What I Learned About Cross-Dressers as a Dominatrix
Neither drag queens nor trans females, they're men who dress as women as a private kink.
In my last post, I described my one and only practice session at Mistress A.’s dungeon, which featured my introduction to Betty, a cross-dresser. Cross-dressers can be defined as men who dress in women’s clothing as a sexual kink. Not to be confused with trans females or drag queens, cross-dressers are cis-males who often consider themselves heterosexual, even if they have bi fantasies.
Betty was the first cross-dresser I ever met. At that point, I didn’t understand the sexual excitement some men glean from dressing up in women’s clothing. Once I became a professional dominatrix, I would meet many more cross-dressers.
And so I began to better understand the impetus to cross-dress while also gaining insight into the many ways a man’s kink for cross-dressing might manifest.
I even ended up interviewing several cross-dressers (both clients and acquaintances) to get their take on this kink. Here’s what I learned:
Cross-dressers are not trans females
Adam, 33, was a client of mine who goes by the name Adriana when he’s cross-dressing. When I asked him if he saw himself as trans, he demurred. “I love trans people, but being trans is nowhere on my radar. I love being a guy who dresses up as a girl. If I identified as trans, I would be femme 100% of the time and date only men, but I love women! But at times, I also want to feel like a woman.”
Juan, 55, a cross-dresser I met on X, shared a similar sentiment, explaining that his desire to cross-dress has nothing to do with wanting to live full-time as a woman. “I wouldn’t dress up to go to the grocery store. If I do go out dressed as a woman, it’s only to private parties where it’s acceptable.”
Sabrina, 40, a cross-dresser whom I also met on X, concurred, sharing that he wouldn’t want to cross-dress every single day. “Maybe I do it a few days a week in the evenings.” He also only wears women’s clothing around people who accept it. “I can’t go out with my vanilla friends dressed as a woman.”
Of course, I have encountered cross-dressers who do want to transition, but there is typically a sense of sexual excitement in that process. They want to transition at the behest of a dominant woman. I don’t think the desire comes out of gender dysphoria but rather one to be “sissified”: the act of being humiliated by being forced—with consent—to be feminine. And as I said, this is usually within the context of a relationship with a dominatrix.
How do cross-dressers define their sexuality?
It might surprise outsiders to learn that many cross-dressers define themselves as heterosexual. This is Adam’s case, though he uses female pronouns when cross-dressing and fantasizes about having sex with men.
Sabrina also sees himself as straight: “I’m only attracted to women. Even when I come across another cross-dresser whom I find attractive, the attraction is in the woman I’m seeing in that person. The feminine form is very attractive. I have an attraction to myself when I dress up.”
Brad, 55, sees himself as bisexual. However, he explained that he’s only interested in sex with other men when they’re cross-dressing. And he echoed Sabrina’s sentiment: “The more they pass, the more attractive they are to me.”
For other cross-dressers, they only enjoy sex with men while dressed as women because it’s degrading. Juan, 55, shared that when he cross-dresses, he likes being forced to do things he normally wouldn’t do. “I’m not attracted to men, but being forced to service a man by a dominant woman gets me off.”
Adam agreed, calling the practice of sexually servicing men while dressed as a woman “forced bi.” He explained: “There’s no worse feeling of degradation.” And therefore, no more headier sexual high.
Cross-dressing as humiliation
For Isaac, 35, the act of being made to cross-dress is humiliating in itself. As I mentioned, it’s all part of being “sissified,” or participating in one’s own emasculation.
“I’m tall, athletic,” he told me. “No one would ever think there’s a feminine side to me. Cross-dressing is about putting myself in the shoes of the damsel in distress. I want to be made to do girl things. Having to sit on the toilet instead of standing. Cleaning a house in a French maid outfit. I want to be penetrated by a woman but not receive any pleasure from my penis. I just want to be taken like a girl.”
I try to unpack the idea that being forced to dress like a female could be humiliating for a man. Part of me is offended. What’s so humiliating about being female? A cross-dresser named Bill, 60, helped me comprehend:
“In society, we are asked to be male or female. Being forced to be a female distances a man from his masculinity. It means a woman is taking that away from me. She is taking control of my sexuality.”
And, for Bill, finding humiliation in being feminized doesn’t degrade women. Instead, allowing a woman to feminize him is the highest compliment he can pay a female. “It’s about worshiping a woman as a goddess.”
