Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/563684.
  Rating:
      Explicit
  Archive Warning:
      Choose_Not_To_Use_Archive_Warnings, Underage
  Category:
      M/M
  Fandom:
      Homestuck
  Relationship:
      Dirk_Strider/Jake_English
  Character:
      Dirk_Strider, Jake_English
  Additional Tags:
      Sex, cross_dressing, Oral, Anal
  Stats:
      Published: 2012-11-15 Words: 3218
****** Silk on Skin ******
by Leticheecopae
Summary
     Dirk learns about one of Jake's more secretive past times while in
     the medium.
Notes
     Written as a fill for Borishu over on tumblr. Sorry for any grammar
     or other mistakes, please enjoy!
See the end of the work for more notes
You don’t know where Jake is and it scares you. You woke up in one of the tombs
to the space besides you empty and cold. Fear had gripped you immediately as
you went to find him. The air in the tombs is breathable this far down, and you
both use it to your advantage, removing the masks so you can run hands over
each others faces, kiss each other breathless. You had both gone to bed in
nothing but boxers and briefs, wrapped around each other so you could press as
much skin as you could together, Both of you starved for the feel of skin on
skin; you had a lot of catching up to do.
You were quick to put on pants and had started your search, looking through a
few tunnels you had already explored, finding the slightest of trails down one
of them, a set of Jake’s foot prints pointed the opposite direction. You turn
down one of the tunnels you had already explored the previous day, and your
eyes catch light. You remember the room, a large one filled with old items,
treasures, and even a dusty old bed. It was larger than anything a human would
ever need, and again you wonder what had lived here at one time. You hear
rustling and peek in through the crack in the door. What you see has you hard
almost instantly.
Jake is wearing the shortest shorts you have ever seen, his ass barely peeking
out of the tight brown bottoms. His thighs are outlined by what look like
straps, keeping up thigh high, deep green stockings that stick out of some of
softest brown leather boots you had ever seen. The boots have a low heel and go
up to his knees. Both thighs bare holsters, thinner than the ones he usually
has, with green stitching in the leather.
He shifts and you tear your eyes away long enough to look at his torso. The top
matches the stockings, tight against his back and outlining muscle, the hem
stopping a good few inches above his hips. It lets you see something around his
hips, a circle of fabric, sheer and lacy that peek out of the shorts that
barely span the width of your palm on the sides.
Jake is looking in a mirror, the light of the lantern he had alchemized gently
glowing over his body, allowing you to see him in the reflection of the mirror.
You can see how the shirt makes a V down over his breast bone, his navel
peaking out from beneath it. In the V you can see the barest glint of a skull
pendant in the middle of pale skin, just below his tan line.
Licking your lips, you look at his face and blink in surprise. His mouth looks
darker, an earthy red that makes you swallow. His eyes were outlined in purples
and browns, highlighting the creases and making them look more sultry than you
thought possible. You see flashes of metal in his ears and for a moment you
feel like your heart may explode. He turns to get a good look at his own ass,
and you can’t help but let out a small sound, something akin to a growl. Jake
jolts and has a gun pointed at your head in a second, breathing hard. His
cheeks, which were already tinged pink, darken as you gently push in the door.
“Christ, Dirk you gave me a start.” He says, voice nervous as he wraps his arms
around his chest, trying to cover himself. Its not a body language you’re
familiar with, but you want it to stop. You step inside, closing the door to
keep any creatures from finding you. Stepping forwards you swallow hard as your
mouth practically waters to kiss him. You can’t stop staring, and without the
shades on your face you’re positive he can see how hungry you look. “D-Dirk?”
You slide your hands over his hips, feel the soft leather of the shorts and the
smooth, silky lace thing that peaks over the edge. He shudders and puts his
hands on your shoulders, not quite able to look you in the eyes. You lean in
and kiss his neck and make a low moan when you smell something on him, dark and
blooming like what you think jungle flowers would smell like. A shiver goes
through him as you lick at his neck, tasting his skin while your hands grip his
ass through the shorts.
“You taste so good.” You mumble over his throat, moving so you can kiss along
his jaw. He shudders and turns to meet your mouth. You can taste the waxy tang
of lipstick along with him, your tongue sliding into his mouth and he moans
when you push yourself against him, feeling his own erection pressing against
yours. When you pull back his lipstick is smeared and he’s panting. You
involuntarily buck at the image. His eyes flutter closed for a moment before he
looks at you again.
“Y-you don’t find this strange?” He asks, arms wrapping around your neck.
“Are you kidding me?” And it comes out stunned. “My boyfriends standing here
looking hotter than hell and you think I’m going to be pissed?” The smile Jake
gives you is gorgeously shy, different than what you’re used to.
“W-well most people would be a bit surprised to find out that their significant
other likes to dress in the opposite genders drawers.” Jake says softly and you
pull him tight against you and get another gasp. You kiss him again hard while
one hand slides around the waistline of his shorts, the feeling sheer lace
against the pads of your fingers making you cock twitch.
