Is crossdressing offensive to women? That question has haunted me for while now. I didn’t want to ask it, even privately—but it finally caught up with me during a conversation with my wife.
We were deep in it—talking about gender, about me, about whether I might be transgender. And somewhere in the middle of all that, she paused and asked something I didn’t expect:
“Are you just trying to become this idealized version of what you think a woman is—without the parts men don’t see?” (paraphrased)
It wasn’t judgmental. It wasn’t said to hurt me. But it stuck. And it’s been echoing in my head ever since—because honestly? I hadn’t let myself ask that out loud. Not really.
So now I am.
Is my crossdressing offensive to women? Is it hurtful? Is it mocking? Is it disrespectful in ways I don’t fully see?
Let’s unpack that.
Why Is Crossdressing Offensive Even Comes Up
Because I get it. I really do.
From the outside, crossdressing can look like someone putting femininity on like a costume. Heels, lipstick, fake lashes—just the fun stuff, right? And for women who’ve had that same femininity used against them their whole lives, that can absolutely feel insulting.
If your body has been policed, your beauty picked apart, and your identity reduced to how you look, it’s gotta sting seeing someone step into that space casually—especially if it feels like they’re doing it just for fun, or worse, for sexual thrills.
So yeah. I think it’s a fair question.
But I also think the answer depends on intent, identity, and what someone’s really doing when they dress.
Why I Crossdress—and What It Means to Me
I don’t crossdress to mock women. Or to copy them. Or to make a spectacle out of femininity.
I do it because when I dress, I feel more like me.
It’s not about pretending. It’s not a performance. It’s not drag. It’s not something I put on and take off like a party outfit. It’s something that helps me feel soft, centered, and calm in a way nothing else does.
And yes—sometimes it’s beautiful. Sometimes it’s messy. Sometimes it’s arousing, even. But it’s never a joke.
I’m not trying to be someone I’m not. I’m trying to let out a version of me I’ve always kept hidden.
So… Is Crossdressing Offensive When It’s Sexual?
Here’s where things get complicated.
There’s a whole corner of the internet where crossdressing overlaps with fetish—sissification, humiliation, forced femininity. And yeah, that can absolutely feed into stereotypes that feel objectifying or gross.
But for some people, that’s part of how they explore identity. And honestly? I think it’s okay to say that even if it’s sexual, it can still be real.
Still, that’s not what this is for me.
This part of my life—Michelle—isn’t about fantasy. It’s about finally letting myself exist. And even though I’ve felt turned on by it before, that’s not the point. The deeper pull is emotional. It’s tied to safety. Belonging. Truth.
And I think it’s important to make space for both. There’s nothing wrong with crossdressing as a kink—but it’s not the same as crossdressing as an identity. Both exist, but they’re not interchangeable.
Is Crossdressing Offensive to Women? Or Just Misunderstood?
This question has no clean answer.
For me, the answer is no—not when it comes from a place of honesty. But I also think it’s possible to do harm even when you don’t mean to. And if a woman sees someone like me and feels uncomfortable or hurt, I want to hear that. Not to defend myself—but to learn from it.
Because femininity isn’t just something I admire. It’s something I crave. Something I’m trying to embody in the only way I know how.
But I also know that being seen as a man who “plays with femininity” carries baggage. Privilege. And even if I don’t feel like a man on the inside, I still benefit from how the world reads me when I take the dress off.
That’s part of this too.
I Want This to Be a Real Conversation
So here’s where I land: I don’t believe my crossdressing is offensive. But I do believe it can raise questions that are worth taking seriously.
If you’re a woman reading this—and you’ve ever felt uneasy seeing someone like me—thank you for even making it this far. I’d genuinely love to hear how it’s felt for you.
This isn’t about getting permission. It’s about listening.
And maybe, together, making a little more space for all of us to be complicated and real.
4 Comments
Amanda · July 20, 2025 at 2:07 am
I think the short answer to your question is ‘some are’. It’s a question that’s difficult for us to answer, firstly as it depends on the individual and secondly because we’re not the target audience for that particular question. Some women are fundamentally opposed to the very idea and there’s not a lot we can do about that particularly if their offence has religious roots.
But many more are open minded and are not so much offended by crossdressing as they are by how it is done and then what is then done with it. Most women are compassionate in nature and it’s certainly my experience that they are happy to treat CDers in the same way that they would treat any woman unless we give them good reason not to. The obvious example here is Dylan Mulvaney who has treated the whole woman thing as a big joke and is widely rejected as a result. Of course, DM is an extreme example but inappropriate outfit choices or exaggerated ‘feminine’ mannerisms (and I use the quotation marks to suggest that many of these mannerisms have no relation to women’s behaviours and have more basis in drag parody) soon suggest that the motives for CDing are performative (and perhaps sexual) rather than from any genuine need to conform.
Personally, I think we have a duty to be the best that we can possibly be and providing we respect, and conform to, what society expects from a woman without resorting to over the top stereotypes, women will not only not take offence but will understand that all we’re trying to do is to belong and welcome us into their world. Seek acceptance and we will almost always get it, demand it and the only thing we’ll get back is offence!
Michelle · July 21, 2025 at 10:20 am
You’re right, it’s not really a question we get to answer for women, and I think sometimes I forget how much nuance there is in how people see us. That part about exaggerated behaviors and parody really stuck with me. It’s something I’ve been reflecting on a lot — how easy it is to fall into patterns that feel affirming in the moment but might read totally differently from the outside. You nailed it with the difference between seeking acceptance and demanding it. That’s something I’m still learning.
Violetta · July 21, 2025 at 10:56 am
That is a question difficult to be answered. I also don´t want to offend women. I like to be that part-time-lady that I am because it feels good to me. And since I was a boy of about 6 or 7 I was attracted by pantyhoses and nylons, I don´t know why. It just feels good to me to slip to the feminine side. And I want to look so much female as it is possible for me. And I know – I´ll never be a woman…but to feel female is a wonderful feeling. And is it sexual? I must confess – Yes a bit, for I like negligees and stockings or straps…it feels good. But that is only in my private room. Thanks for your kind visits to my blog,
All the best
Violetta
Michelle · July 21, 2025 at 4:41 pm
I really hear you on wanting to feel as feminine as possible—and how good it can feel just to have that space, even if it’s private.
I don’t think there’s anything wrong with it having a bit of a sexual side either. (Guilty!) That’s human. I feel like what matters most is that it’s about connecting with something real inside ourselves, not about making anyone else uncomfortable.