#tw crossdressing

[letstalktea]

Contents: gn!reader (you/your), amab!Kylar (he/him), crossdressing (forced)

Word Count: 583

You finished putting the lipstick on him with a smile plastered from end to end on your face. "You're so cute that I'm almost jealous."

He couldn't help but blush as he stared at you dressed in the skimpiest lingerie he'd ever seen that framed your best assets perfectly. You were so lewd dressing up like that, especially in front of other people. It was okay when it was just you and him, but not in front of those creeps. They would take advantage of you.

"It's almost time for your show." You placed a finger just below his balls and enjoyed the way he shook as you trailed over the lace of the fabric that could barely contain him. "You ready, Princess?"

You were sure the audience would adore him as much as they did you. He was practically sweating as his eyes glared at you. 

"Don't look at me like that." After all, you weren't the one that was in trouble.

It was all him that came storming in hoping he would – or rather, wouldn't – find you dancing on stage. It was just unfortunate he'd found you with your shirt freshly torn off and your breasts on display for everyone to gawk at. After that, he got a little too comfortable with swinging his knife around and everyone started freaking out.

Briar had not been pleased. It took a lot of convincing (and a few promises to get a lot more risque for the next few shows) to get them to offer Kylar any kind of clemency. Clemency that came in the form of him earning back what he’d lost them: an audience and all of his profits. You would be damned if you let someone drag him off the stage though, so he had to milk as much as he could from the people who would be watching him.

You knew the audience well. You knew they liked them pretty and you knew they liked unraveling people's secrets. Well, he sure had one of your favorite secrets hidden under the skirt you'd forced onto him.

It wasn’t fair how cute he looked dressed up like a little goth slut. And the way he continued to glare at you as if he was looking for his chance to grab you and drag you away from all of this? Absolutely precious. Oh, you would love to be a member of the audience just to see how he performed, especially because you knew he wouldn’t have a clue how to dance. There was something charming about amateurs. 

“Are you angry with me?” You put on your sweetest voice as you leaned down to his level, brushing your lips against his ear as you dropped your voice and whispered to him, “I promise they’ll love you as much as I do? After all, you’re a cute girl with an even cuter dick?" You flipped up the edge of his skirt to cup his balls with a gentle squeeze as you leaned forward to whisper in his ear. "They'll eat you up."

Literally, if the audience had their way. A small part of you burned up thinking about how hot it would be for them to grab both of you and molest you side by side, but you would also probably kill anyone that touched him. Then you would owe Briar even more than you already did. Then again… maybe it wouldn’t be so bad to see him forced to dance a few more times.

[geckyklok]

🖤⛓Welcome to the most metal maid cafe ever⛓🖤

[hero2222-nsfw]

Another starter idea: Vio dressing up as a girl for 24 hours and walks around town...needless to say the clothes don't stay on him.

[princess-josie-riki]

Cartman: "All right! But don't make me do anything embarrassing."

Cuts to Cartman bursting out of the boxes in Poppy Playtime's dress.

Cartman: "I'm gonna kill him!"

Kenny: (disguised as Huggy Wuggy) ("Actually, I thought that dress was rather slimming on you.")

Cartman: "Oh, really? I thought it was a little revealing..."

They both hear Mommy Long Legs' laugh and run.

[owlclawstudios]

During ww2 henry was drafted into the us army Mabel wanted to keep henry safe and fight for her country how ever wonen in her country weren't allowed to fight on the battle field since many women worked as mechanics and nurses Mabel needed to disguise herself as a man to join the army, she cut her hair short and wrapped bandages over her chest and put on mens clothing she learned how to speak in a low voice she took the alias billy carter and she enlisted in the army without getting detected

[onikiribattousai]

Neko Maid Hoozuki and Sebastian, because I love drawing guys in maid outfit

FYI, they were wearing wigs

[malew1fed]

found some old girlclothes today and wore an actual bra for the first time in like 6 years today, and man, the power that crossdressing makes me feel?

unprecedented.

want to dom the shit out of a cute thing, my broad shoulders accentuated by bra straps and my tits creating cleavage, accented by my chest hair and the flexing of my biceps. blue jeans and workboots, boxer briefs creating a dissonance between my top and bottom halves. reeking of power and self esteem, sex appeal. want to be covered in stains at the end of it, jeans stained from fluids from fucking, bodies covered in sweat. their hole leaking my cum.

the masculine, the feminine, the threat of my hands and my strap and my gaze.