“Well I’m not most people,” you kiss his nose to get him to blush harder. “And
I think you look gorgeous.” He looks at you with thankful eyes with the
slightest gleam in them that makes your heart skip. You don’t really understand
why he thought you wouldn’t like this. Yeah you know from what little you’ve
learned about the culture of his time it wasn’t the norm, but you lived in the
middle of the god damn ocean; you could care less what he’s wearing, everything
just accentuates what you fell in love with. You give him a sly grin and pluck
at the fringe sticking out of the shorts. “If I remember correctly drawers
means underwear in that dialect you love so much.” The blush reaches his ears
as you lean in and kiss the reddened tips of them.
“Let me see?” Its soft and gentle and his shivers under your hands. He nods,
pressing his head against your chest as you walk him backwards towards the bed
that was once meant to be used for the dead and will now be used for the
living. He kisses at your neck, leaving red smears over your skin until the
back of his knees hit and you push him back. The bed is dusty but it means
nothing to you both as you help him slide back on the bed, getting him in the
center before grabbing the soft leather of his boots. You pull them off slowly,
exposing his calves which are wrapped in the silky texture of the stockings.
Taking one in your hands you nibble at the flesh through the fabric just
beneath the knee and he gives a giggle, a sound that you never thought you
would hear out of him. There is something about him in these clothes that makes
you feel something clench. Its still Jake, strong as steel, blow your head off
Jake, but he’s looking at you with such a different look. Usually its purely
predatory when you do this, wanting to take all of you, fuck you soundly till
your sated. You’ve been in him a few times, but not nearly as many as he’s been
in you. The look on his face though, its telling you to just take him, take him
and make him yours in the middle of the tomb.
He shivers when you slide your hands up his legs and undo the holsters, setting
them just next to the bed where he can reach them easily. He lets you do it,
going slow and at your pace instead of being demanding. Its odd yet refreshing,
making you smile just slightly as you look him over. Jake’s trembling just
slightly as you climb to sit between his spread ankles, hands wrapping about
them. Trembling pants escape his lips as you slide your palms upwards until you
are kneading Jake’s thighs and making him buck in just the smallest motions.
The outline of his cock is pressed tight against the dark leather of his
shorts, the top of the material just barely covering him. Leaning forwards you
undo the button slowly, loving the way he arches up into your hand. Jake makes
little pants as you pull down the zipper, deep purple silk pushing into view as
you look. The cloth barely covers him, the head of his cock poking out of the
top, red and flush with pre-cum shining dully in the pale light of the lantern.
His hands ball in dusty sheets as you look him over, his erection straining to
push out between the open fold of his shorts.
Outlining him with your finger he shudders and presses his fists into the bed.
There is something else under the shorts, going around his waist, something you
can’t fully see with them still on. Moving forwards so you can lean down to
kiss his navel you grab the shorts and help him raise his hips, slipping them
down slowly as you kiss his belly. When you have to move to get them off he
pulls his legs to his chest, letting you remove them quickly before throwing
them over the side of the bed near the holsters. Without the bottoms you can
see just what Jake had hidden underneath.
The clasps on the stockings are connected to more deep purple lace that
surrounds his hips, outlining the bone and the muscles of his stomach. The
cloth covering his cock you notice is not connected, but underneath the straps,
a strip of cloth held by thin stringy straps around his hips. You push your
hands against the underside of his thighs, spreading his legs so you can see
how the cloth tapers off after his balls, barely covering them, to becoming a
barely there strand of cloth. Rubbing your thumbs over the insides of his
thighs he bucks again and moans.
“You look beautiful like this Jake.” You say softly and lean in to kiss his
thighs.
“D-Dirk,” he pants as you nuzzle his balls, feel their heat as you pull the
thong to the side. Gently you suck them into your mouth, getting a snap out of
hips that makes you take more in as Jake groans low. “Oh christ Dirk please.”
His voice sounds high as you suck and lap at the package in your mouth. Jake’s
hands tug at your hair and you come off with a soft pop.
“Please what?” You ask and move forwards just a bit, tongue darting out to lick
him through the thong.
“Dirk, oh christ,” he pushes your head down a bit, pressing your chin into the
silk covering his cock. “Please, Dirk, use your mouth.” He begs and you
shudder. He’s never been this needy and it makes your cock twitch. You decide
not to make him ask twice as you press a kiss to his dick, getting a moan and
fingers twitching in your hair. Pulling back the fabric you leave it on, making
it catch on the base of his cock and balls, framing him on one side. Licking a
long line from balls to tip you start, pulling moans from him as you lick and
nibble, swirling your tongue over the head, making sure to lap at the precum
that has collected there. When you play with the tip he hisses, pushing at you
to take more, and you do.
The groan he lets out is one of the most beautiful things you’ve ever heard.
One of your hands play with his balls, rolling them as you slide the other up
to run over his stomach, pushing up the shirt he is wearing so you can touch
every single one of his ribs. You trace his muscles with your fingers as you
trace the head of his cock with your tongue, swallowing him down while you
flick over the pert nipples on his chest. Moans and small curses flow from his
mouth as he bucks into yours, getting you to go as far down as you can at the
angle you are at. When your nose finally brushes the curls of hair at the base
he tugs you off, making you pant just as much as he is.
