The Secret Lives of Married Men Who Cross-Dress

Of all the things that are blatantly gendered in our society – from bathrooms to fairness creams – perhaps, clothes carry the biggest gender binaries in every stitch of their fabric. We’re constantly under watch and repeatedly told off for what we choose to wear by family as well as friends. Men are supposed to stick to shirts and pants and boots, while dresses and sarees and gowns are only for women. At least, that’s what we’re taught as kids and the rules seem set in stone. If we happen to see a man in what is considered women’s clothing, it’s showcased in films and comedy sketches to play up the “ridiculousness” of cross-dressing. A man in a dress, or a woman in a suit and tie, is a punchline at the end of the day. 

Of course, there are men who cross-dress professionally, serving as beacons for the queer community in the form of drag queens. Then there are also transgender people who don’t wish to conform to the sex assigned to them at birth and instead align with the gender they’ve always felt most comfortable in, including in terms of clothes and hair.

However, there is also a large subset of cisgender men who love to cross-dress just because they feel like it. The desire to cross-dress for their own pleasure, however, makes them feel shunned by the world, so they instead practise cross-dressing only in spaces of their choosing. Their struggles with visibility, however, might be causing a strain on their mental health. 

Rutuja Thukarul, a clinical psychologist and queer-affirmative counsellor, said, “People usually associate cross-dressing with homosexuality, but in reality it doesn’t have any relation to sexuality, except for some who feel sexual pleasure because of cross-dressing.” She added, “Some men who cross-dress might happen to be queer, but we should remember that correlation is not causation.”

The practice of dressing in a way that is conventionally different from the way the gender one is assigned at birth dresses is known as “transvestism,” and this includes cross-dressing. However, the term has been largely rejected due to the negative connotations associated with it. 

We spoke to four married men who secretly love to wear clothing associated with women, but have to keep that part of themselves hidden from the rest of the world.  

The Beginning

Som is a 38-year-old engineer who works for a multinational company, and like all the men we spoke to for this story, preferred to share only his first name. When speaking of his cross-dressing adventures, Som preferred to refer to himself as Savita. Married for over 12 years, Savita has one kid, and keeps her cross-dressing desires entirely hidden from her family. She said, “I was perhaps 11 or 12 years old when I used to cater to my sexual needs by sniffing my mom’s underwear.” For Savita, it was nothing more than a way to associate with a vagina through the clothing. Soon, she started to look for other ways to draw pleasure from the underwear and decided to start wearing them. 

While the act of cross-dressing can be sexually arousing for some, for others, it may serve as a means to explore the thrill of being the opposite gender, even if it is just through wearing clothes. Sam, a 35-year-old writer and performer based in Mumbai, India, said, “As a young boy, I always wanted to know what it would feel like to dress up [as a girl], grow my hair out, and just be a girl for a day. I remember resisting it so badly as I was already a weak, wiry, and short kid. Add femininity to the mix and I would’ve been traumatised.”

But Sam would still sneakily tie his hair with a clothing clip when no one was around. He referred to this memory as “cross-thinking” when he experienced it for the first time. He added, “By the time I was in my teens, the urge to dress in women’s clothes was beyond my control. I knew where a few of the women in my family kept new clothes in the cupboard, and so I wore those clothes – sometimes even braving to step out in them.” 

Sam equates wearing a bra for the first time to using recreational drugs. He said, “It was in that moment [that] I completely embraced who I am. And I really wasn’t afraid of myself anymore.” 

This escalated to full-blown, private dress-up sessions where Sam was wearing everything from corsets and pantyhose to padded bras, and eventually makeup.

The desire to wear women’s clothing might manifest in different ways for others. Ankit, a 35-year-old consultant from Guwahati in India, was high on MDMA when he had his first chance encounter with cross-dressing. Ankit identifies as bisexual, and was tripping with his wife and their third sexual partner, a man. “We were role-playing and performing various sex acts on each other. Suddenly, I had the urge to wear women’s clothing. So I asked my wife to give me one of her babydoll dresses to wear,” he said.

In Marguerite Kelly’s advice column for The Washington Post, George Brown, a professor of psychiatry, points out that, “The behaviour probably isn’t inherited or nurtured, but it may be triggered in the womb – perhaps when the fetal and maternal hormones mix at some critical juncture – and it affects men much more than women.”

“Apart from wanting to experience femininity from a much closer and traditional manner, many men cross-dress to de-stress, which for some could be gender euphoria and for some just a joyous experience in itself without wanting to change their sex and/or gender,” added clinical psychologist Thakural.

The Thrills

The fact that all the cross-dressing these men do has to be in private is reason enough for most people to not try it entirely. Then, why risk it at all? 

