Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/350391.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Homestuck
  Relationship:
      John_Egbert/Dave_Strider
  Character:
      John_Egbert, Dave_Strider, Bro_Strider, Dirk_Strider
  Additional Tags:
      Crossdressing, Boys_in_dresses, First_Time
  Stats:
      Published: 2012-03-03 Chapters: 1/2 Words: 1910
****** The Icing On the Cake ******
by TheSpaceCoyote
Summary
     "Bro must've known. He must have been plotting this the whole damn
     duration of John's visit. He had seen the way you two dodged around
     each other with stuttering statements of "no homo," the way that
     every touch that got too tender or too intimate was either brushed
     off as "ironic" or a "prank."
     That's what made him hang the two dresses out there in the room. He
     knew you two would take the bait. You knew that he knew, and yet you
     hadn't let it stop you when you had proposed to John that this would
     be the ultimate gay chicken test."
     In which Dave and John experiment in crossdressing.
Notes
     Well, both Ahmerst and Gutennachte on tumblr have been dabbling in
     boys in dresses this week, and in one of the livestreams people said
     they wanted some more so....I did a lil with Dave and John <3 Enjoy!
     (Also I love Dave kind of being terrible at sex, it's way cute)
 
 
 
"You done in there yet, Egbert?" You holler through the bathroom door, giving
it a light backhanded rap. John's splutter comes amidst the audible sounds of
rustling fabric and fumbled zippers, but you can still hear him.
"A-ah, almost! Jeez, give me a minute, Dave!"
You would chuckle, but your current situation impairs you from doing anything
more than pulling a wry smile. You cross your legs and try not to think about
it, but the clack of the shoes you have on pulls you back to reality. As does
the soft sheer feeling of your stockings rubbing against your calves. 
Your Gay Chicken Battle had just flamed into the Great War of Crossdressing
which had claimed many casualties already. Namely, your sanity, your dignity,
and your masculinity. And John's were surely mortally wounded and would perish
despite the best efforts of the med team. There was no hope for them, not in
the face of so many daunting frills and zippers and buttons and bits of lace.  
Bro must've known. He must have been plotting this the whole damn duration of
John's visit. He had seen the way you two dodged around each other with
stuttering statements of "no homo," the way that every touch that got too
tender or too intimate was either brushed off as "ironic" or a "prank."
That's what made him hang the two dresses out there in the room. He knew you
two would take the bait. You knew that he knew, and yet you hadn't let it stop
you when you had proposed to John that this would be the ultimate gay chicken
test. You dared him to, and when he had dared you back you had shrugged it off
like it was no big thing. And it wasn't novel to you--Bro had had you try on
one of his stupid dresses before back when you were younger and stupider and
convinced of his lie that it would up your level of irony a millionfold.  
But trying on the dress in front of John, and then seeing John in a dress in
turn might end up being a little more than you'd bargained for. 
You palm your face, tersely rubbing the bridge of your nose. You really, really
hope Bro doesn't come by right now. Before when you'd worn his dresses you'd
sworn it was only due to his coercion, or the promise of a lesser beatdown next
time you strifed. If he saw you willingly dressing up like a virginal
schoolgirl he would have a fucking field day and all your credibility would be
crushed under the heel of a bright orange Mary Jane. 
Yeah, orange. Fuckin' orange. Bright sherbet orange plastered all over your
body in the form of a frosted Jello mold dress, a pair of candy-striped
stockings, peachy gloves--the whole fuckin enchilada. It feels like Bro has
branded you in his favorite shade of atomic-tangerine, and that only further
adds to your humiliation.
"Dave?"
John's quiet voice sounds right next to your ear, like he's pressed right up
against the door on the other side. You turn your head. 
"Yeah, bro? You all right over there?"
"Uhm." You hear him fumbling and fussing, shoes clacking against the tiles and
you can practically see him nervously hopping from foot to foot in your mind's
eye. 
"Yeah, I'm fine just, uhm. Uhh. I'm going to come out now, okay?"
"Sure, bro." 
You take a step back as the door swings open, revealing John standing awash in
the mellow light of the bathroom. He's hugging himself and biting his lip and
he looks super nervous, but you can't pay too much attention to all that.
Because he's wearing the dress. And while you expected that you didn't expect
him to look…well, you didn't expect to like it. 
John looks like a damn cake in that dress--a TLC bride's dream, quintuple-
tiered with baby blue icing crossed in lacy patterns at the bottom. It's like
spun sugar, bubblegum cotton candy just barely clinging to John's skinny frame.
It's light--airy.You suppose that it fits him like that. 
Even though you'd thought your Bro to be an utter shithead for baiting you two
with these dresses, you could practically kiss him right now for blessing you
with the image of John Egbert in a fetishized Cinderella ball gown. 
"John," you breathe, voice softer than you've ever heard it, "John just…Christ,
man."
John whimpers and hides his face, shaking his head back and forth in dismay.
"Jesus, Dave! This is…so fucking embarrassing…" He groans. You can see his skin
bright red and burning up between the fingers of his gloves and wow that
material is pretty and dang you kind of want to touch it and what the fuck are
you thinking. 