When does cross-dressing start—and why?
“As soon as puberty hit,” Adam told me, “I was thinking about panties.” When his mom’s friend came to visit, he went through her bags while she was out. “I could see her panties at the top of the bag and had to get a hold of them. I wasn’t sure what I was going to do with them. I just wanted to touch them.”
He said he took the panties to the bathroom and just looked at them. “I felt like I had bear claws, and I was touching the lightest substance on earth. I put them on, and they felt electric. They touched parts of my body that had never been touched before. The panties constricted me and held me very tight. I felt like I weighed sixty pounds. My heart raced. It pounded so hard in my chest, and I felt my heartbeat in my fingertips. I was scared of possibly fainting.”
Adam was quick to add: “I’ve never been molested or abused.” He said that often past girlfriends have asked this when he was honest about his kink for cross-dressing.
The fact that Adam’s cross-dressing urges emerged in puberty aligns with the stories of the other men I spoke to. Jeff’s fantasies also started in puberty when the 24-year-old began getting into his sister’s dresses when she wasn’t home. “I would masturbate in her dresses and underwear. I tried her makeup, but it wasn’t as much of a thrill as the clothes were.”
Juan’s first cross-dressing experience also happened young, though for him, it was pre-sexual. “I was 8 or 9 years old when my sister dressed me up for the first time. My sister had some friends over, and I loved the attention the girls gave me. When my sister showed me dressed as a girl to my parents, and they got upset, even that was exciting. It was more about attention than anything else.”
Cross-dressers are often in relationships with women
The majority of the cross-dressers I spoke to were in committed relationships with women. Adam has a girlfriend he used to dress up with, though she no longer has any interest in his cross-dressing. He said she’s open to him doing it with other women as long as he doesn’t tell her about it.
Like Adam, Juan’s girlfriend is also aware of his cross-dressing. However, his girlfriend does sometimes participate. When she’s not participating, he runs everything he does by her first. “Everything is transparent.”
Brad, on the other hand, isn’t out with his girlfriend. When asked whether she would be okay with his cross-dressing, he said, “She wouldn’t like it.” When asked if sexually servicing other men while dressed as a woman is cheating, he stated, “Probably.”
Still, Brad doesn’t want to leave his girlfriend. “Once I do it a couple of times, the excitement wears off, and I go back to being a vanilla guy.”
Paul, 35, another cross-dresser, told me he also lives a double life. His wife knows nothing about his cross-dressing or his having sex with men.
Kevin, 48, doesn’t have a girlfriend but wants to find one who’s into his cross-dressing. “It’s very hard to find women who are truly interested, though. Too many have fooled me into just wanting money.”
Cross-dressing is taboo
Though all the men I interviewed seem to enjoy cross-dressing, not all are at peace with it. “I wish I didn’t think about it so much,” Brad told me.
Adam agreed. “The urge keeps coming back. I want it to go away.”
Many social factors make cross-dressing difficult, especially if a man feels compelled to hide it from his significant other. Cross-dressing is definitely still taboo.
Cross-dressing can be beneficial to a man’s sense of self
Sabrina is thankful that he discovered cross-dressing in his 30s. “Cross-dressing lets me inhabit the feminine and masculine at the same time. It gives me the best of both worlds. I can be masculine in my daily life and feminine at other times, and that gives me acceptance and confidence about that side of myself.”
He shared more about what influenced him to start cross-dressing: “When I developed in puberty, I discovered my testes were undescended. I didn’t develop the masculinity, so I questioned whether I was masculine or not. I wasn’t as masculine as most men. I was quite dainty, in fact. My voice didn’t deepen, and my features were feminine. I wondered if I was meant to be a woman. I always had that question in my mind. When I started dressing up, things pieced together.”
Sabrina also explained that he never felt confident being photographed when he was younger. However, when he began to cross-dress, he started modeling for different photographers. “As a female, I saw that I was attractive. I liked to have photos taken. I went out to events and was amazed by how supported I felt. People thought I looked very attractive, which gave me confidence I’d never had before.”
I remember being photographed as a young woman and how that gave me confidence, too. As vulnerable as it made me feel at first, being photographed was also empowering. Before I started working as a dominatrix, which necessitated I pose for publicity photos, I didn’t realize how attractive I was. When I saw how beautiful I could look in these photos, I felt power in that. There was power in my transformation and in exploring my identity. Cross-dressing, for men, can be that, too.