The Fetishization of Crossdressing

I believe that most people think a lot of kinks and fetishes are weird.

I mean, if you think it’s hot when a girl wears stilettos or a leather skirt that’s one thing. Those are pretty… hm, common things to be attracted to? I don’t think it’s much of a stretch to say that most straight dudes think a pretty girl wearing a tight skirt is attractive. I think most guys would understand and agree if one of their buddies told them that they think girls in high heels are hot.

When someone has a kink or a fetish that is oddly specific that’s when things can get a LITTLE out of the ordinary. For a while I had a guy who emailed me on the regular asking if I would wear a very specific type of dress for a photo shoot. I mean, I get these requests from time to time but they are usually along the lines of “wear a schoolgirl skirt” and “wear a latex dress”. I mean, I would love to wear a latex dress but girl, they are expensive. If you want me to wear one, then buy me one, lol.

The dress he requested wasn’t “sexy” in the traditional sense. I don’t want to get into toooo much detail as I don’t want to call him out but for the life of me I couldn’t understand why this dress was so alluring to him. A French Maid dress? Yes, I get that, but the one he kept asking about? I couldn’t figure it out and the more he requested it and the more in detail he got in describing it the weirder it became. I became pretty uncomfortable after a bit and thankfully he has since backed off.

Again, consent is necessary for anything sexual.

Sometimes I get invited to add a photo to a group on Flickr. Most of the time the groups are along the line of “t-girls in pretty dresses” or something like that. Something pretty broad and general. But other times the group is very, very specific like “t-girls who hold their purse in the crook of their arm” or something like that. It’s like… why is that hot for you??

I don’t spend too much time thinking about why someone thinks something is arousing. I mean, I don’t WANT to think about it in the first place, but I also know there’s usually not a reason why someone thinks something is erotic. It’s usually just how someone is wired.

I grew up knowing that although wearing girl clothes wasn’t wrong, I also knew it wasn’t something most boys did. It was ingrained in me at a very early age to hide this part of me. When I was five and entered kindergarten the WORST thing a boy could do was doing ANYTHING that a girl did. If you colored with a pink crayon or jumped rope then you were teased. Mercilessly.

We have a need to belong, to have friends, to be part of a community. We are not meant to isolate from the rest of the world (at least not for very long). We need collaboration, cooperation, and to socialize.

Being ostracized from the other kids in your class was traumatic. No one wanted to be left out.

So, I learned really early to not do anything that could lead to this. I learned to pretend to like certain television shows or to play sports that I had no interest in doing. I went along with the crowd. I assimilated.

And yes, hiding my crossdressing was part of that.

It still is.

When most people get their first exposure to crossdressing it’s usually portrayed for laughs or in a sexual way. If a boy ripped his pants in a cartoon and the tear revealed he was wearing pink panties with hearts on them it was meant to be HILARIOUS. As we grew older and our entertainment became more adult we would see movies that sometimes showed a man wearing lingerie as a kink or again, for laughs.

This annoyed me.

I would see things like this and for a split-second feel… hm, represented? But then it would quickly turn into a comedic or sexual scene. And not “sexy”, more like… creepy.

I didn’t like how crossdressing was portrayed. I’m not saying it needed to be shown as some sort of dramatic moment, but I would have loved to have seen crossdressing as something more… subtle, I guess? Like how groundbreaking would it be see to a television show where the husband and wife get ready to sleep and he changes from a suit into a black nightgown and…. that was it.

This sexualization made my life more complicated. Whenever I came out to someone I had to make sure they knew that THIS wasn’t a kink. I had to acknowledge that YES, to SOME it is INDEED a fetish but for me it was just what I wore. It was exhausting to come out since so much of “the talk” focused on what crossdressing WASN’T (at least to me). And to be fair, to most people their experiences with “men wearing lingerie” was almost always portrayed as kinky so it’s not surprising that someone had that assumption.

Look, I am very sex positive. I think a healthy sex life is very beneficial. I am not here (or anywhere) to kink-shame. If this is a fetish to you, awesome. If a t-girl holding her purse in the crook of her arm turns you on, enjoy this picture:

My point is that the sexualization of who we are and what we wear will forever complicate our lives and impede acceptance of who we are. I’ve written before about how I am terrified of being outed as a crossdresser more than I am terrified of being outed as a t-girl and that is solely based on the misconception of what *this* side of someone is about. As sexually charged our society is, it’s really odd to see how repressed we are. We giggle and become squeamish about sex.

I do admit I overthink about most things in my life, but am I alone in this? Does the sexualization and fetishism of crossdressing irritate anyone else? Did you have to “unpack” crossdressing as a kink when you’ve come out to someone as well?

Love, Hannah

5 thoughts on “The Fetishization of Crossdressing

  1. In early life my exposure to cross dressing (other than my own) came primarily through television. Most had a primitive level of sophistications: Man wearing dresss…that make me laugh. I found these to be cringeworthy at best. Other portrayals suggested the stereotypes of transgender people as either gay or fetish practitioners. Both made me uncomfortable, I suppose because I was young, confused about my gender identity and sexuality. I didn’t want to be like that…but thats all I saw.

    Strangely, in married life, cross-dressing as a kink provided a bit of camouflage…at least we could pretend it was just for fun and not something deeper. But there were rare, sensitive portrayals of transgender people. I remember one in particular from Hill Street Blues. With those instances I felt a connection to something not sexual, something defining. And that scared the crap out of me too, and still does to some extent.

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  2. When I first thought about wearing panties or some other such girls clothing item yes I did get a tingle as it were thinking how wonderful it would be to be dressed so pretty.
    But was that because I was exposed to the laugh off thing or kink thing about it?
    Yes I do believe so, now I understand that the real reason I wanted to wear them was because it was just me, it took me a long time to figure out they were just clothes, the clothes I preferred to wear.
    So many things in our society effect how we see things and until we figure ourselves out we will always feel that if we reveal this to someone they will not understand it and will only have a few times being exposed to trans folks.
    It’s why I do think it’s so important to be as visible as possible. Show folks we are just people just like they are trying to live our lives

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  3. Well thought out and well written Hannah.
    When I started down this path at age 12 it was a pure fetishistic sexual turn on. Now I am old and the pleasure I get from dressing has changed. From the creative pleasure of putting together looks to just enjoying the relaxing feeling of wearing women’s clothing.
    Gendre Amore

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  4. “Does the sexualization and fetishism of crossdressing irritate anyone else?”

    No, but that seems to be the consensus. I seem to be the only one on the internet that views crossdressing as a purely sexual thing (or pretty close to it). I guess I’ve never understood why it should be offensive to anyone else. After 47 years it’s never really changed for me in that regard. I think I told my wife within a month or so of dating that I’d been doing it since my earliest memories and really didn’t want to find someone just to lose them because they thought X. I never expected her participation in it in the bedroom as a requirement or something but it’s been 27 years now and I’ve found if I play my verbal cards right it’s easy to get her wrapped up in whatever I’m doing.

    I’m curious as to how the OP/Hannah goes between genders or doesn’t with her wife for sex? I believe I had read her wife prefers the male “side” for that type of thing and this site/blog seems to portray a nearly full time Hannah, which is why I ask.

    Thanks for reading if you made it this far. Also, maybe it was the water in St. Josephs Hospital in St. Paul where I was born in ’74. 😉 I still visit but have lived in Orange County since I was 5. I hope no offense was taken by anyone, if so it was unintentional.

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    1. Hi! I am very much part time. My website discusses my femme side because I don’t think my male life is interesting. 🙂 As for any intimate details between my wife and I, they will remain between my wife and I.

      Love, Hannah

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