Ask Hannah!

Do women like crossdressing?

Okay, a few things before we dive into this question.

I am going with the assumption you are referring to cis woman and the definition of crossdressing (for the purpose of this question) that I’ll be using is about as simple as it gets: one gender wearing clothes that is intended for a different gender.

And! I am mostly going to talk about gender identity as a binary here.

Let’s get started.

Do women like crossdressing? I don’t know, I haven’t asked all of them.

But let’s frame this question a LITTLE differently. Is that okay? Thanks.

Do women like their cis male partner crossdressing?

“Like” may not be the right word. I am not sure how many cis women are necessarily happy that their big tall strong manly man husband wears panties. I can only speak for my relationship but I wouldn’t say my wife LIKES that I crossdress…. but she understands and accepts that I like it and that it is a part of who I am. I think many people are glad that their significant other has SOMETHING, be it crossdressing or hot yoga or hiking or whatever that brings joy to their life. My wife doesn’t understand why I love wearing what I wear but she doesn’t have to. Put the stiletto on the other foot and I don’t understand why she loves listening to murder podcasts right before she falls asleep. I think she is happy that I have this side of me that makes me feel the way I do.

I think for a lot of people as long as their partner’s interests don’t go toooo crazy or dominate toooo much of their lives AND are honest about this side of them, it’s (usually) good.

At the end of the day, I don’t think for many of our partners they really care don’t what color our underwear is. BUT the concern can come from the other things that crossdressing can bring.

I don’t care he wears panties, but I’m scared he will want to transition

I don’t care he buys dresses, but he is spending a LOT of money on clothes

I don’t care he goes out en femme, but he is going to places that I’ve asked him not to

I don’t care he wears lingerie, but he is always lying about this side of him

I can’t speak for every wife out there, but these are the most common things that I hear from a lot of partners of crossdressers. For some, it’s not about the CLOTHES themselves, it’s about the other things that we as crossdressers have a tendency to do.

Crossdressing under the influence of the Pink Fog may cause us to do things that we normally wouldn’t do and may cause us to make poor decisions that are not well-thought out. It’s not unlike drinking too much.

So yes, it’s safe to say that crossdressing, because of everything that can come with it, may not necessarily delight our partners.

Do some women have a kink that their man dresses? Sure. I know for a lot of us we hope that our partners have a fetish of men crossdressing which can open the door to all sorts of fun but I am not sure how common this is. I could be wrong but I don’t think it’s very typical.

If your question is “do women like TO crossdress?” that is a completely different question. Again, we are going to use the definition of ‘crossdressing’ at it’s most simplified: one gender wearing clothes originally designed for another gender OR clothes that on a societal norm level are typically associated with a different gender.

For starters, let’s acknowledge that people wear the clothes for many different reasons. Practicality, style, comfort, an occasion, or for fetish reasons.

If a cis woman wears “men’s clothes” it might be for practical reasons (such as the joy of having pockets). I know some cis women who wear men’s t-shirts because the fabric is a little thicker. Some cis women tell me that some t-shirts designed for cis women don’t hang long enough or the neckline is too plungy.

Cis women might wear clothes because of the style or it’s trendy, even if it’s a little uncomfortable or expensive. They might be wearing it for the ‘gram. And that’s okay.

Wearing an outfit for an occasion, be it a Target run or the coronation of royalty is pretty self-explanatory.

Same with comfort. Choosing leggings or pajama pants or flip-flops might not be as glam as a floor-length ballgown but are arguably comfier.

Do some cis women wear something because it arouses them? Sure, of course. It is erotic to a cis woman to wear something that is designed for a cis male? For some I think it is… however I think there are many, many, MANY more men who are turned on when they wear lingerie than cis women who fetishize wearing neckties.

