants aren't actually coercing their submissives into doing things they don't want to be doing. PINK's boyfriend is begging to perform oral sex on a man. For these reasons, it is likely that PINK's boyfriend has a deep-seated interest in engaging sexually with men. Perhaps because of his fears surrounding homoerotic desires, he has come to see himself as less masculine and more feminine, and is seeking to engage with this side of himself in a setting in which he is "powerless" to object to performing sex act on men.
Mea culpa. I should have said closet bi guy, or simply in the closet.

unfortunate and unsuspecting third partner
All kink requires informed consent. PINK would need to find the right guy for this, and that would involve full disclosure.

@23: "And such services are typically pitched with a drink in hand."

They were perfectly kind and sober at the time.

The idea of inviting a stranger into the house quashed that, but it definitely left my friend with a "hrmmmmm". It was taken well, just not tempting enough to follow through and examine any caveats.
@27: I imagine wondering if/how she should be supportive when he's internalizing the homophobia? It's obviously causing discomfort for her when he's in "manly" mode and expressing unironic slurs but also when he's embracing the taboo and desiring the same pile-on in sissiness. There's a disconnect she's curious how/if to bridge, and it can't be enjoyable when he moves off-scene but still spouts hateful language or callously fucks with her with his "just kidding!"
I'm with BDF @6 and Jaymzb @9, though I'd emphasize less the strap-on aspect than the "let's get a bunch of toys and play with them" aspect.

Some dildos, some small butt toys, maybe a dildo-harness if he expresses interest in that. I'm really surprised that the LW describes "forcing" him to do gay things in the form of watching gay porn and writing a fictional "coming out as gay" letter to his friends and family. That letter seems way more advanced than licking a dildo would be. (Or two fingers of her hand, while she says, "that's right, suck my cock you cock sucker", if they can't afford a dildo.)

Re "upsettingly homophobic comments that I've called him out on" -- I'd want to know:
- whether his friends routinely make homophobic jokes
- what his reaction is when she calls him out on it; and
- whether he has gotten better or worse over time.

If he is expressing more homophobia over time, I wouldn't go any further without both personal therapy for him and couples therapy to get an objective perspective on how he reacts when confronted with his homophobic remarks. He might be headed to a crisis of some kind. Better to have professional help with that.
@27. UndeadAyn. In this case, I have to be careful to make sure I'm clear in saying that forced bi, the eroticization of the shame of having to confess to being gay, or of being made to bottom as gay, _isn't_ necessarily homophobic. I wear pink shirts and black underwear (man, those Calvins are snug). No tatts. Taking it up the ass isn't shameful for me. I represent some sort of norm here and PINK's boyfriend some sort of imitation, parody or deviation--but this doesn't mean the deviation is somehow improper or invalid.

I'd think the scenes and the other times, the not-scenes, have started to bleed into each other in disorienting ways. The times when he utters homophobic remarks could easily in his mind be extensions of the scenes--'who I revile and find disgusting is gay bottoms ... and, oh no, later, you're making me be a gay bottom, or to suck cock, or to do these things hypotnotised...'. The times when he ventures, but won't talk about, his actually being gay are a different case, which could be part of his fantasy life--but could also be an expression of a problem, an underlying problem of confused psychosexual identity that his sex life is also trying to address. The last would seem the more likely to me on the strength of the LW's comments. Certainly she should not accommodate his homophobic remarks off-scene. But I'd think she's written in because he makes enforcing this kind of scene/not-scene distinction hard for her. She tries to ask e.g. how serious were you in suggesting you might be gay, and he takes a swig of beer, draws on his Marlboro and clams up. But the point may be getting closer when she needs to press the issue in a context where he can't lash out--physically, and to a lesser degree emotionally. She shouldn't feel she's barred herself from opening this discussing because she's so enjoyed domming him and could seem to have been complicit in his gay-abjecting persona in the past.
A discussion on the N-word has given me an idea regarding Guy's "homophobic" remarks. Just as black people can use the N-word and it's fine because they're part of the in-group that has reclaimed that slur, gay men can call each other "fag" and make gay jokes. I'm wondering if Guy, in some sense, feels that he has now come out to PINK as queer and is therefore entitled to make gay jokes? I'd want to know more about the nature of the comments. They do seem like they're part of an effort to tell her something. But I would say to him, "honey, unless you're openly identifying as queer, you don't get to say that. Is there something you're hinting at?"

I'm also wondering whether Guy ever, in fact, presented himself as straight, or whether PINK just assumed it. It could be that in his mind, he's bi and always has been, he just never stated it directly. (I recently met a very cute guy who assumed I could tell he was gay "from his mannerisms." Well, no -- not when I know lots of fashionable straight and bi guys, and when he'd spent most of an evening dancing and flirting and holding hands with me!)
@35: "I'm wondering if Guy, in some sense, feels that he has now come out to PINK as queer and is therefore entitled to make gay jokes?"

From the way she frames it all, they're insults and disparaging comments not "jokes" on any level.

@34: "I'm clear in saying that forced bi, the eroticization of the shame of having to confess to being gay, or of being made to bottom as gay, _isn't_ necessarily homophobic."

I understand context and so does she, but this obviously is taking on a darker tone in and out of scene and she definitely needs some realtalk. I almost wonder if he's limiting himself because he enjoys the feeling of power over another. I mean, being a Trumper's caricature of a "manly man" and queer certainly requires compartmentalization but isn't at all uncommon.

What his exact deal is certainly will require serious and active communication to reestablish boundaries in and out of scene, perhaps requesting a third party mediator if she feels he's worth pursuing anything further with. Well above my paygrade, especially not knowing much about the situation.
Undead @36: We don't know the nature of the comments. She described them as "upsettingly homophobic comments." What about the comments upset her? Were they disparaging and insulting, or was she just upset about the fact that he made a gay joke or used a slur in the first place? Someone affecting a camp accent, snapping his fingers and saying "You go, girlfriend!" would upset some people but not others. Without examples I can't make a determination on whether these comments would be acceptable coming from a gay man or not acceptable at all.
@37: "Someone affecting a camp accent, snapping his fingers and saying "You go, girlfriend!" would upset some people but not others."

Out of context and abstractly sure! But someone regularly administering sissy humiliation scenes is necessarily going to have a finer grasp of this. He's playing games with her and either intentionally disrespecting boundaries or whatever turmoil is leaking out into homophobic outbursts, and she mentions that it's intrinsically tied to his "macho" persona.

Regardless, she isn't comfortable with how he's actively performing in public and she deserves more respect for her role and participation.
Thanks Sublime and CMD for walking me through that.I learn a lot on this site. It's hard for me to wrap my mind around humiliation play at all because it's so not my thing, so I think I missed the part in which it's not the humiliation itself that is the turn-on but rather the deeper desire. The humiliation is just wrapped up in it because of whatever socialization / life experience / personality quirks, etc, and then becomes a part of the sexual exploration of the thing that the person desired in the first place. Correct? Well if not that's OK as it's moreso just a detached curiosity on my part. I think there's an aspect of part of what CMD says that I relate to- it's always easier to do something new that you want to try but are nervous about to have "permission" or to have a "request" to do it.

Re: the foot fetish house cleaner, sorry I misremembered that post and drew up a poor analogy.

@36. UndeadAyn. I suspect he would panic at the thought of a 'third-party mediator'. But I don't know.
@40: I mean if he continues to refuse to respect her boundaries and discuss what's going on otherwise, and she wants to stay in a relationship with him and not feel so uncomfortable. What options would she have otherwise?

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