“Fuck me, please, Dirk I-I need you to. Like this, please-” he trails off when
you un-captchalogue lube. You stand up on your knees and he stares at the ridge
in your pants. As you pop the cap he sits up and starts undoing your fly,
sliding down the zipper and pulling you out of the cloth of your boxers.
Covering one palm in lube you go to shove your clothes down with the other hand
but he stops you.
“Keep them on, please.” His voice holding the slightest plea. It makes you
shiver and you can only nod as you settle back on your heels. Jake lies back
down, legs spread wide as you pull the back strap of the thong from his flesh,
sliding slick fingers between his cheeks and making him groan. When he sounds
like he is about to complain you slide a digit inside, feel his body tensing as
you do so before he takes deep breaths. You slide in deeper, feeling him clench
and relax with each inch. In only a few shallow thrusts he’s begging again, his
demanding side coming through now that you are inside him.
“Faster,” he begs. “Dirk go faster.” The way he says it makes you groan as you
lick the underside of his shaft, getting a moan as you slid in a second
finger.You move the digits inside him for a few moments while you lap at his
cock, his hands wrapped in your hair. “Just- please, please.” And he rocks down
on your hand, thighs bunching and you can’t help but slide in the third. His
back arches off the bed, cutting off your air for a moment as he thrusts in
deep. After a moment a small cloud of dust shifts around you both as he flops
back down. With three inside him you spread Jake wide, scissoring and pressing
against his walls, your mouth on his cock, pulling sounds of pleasure from him
until he pulls you off again. You gasp a little and feel your cock throb as he
looks at you with half lidded eyes, his lipstick smeared and eye shadow
smudged.
“In me,” he says and can’t help but obey him as you grab the lube and slick
yourself up. It gets on your pants, your boxers, but you don’t care. Jake
wanted them on, so you are going to keep them on. Pulling the thong to the side
again you line yourself up and look up at him. Green eyes look at you almost
pleadingly as he reaches a hand towards you; It’s a gesture he makes every
time. Taking it in your own you squeeze his fingers while you push inside, the
other hand on his hip to keep him steady.
Even after all the prep he’s tight, so tight, and you go so slow even as he
immediately starts to beg you to go faster, fuck him raw; just ‘please, please,
please’ while he squeezes your hand. You don’t, just slide inside until you’re
fully sheathed inside him. Jake pulls you forward so he can wrap his arms
around your neck, holding you tight. He kisses you hard as you start moving,
feeling him clench and relax around your cock, both of you moaning into each
others mouths. The strap of the thong rubs along your junk with each thrust,
another sensation as you slowly speed up.
“Strider, please. Oh crikey, please just-” he pants as he locks his ankles
around your back. You can feel them pushing your jeans down over your hips as
you fuck him slow. A few more scattered words escape before your push your
tongue past his lips, fucking his mouth with it as you speed up your thrusts.
He moans deep and you reward him by wrapping a hand around his cock, jerking
him harshly. His head falls back.
“Strider please, I need, fuuUUuuck harder.” His hips jerk up with the words and
you comply, speeding up your rhythm and going deeper, harder. Neither of you
last long as you start to slam in hard and rough, stocking clad legs tightening
around your waist till they are almost bruising. You run one hand over his
chest, feel his muscles clench beneath your touch. A few more harsh jerks from
you hand on his dick and he is cumming, thick and sticky over your fingers.
“Dirk.” The words come out between clenched teeth as everything goes tight, the
clench of his body pulling orgam from you. He keeps moaning as you rock gently
in him, riding out your orgasm till you are barely able to hold yourself up
above him. You lay on top of him, panting hard as he holds you.
“Should get dressed up for me more often.” You pant and he chuckles, you both
sound tired.
“Whenever you want Strider.” A small pained sound leave his throat as you slip
from him, rolling off him to lay on your side. He shifts to put his back to
you, allowing you to pull him against you and spoon him. You’re both sticky as
all get out, your clothes ruined with lube and his garter belt stained with
cum. Taking out a towel from your sylladex you wipe the two of you off as best
you can, straightening Jake’s underthings as you go, before throwing the soiled
towel across the room. You pull away only a bit to remove your pants and
underwear before leaning over the side of the bed and grabbing the leather
shorts. They are a little big on you, your hips leaner than Jake’s, and as you
slide them on Jake throws off his shirt, leaving only stained silk and
stocking. When the shorts are up and zipped Jake smiles at you, and you lean
down and kiss him before lying back down and resuming the spooning.
“Maybe you should dress up for me.” Jake chuckles as he grabs one edge of the
dusty bed cover and throws it over you both.
“You’ll have to pick out the outfit.” You murmur in his ear and feel the
slightest tremor go through him. Smiling you kiss the back of his neck and
allow sleep to take you, arms wrapped tight around him as you enjoy the feeling
of his skin.
End Notes
     Can you believe this started as a drabble?
Please drop_by_the_archive_and_comment to let the author know if you enjoyed
their work!