[rageagainsttheapathy]

An addition! To my Steve Becomes A Rocky Horror Performer au (link to part one here)

So! Steve has just been cast in the part of Dr Frank-n-furter, and he really did NOT expect to get this far, but he isn’t too worried. He had been while working up to the audition, because he had Zero experience in theatre, like, even less than most people because he’d never even BEEN to a stage show until his Adoptive Gay Parents took him and Robin with them to a midnight showing.

But the audition has passed! Steve has the part! Rehearsals start soon, but he knows the songs, he’s got his lines, and he’s sussed the fact that in order to pull off the part of Insane Sexy Alien Transvestite Doctor, all he really needs to do is walk into the room like he knows he’s the sexiest person in it which, hey! Finally a good use for the EXACT skill set he spent all of high school honing.

And then the casting director hands him a pair of platform heels and a case of makeup and tells him to get practicing.

Naturally, Steve calls Robin, freaking out down the phone about ending up looking like a clown with broken ankles, “fuck this was such a bad idea I’m gonna ruin the entire show for everyone help”

To which Robin replies, “Why the hell do you think I’m going to be able to help? I can barely walk straight in sneakers and I own three (3) items of makeup, all of which were gifts from distant aunts.”

“For gods sake Robin I need moral support GET OVER HERE”

Needless to say, it takes some work. Steve is not an artist, and makeup turns out to be incredibly easy to Mess Up. He spends multiple hours hunched over his bathroom sink swearing while Robin lounges on his bed offering unhelpful advice without looking up from her magazine, and cackling at him when he suddenly realises that he has makeup but not makeup REMOVER. His skin may never recover, honestly.

And then there’s the heels for Dr Frank’s costume. The first time Steve puts them one and tries to walk, he almost gives himself (another) concussion. There’s a whole different centre of balance to walking in heels, but Steve is an ATHLETE goddamn it, he is GOING to master the Sexy Strut™️ if it’s the last thing he does.

And, after a week of wearing his borrowed platforms around the house while he does chores and trying to mimic the hip sway that he’s always enjoyed seeing girls do, master it he does.

He demonstrates said mastery by striding confidently into the living room in full costume while Robin wolf-whistles and waves a wad of dollar-bills at him like he’s a stripper.

[letstalktea]

🔞Definitely thinking of M!Corrupt!Sydney with a F!PC. Specifically thinking how he puts on a dress when he goes out and won't take his hands off of her. It's just a little female kinship. That's what everyone thinks, but they don't notice how he's sitting next to her in the movie theater with his fingers buried in her cunt or how they both go into the same tiny stall in the bathroom during the credits so he can finally give her the real thing. They don't notice how he follows her into the dressing room at lingerie stores so he can tell her what he likes on her, or how he tries them on too just to see her get riled up.🔞

[incorrect-joseimuke]

Mitsutada, crossdressing: Can't you give a free sample to a pretty lady?

Sada: Sure! Do you know one?

*Beat*

Mitsutada: Care to give a free sample to an ugly lady?

Sada: No, ugly ladies hafta pay...

[geckyklok]

I guess Daisy really is best girl 👀

[decaydanceredacted]

i want pete wentz to forcefully detrans me. i want him to make me put on a skirt for him and call me a good girl while he fucks me like a girl. he transed my gender and i want him to take it back. pete wentz giveth and pete wentz taketh away.

.

[princess-josie-riki]

Ammo Baron: (sees himself wearing skimpy woman's clothing) "Holy shit! What the fuck am I wearing?"

