Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/7804042.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Twenty_One_Pilots
  Relationship:
      Josh_Dun/Tyler_Joseph
  Character:
      Josh_Dun, Tyler_Joseph
  Additional Tags:
      Alternate_Universe_-_No_Band, Alternate_Universe_-_High_School,
      Crossdressing, pastel!Tyler, Smut, Blow_Jobs, Public_Blow_Jobs, Tyler
      likes_to_wear_dresses, and_Josh_likes_to_encourage_Tyler_to_do_exactly
      that, and_it's_all_p_cute_until_it_also_gets_p_hot_ok, that's_all,
      ENJOY!!!, (_also_tyler_in_dresses_is_my_kink_ok_can_u_blame_me_)
  Series:
      Part 2 of Underneath_your_clothes_-_crossdressing_au
  Stats:
      Published: 2016-08-18 Words: 3154
****** Dressed Up ******
by heavydiirtysoul
Summary
     Tyler wants to buy a dress for his sisters birthday, and he's only
     trying it on to make sure it'll really fit her. Flirting with the
     cute shop assistant is an added bonus, fine, but the fact that he
     seems to really dig Tyler in this dress definitely won't have any
     influence on his decision wether to buy it. Not at all. Not the
     tiniest bit.
Notes
See the end of the work for notes
Tyler wasn't a materialistic guy.
He'd always liked vintage shopping; browsing through thrift shops and flea
markets for hidden treasures was one of his favorite pastimes, so when he found
the random flyer for a vintage shop summer sale at the school's blackboard, he
didn't take long to decide that he'd go – he had nothing better to do anyways,
and maybe he'd find a cute dress for his sister. It was her birthday in a few
days, and he still hadn't figured out a good gift idea he liked, so he decided
to go today, right after school.
He waved goodbye to his friends, telling Mark to let his Dad at the bus stop at
home know that he'd be late today, and off he was. The shop was close by, it
only took him a few minutes of walking to get there.
 
The bell on the door of the shop was small and light, making the tiniest noise
as he entered the store. It was the generic vintage shop, exactly the kind of
place he'd spent hours in as a kid – Tyler had always had a faible for
sundresses and pastel colors, getting giddily excited when he could help his
mum or his sister pick out clothes.
His parents had given him every chance to embrace his feminine side -- or any
side, really, they were open and happy to let their son explore whatever he had
set his mind on. His childhood was a happy time for him, limitless, free, his
need to experiment and find himself in a world that was much too keen on
restraining people in their personality always being supported by his family,
so he was confident enough to walk into an all woman's shop without even
bothering to care what others might be thinking.
It was a well-sorted place, the dresses, skirts and shirts in order by color
and size, and for a moment, Tyler could feel the familiar, childish excitement
buzz in his fingertips – the fabrics were soft and silky as he let his hands
dance over them, and he almost shuddered with nostalgia.
He was drawn to the clothing rack with the violet, dark pink and magnolia
dresses, eyes fixed on one specific piece with a laced up corsage, pretty
valance cascading in waves, and it even had a petticoat in a soft, gleaming
white, almost pearlescent. He eyed the dress curiously, itching to maybe try it
on, but he couldn't find a salesperson to ask about it – he didn't want to come
off odd, and sometimes, if the dresses were expensive, the shop wouldn't allow
them to be tried, or only after buying them.
Tyler didn't like those shops very much; while he could appreciate a store
wanting to make the dress perfect with fitting it exactly to your own body
after buying it, he couldn't really ask them to change the dress to fit the
body of his sister without them knowing her measurements. He really hoped the
shop he was in right now wasn't like that, since he really liked the dress and
could see his sister wearing and loving it just as much.
 
