The Link Between Cross-dressing, Sissy Play & the Queer Community

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Here’s a hard dose of reality: trans people are not “supposed” to discuss gender exploration, especially in sex.

We’re not supposed to talk about how it can be enjoyable to play around with gender roles, or else we’re suddenly targets for harassment by bigots.

Transphobes are quick to claim that our entire gender identity is actually some extension of our freaky sex lives. They’ll claim that we’re not actually trans, but instead, this is all some kind of perverse 24/7 cross-dressing kink. It’s sick, twisted, and especially because it involves the general public without their consent.

Clearly, that’s not true, so what’s the truth with trans people, cross-dressing, and kinks?

Trans people, like our cis counterparts, can enjoy playing around with gender presentation during kink and sex. Gasp! It’s true. Obviously, not all trans people enjoy it, but there’s a small group of trans people who do and would like for it to stop being seen as evidence against their transness.

Sissy? Cross-dressing? What?

Let’s break down some loose definitions so we’re all on the same page, right?

First off, cross-dressing is a sliding scale behavior usually defined as people dressing in clothing that’s “not for women/men”. In most countries, cross-dressing had a legal definition that led to many people getting arrested for not wearing clothing meant for their sex. As society changed, so did the definitions for cross-dressing. For example, most communities would hardly consider women wearing pants as cross-dressing but back in 1900 it would be!

Nowadays, cross-dressing is done for performative reasons (for things like drag or even Halloween), pure enjoyment, or for a sexual thrill. Being trans is not cross-dressing, as it isn’t about subverting your gender identity by dressing “as the opposite gender”. If a trans woman wears a dress, she’s just a woman in a dress!

Cross-dressing is an umbrella term. Kinks like “sissy play” and “forced feminization” are under that umbrella. 

Sissy play is a type of dynamic where a man takes on an almost alter ego that’s a caricature of a stereotypical woman. The sissy dresses in extremely feminine clothing, including lingerie, and heels, and might even wear breast forms to create a more alluring silhouette. Usually, the alter ego has a completely new name like “Candy” or “Bambi”, and behaves like a stereotypical airhead.

Forced feminization is a kink where the man is being “forced” to dress and behave in a stereotypically feminine way. The main difference between sissy play and forced feminization is that people who engage in sissy play might do it solo, while forced feminization requires having others dominate you by “forcing” the person to dress up.

I’ve put “forcing” in quotations because the forcing is consensual, and the person being feminized can decide to end things at any point in time. It is a BDSM dynamic, and the submissive can say their safe word without repercussions. 

With that out of the way, let’s break down some commonly asked questions!

Does cross-dressing make someone trans?

Short answer: no!

Long answer: no, cross-dressing does not make someone trans.

Being a trans person is more than just “wearing clothes traditionally made for another gender”. Transness is a whole state of being, and what you wear isn’t what makes you trans. If a trans man is wearing a dress and makeup, he’s still a trans man! 

Just because a cis het man enjoys dressing up as a slutty kitty on Halloween does not make them a trans person. Plenty of people enjoy playing around with gender as a cisgender person. There are tons of people who want to be called “daddy” and aren’t men, plus plenty of men who enjoy wearing lingerie for a thrill!

But… does cross-dressing turn someone trans?

No, cross-dressing isn’t the reason why people are trans. 

It is true that lots of trans people do start to understand their gender identity after dipping their toes into more casual forms of cross-dressing. 

Personally, I dressed up as a man as a kid for Halloween or during school plays and felt incredibly at peace with myself. I felt powerful like I suddenly became an idealized version of myself. They were such euphoric moments for me that I dreaded taking off my outfit and having to “become” a girl again.

So yes, lots of people realize they’re trans through playing around with cross-dressing but it isn’t the cause of our transness.

If I’m a trans man who enjoys a sissy kink, does that mean I’m not actually a man? If I’m a trans woman who still participates in it, am I just a pervert?

You are not weird or perverted for participating in sissy kinks! 

There are trans men or transmasculine people who enjoy dressing up for forced feminization scenes, and it’s really not that uncommon! You’re not weird if you enjoy them, and you are not less transgender for engaging in them either.

As for the trans women who are into sissy kinks, that’s obviously still ok! You’re allowed to be in that space, and sometimes it’s easier to find sex partners in these spaces, especially since these cis men are actively seeking out a feminine person with a penis. These spaces might be familiar to you, and easier to navigate than the vanilla hookup scene where people can become horribly transphobic in their rejection.

So don’t worry, you can be into cross-dressing and still be trans, it’s not as cut and dry as some people (ahem, bigots, ahem) would want.

Wouldn’t dressing up as a woman during sex make a trans man dysphoric?

For some people, kink can involve playing with typically “uncomfortable” feelings or sensations.

There are practices that outside of a sexual nature might be deeply unpleasant to experience, like public humiliation or physical pain, or even people interested in playing with kidnapping or rape fantasies with their partners. During sex, these might feel thrilling and novel like a spicy hot sauce over your favorite pizza but that doesn’t mean you want these things to actually happen to you outside of the safe space of kink and sex. 

There is also the aspect where exploring dysphoria during sex through forced feminization can allow the trans person to experience it in a comfortable and safe environment. If at any point in time the trans guy feels overwhelmed with dysphoria, they can say their safe word and end the scene. In an ideal kink scene, there will be aftercare as well, which will be tailored to gender affirmation.

Why would a trans man enjoy cross-dressing as a woman?

I was actually asked this question back when I was exploring sissy play on an online kink community.  A cis het man (who I later found out was a chaser… groan) asked me a strange question. If I was looking to play around with someone dressed as a hyper-feminized woman, why didn’t I just live my life as a woman?

I replied that people dress up as French maids during kink play, but that doesn’t mean they want to get a job in sanitation or move to France! Someone can enjoy putting on a costume and engaging in particular kinks without wanting those kinks to be their entire life!

The man’s question felt ridiculous at the time, but I now understand the flawed logic, especially if someone misunderstands what it means to be trans.

As I’ve said above: being trans isn’t about what you wear, it’s about your internal sense of gender identity. You don’t have to perform or wear anything to be trans, you just are.

Do all trans people enjoy playing with gender during sex?

Do all gays watch RuPaul’s Drag Race?

Do all cis people want to get married and have kids?

Do all hetero people “live, laugh, love”?

Except for that last part, obviously, the answer is no! There is not one right way to be cis or gay or queer or trans. Lots of trans people just don’t enjoy playing with gender during sex, and that’s completely understandable!

There are trans people who feel like the forced feminization community is actively harming trans women’s lives. A visualization by lawsuit.org shows that conservative states in the US are far more likely than their progressive counterparts to search for transgender porn (using terms like “shemale” or “tranny”), and these people are paradoxically also those dominants who seek out “sissies” online.

Due to transphobia, These conservative men perpetuate transphobic ideas within their kink scenes, and for trans women who just want to date people who aren’t total assholes… it can be a real pain to have to constantly come up against people who think they’re sissies for just being trans women. Trans people, sissies, transvestites, and crossdressers are completely different things!

So no, not all trans people want to engage with those kinks, and that’s fine! Having these kinks also doesn’t make you less trans, and I want to especially underline that you’re not trans for cross-dressing either.

Was that a huge jumble of possibly confusing terms and words? Yes, but heck, gender and sex is a huge messy chaotic pile so… definitely get used to it and enjoy the ride