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Cross-dressing Experiences


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#1 Keil

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Posted 28 April 2012 - 10:15 AM

Speak as much as you feel comfortable.

During an Earth Day Carnival at my school, there was a clothing swap. An amazing sized small Invader Zim sweater caught my attention and I snagged it before anyone else could. I put it on and it was really snug. I'm a relatively small Asian so I thought the small sweater was perfect for me. The sweater was comfortably tight on me. The sleeves were tight on my non-existent muscles and the bottom part of the sweater was snug covering the top of my jeans. So then I walked out of the carnival feeling like I rocked it.

One of my guy friends wolf whistled and said "nice ass" to me and I didn't think twice because he's usually that friendlily obnoxious. When I went to town to drink, a classmate from EMag told me that she wished she had a sweater like mine but it got sold out at Claires (or some girl's clothing store). At that time I realized that this was a girl's sweater. I didn't give a fuck and still went to the bar to drink.

It never really occurred to me, but there are intermediate level gender-assigned clothing in our society. I'm not talking about guys wearing dresses and girls wearing tuxedos. More like guys wearing jeggings and girls wearing jerseys on a normal occasion.

What does everyone wear that are assigned only to your respective opposite gender?


I admit that I have a couple girl's white shirts because men's shirts were either too big or too loose and I actually like how they feel on me.

#2 yeah

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Posted 28 April 2012 - 11:35 AM

I guess this isn't that strange, but I prefer getting mens' tees over girls' fitted ones when I can. There's always some shit going on with the girls' tees, usually for me the fabric getting baggy around my (small) waist. I can't really tie an already snug shirt back with a ponytail holder because it just looks weird. With the guys' t-shirts I can tie/pin it until it's perfect. And, if you'll look, they always have cooler things on them. Space Invaders > odd feministic slogans.
I also love wearing ties and fedoras ;D what else... accessories, yeah. I always wear a belt with jeans, and I only buy thick mens' belts with big buckles. Can't stand those little stringy womens' ones. I cringe whenever I see people wearing them, lol. Dunno if this counts, but my preferred hair gel brand is American Crew.

#3 Sweeney

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Posted 28 April 2012 - 11:58 AM

I have a hoodie jacket that is a girl' cut. It's from Shrek the Musical.

#4 Irradium

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Posted 28 April 2012 - 12:03 PM

I personally have very little experience with transsexualism.
The most I've done is probably learning to walk in heels to win a bet. :)

#5 Random

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Posted 28 April 2012 - 12:40 PM

Girl's wearing jerseys can be hot.
Guys wearing jeggings are fucking weirdos.

#6 Honey

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Posted 28 April 2012 - 01:07 PM

I love it when guys are wearing tight clothes even they don't have muscels to show off ;)
I like this kind of androgyny especially asian guys have.

Do you know this Japanese Takarazuka theater? Where all roles are played by women? PIC PIC2
When the play a man's part there's still something femal left-- and that's sexy I think :3


I'm quite tall for an Asian girl and I also was dressed as a man.
Some guys said I looked like a Yakuza but the gilrs loved me XD

#7 Guest_Kate_*

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Posted 28 April 2012 - 02:06 PM

Girl's wearing jerseys can be hot.
Guys wearing jeggings are fucking weirdos.


PREACH IT <3

#8 Chappy

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Posted 28 April 2012 - 02:10 PM

Well as long as your not going for skirts and dresses I think you're fine.
Seriously I've seen an Asian guy who dresses girly, but to the point where his shirt was tighter than some of those very chested females.
I think guys are nice in tight shirts but just make it seem natural not overly tight.
I have to say I've never seen a guy in Jeggings and I probibly never do.
I think females have an advantage (not that I'm pro-feminist, they freak me out) to be able to wear both gender clothing and society accepts it ;/

#9 Turnip

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Posted 28 April 2012 - 02:33 PM

Girly men cross-dressing is hot ♥ ♥

Also, I always preferred boys shirts over girls ones when I was younger! They're nice and baggy and have room for you to breath in, and sometimes had cool video game character designs on them rather than idk, princess~*~* xoxo on them :p
(And I'm wearing a men's shirt right now!)




#10 Romy

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Posted 28 April 2012 - 02:45 PM

It depends to what extreme you take it i guess.

Some guys pull off woman's clothes very well.
Even I have o admit that one of my favorite shirts (before i grew out of it) was a fitted women's shirt with a picture of a trolley.

#11 Melchoire

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Posted 28 April 2012 - 02:46 PM

I had pink head phones for a while...does that count?

I always found that it's way easier for women to get away with wearing men's clothes but not the other way around.