You're thinking about wanting to touch John and no, damn it you put those
feelings to rest. You'd dug up those feelings, pissed on them and then buried
them again upside down. They were gone and desecrated so what were they doing
here, making you hot and bothered and wanting your best bro as more than just
that.  
Even though the layers of your bloomers and the dress it's very obvious that
your tenting. And it seems obvious to John as well, the way his eyes drift down
to your nether regions. You swallow hard, hands balled into fists, trying to
remain as stoic as you can with a boner poking through your dress. 
You can't do it.
You surge towards John and grab his wrist, pulling him forward to you and
jamming your lips together. John whines in surprise and tries to pull away, but
you've got him, and after a moment his resistance seems to melt. 
Well. You weren't expecting that. Though considering 90% of what's happening
today has come out of bumfuck nowhere, you're not sure whether that's much of a
valid distinction. 
You start sinking to your knees, pulling John with you. He comes willingly,
knees buckling and hitting the tile. He bends backwards as you gently push at
his chest until he's laying spread eagle against the bathroom tile, dress
fanning outwards from his hips like a puddle of frosting. 
"This," He opens and closes his mouth a few times, trying to find his voice,
"This is okay, right?" His fingers tighten on the back of your neck and you
crane forward, letting him bring you closer. His eyes keep moving around,
flitting behind your shoulders and above your head as if he suspects Bro or his
Dad (magically transporting from thousands of miles away) to walk in on your
impromptu love nest. 
"No, dude," You simper, papping his cheek, "This is totally not okay. I
definitely don't have the hots for my best bro even when he's in a goddamn ball
gown, and that's why I'm definitely not going to do this." And then your hands
are down at John's knees and you're pulling his thighs apart. 
The force with which you had spread John's legs had tore the tights along the
seam right at the crotch and damn, that was practically an invitation. Flight
traffic controllers waving you right into John Egbert's awaiting asshole. You
pull down your bloomers and slowly wriggle yourself out, hard and ready for
landing. You investigate the tiny lump in the pocket embroidered on the chest
of your dress and are pleased to find its a small tube of lube. You don't want
to think that Bro had expectedthiswhen he'd left out the dresses, but you're
still internally singing his praises. 
You don't know all that much about sex with dudes, but you figure it's just
like putting figure A into slot B with a little bit of lube to slick the way.
Like fitting a piece of furniture together. Though John admittedly is a little
bit more sexy than a flimsy Ikea chair. 
You cover your own dick with the gel and decide to wing it, grabbing John's
hips and levering him up. He suddenly jerks and pushes himself up on his elbows
but you're already pressing against him, trying to dig your cock into his
body. 
"Ow, Dave, fuck--Dave, Dave stop!" He kicks out his heels, shoes grinding
against the tile,  and pushes himself away from you, looking up at you like
you're crazy. You try to grab him again and pull him onto your dick but he
pushes a hand in your face. 
"What the fuck are you doing?" he cries, voice shrill and offended. You lift
your hand off his hips and pull at his wrist, dislodging his fingers from your
face. 
"Uh, didn't think that was really up to much debate here, Egbert. Thought I was
gonna fuck you and all but maybe I'm getting some mixed messages. Would you
rather have a nice massage? Or maybe you just wanted our dicks to shake hands
and then go about their merry ways."
You cross your arms. You're not pouting, no way. You just wish he wouldn't be
such a bitch about you doing what you knowhe wants. 
John looks up at you, mouth agape. He tilts his head to the side and furrows
his brows like concentrating, trying to look through your mind and unravel the
tangle of Strider senses.  
"Dave, seriously? I would've thought…." John trails off, looking away, before
bringing up his hands and making a scissoring motion.
"You gotta, y'know. With your hands down there first before you…yeah." His
vague explanation doesn't really click with you at first, but then you get it
and your mouth forms a silent "O" before you feel your cheeks light up with
embarrassment. 
John has apparently watched a lot more gay porn then you have. Which would
basically mean any gay porn at all, since you didn't really make a habit out of
it. 
"All right." You breath deep, in and out, "All right."
You figure you should take off the gloves but, well, you've already fucked this
up royally so far and if you make John wait you fear he's going to change his
mind. So you dribble the lube onto your index and forefinger, rubbing them
together until the silk of the gloves is soaked and sticking to your skin. 
You slowly ease your fingers into him and John "oohs" softly, arching his spine
and causing more of his dress to spill off of his hips. 
"Oh God, dude that feels…that's so weird…" he mumbles as you press in more and
more. His hand scrambles for something to cling onto, but the smooth tile floor
provides him with nothing so he just settled for throwing his hand over his
face, one finger hooked into his lip. 
You can feel the slime of his insides through the fabric of your glove as your
prepare him. You swallow, wondering if the silk rubbing up against him is
uncomfortable at all but with his hand covering half of his face you can't
really tell. At least the noises he's making seem to indicate that he likes
it. 
After awhile you look up and you see that John has moved his finger from his
lip and is now biting into the knuckle, and you're not sure if its from nerves
or because it hurts. You gently rub his leg anyway, the fabric of your own
gloves rubbing against his tights and creating a soft and silky friction. 
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