„You're not the usual customer, I'll admit that.“ The voice caught Tyler off
guard, and he almost dropped the dress, shoving it back onto the rack with a
small jump.
„Geez, you scared me“, he huffed, palm of his hand placed on his heart, turning
around to find himself face to face with another guy, a bit older than himself,
leaning against a rack with a smug grin.
If there had ever been a guy that looked like he wouldn't be working in an all-
woman's dress shop, this was him. He had bleached hair with a soft shimmer of
blue, half washed out already, a nose ring, gauges and a full sleeve of
tattoos, wearing skinny jeans, a NASA shirt, pink converse. Tyler knew he was
staring, but he couldn't help it.
"You don't look like the usual guy to work in a vintage dresses shop either."
„Uh, okay, that's true, I guess.“ The other seemed to be utterly unimpressed
with Tyler's obvious fascination, still leaning against the rack, casual. „So,
can I help you with anything?“
„Sure“, Tyler muttered, reaching to grab the pastel-violet dress he'd picked
out before, holding it up with raised eyebrows. He knew he was blushing, all
the pride of confidence in his own femininity nothing more but a memory by now,
standing in front of one of the most attractive guys he'd ever had the pleasure
of laying eyes on.
„I was wondering, um, so – actually, I need a gift for my sister. It's her
birthday soon, and I think she'd really dig this one.“ He nodded towards the
dress again, although it was obvious what he was talking about. „So, uh, she
and I actually have pretty much identical measures, except for, you know – I
don't really have... ah, whatever. Anyways, I was wondering, do you think I
could try this on?“
He could feel the intense stare from the sales guy, and Tyler felt like
squirming in place, like an ant under a looking glass, exposed. Maybe he'd just
laugh and call him a pervert, just here to try on woman's clothes, kick him
out, shake his head at the weirdo, but to his own suprise Tyler found the guy
shrugging, then nodding casually.
„Sure thing, can't think of a reason why you shouldn't. You might need help
with the lacing though, so just call me when you want me to tie the thing up.“
The guy gestured towards the single small changing cubicle in the corner of the
shop before taking the dress from Tyler and untangling the various bows and
laces while Tyler stood next to him awkwardly, eyes everywhere but on the other
guy's surprisingly delicate fingers working with the fabrics.
„There you go“, he finally said, handing the dress back to Tyler and holding
the curtain of the cubicle open for him, leaning against the frame again –
always so casual, and Tyler almost envied the other guy for his radiating
confidence.
The heavy velvet curtain fell close, and Tyler could hear steps moving away.
„I'm Josh, by the way. Just call when you need help.“
 
So now the guy had a name, and Tyler was glad to know it as he soon found
himself all tangled up in countless fabrics – it was a mess, and he wasn't even
sure if he had put the dress on the right way or if it was upside down or
turned from the inside out. He was in his briefs only, one of the hooks of the
corsage awkwardly stuck in the waistband of them, and he felt like crying - or
maybe even hysterical laughter due to his own helplessness.
„J – Josh?“
„Yeah?“, the voice came from the other end of the shop, and soon enough steps
were closing in.
„What's up? Need help?“
„Uh, I think so, yeah.“
„Okay, can I open the curtain? It's just you and me in the shop, don't worry.“
Tyler nodded before realizing Josh couldn't see him, so he took a deep breath
to gather some confidence, popping his head out of the cabin first, slight
blush and defensive expression on his face.
„You have to promise not to laugh. I messed up pretty bad.“
„It's okay“, Josh nodded, serious undertone in his voice despite his huge grin,
encouraging, almost. „Those dresses are complicated. No need to be ashamed.
Now, come on, let me help you.“
Tyler pulled the curtain to the side, stepping out, half naked and covered in
violet lace and silk, and the color surely didn't fit his excessive blush at
all – but Josh looked somehow weirdly pleased, big eyes and honest admiration
on his face.
„The color suits you very well.“
Tyler wasn't sure if he was just being polite, but he suppressed a lame joke
and remained silent, pressing his lips into a thin line while Josh worked the
dress with trained hands and focused movements.
„There you go“, he finally said, fingers ghosting over Tyler's waist for a
moment as if he wasn't sure about what to do with his hands now that he was
done. „I'm going to lace up the back real quick. Tell me if it's too tight.“
Soft fingertips were brushing against Tyler's back in a quick rythm, yet it
didn't feel hurried, and every touch left the tiniest trace of a shudder on his
skin, and he was sure that by this point Josh must've noticed the soft
goosebumps on him.
The other was silent, working, and when Tyler suddenly found himself being
turned around by his waist to face the mirror, he couldn't help the gasp.
 
