
Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/256629.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Homestuck
  Relationship:
      John_Egbert/Dave_Strider
  Character:
      Dave_Strider, John_Egbert
  Additional Tags:
      Crossdressing
  Stats:
      Published: 2011-09-24 Words: 2256
****** classy crossdressing shenanigans ******
by orphan_account
Summary
     Done for the (2nd) kinkmeme.
     Original prompt: "john has always been a little curious about wearing
     girl's clothes, in a sort of derpy "urgh man i'm a little weird
     aren't i. they're so pretty though!" way.
     dave is only too eager to make it happen."
Notes
See the end of the work for notes
John had a secret. He was very careful about it—he hadn't told anyone: not his
dad, not his friends. He was pretty sure that his secret was not normal. But,
Dave was John's best bro. That's why he knew he could tell Dave anything
without having to worry about how Dave would react. Sure, Dave might criticize
him a bit, but it would be in his ironic way and John knew that he wouldn't
really meant it negatively. Good friends stood by each other no matter what!
So, John was pretty sure that he could tell Dave his secret when they were
discussing the topic of alchemizing new clothing.
TG: you need some better duds man
TG: look at me
TG: suits
TG: all the way
TG: cutting imps to ribbons in style
TG: im like the butcher bridegroom of lohac street
TG: put on your suit egbert
TG: its time to dance
EB: BLUH!! no way! i tried that and it was okay for a while but now i am trying
something new! that is just too cool for me, i guess. i think clothing should
be comfortable!!
TG: no
TG: it should be awesome
TG: or ironic I guess
TG: but you dont really get irony so thats not an option
EB: but isn't it good to have your own style?
EB: you should try different stuff and maybe you will like it.
EB: i think you should alchemize casual clothing!!
TG: i already did that
TG: and then i switched to suits
TG: besides i am not taking fashion advice from a kid in a lab coat
EB: :P
EB: i'm not wearing a lab coat anymore!
EB: but i guess i do have some weird ideas about clothing
TG: what
EB: i mean i always sort of wondered what it would be like wearing girl's
clothing
EB: it's all so pretty!!
EB: i've never done it because i don't think my dad would have been okay with
it
EB: dave?
EB: are you still there?
EB: you're taking awhile to respond
TG: sorry I had to do something
TG: dont worry about it its not even a thing
TG: so you want to wear girls clothing
TG: thats cool bro
EB: i'm glad! i was worried you might be weirded out!!
EB: i should have known my best bro would support me! :)
TG: ok
TG: egbert
TG: im gonna give you a captchalog code
TG: use it
TG: or not
TG: i mean i really dont care
TG: but
TG: i might stop by lowas soon
TG: maybe
TG: you never know
 
Dave sent John a code and refused to say what it was for before logging off
Pesterchum. It was all a bit suspicious but there were a lot of things Dave did
that John did not understand, so he was not really worried. John used the code
and went about the process of making a cruxite totem and alchemizing the item,
which turned out to be... “The THREE IN THE MORNING DRESS?” While this was very
nice of Dave, and John saw this as a very friendly gesture in accepting his
quirks, John could not help but feel that the dress was not really his style.
John glanced around his living room. There had to be something that he could
combine with this to make it better. He decided to try out random things and
hope for the best. Either way, alchemizing things was fun!
Remembering his WISE GUY SLIME SUIT, he combined the code of the dress with the
code of his copy of WISE GUY. He got the GAMBLER GIRL GETUP, which was a better
color in John's opinion, but looked a bit uncomfortable.
On a whim, he combined it with his PROBLEM SLEUTH game. The result was the
SCALE BODICE which, for some reason, was much too small. It looked more like
something a doll would wear. He decided not to worry about it, and moved on,
looking for other items.
