The first "drag queen," William Dorsey Swann. Born into slavery, Swann began holding "drag balls" after emancipation, attended mostly by former slaves. Swann was often arrested for cross-dressing, and is the first American to lead a queer resistance group. [1903]
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πŸ‘€︎ u/palmfranz
πŸ“…︎ Feb 13 2020
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Non-Canon: It's a ball 3.0: Cross dressing.

Once again we're having a formal ball, and it seems we're cross dressing tonight. I'm sure Nash will look dapper in her suit.

Fuuuuuuck. Right. This is Universe B.

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πŸ‘€︎ u/JonArc
πŸ“…︎ Feb 02 2017
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[DISC] While Cross-Dressing, I Was Hit on by a Handsome Guy! :: Chapter 36 guya.moe/proxy/imgur/CNeB…
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πŸ‘€︎ u/kurisumx
πŸ“…︎ Mar 22 2021
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INTJs and their obsession with maid/cat cross-dressing femboys

I have made multiple INTJ friends throughout the years and a surprising number of them where obsessed with maid/cat/fem/crossdresser/boys back in highschool and college.

Is this a thing with other INTJs or was it just exclusive to my cohort of INTJ friends (many who’ve never met each other).

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πŸ‘€︎ u/LeanTangerine
πŸ“…︎ Apr 21 2021
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New to cross dressing how do I look
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πŸ‘€︎ u/Sissyboyinlondon
πŸ“…︎ Apr 11 2021
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I really really wish I had the confidence to wear my cross dressing outfit in public

I really love wearing my dress, choker, makeup and edgy barbed wire leggings. They make my feel so cute and I wish so hard that I had the confidence to wear it outside my apartment room.

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πŸ‘€︎ u/EccentricEgotist
πŸ“…︎ May 07 2021
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What do you call a cross dressing vampire ?

Dragula.

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πŸ‘€︎ u/VERBERD
πŸ“…︎ Dec 01 2020
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Update: Dead Bedroom due to Cross Dressing

Original post: (sorry not sure how to link!) https://www.reddit.com/r/DeadBedrooms/comments/jvsmtf/dead_bedroom_due_to_cross_dressing/?utm_medium=android_app&utm_source=share

TL;DR: My (27F) boyfriend (31M) had a cross dressing kink and didn't like to touch my vagina. 4yr relationship. Completely eroded my self esteem.

So I posted here around 3 months ago about my awful DB situation. I really appreciated all the honest advice I was given.

I bit the bullet and ended things. Moved back to my mum's place. I spent all of December quite miserable and felt awful but gradually the fog lifted.

Tomorrow I'm moving in to my new apartment, on my own. I downloaded Tinder and met this amazing guy, we've been on two dates and I've had the most amazing sex of my entire life with him. We're planning a 3rd date but even if things don't work out with him it's shown me that there are men out there that despite your body not being perfect, will worship every inch of you and make you feel irresistible. Both physically and emotionally.

So I just want to say: thank you to you all. I hope you find the courage and strength to leave your DB if you can, I'm sorry I waited so long!

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πŸ‘€︎ u/cappuccinolover90
πŸ“…︎ Feb 18 2021
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I'm just curious about how much we share with others about our cross dressing.

Feel free to add your own category or share.

View Poll

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πŸ‘€︎ u/CeeCeeChville
πŸ“…︎ Apr 25 2021
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The Notorious 1880 Police Raid of the Cross-Dressing Ball at Temperance Hall mimimatthews.com/2016/07/…
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πŸ‘€︎ u/AvaWelles
πŸ“…︎ Jul 26 2016
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Harold hid his cross-dressing for years. He felt bad when he finally told Patricia after 20 years of marriage and 3 chicks, but he had to be true to himself. She went to stay with her mother. Harold put on his fake eyelashes, fishnet stockings, wig & strutted his stuff. Harold never felt so alive! external-content.duckduck…
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πŸ‘€︎ u/bluesimplicity
πŸ“…︎ Apr 12 2021
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Cross-dressing for the first time
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πŸ‘€︎ u/pedoro_pedoro
πŸ“…︎ Mar 03 2021
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F1nn5ter cross dressing King tbh
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πŸ‘€︎ u/dsorgen
πŸ“…︎ May 12 2021
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Punekar chaddi's take on cross-dressing np.reddit.com/r/pune/comm…
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πŸ‘€︎ u/MeraFurryAccount
πŸ“…︎ Mar 01 2021
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Sitting Down with a Pro Cross-Dressing Idol Wrestler (ft. Ladybeard) | Trash Taste #44 youtu.be/jePOmeSAgdg
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πŸ‘€︎ u/GregHall44
πŸ“…︎ Apr 17 2021
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Christians who believe it's cross dressing for a woman to wear pants, please answer this.