The wavy fabric cascaded down his body in the prettiest ways, framing his thin
shoulders with clouds of tulle, his waist almost perfectly curved into an
hourglass shape, the huge bows on the circle skirt only amplifying the great
effect the dress had on his figure.
„You look stunning“, Josh said in a somehow muffled voice as if he was
repressing something, and Tyler's eyes were as big as the moon as he gazed at
himself in the mirror, unbelieving upon his own reflection.
The fact that Josh was standing next to him, slightly to the back, drinking up
his appearance in the mirror like he was dying of thirst only made the whole
thing better, and Tyler almost giggled.
„Are you okay?“, he asked, slightly poking fun at the other for his obvious
admiration, batting his eyelashes in a very coquettish way, and Josh turned
crimson red in a matter of seconds, turning on his heel immediately to walk
away, and for a second Tyler thought he'd gone too far with their little game,
feeling self-conscious and exposed suddenly.
Anyone could walk in the shop at any moment, and he surely didn't want to be
caught in a compromising situation like this, so he almost fled back into the
cubicle, tearing the curtain close behind him with a quick, hasty motion.
„Hey, wait, uh, – I don't even know your name.“
„Tyler“, he snapped, while already trying to fumble out of the dress, failing
horribly thanks to the laced up back, „but why do you care?“
„Tyler, hi. Uh, I care because I have, um, I think it's the perfect addition
for your dress – I mean, your sister's dress. Look.“
A shy hand sneaked through the curtain – stockings, delicate and softly
glittering, with little bows on the top hem, and Tyler took them cautiously.
„I – I'm not sure I'd need to try those on. I mean, stockings fit everyone,
right?“
„Just do it, man. Gotta know they fit the dress, okay?“
 
Maybe it had just been an excuse, but Tyler agreed and slipped into the
stockings – it felt weird at first, uncomfortable, but after a few moments of
deep breaths and self-conscious gazes into the mirror of the cubicle he decided
he'd just trust Josh with this.
It did look cute, the way the stockings shaped his legs, making them look even
tinier and more delicate than before, and Tyler couldn't help but notice how
weirdly at home the whole outfit made him feel. He didn't feel like himself
anymore, necessarily, more like someone else, someone prettier, someone coy and
kittenish and flirtatious and definitely more feminine than he was usually in
his basketball shorts and loose vests.
He tiptoed out of the cubicle, making his way up to Josh silently, letting his
hand ghost over Josh's shoulder for a moment, unsure if he should just pat him
on it to get his attention, instead opting to lean in and whisper a soft 'Hey
there, handsome' into the others ear.
„Woah“, he made, a huffled noise as he almost jumped and hit his elbow on one
of the clothing racks, and his eyes grew wide, scanning the thinly framed boy
in front of him with surprise.
„You look.. I mean, you're gorgeous. Your sister will love the dress, I'm
sure.“
„Hm-mh“, Tyler made, twirling in front of the closest mirror, shooting short
gazes across to Josh, beaming. „Or maybe I'll keep it for myself. I don't
know.“
Josh nodded, seemingly absent-minded, lips pressed together in a thin line, and
Tyler wondered for a brief second what was going on – but then Josh tried to
low-key adjust his pants, and now it was Tyler's turn to worry his bottom lip
between his teeth.
„Umm, are you okay, Josh?“
„Sure thing. A-okay. All fine, don't worry“, he almost stumbled over his words,
crimson red with embarassment as he noticed Tyler's gaze, and Tyler knew that
Josh knew that he knew and all of that resulted in an awkward silence neither
of them knew how to get rid of.
„Uh, you could, um, help me out of the dress again, please“, Tyler muttered
eventually, fingers nervously entangled in some of the lace bows on the skirt,
and he avoided Josh's gaze, but the thought of being able to turn the other on
with simple movements like twirling in a dress did give him a certain
satisfaction.
„Right. Yeah, sure. Let's go back to the cubicle, don't want to have you stand
half-naked in the middle of the shop.“
 