Rahi is a 50-year-old VP at an IT firm. He said that despite all of the initial risks, he loved looking at himself in the mirror and witnessing a gender-fluid version of himself reflected back. Married for over 20 years now, Rahi has told his wife about his desires over time and she has slowly wrapped her head around it. 

For Savita, it worked more as a tool to masturbate. She said, “It is an autoerotic act for me. The desire to feel what a woman feels [during] sex and the desire to express those feelings as a woman does in a sexual context is my biggest drive.”  

Sam feels that for crossdressers, femdom (short for female dominance) is a big part of their lives. Shaming, something that causes trauma in the outside world, can become a thing of sexual freedom and absolute happiness inside the bedroom. He said, “I love to be shamed, I loved it when my exes told me that I’m too feminine. The whole feminisation process, domination, shaming, and taunting is an extreme turn-on, and to find partners who were into it was nothing but blind luck.”

Ankit has been married for six years, five of which have been in an open marriage. He is lucky enough not to have to hide most of his clothes like the other men we spoke with. When asked why he prefers women’s clothing to men’s, he said, “Men’s clothes aren’t sexy in my eyes. By sexy, I mean provocative. A male thong or crop top were originally designed for women and later adapted for men. Women have so many options for sexy clothing: mini skirts, short shorts, bodycon dresses… the list just goes on.” 

So, despite the risks, the desire to have experiences that they wouldn’t ordinarily have drives them to try on clothes and accessories that are not, strictly speaking, associated with their own gender. Sam added, “All my life, when I saw a woman, more than wanting to date them or be with them, I wanted to be them. I wanted the same hairstyle, the same confidence, and to be real to who they are. I want the high ponytail, I want the winged eyeliner – I just want to be how they are.” 

To feel the transformation, Ankit likes to wear a chastity cage and a butt plug, even if he’s in men’s clothes, as it allows him to feel feminine underneath what he’s wearing. He said, “I’ve worn the chastity cage 24×7 for more than 20 days in 2022. I wore it to work, for grocery shopping, to meet relatives and so on. I once wore a butt plug while going to a movie.”

The Secrecy

The trickiest part for most men who cross-dress in private is the dual life they have to lead, especially when they have felt cornered by society to the point of having to get married and live the quintessential hetero life. But, deep down, they feel suffocated. Savita said, “My partner has no clue about this side of me. I’m afraid if she ever finds out, it will be the end of either our marriage or our lives.” In order to keep her lingerie and wigs hidden from her wife, Savita has to stash them away in her work locker and only brings them home when her wife is out of town. 

Sam, who has been married for two years now, hasn’t yet told his wife about his cross-dressing, either. He posits that Gen-Z women are way more empathetic and kinder in this regard. “The whole BTS fandom is clear evidence of it too,” he added. Empathy and kindness are needed more now than ever, especially since bullying on the internet is at an all-time high with alpha and beta males fighting over who can be douchier when stringing hate-filled sentences together on Twitter. 

Thankfully, for Ankit and Rahi, their partners are aware of their cross-dressing desires and support them up to a point. Rahi said, “My wife started observing me when we were out shopping, and noticed the things I would pause and look at longingly. So, after a few open conversations, I told her that I identify as queer and want to dress in women’s clothing.” 

Ankit’s wife even gave him a saree, and has started helping him get dressed under the condition that he only does it within the confines of their home, until she feels comfortable with him cross-dressing in public scenarios.

The Stress

While there are men who find support, either with their romantic or sexual partners, many still choose to keep this aspect of their lives hidden. In extreme situations, this can lead to depression, guilt, and stress brought on by disapproval from their partner or the fear of societal shaming. 

Psychologist Lakshmi Sreenivasan, a trauma-focused and queer-affirmative counselling practitioner, said, “There is no need to treat someone who likes to cross-dress because there isn’t anything to treat. But if someone is experiencing severe shame, anxiety or ridicule, therapeutic interventions can help address these negative effects.”

She agreed that people cross-dress for different reasons – be it for fun, sex, entertainment, or even for political reasons. She added, “But, more often in India, we see that people prefer to do it in absolute privacy.”

Eventually, it all boils down to cross-dressing being a form of expression. And the only thing to do away with is the shame and the guilt that can sometimes come with it. Sreenivasan said, “Society needs to open up and allow individuals to thrive as themselves, without binding them to patriarchal norms.” 

For Ankit, Sam, Rahi, and Savita, things remain more or less the same. As long as they have their privacy and their little slice of joy, they are okay thriving in those moments. As Sam said, “Masculinity is conformity. Conformity to every single norm, societal flaw, tradition, conservatism, and atavistic rules. Femininity for me is rebellion. The complete loss of who I am is satisfying to my soul.”

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