I'm studying this cross dressing topic and it's proven to be tough. Here's a question I have

Aren't women's pants a woman's garment? In the same way men and women during bible times wore tunics and robes, they had differences but they generally wore the same garments. Couldn't it be the same with pants? There are pants for men and pants for women

Women's pants are curved while men's are not. Isn't that a difference?

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πŸ‘€︎ u/yoursausageboi
πŸ“…︎ Mar 30 2021
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I am new to the cross dressing world what do you think of some of my choices for clothing so far? reddit.com/gallery/msiwjs
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πŸ“…︎ Apr 17 2021
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[DISC] While Cross-Dressing, I Was Hit on by a Handsome Guy! Ch. 31 twitter.com/HachirumiScan…
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πŸ‘€︎ u/Hachirumi
πŸ“…︎ Feb 04 2021
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Me 2nd time cross dressing. Let me know what u think.
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πŸ‘€︎ u/Milla115
πŸ“…︎ Mar 22 2021
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Cross dressing Naruto at an all girls school | SasuNaru fic

Alright I read this YEARS ago and I remember enjoying it because it was super funny and NO Sakura bashing. I wanna reread it again and I’m having trouble finding it on ff.net.

Basically, Naruto (with Kakashi’s aid and blessing) disguises himself as a girl to get close to his crush Sakura who goes to an all girls school. Unfortunately, he ends up catching the eye of Sasuke. Sasuke finds out that Naruto is a guy and he strikes a deal with Naruto to become his fake girlfriend so fangirls will finally leave Sasuke alone.

Pretty sure that’s accurate so I hope someone can help me out!

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πŸ‘€︎ u/kitanero
πŸ“…︎ Mar 18 2021
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The loneliness or cross dressing alone

One of the things I don’t like about cross dressing alone is it’s relatively lonely. I used to dress up years ago and I was doing it for the photos but I always wished I had company l used to go out when I was living in the city but here in the country there’s no where to go So here I am unexpectedly finding myself alone in the house and so I used the opportunity to wear at least a silk camisole and paint my nails but it feels empty I like how natural the clothes feel but besides me looking at mysel in the mirror who am I doing this for no one there to see me and I have to tell you that’s part of the fun it’s why I use makeup and lipstick on my zoom meetings I like presenting to the world without feeling like a freak feminine I love that people see me I guess second-best is photographing and posting here .I have awesome mirrors full length and want to use them to photograph myself but I promised I wasn’t going to start until I lose the weight and fit into the corset so for now I just play around a little bit

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πŸ‘€︎ u/tonit2112
πŸ“…︎ Apr 21 2021
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[DISC] While Cross-Dressing, I Was Hit on by a Handsome Guy! Ch. 30 mangadex.org/chapter/1192…
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πŸ‘€︎ u/LonelyGoose1
πŸ“…︎ Feb 01 2021
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Why is cross dressing so popular in Asian cultures?

So I’ve recently gotten back into the dating game. I’ve noticed that there’s a lot of Asian cross dressers, mainly from the Philippines. Idk it’s just something I’ve noticed over the past few months

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πŸ‘€︎ u/Apoopot
πŸ“…︎ Mar 29 2021
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Cross dressing versus trans

This might be a little rambling because I'm confused about the subject but I'm not sure exactly what it is that confuses me. So I saw an interview with Eddie Izard where she answered a question about the trans experience. I was surprised because at that point I thought she was a cross dresser and didn't realize she actually identified as female. So I guess my question is what is the relationship between being trans and being a cross dresser? I'm not talking about a man who has a preference for women's clothes, I'm talking about men who identify as men but go in full on drag. It's like cosplaying as a woman.

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πŸ‘€︎ u/See_Bee10
πŸ“…︎ Feb 24 2021
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My sister walked in on me cross dressing

Said something like β€œNice legs, bro” and then we proceeded to have like an hour long conversation about completely unrelated stuff while I’m literally just laying there in a skirt.

I love my sister.