He tried again, combining the THREE IN THE MORNING DRESS with a HARLEQUIN DOLL
(because why not?) and creating the MIDNIGHT ARLECCINA DRESS. Oh my. It was,
well, it certainly looked comfortable. And also frilly and pretty and John
really, really wanted to try it on. He glanced around nervously, as if he could
sense the eyes of a troll watching him at this moment in his timeline if he
simply looked hard enough. He scurried inside his house to his room. Trashed by
imps or not, he felt safer here. Sending up a quick prayer to gog that Rose was
not watching him at that moment, John undressed and put on the MIDNIGHT
ARLECCHINA DRESS.
The dress was soft and lightweight. It was vividly colored, with diamonds the
color of pool balls running up the entire length. It came with white stockings
and black shoes, and poofy white bloomers that John blushed about, but put on
anyway. John glanced around guiltily. He was probably enjoying wearing the
dress too much. He could just hear the lecture he would get from Karkat if he
happened to see him like this. Remarkably, he didn't hear any dings to signify
he was being pestered (or trolled) on Pesterchum.
Instead, he heard a knock on his bedroom door.
John walked over to the door nervously. Imps didn't knock, so it had to be a
person. He really hoped it wasn't Rose. She would never let the psychoanalysis
end. He opened the door a crack and peeked through. “Oh, Dave! Hey, you
actually came by,” John opened the door all the way and took a few steps back
to let Dave into the room. After all, Dave was probably expecting to see him
wearing a dress, so it didn't matter if he saw John now. “Thanks for the code
for the dress! I ended up combining it with a few things to see what I'd get
and I really liked this one.” John turned on the spot to show of his handiwork,
enjoying the way the movement made the skirt flutter around his legs.
Dave Strider had come by expecting to see John in a long, dark green dress. He
had prepared himself for the sight, and had assured himself that he could play
it cool around John long enough to imprint the image forcefully in his mind for
later reviewing. He had not expected to see John derping around in a short
dress and white stockings that ended suggestively mid-thigh. But it was cool.
No big deal. Dave was chill as the fucking polar ice caps.
And that explained why he suddenly strode forward and grabbed John's shoulders.
Irony, man. Learn it.
“Dave? Uh, is there something wrong?” John grinned a goofy, bucktoothed,
nervous little grin, like he wasn't quite sure what Dave was doing but he
wasn't all that worried.
Dave felt his pulse quicken. John was too trusting. Too easy to take advantage
of. He needed someone to protect him, a valiant Knight to guard his honor, to
save him from the impudent advances of...oh, screw it. Dave leaned forward and
caught John in a kiss.
John opened his mouth in shock, and stumbled backwards a bit. Dave took
advantage of this and followed John back while deepening the kiss. He walked
John unsteadily across the room until they met with the bed, which John fell
back upon, breaking the kiss. Dave crawled up on the bed to kneel over John,
panting. “Egbert, what the fuck.”
John sat up, supporting himself with his arms as he leaned back a bit. “Uh, I
think that's what I'm supposed to say. This is unexpected, Dave!”
Dave scoffed. “I come in here and find you in this frilly little dress and you
expect me not to do this? It's like an invitation, bro, fancy script and
everything, 'you're invited to attend a private showing of John Egbert's legs!'
I think I'm obligated to accept.” He sat back and put his hands on John's
thighs, just above where the stockings ended.
John blushed vibrantly and clenched the sheets beneath him. “D-dave! I'm not
sure I'm comfortable with, um, all of this. I mean, I don't like guys.”
“Egbert. Shut up. You're so deep in the closet you're chilling with the
boogeyman.” Dave considered his options: stockings on or off? He rubbed John's
thighs as he tried to imagine both possibilities.
“I am not! I like girls,” John tried to look offended, but it ended up looking
more like he was pouting.
Dave noted that John didn't look uncomfortable, and wasn't trying to shove Dave
off of him. “You mean you like dressing like girls. It's not the same thing, I
thought you understood that,” he smirked. Yes, stockings on would definitely be
the better choice. John looked like he was about to come up with a retort, but
Dave's hands slid up John's legs, and one hand cupped the bulge in the little
bloomers.
“Ahh!” John's arms gave out, and he fell back onto the bed. “Dave! What do
you—nngh!”
