Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/849509.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Homestuck
  Relationship:
      Bro/Dave_Strider, Bro_&_Dave_Strider
  Character:
      Bro_(Homestuck), Dave_Strider
  Additional Tags:
      Crossdressing, Crossdressing_Kink, Bondage, thigh-highs, thigh_highs,
      Oral, Anal, Rope_Bondage, Anal_Sex, Oral_Sex
  Stats:
      Published: 2013-06-19 Completed: 2013-07-04 Chapters: 2/2 Words: 2070
****** Bubblegum Bitch ******
by Cora_knight_of_breath
Summary
     Bro catches sight of a short blonde girl in a club. What happens when
     she has more under her skirt than expected?
***** Cross Dresser *****
Bro felt his body move easily with the beats in the club. He was drunk, but not
so much that he couldn't gather his whereabouts. He could easily identify the
people around him. He just chose not to as their bodies blurred and moved with
his. This was how he spent his nights: going from club to club, picking up
girls.
A smirk formed when he saw a blonde girl in a baggy red skirt and plaid skirt,
red thigh-highs rising up from black flats. Bro slyly worked his way over to
her, taking in the bubblegum scent drifting from her. She sensed his presence
and allowed herself to dance against him. He placed his hands on her hips,
allowing the music to guide him. She slyly worked herself back ever-so-
slightly, grinding against him. She smirked slightly, her red eyes looking at
him from behind aviators. She grinded against him, her back pressed to his
chest. He had been half-hard at just the scent drifting off her. The grinding
helped turn it into a full-on boner. He couldn't resist grinding back, which
caused a bigger smirk. He wrapped his strong arms around her, whispering in her
ear.
"You give all guys at clubs boners?"
Her response was soft. "Only ones I'm interested in having fuck me."
That was too much for Bro. In a moment, his lips were pressed to hers. Her
lipgloss tasted like she smelled: bubblegum. His tongue twirling in her mouth
eagerly, rubbing against hers. She broke the kiss after a moment.
"Even though few would notice it, I suggest taking this somewhere
more...private."
He smirked. "Like hell if I'm waiting for a trip to a hotel."
He pulled her along, into the bathrooms. In a moment, they were in a stall and
she was pressed against the closed door. Their lips mixed eagerly, tongues
dancing as her fingres tugged at her hair, knocking off his hat.
Bro could sense that she was nervous. She was clearly more talk than act. Maybe
even still a virgin. No one had likely caught her in the lie.
Bro nipped at her kneck as his hands slid up her skirt. She gasped, her eyes
closing. She wasn't about to give up, it seemed. She was determined to stick to
the lie, even as Bro's leather hand slid inside her lace panties to rub at her
dick.
Yes, dick.
The girl pinned to the stall was the notorious Dave Strider. No one had ever
actually caught on to his actual gender. They always fell for it. Bro was
different, though.
"I have to admit," he whispered in the blonde's ear, "you're pretty
convincing." He rubbed his gloved hand along Dave's dick, helping it harden
fully as the young boy moaned. "It just takes more than that to trick me."
"G-God!" Dave nearly screamed as Bro's rubs became faster.
"I say I teach you about lying. I'm going to fuck you senseless here, and then
I'll punish you at my place."
Dave nodded. "Y-Yes! Please!"
Bro slid the boy's panties down to mid-thigh, rubbing along the thigh-highs.
God, they were sexy. Guys crossdressing in general were sexy, of course.
"You can admire the lace later!" Dave barked. "J-Just fuck me!"
"Forgetting something: lube."
"P-Purse!"
Bro pulled it out, chuckling at the bubblegum scent that came when he opened
it. This kid must have an addiction to that scent or something.
He slathered two fingers, slipping them into the boy. A deep moan came out. He
was clearly a virgin in this area, at least. Whether or not he had fucked
someone was another matter, but he was too tight to have ever been fucked by
someone else.
Bro slowly thrust his fingers, working to loosen up the younger boy. No matter
how much preparation he gave Dave, he would never be able to handle Bro's dick.
It was good to help a little bit, at least.
"J-Just put it in!" Dave begged.
"You asked for it, kid."
Bro slathered his part and slid it in, causing Dave to wince a bit. Bro slowly
thrust, one gloved hand firmly grasping Dave's dick as the other held his hip.
He slowly jerked Dave off as he thrust, turning the young boy into a moaning
mess. His thrusts came hard as he tried grasping at the door of the stall best
he could. He screamed out as he cummed, his liquid covering the door and his
skirt. Bro continued thrusting a bit, listening to the screams of the boy. Soon
he pulled off, stepping back.
"Suck me off," he instructed. "No way am I climaxing at this rate."
Dave nodded, panting, and sank to his knees, turning to face the man before
him. He watched as Bro slowly licked the cum off his fingers, not sure where
his eyes were. He took a deep breath before sliding his mouth around his dick.
He could only take in half, but he supported the rest with his hands. As he
bobbed his head, his hands twisted along the part. He sucked eagerly at it,
twirling his tongue along it. He rubbed the top of his tongue against the tip,
taking pleasure in the moans sliding from the older man. Soon his mouth was
full of cum. He tried to swallow it, but he only got a bit down. Most of it
ended up splattering over his face. He held his mouth open, panting. Bro sank
to his knees, licking the cum off the boy's face. Dave eagerly pressed against
him, finding himself oddly turned on for the second time. Soon, it was all off
his face and his panties were pulled back up.
"Hope you like bondage and pain," Bro whispered in his ear as they left the
restroom. "My place is next."
Dave honestly found himself enjoying that idea, though not nearly as much as
Bro did.
