A friend raised an interesting topic the other day. Why does a man have to be dressed as a woman for this type of role play? I don't have an opinion on it. But, it was a thought provoking conversation. What are you thoughts?

Ooooo That is provoking. What first comes to my mind is the evolution of gender play in the scene, and then contrasting attitudes in the mid 70’s to late 80’s to what is seen now in 2021.

Tracking backwards - when I was first exposed to this aspect of play late 70’s early 80’s as a youngster who had gotten his hands on fetish material (e.g. The Esoteric Press family of fetish newspapers, Centurions Transformation, Forced Womanhood), the classical ‘societal ‘ “gender roles” were more or less black and white, despite the few folks who were open about their choice of gender identity, I feel that most gender play was clandestine because switching birth assigned roles was generally not accepted; contrast those dispositions to what is common today and we might easily understand why that question could come up. So, I am thinking that there is not a right or wrong answer yet the question of sissy play being misogynistic hinges on how views are framed that could end being philosophical circular argument.

I've heard this argument several times.

It's important to note that an enormous amount of humiliation play involves berating the submissive for things that are not actually shameful but are often shamed by society. It's not shameful to have a foot fetish or a small penis and yet we release all kinds of cruelty upon our pin-dicked little footfreaks. The point isn't that those things are bad -- the point is that it's hot (and sometimes very cathartic) to hit the sexy shame button repeatedly.

I find it much grosser to humiliate a submissive over things that are actually shameful. He's turning his genuine wrongdoing into a sexy game and asking me to enable him.

Im going to take a stab at this interesting question...

While i don’t do sissy or slut play, Strapon play is my all time favorite. Its easy and tempting to bend genders in a strapon scene.

But I don’t think you have to do it that way. The way the session works for me is not to switch genders but for me as the powerful man getting pegged by a more powerful dominant woman. In my mind that the natural orders of things. I can still be a man she can still be a woman and she can totally have her way with me as i submit to her. I love the thought of her having more power than me. This setup had les to some intense pegging sessions.

Rather its sissy, slut or strapon play many who are interested are probably interested in exploring gender roles and that probably leads to some of it.

100% agree.

Ironically I just visited here to post something on this topic. A friend asked me if I was offended when men wanted to be made into a caricature of a woman. (His words, not mine.) He wanted to know how that was any different from appropriating someone's culture or race.

Gender appropriation? Any thoughts on this?

By the way I was recently interviewed on the topic of gender play here:
https://simplysxy.com/articles/2021/02/15/how-to-explore-enjoy-gender-play/

Great interview and I love the photos. While I respect women who don't care for sissy/slut play because they find it disrespectful to women, it really hasn't bothered me. In fact, I've had fun with it, especially when the dom has a hint of male attire and is smoking a cigar. A lot of gay men, think Rocky Horror Picture Show, associate lingerie and high heels with be slutty. As long as it isn't intended to hurt a woman's feelings and the intentions are all fun and games, I'm cool with it.

I agree. There is no right or wrong answer here. Gender play always had a feel of naughty to it. When I've dressed as a pimp and my slave as a hooker, it was fun. Someone could say that I was making fun of men. Well, I guess I was. lol. But, all in good fun.

So true. Words of wisdom.

Great interview Mistress Ayn.

This is not a fetish of mine, but I did get seduced into doing it once. It was a "lost in translation" moment. And the description is admittedly over the top, but here goes.

I met a lady named Gina in the late '90s via the old New York magazine personals sections that offered a wide pallet of services: domination, escort and massage. She was assertive and unique. Brazilian, zaftig, somewhat petite with a deep voice and seductive accent, bronze tan, and long blonde hair. We were the same age, around 40. She advertised in the old New York magazine personals section. (No pictures.) When I called her that voice was enough to make me make an appointment. I told her about my sub Tarzan / Amazon role play and she was fine with that.

She was dominant in our first two sessions. Some body worship, foot worship, spanking and general abuse. In the second session she wore this skin tight jungle print dress. She drove me nuts with it and I loved it. At the end I said something like, "Tell me where you bought it so I can make a Tarzan thong to wear the next time." I used to make my own outfits. Maybe something was lost in translation, because she then said, "The next time YOU wear the dress, blond wig and lipstick and I'll give you extra time." Me being intimidated and horny, I said yes.

A couple of months later I called her for a Saturday morning appointment hoping she had forgotten. She remembered. With dread I followed Gina's "trainee" as she called her (around 30) to take me into the room we were going to play in. She was also from Brazil and spoke little or no English. She helped me into the dress, which was way too tight, a blonde wig and red lipstick. I also had backless high heels which were too small for me. I looked at myself in the mirror and it was ridiculous. The trainee giggled and left.

Gina immediately came in, with red lipstick and nails, in a black corset with her breasts flowing out of them. She was a vision. She checked me out, spanked me a bit and saw I was immediately and tremendously aroused. She got on the bed, ordered me to join her and worship her breasts. Soon after with one hand she grabbed the wig and threw it aside, then quickly got the dress off of me, and threw it to the other....

When it was over there was red lipstick all over her face and breasts, and all over my face and parts of me. She turned to me, we laughed, and said, "I couldn't let that" as she grabbed me "go to waste." Unconventional? Yes. Dominant? Absolutely. I was completely intimidated and there for her. (After that she took me to the bathroom and scrubbed the lipstick off me like I was a child or a pet.)