Clothes and emotion are linked. Some men feel powerful in a suit. Some little kids feel confident in a Batman costume. Some people feel beautiful in a princess dress. But crossdressers connect with clothes on an entirely different and elevated level. We wear what we wear for a lot of reasons. It could be comfort (leggings!) or sensuality (lingerie!) or because a dress or a skirt is a representation of our gender identity. I present en femme because doing this is a reflection, a manifestation, of my gender identity. Do cis men wear a suit for the same reason? Do cis women wear a skirt for the same reason? Maybe… but I don’t think at the same… intensity, if you know what I mean.

Historically pants (or trousers for my readers across the pond) are FOR MEN and yes, women wear pants but women have the option of wearing pants designed for women.

And yes men have the option to wear panties designed for men but on a societal level a woman wearing pants at the office is not equal to a dude wearing pink boyshorts in a gym locker room.

So yes, girls wear girl pants and some girl wear Boy Pants (again, the practicality of pockets can be appealing). A girl wearing “boy clothes”, a girl crossdressing (again, using the definition at the start of this post) is not a big deal… not as big deal as a boy wearing a skirt, anyway.

bUt iT’S nOt FAir tHAT giRLs caN CRossDreSs but boYs CAN’t.

Listen, we’ve been over this, but society did not one day collectively decide it was okay for women to wear pants. This did not happen suddenly or without consequences.

If we want the same societal acceptance to wear a skirt that women have when it comes to wearing pants, wonderful, then we had better start fighting for it.

I don’t view a cis women wearing pants as crossdressing. Pants have been “de-genderized”. Women did that. Women waged and won that battle. And honestly? Good for them. If my wife is wearing jeans she is wearing “girl jeans”. Jeans that are designed for the cis woman’s body. If men want a skirt to be de-genderized, it’s a battle that men will have to fight.

And to be clear boys can absolutely crossdress. As of this writing it is not illegal to wear a dress if you have a penis (but I suppose that day is coming) however you’ll probably turn a few heads and, let’s be honest, opening yourself up to less-than-welcome comments, to say the least.

So! Do women like to crossdress themselves? I don’t know, I don’t think a cis woman CAN crossdress the same way a man can crossdress. A girl can wear her boyfriend’s t-shirt and a pair of boxers to sleep in but I don’t think she is necessarily crossdressing (using the definition above) . But her boyfriend wearing her nightgown? Yes, that is crossdressing.

Is this fair? Eh, maybe not… but I think cis women have earned the right to wear what they want by fighting for it.

I have no idea if I answered your question but there it is.

Love, Hannah

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5 thoughts on “Ask Hannah!

  1. Thanks for providing a thorough review of the various ways women may view cross dressing. Its interesting how often cross dressers ask it of each other, and odd, since there are lots of women we could ask. If asked, women’s perspectives will be all over the spectrum, but for certain, a closer relationship will elicit a different response. What is tolerable or even enjoyable part of casual acquaintances, might often be intolerable in an intimate relationship. That is perfectly understandable.

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  2. My late wife seemed to enjoy my cross dressing. We would shop for clothes together. She would even buy clothes for me. She seemed to enjoy me wearing nightgowns to bed. So she may have been an exception.

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  3. I’ve had girlfriends who have thought it was absolutely disgusting, others who found it interesting, but only one who thought it was a turn-on.
    My wife sees how happy it makes me but it makes her uncomfortable to see it. She doesn’t understand why I need to do it in public after 30 years in the closet. I ask, why do we do anything we enjoy in public? Why must we socialize with people of similar interests? Would Football fans be satisfied watching games alone on TV or would they like to go to the stadium to cheer on their heroes? If you love a form of self expression , you do it in public!

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  4. I just want to say Ms. Hannah, that “you are terrific for your logical and incisive thinking on a difficult subject”. The clothing is definitely not the single issue as much as the full monty, the presentation. makeup, gestures, accessories, manners, voice, accent, unity of the presentation, and the footwear. It becomes a collective ticket to inhabit a glamorous universe otherwise blocked if confined and stuck on one side of existence. A magical place to be pretty with or without company or endorsement. A deeply satisfying and calming form of warm excitement, and alternative living, a rest for the soul for the hard job of being any gender, or the various identities on the sliding scale of gendernous. An inconsistency that assists the process of being a whole single person.

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