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πŸ‘€︎ u/dosdrasm
πŸ“…︎ Nov 07 2020
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So, is this a cross-dressing bull moose or did Beastars skip a groove on the biology again? (From S1:E2)
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πŸ‘€︎ u/Ferrous_Patella
πŸ“…︎ Jan 07 2021
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THE VIRTUAL VICTORIAN: DETECTIVE CAMINADA AND THE CROSS DRESSING BALL... virtualvictorian.blogspot…
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πŸ‘€︎ u/sleepyhamster
πŸ“…︎ Jul 03 2014
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Cross-dressing dramas that aren't terribly sexist

I'm a sucker for the gender-bend trope, but I get frustrated by the sexism (and inherent transphobia) in dramas like To The Beautiful You and even Sungkyunkwan Scandal. Are there any shows with the trope that you think do it particularly well?

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πŸ‘€︎ u/emilyrose021
πŸ“…︎ Feb 28 2021
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My wife caught me cross dressing and told me it was over.

So I packed all her clothes and left.

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πŸ‘€︎ u/jgudnas
πŸ“…︎ Mar 07 2019
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First time cross dressing
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πŸ‘€︎ u/kieranphillips69
πŸ“…︎ Jan 21 2021
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I tried cross-dressing but don't think it drastically changed how I feel.

Check my past post history on here for previous context if you need it.

Anyway, so my mom and sister helped me put on two different outfits and makeup but I don't really feel like it made a big difference one way or the other when it came to deciding my gender identity. I mean yes, I found the outfits comfortable and the makeup felt nice to put on, but I don't think it really made me feel more feminine or anything like that. It just feels like "I like wearing this, it's comfortable for me", but I don't know if that means I'm just a cis dude that likes cross-dressing or if it's further evidence I might be trans.

The way it felt in my head was, I was already jumping ahead to "looking feminine" that me not actually being feminine made it not leave a strong impression despite me being comfortable wearing the clothes and makeup.

Have any trans women felt this way before? Do you know about what I may be feeling? Thanks again for any responses.

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πŸ‘€︎ u/zeldafan165
πŸ“…︎ Mar 15 2021
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Oregairu x Tsutaya Collab Illustration. Saika Cross Dressing go brr
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πŸ‘€︎ u/reiikaza
πŸ“…︎ Dec 11 2020
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Soooo cross dressing

If a boy wears a skirt or a dress do you think you'll think him as gay. And do you think majority of people will think that. See I want to wear a skirt but don't want constantly tell people I'm not gay I just like to wear skirts.

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πŸ‘€︎ u/iMistaken0X
πŸ“…︎ Feb 08 2021
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[DISC] While Cross-Dressing, I Was Hit on by a Handsome Guy! Ch. 24 mangadex.org/chapter/1137…
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πŸ‘€︎ u/LonelyGoose1
πŸ“…︎ Dec 18 2020
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Collectivism, determinism, non-dogmatism, environment friendly, sounds nice but impractical, open about sex, cross-dressing, homosexuality, facilitating trans-surgeries, contextual, esoteric, vague, highly prone to interpretation, flexible, deconstructs more than constructs, female reverence etc....
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πŸ‘€︎ u/Anime-X-Kshatriya
πŸ“…︎ Jan 21 2021
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What was it like your first time cross-dressing in public?
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πŸ‘€︎ u/blern8792
πŸ“…︎ Feb 13 2021
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[DISC] While Cross-Dressing, I Was Hit on by a Handsome Guy! (Ch. 27) mangadex.org/chapter/1162…
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πŸ‘€︎ u/TrashGuys4Hire
πŸ“…︎ Jan 07 2021
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My sona Hush cross dressing (itzyshiu@twitter)
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πŸ‘€︎ u/HushTheBlues
πŸ“…︎ Jan 02 2021
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[DISC] While Cross-Dressing, I Was Hit on by a Handsome Guy! Ch. 26 mangadex.org/chapter/1156…
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πŸ‘€︎ u/LonelyGoose1
πŸ“…︎ Jan 02 2021
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As you can see this was taken moments before i got kamikazed by a purple tiger manhandling a fire flamingo cross dressing as an umbrella
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πŸ‘€︎ u/wolfharp
πŸ“…︎ Apr 01 2021
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[While Cross-Dressing, I Was Hit on by a Handsome Guy!]
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πŸ‘€︎ u/Certainlynotwrong
πŸ“…︎ Feb 26 2021
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John and Yoko cross-dressing
πŸ‘︎ 792
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πŸ‘€︎ u/Ghost_Artist2000
πŸ“…︎ Nov 29 2020
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