#12 NapisaurusRex

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Posted 28 April 2012 - 07:51 PM

Well, it's more acceptable for women to wear men's clothing most of the time than the other way around. I generally wear female clothing in shades of grey, black, and pink most of the time. At night though, I like to wear boy t-shirts and long sleeve shirts. During the summer, I wear a lot of wife beaters from the boys' area at Dollar General and I wear men's shorts because they're a lot cheaper, longer, and fit better than women's.

#13 Keil

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Posted 28 April 2012 - 09:22 PM

For all those who never saw men in jeggings: there's hardly any different from really tight jeans. Their crotches are just more noticeable and seeing them is like seeing your grandma shave her legs; it's not that completely disgusting but you still try to evade the sight of them.

#14 Frizzle

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Posted 28 April 2012 - 09:29 PM

I have a pair of black and pink heelys.

#15 Bazzel

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Posted 29 April 2012 - 03:41 AM

Im wearing a Guys Hoodie... Erm...

My ex however.. Tried on my Underwear and Skirt once.. He was curious if it fit...Posted Image

#16 luvsmyncis

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Posted 29 April 2012 - 06:33 AM

I have a pair of black and pink heelys.


Nice. Very nice.

My hair is very long at the moment, but prior to this last year, I've always had it cut very short.You couldn't pay me to wear a dress. I always wear a black blazer and pants to weddings or funerals or dances or any other formal event, so everyone in my extended family thinks I'm a lesbian. I've been called 'sir' many times in my life and I am flat chested. I used to find my own androgyny very comfortable, because I don't find being sexualized by men very appealing.  

#17 Sage

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Posted 29 April 2012 - 08:23 AM

I love, love, love wearing boxers. Not those boxer-brief thingies, those are wierd and more often than not ride up clean to my goddamn throat, but real boxers with the hole in front and everything. They're comfy! Also for some reason my (now ex-) boyfriend thought it was hot. So that was nice, too.

I've got a lady tuxedo (dresses are for people who don't freak out when stared at) but I can't afford to get to the wedding I'd bought it for now. Bleh. At least it's a sweet-ass tuxedo.


Also, no one should wear jeggings. They're just... fuckin' stupid.

Edited by cuddlydemon, 29 April 2012 - 08:25 AM.


#18 Bone

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Posted 29 April 2012 - 08:29 AM

I personally have very little experience with transsexualism.
The most I've done is probably learning to walk in heels to win a bet. :)


There's a huge difference between transsexualism and cross-dressing. Trust me. ;)

Nice. Very nice.

My hair is very long at the moment, but prior to this last year, I've always had it cut very short.You couldn't pay me to wear a dress. I always wear a black blazer and pants to weddings or funerals or dances or any other formal event, so everyone in my extended family thinks I'm a lesbian. I've been called 'sir' many times in my life and I am flat chested. I used to find my own androgyny very comfortable, because I don't find being sexualized by men very appealing.


What about people who have an androgyny fetish? :lookaround:

#19 NapisaurusRex

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Posted 29 April 2012 - 11:38 AM

I used to find my own androgyny very comfortable, because I don't find being sexualized by men very appealing.


Used to? What changed?

#20 Sweeney

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Posted 29 April 2012 - 12:08 PM

Used to? What changed?

Her hair.

#21 trizzle

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Posted 29 April 2012 - 01:16 PM

I usually buy guy hoodies because when I'm just slouching around and being a general slob I don't want to wear tight things, I like keeping it loose. Also I think the general cut of a guy hoodie looks nicer than those fitted girl ones that look like they're purposely designed to flaunt tattybojangles.

There's a guy in our year who wears tights/leggings/dresses to some parties and everyone is fine with that (his girlfriend too) because that's just who he is. He prefers the look and feel of girls clothes, just like I prefer guy hoodies.

#22 NapisaurusRex

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Posted 29 April 2012 - 01:21 PM

Her hair.


huh. I didn't know hair length was directly related to intrinsic comfort. Mine makes me uncomfortable, but mainly cause I choke on it in my sleep.

#23 Sweeney

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Posted 29 April 2012 - 01:28 PM

huh. I didn't know hair length was directly related to intrinsic comfort. Mine makes me uncomfortable, but mainly cause I choke on it in my sleep.

It's not. But it is directly related to percieved androgyny.

#24 Galadriel

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Posted 29 April 2012 - 02:28 PM

When I was younger, my cousins dressed me up and put in heels and made me dance to "Sweet Transvestite"...




#25 trizzle

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Posted 29 April 2012 - 02:31 PM

When I was younger, my cousins dressed me up and put in heels and made me dance to "Sweet Transvestite"...


Haha this reminds me, I used to dress up my little brother and put make up on him. He pretended he hated but I never saw him putting up much of a fight Posted Image


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