Dave had reached inside the bloomers and taken John's dick. He pumped John
lightly, enjoying the way John's breath was coming in short little gasps. Dave
slid his hand down further, fondling John's balls while stroking the apex of
John's thigh with his thumb. After a minute he let go in favor of pulling the
bloomers down John's legs just enough to expose him completely. He observed his
work.
John was breathing shakily, hands clenched, knuckles white, eyes teary behind
glasses. He looked up at Dave, unsure but needy, an unspoken request on his
slightly parted lips.
Fuck. To hell with being calm and collected, Dave had needs. He palmed his
crotch before unzipping his pants and putting out his own cock, which was
already fully erect. “Goddammit, Egbert. Why do you have to look so fucking
tempting?”
John offered up a shaky smile. “I promise, it's not intentional!” He tried to
pull himself out from underneath Dave, suddenly more nervous at seeing Dave's
arousal. “I mean, I was just going to put on the dress and maybe wear it for a
little bit, but then you came over and when you started kissing me it was sort
of okay but I'm not really even into those things and—ack!”
Dave pulled John back by his legs and sat down on them, holding John in place.
“Ok Egbert, listen up. Rule one, you are banned from speaking. Rule two, you
are going to lie there and deal with it,” he leaned forward and initiated
another kiss. John was completely still at first, but he hesitantly opened his
mouth (after Dave's tongue had prodded his lips insistently enough). Dave's
tongue slid against John's trying to encourage his to be an active participant.
Ever so slowly, John responded.
John was not a very good kisser, but his reaction gave Dave some
encouragement—he hadn't been totally sure of John's compliance in all of this,
and he really didn't want to force his best friend into something he would hate
him for later. Dave pulled away and nuzzled into John's neck, mouthing just
under his jawline. “God, John,” he thrust his hips forward, rubbing his aching
cock against John's.
The Heir of Breath cried out breathlessly, and Dave almost commented on the
irony. He repeated the motion, and was rewarded with a similarly attractive
noise coming from John's mouth.
“Dammit, Egbert,” he huffed into John's ear, continuing to grind against him,
“When we beat this fucking game, you're going to have to wear dresses more
often.”
John's arms reached around Dave's neck and flailed, trying to find something to
hold on to. “Dave! Ohgod, I've never—” His nails dug into Dave's shoulders as
he clutched Dave to him tightly, and whined.
Dave chuckled, still smug despite the situation, “Never what? Bumped dicks with
another dude? No problem, bro.” He managed to sound cocky, though not quite as
composed as he usually did.
“N-no, I mean,” John moaned, “not even by myself.”
Had it been any other situation, Dave might have frozen in shock. But he sure
as hell wasn't going to stop moving, even for such an admission. “Fuck,
seriously?” No wonder he was in denial.
“Yeah,” John turned his head and breathed the word into Dave's neck, making
Dave's neck hairs stand up.
Dave smiled broadly into the crook of John's neck, getting an idea. “Never
jerked it to the thought of someone before?”
“Wha? Dave, no—”
Dave pressed his lips to John's ear. “Never reached down and touched yourself,
imagining someone else's hands?” He slipped one of his hands down between them
and grasped both his and John's hard-ons, stopping his thrusting in favor of
pumping his hand.
“Ohh, god, what are you—”
Dave started to thrust into his hand, even as he continued to pump himself and
John. “Never dreamed about getting fucked and woken up covered in your own
cum?”
“Dave! I—I think I'm—!”
“Come, John,” Dave whispered in John's ear.
John came with a high wail, and Dave followed soon after. Dave sat up after a
few minutes of breathing heavily, collapsed on top of John. John was laying
spread-eagle on the bed, eyes closed and panting. The skirt to his dress was
bunched up around his waist and splattered with semen. He opened his eyes and
turned his head to look up at Dave, face flushed.
Dave smirked. “Congratulations, Egbert. Now you're a man.”
End Notes
     This is bad and I should feel bad. Protip: I do.
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