The awkward silence continued as Josh's fingers ghosted over Tyler's back
again, untangling the laced up back carefully with measured movements, and even
though Tyler knew it wasn't helpful, he couldn't help the badly suppressed moan
as Josh's fingers grazed his lower back.
There were many things he'd expected as a reaction to that, but Josh throwing
him around with a swift motion so his back crashed against the wall of the
cubicle wasn't one of them.
„Such a tease“, he muttered, Tyler's wrists caught in his hands, pushed against
the wall above Tyler's head, and he was staring, mouth open wide upon the
intense gleam of lust in Josh's eyes. „I -“, „Shh, princess. Now is not the
time to talk, alright?“ Josh's voice was.. different, rougher, yet soothingly
warm, like dark honey and coarsely ground coffee, and Tyler gasped sweet
profanities as Josh's teeth left the tiniest marks on his neck.
„Keep your hands where they are, princess“, Josh ordered, and it took Tyler his
all to not let them fall down and into Josh's messy, blueish hair when he
started to let his delicate hands wander up Tyler's thighs, softly tugging on
the hem of the stockings.
„So pretty, aren't you? Such a pretty princess. And so innocent, hm? Never been
fucked in a dress before, have you?“
Josh's gaze locked with his, and Tyler shook his head slightly – he'd never
been 'fucked' anywhere, and he articulated the thought, small voice, almost
embarassed. Josh snapped out of the growly, seductive state immediately and
gave Tyler big eyes, his hand cupping Tyler's cheek softly within the matter of
a moment.
„That's okay, shh. I have an idea.“ The gleam was back in Josh's eyes, and as
he sunk down to his knees, thoroughly tugging on the stockings to bring them
down and let Tyler step out of them, the younger boy had a very detailed idea
of what exactly Josh wanted to do.
He was almost painfully hard in his briefs now, and he couldn't help the squeal
as Josh finally pulled down his underwear to let his dick spring free, pressing
soft butterfly kisses to Tyler's inner thighs, and the tulle and silk shifting
against their skin made them both weak in the knees.
 
Where Josh's hands had been delicate and tender, his lips were rough and
demanding without ever being too much – the stubble against his thighs was on
the verge of being painful, burning harshly on sensitive skin, but the
overwhelming mixture of pain and pleasure was enough to make the dressed up boy
moan in the prettiest octaves.
Josh's hand finally found the perfect pace around Tyler's cock, soft kisses
ghosting on the head, short, quick flicks of a heavy, warm tongue against his
slicked up skin.. Tyler was teary eyed with need at this point, whimpering
breathless begs and sweet nothings.
„Please, please, Josh, please“, an endless stream of muttered out words like a
mantra was falling from swollen lips, worried between teeth, and his eyes were
closed, the new, yet oddly familiar feeling of his nerves straining with sweet,
close to unbearable ache numbing out every other sensation.
Tyler wasn't even sure what he was begging for at this point, the movement of
Josh's hands and his lips finally closing around Tyler's dick pushing him even
closer to the edge, and he felt like collapsing into himself; into a panting,
sobbing mess of blurred out vision and blood rushing in his ears. But Josh knew
what he was doing, keeping Tyler on his toes, one hand reaching up to press him
to the wall, keeping his hips in place and giving him no chance to buck up into
Josh's mouth – even now, the older boy was completely in control, and Tyler was
close to losing his mind with every nerve trembling to the point of breaking
down completely.
„Please, just let me--“, he muttered, and Josh hummed against the sweaty skin
of his cock, tongue circling tiny patterns against hypersensitive skin, and
before Tyler could object, Josh had gotten up again – the loss of contact for a
mere second already caused him to whimper with pain, but Josh was leaning
forward now, his whole bodyweight pressing against the younger boy.
„I want to see you come,“, he whispered, soft smile tugging on his lips as he
let his hand sneak under the layers of silk and lace, finally closing around
Tyler's dick again, and Ty's head fell back against the wall with the
overwhelming sensation of being so, so close, knots in his stomach, every inch
of his body aching for release.
„Look at me, princess. My pretty, dirty princess. Will you come for me? Would
you do that for me, mh?“
And with a last few, quick strokes, Tyler could feel his every muscle tense,
coming undone - falling apart beneath sloppy strokes from fragile, tender
fingers and intense gazes from eyes as dark as the universe and just as pretty
and maybe even just as dangerous if you got lost in them.
Waves of pleasure were crashing into him and pulling him under, and for a
second, he was sure he'd lose consciousness, unable to draw in just one breath.
But Josh soothed him through his climax, hushed words and sweet nothings and
soft, barely visible motions against his skin, tickling the last rushes of his
orgasm out of him with practiced hands.
Tyler collapsed against Josh's chest with a gasp, eyes wide, an exhausted smile
plastered on his face as Josh trailed soft kisses along his collarbone.
 
Needless to say, Tyler bought the dress; and his sister got a necklace for her
birthday.
End Notes
     I just really like Tyler in dresses okay
     PROMPT ME @ www.badkittyjosh.tumblr.com
     also shoutout to the wormler stans, y'all #duncumsquad
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