***** Apartment Shenanigans *****
Chapter Summary
     Bro takes back to his apartment and shows him a few kinks he has.
Chapter Notes
     (by popular request it is done)
See the end of the chapter for more notes
Dave looked around at the room, feeling a bit nervous. There was a hook
attached to the ceiling, which he stared at for a good time. There was no
canopy, and Bro didn't really seem like the kind to own one.
"Sit on the bed."
Well, that seemed odd. Dave really had no right to protest, though. So he sat
in the center of the bed in the required position, trying to watch as Bro
pulled out ropes and what looked like two gags. He carefully climbed up behind
Dave, tying his hands behind his back so that the palms were against the
elbows. He then tied the bound arms to the hook with more rope. Dave was
feeling nervous, sitting on the bed with his legs pull up to his chest as Bro
bound him. He didn't even get to take off his clothes.
Dirk then worked to spreading out his legs. They were bound to the footboard,
spread apart. Dave was about to protest, but then Dirk put a gag in his mouth.
The other one turned out to be a blindfold, which was readied as well. Bro slid
off Dave's sunglasses, seeming to stare at the younger boy's red eyes for a
moment. A thumb, rough and calloused, gently rubbed under the eye before he
gently kissed Dave's brow. Dave watched as he crouched down in front of him,
ignoring the blindfold.
"Well, I hope you're ready."
He lifted up Dave's skirt, blocking his actions from the boy's view. Dave was
near protesting, wanting to watch whatever Bro was doing. He could only rely on
feeling now. So he closed his eyes, even though Bro had basically given him
permission to watch.
He focused on how it felt as the soft lace of the panties were slid so that his
dick was out, Bro's leather gloves carefully holding it.
He focused on the warmth of Bro's tongue on the throbbing member.
He focused on how each suck felt, how each vibration as the older man hummed
felt, and how it made him ready to scream as Bro lightly grazed his teeth over
it.
He let out moan after moan, wanting desperately to buck his hips as Bro began
to bob. All of him was taken in with ease. It was no problem for the older man.
So Dave's entire dick felt the pleasure of Bro bobbing. It made him lightheaded
as it became harder by each moment. He was desperately trying to call out
warnings as he came, but Bro didn't seem to care. He took it all in, swallowing
it, and licking up whatever strayed from his mouth. Dave was left panting,
exhausted and ready to collapse against the ropes.
But he noticed the lump in Bro's pants and just couldn't resist the urge as Bro
untied the gag.
"You can relax now, kid."
"No," Dave quickly shot back. "I want to get you off. Just...let me try
something."
Bro chuckled, untying the younger boy. "Okay. What do you want to try?"
"Strip. Then put your hands against the headboard."
Bro did as he was told, leaving on his hat and sunglasses. Dave tied his
wrists, checking the ropes to make sure they were secure, before removing Bro's
shades and hat. He looked into the Strider's orange eyes, into the warmth of
the unique color.
"Spread your legs."
Dave slowly slid off his skirt and shirt as Bro did as he was told. He put his
own dick back into his panties before positioning himself between Bro's legs,
feet bent so Bro had a nice look at his panties.
"What are you pl-"
"Shush," Dave cut him off.
He took a deep breath, calming himself, before rubbing one of his feet against
Bro's part. Bro failed to hold back a moan at the feeling of the lace thigh-
highs against it. Dave toyed with it, using both of his feet. He was gently,
but he was also plotting. That much was apparent as on of the laced big toes
pressed into the slit at his head. He moaned loud as he twirled around,
becoming coated in precum. Dave used the new liquid to rub along the rest of
the part, almost as if applying lube with his feet. 
The faces and noises coming from Bro drove Dave nuts. He pulled off the lace
panties, positioning himself over Bro. He slowly slid himself down with a moan,
slowly taking in Bro's dick. He heard Bro moan his name, tugging against the
restraints. He slowly started riding him.
Thrust up.
Thrust down.
He moaned, pumping his part as he continued. His lace legs rubbed against Bro's
thighs as he rode him, bringing him to a quick climax. The liquid filled Dave
to the brim, bringing out a loud moan. Dave continued riding a bit before he
climaxed all over Bro, panting.
"Lick it up," Bro commanded as Dave slid off.
He nodded, panting, and carefully crouched by Bro. He licked along his thighs
and along his part. He then worked his way up his stomach, licking as slow as
he could. Soon he was licking along Bro's chest. He up to his neck, even though
it was clean.
"Gonna help clean up the mess you made, too?" he whispered.
Bro nodded. Dave loosened the ropes enough to let Bro's head lay flat before he
positioned himself over his face. Bro carefully licked along Dave's ass,
sliding his tongue into the hole a few times. A low moan escaped Dave as the
tongue thrust itself in and out. He was already becoming hard, though it was a
bit painful. Once Bro had finished, Dave moved so his cum-covered part was over
his mouth. The older strider slowly took it in, sucking on it. Dave gripped the
headboard desparately as Bro sucked. He started to slowly thrust himself in and
out of Bro's mouth, taking in the warmth. He was hard enough that it hurt, and
Bro was quickly pushing him over the edge once again. He was moaning out to
him, sounding like a horny porn star. Once he reached his climax, Bro choked a
bit because of the position, but he took it in with ease.
Dave slowly got to work untying him, only to be pinned down by the old man.
Their lips crashed together, Bro's tongue instantly invading his mouth. After a
bit of tongue wrestling, Bro released the panting boy from the kiss.
"Get some rest. I might want more in the morning."
Chapter End Notes
     (done unless you want morning sex. Maybe over a breakfast table to
     something. In the shower. I could do it in a variety of places for
     morning sex. But only if you want it)
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