[just-rogi]

I’m fucking venting here bc I’m angry and don’t have anyone to talk to and I’m not sure if this is political correct or right or whatever but I’m fucking pissed - I’m a public school teacher who works in the inner city and this year alone there have been two shootings in my neighborhood involving students not dying school hours- and one student who went missing due to gang ties (they were found ALIVE a DAYS later) -

I’m fucking TIRED I’m FREAKED OUT and I’m ANGRY because I have to go into work tomorrow and I have to have that conversation with the kids during our SEL block because they will have questions and bc they are in middle school some will not know how to process it and will joke while others will be genuinely upset

and I feel nauseous thinking about the fact that my mother and four of my closest friends are all going through the same fucking shit as teachers at different schools right now- and my roommate who is trans- and unrelated to his identity is also kinda an asshole- has been shitting on me all night about how I’m not I’m danger like he is and how I don’t know his pain (and while I’m not making excuses I’m an openly gay teacher who works directly with the lgbt students and activly educated my kids on trans rights AND I work for a nonprofit organization that directly works to protect trans and queer rights and JUST LAST WEEK put out a video for our organization on antitrans laws - I’m not saying I fucking get what it’s like to be trans but Jesus fuck I’m fighting the fight for trans youth more than you are working at Whole Foods) why the FUCK are you quantifying suffering, why the FUCK are you lashing out at ME of all people, and why the fuck are you telling a public school teacher in inner city Boston that I have no idea what it’s like to be afraid- motherfucker I’m angry I’m sorry but why the fuck are you monopolizing suffering why do you think you have the right to talk to me this fucking way. I get you are scared but you work in Whole Foods in Massachusetts- the bluest state there is- )

there is no fucking cap on grief- sorry I’m upset at this as well but you saying it doesn’t directly effect me is just so fucking ignorant and suffering shouldn’t be quantifiable mf we are on the same fucking side why are you infighting right now (and I know this isn’t relevant and this is entirely unrelated to him being trans but god he is so fucking sexist- saying shit like I have no idea what it’s like to have my bodily autonomy at risk as if roe v wade didn’t get overturned THIS year???) sometimes it pisses me off like fucking sorry I’m being over emotional and overreacting to a school shooting as a fucking public school teacher GOD I should be allowed to be angry too in my own goddamn apartment-

you don’t get to sit on your high horse and say you suffer more than me and that I’m not allowed to be afraid ok I’m done I’m gonna go in tomorrow and make sure to hug my one openly trans kid extra hard bc I know they are suffering just like I know my roomate is suffering and needs a place to express his anger- I get I’m an easy target bc I’m a safe person to lash out at and I’m not telling anyone how to grieve and I know a lot of this is just knee jerk reaction to violence and anger- I just wish he wasn’t expressing it at the one fucking person who doesn’t deserve it, like fuck, the one thing people always say about public school teachers is that we have it TOO easy, especially the night after a school shooting

*Also fuck terfs and fuck anyone who is using a tragedy as an excuse to hate trans people*

[werewolf-cuddles]

Motherfucker went from 'yeah it's gay men mocking women' to 'but it's those trans trenders to blame' like fuckin pick one? Are you on the side of gay people or not? Also 'minstrel act' nice. Nice. Just gotta slide in that casually racially loaded language

It's sad how fucking predictable this shit has become

[im-fuck3d-90]

Guysssss! I have a problemmmmm!!!

Okay, so! You guys know that I'm a trans-masc demiguy. As part of the demi part of the guy, I occasionally crossdress; sometimes even out in public! (Ofc I'm not doing this rn with all the bs going on in FL!!!) Well, I've also experimented with different religions when I was a teenager and tried to determine what religion is best for me (I've settled on The Satanic Temple brand Satanism!), and part of that was researching traditional dress and various sins, etc. etc. So, my problem is that, while I'm a Satanist and don't believe in any god at all, and am skeptical of supernatural things (personally, supernatural happenings could come from higher dimensional beings, aliens (it's statistically impossible for us to be the only life in the universe!), lapses in space-time, etc.) I have this want to sometimes wear a hijab! As a Satanist, participating in religious dress can be kinda... ugh... And like, as a trans masc, wearing strictly fem clothes feels like,, dangerous... But also, in terms of my own feelings towards things like, being seen, anonymity, style, etc. I feel like,, I want to... It feels so weird! Like, I know in my heart and soul what my gender is (and part of that was actually my moots!), but I know that if I'm visibly queer (I would wear a pronoun pin on my hijab which includes the trans flag), or appear Muslim in America rn, I could very, very likely get assaulted or killed...

I'm moving up north by the end of summer and I just... Do you guys think I'd be able to get away with it? Should I do this? Is it okay if I do this? I find the hijab nice to wear; is this offensive? Pls reply with your thoughts!