Have you ever tried cross-dressing?

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I would like to know how many people here on WP have tried cross dressing. For those of you who don't know, cross dressing is when you dress up in clothing often associated with the gender opposite to you own. It can be fun if you're really into it (in my humble opinion of course)

Personally I would find it fun if I ever get the chance!

But what I would really like to know is the experience you've had with cross dressing. Was it fun? How did you felt while doing it? And did you have to deal with those annoying, traditional people who are against cross dressing?

So what's your story?

I loved wearing dresses, butterfly wings, and tutus when I was closer to my toddler years. My babysitters promoted this behavior and liked to dress me up. I unfortunately didn't develop those interest; my dad tried to prohibit my feminine activities, for worries that they would "turn me gay." Joke's on you, papa~!

I've really wanted to try out drag. Especially the makeup. I could rock bearded drag so hard.

I can honestly relate to your problem with your dad. I think that my dad might be a bit more open-minded about the idea (although it might take some time ). I'd LOVE to be on a drag! even if it's just for once!

I'd probably look like this in my drag:



Proud and pretty and full of attitude!

Also, don't let your love for your father present you from being yourself! You are not your father and your father is not you! That is a FACT and it is futile to deny that!

Last edited by The_Blonde_Alien on 07 Dec 2015, 4:04 pm, edited 1 time in total.

Once I wore high heels.

How was it? What happened afterwards?

No worries, Blonde Alien, the love I have for my father is minimal if at all existent, so I'm no longer tied to his expectations.

On topic, the style of clothes I'm most interested in is victorian. I think going for an androgynous or male-objectified look would be enjoyable also.

I have! But since I'm a pre-everything trans guy it's not like anyone would've been able to tell I was "crossdressing".

What do you mean by "pre-everything trans guy"? Also, are you hiding in the closet? Life isn't about meeting someones expectations, let it be friends or family. Life is about expressing who you are and being unique! It's bad enough that we're living under the thumb of Christianity's imperialistic agendas, and doing that isn't going to help us transgenders and crossdressers be socially accepted in the general public that is, unfortunately, driven and controlled by the Christian Church!

Honestly I think Christianity as a whole is no different than the Star Wars Empire!

First appointment with my first gender therapist (this was back in the day), years before I even really started to transition. I came right from work in my office wear. Pants, oxfords & collared shirt, so I looked like any other guy, not like a (trans) woman, at all. She asks,

"Have you ever cross dressed?"

Me: "I am right now."

She didn't think it was very funny...

LOL! Well I think it's funny, and any therapist savvy in the ways of transfolk would have at least appreciated the irony.

I'm no one to tell anyone else how they identify but for information sakes, "pre everything transguy" often relates to a person who was born with a female body, identifies as a transgender/transsexual man, and is seeking medical transition in the form of hormone replacement therapies and surgery, but hasn't started this process yet.
For me, I cross dressed like hell for years, mostly in my early - mid 20's. I was considered very attractive dressed in this way, which only confirmed my suspicions that I was trans and had to do something about it. I don't know if it was fun per say, but it was very informative. Nowadays I'm much more shy about cross dressing which is odd considering I imagined that as transition went along, I would be MORE into it.

Oh geez, that picture. Just... it... well.... whaaa... I could go on about what I think of it but that probably wouldnt be very bright. But I had to download it, yep. Who exactly is this character?

That bare-shoulders look gets me every time, it really does. I dont even know why. Bare back will do the same.


Now as for myself... ehhhh, I dont know if this counts, but I'm into cosplay, and I absolutely will dress up as female characters (or just super-feminine male ones, which ends up being the same exact thing to most people). These outfits obviously arent "normal" clothes, but it's the same concept.

I get nervous every time I do it. I always imagine people laughing at me, as I've seen happen to others that do this at conventions. Every single time, nobody ever laughs. People often seem to like it (and some can get a little weird about it)... I'm never quite sure what to make of that. Though I'm aware that I'm a bit on the androgynous/feminine side to begin with, but still.

Hell, when I initially started doing it, NOBODY I knew was surprised. Like, okay, you're doing that, we kinda expected it. And... I dont know what to make of THAT either. Even had one of them, who is straight, say "Wow, you sure make for a pretty girl" just out of the blue once while I was at a convention with them. I had sort of a mental Windows bluescreen moment in response to that.

But anyway, once I get past the paranoia bit though I generally enjoy myself. Usually.

Until I have to deal with the elevators. Waiting 2000 years to get on one kinda ruins... anything.



Now as for dealing with acceptance and such, well... as I said, friends werent surprised and didnt have any problems. And I know my family wouldnt either... my father in particular, I know him well, I do, and he would say something like "I dont see the problem here, why are you embarrassed?", because he tends to think that way about damn near everything (as in, he is a very smart guy but he can be just a BIT dense at times), and that comment would prompt a facedesk from me. I can get embarrassed easily in some situations and dealing with THIS in relation to family is one of those situations.

does it count that i only wear Men size 2 XL shirts? i haven't really worn a dress since i was a teenager.
i wear jeans and jean shorts all the time, and sneakers that i just slide on.

All depends on who is judging you, make of that what you will. I mean, technically if you buy the exact same item of clothing but buy it from the other side of the aisle (in the "other" department), some will be aghast and say it is crossdressing. Of course, women regularly wear men's clothes in our culture but because there is a social hierarchy, that's not seen as deviant.

So, I'd have to ask the motivation question, "Why do you wear Mens shirts instead of womens?"

I wouldn't be able to handle high heels.

Nonsense! Why, our Founding Fathers strutted around in heels, makeup and wigs - what could be more American? All it takes is practice and building up those muscles! You-Can-Do-It!!

Men used to wear corset-like things in the 18th Century as well.