general Have you ever tried clothes for the opposite gender?

[Lucky Bolt 35,063]

Yeah. Guy clothes are really comfy. 

[Oblivion 20,266]

I wore a bra before and stuffed it, I thought I looked damn sexy! 

On 8/7/2015 at 11:33 PM, Kyoshi said:

Nope, never tried any female clothing on, but I will be honest that I have thought of it before, specific things. I have thought before that I might look cute in a skirt, but who knows honestly. If the clothes are actually comfy, I don't see why not. One day perhaps I might try it out. 

Just wear a kilt! which is basically a man skirt! 

[ExplosionMare 18,062]

I have a couple of boy’s shirts cause I wanted a couple of FNAF shirts. The only thing FNAF for girls is a nightgown but I can’t stand those things.

[Rainbow Cloud 17,939]

Yeah, I have in the past out of curiosity when on my own and in private, it's a bit weird but harmless.

[Wasp Child 38]

17 hours ago, Rainbow Cloud said:

Yeah, I have in the past out of curiosity when on my own and in private, it's a bit weird but harmless.

Same, also something I tried once or twice in private, but I wouldn't do again.

I did try wearing women's underwear for a bit, it was surprisingly wayyyy more comfortable than any briefs. I'm pretty sure there are some guys who do just that for the sheer comfort factor alone.

[Treeglow Flicker 13,621]

Currently I'm stuck living both a male and a female life, so I wear both for now until I can completely and safely phase out my male role. I'm not going to miss male clothing when the time comes. Male clothing feels like I'm wearing a costume or disguise. Which I guess technically is what I'm doing.

[Rebel the Wolfgirl 5,601]

No, but...I'd like to try crossdressing sometime.  

[Fluttershyfan94 5,742]

ÙwÚ who's asking? I might do it for you anon OwO.

Obviously my dudes why wouldn't I have, got a cute outfit too. UwU *Giggles*.

Reading the other posts it sounds like it is controversial haha, I feel like cross dressing is for everyone really and if you enjoy it more power to you. More power to me! Powaaaaar!

To me it is self expression UwU a cute expression. 

Edited April 25, 2020 by Fluttershyfan94

[Sphinx-Ara 3,569]

Well yeah, I started in 2014 when I had started transitioning.. but these days as I am feellign I am more bi-gender or perhaps even gender-fluid. I don't wear many female clothing save for leggins.

[BlankFlank777 199]

I've worn dresses and skirts for a laugh a few times. I wouldn't be against trying it seriously but I'd only try wearing stuff that's not overly feminine cause it would clash with everything about my appearance. I just don't care who clothes are made for. I'll wear whatever I think looks nice on me. But so far that happens to just be male clothes.

[Sepul-Coloratura 762]

Not that I have thought of it, but it's a strange dilemma.

It would be such a taboo for a man to wear womem's clothes, but if it weren't taboo enough, it would lose it's merit in the first place. Because I can only picture myself in the situation with impure curiosities.

Not that I have thought of it though.

Edited April 25, 2020 by Sepul-Coloratura

[Splashee 28,563]

Many times I have seen lipstick and wanted to borrow some, but it seemed too expensive.

 

Mascara though, that I have tried a few times.

[Lord Valtasar 12,690]

i've dressed up as an old lady for halloween when i was little but that's about it

[DixonTheAdversary 1,632]

Not intentionally. When I was younger, I accidentally wore a pair of my Grandma's Jeans.

[Fluttershyfan94 5,742]

On 4/26/2020 at 1:21 PM, Super Splashee said:

Many times I have seen lipstick and wanted to borrow some, but it seemed too expensive.

 

Mascara though, that I have tried a few times.

That actually reminds me of that one time I actually offered to model as a female so I got the whole charade. Lot of makeup and some extended eyelashes UwU was very nice. Yet hey that's one thing just model as females but honestly the mascara is scary. 

[Early Sunsets 2,106]

I wore a whole outfit once out of curiosity (yes, including a bra and panties). Honestly it wasn't that bad, but that's just my weird personal preferences. Basically any other guy would find girls' clothes horribly uncomfortable. I'd consider crossdressing if I wasn't 6'2 and didn't have a horribly masculine face. Seriously, my body doesn't fit my personality at all.

[Meson Bolt 2,648]

No. Well, maybe. I bought this one Army hoodie back in AIT (wearing it now matter of fact) and the zipper is backwards. Wikipedia told me that means it's a girl's hoodie, their zippers are on the left while guys' zippers are on the right.

Do I care? Nah. It's a comfy hoodie, and it fits me. Plus it's kind of a cool story.