Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/1136081.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      F/M, M/M, Multi
  Fandom:
      Teen_Wolf_(TV)
  Relationship:
      Derek_Hale/Jackson_Whittemore, Lydia_Martin/Jackson_Whittemore, Stiles
      Stilinski/Jackson_Whittemore, Isaac_Lahey/Erica_Reyes/Jackson_Whittemore,
      Vernon_Boyd/Jackson_Whittemore, Scott_McCall/Jackson_Whittemore
  Character:
      Jackson_Whittemore
  Additional Tags:
      Blow_Jobs, Oral_Sex, Cunnilingus, Semi-Public_Sex, Unsafe_Sex, PWP, 5+1
      Things
  Stats:
      Published: 2014-01-14 Words: 4569
****** Staples Sells Staples So Does BJs Sell... ******
by ziusura
Summary
     Five times Jackson went down on someone and the one time someone went
     down on him.
Notes
     So this was a prompt on tumblr by bdrixhaettc filled here, and it
     turned out longer than it was supposed to so I threw it on here,
     haha.
===============================================================================
                                      One
===============================================================================
Lydia was the first to make him do it, and it didn’t matter how young and
fifteen and thoroughly grossed out from the idea of doing anything but stick
his dick in her, Jackson was—she was going to withhold any kind of sex if he
didn’t. And Jackson might have been stubborn, but he wasn’t nearly as grossed
out by the thought of licking her open as he was horrified by the prospect of
not getting screwed in the right kind of way by a fuckbuddy. It wasn’t a
healthy compromise, but he and Lydia were never really anything but unhealthy. 
She lay back on Jackson’s sheets with an air of disinterest, and spread her
legs without without thought. She was still wearing her skirt and socks, but
her panties and shirt were in a heap on the floor by his bedroom door. 
Lydia looked good like that, even as bored as she looked, and Jackson took a
moment to squeeze his cock through his pants before crawling up on the bed
between her legs. 
He pushed her skirt up around her hips with careful hands and squeezed at the
soft flesh of her inner thighs once it was revealed. And Jackson paused for a
moment, looking at her vulva and letting the fear churning in his gut take over
for a moment. What if he wasn’t good enough? 
But fuck that. Jackson was never anything but the best, so he lurched forward
and barely touched the top of her lips with his mouth, nose buried in her pubic
hair. Lydia trembled slightly and adjusted her legs, and if Jackson didn’t know
any better he’d say it was almost a nervous gesture.
For all the movies and half whispered jokes shared in the locker room that said
said that vaginas smelled like fish, Lydia didn’t really smell anything but
nice. It smelled wet in a different way than cucumbers did, with a hint of
spice that was all Lydia. 
"You going to do anything, or are you going to just breathe on me?" Lydia
asked, and Jackson peered up at her through his eyelashes. She was leaning up
on her elbows and staring sort of frustratedly at Jackson. He could understand
that, in a way; he didn’t exactly like it much either when someone wrapped
their mouth around the head of his dick and didn’t move. 
Jackson looked back down at her pubes and pressed his mouth forward, taking in
the shape of her soft folds and hardening clit with his lips. Lydia sighed
softly, but didn’t ease her body back down onto the bed until he opened his
mouth and slid his tongue between her to nudge at her clit. 
Her legs shifted suddenly, tensing against his shoulders, and Jackson had to
reach up and hold them still to keep her hips from canting up into his nose—he
didn’t exactly want his first broken nose to be from her pubic bone. He licked
at her harder, with more purpose, and Lydia’s scent doubled in strength. Her
hands came up to his head, but she didn’t yank or pull. Lydia was nicer than
him in that regard. 
Lydia’s breath hitched on a strangled moan, and Jackson echoed with one of his
own, swallowed up by Lydia. He struggled to keep from humping the bed with
every one of Lydia’s shallow breaths—he refused to cream his pants.
Jackson was harder than he thought he’d be, and Lydia was thrashing and
writhing more than when he fucked her, and the power surged through his
veins. He could suck on her and move his tongue in quick sweeps across her clit
until his mouth was sore and Lydia was tensing in that way Jackson knew meant
she was close, and then he could pull back and suck on her labia lazily until
she dug her fingernails into his shoulders and scalp in frustration. 
He angled his mouth away from her and tried to catch his breath without getting
pubes up his nose, and Lydia let out a keening whine, like she was begging him
back. Jackson tilted his head and laughed into her thigh, gripping at her leg a
little harder than necessary because he felt like he was about to vibrate out
of his skin. When she grunted at him again, he let go of her leg and replaced
his mouth with his fingers for a second. 
This was way better than he thought it was going to be.
"Jackson," Lydia said breathlessly, and it contained almost none of the
authority it usually did when she said his name like that, but he complied
anyway, pulling his hand away and putting his mouth back on her. 
Jackson explored downwards this time and licked into her. She smelled even
stronger there, and tasted better too. Her vagina spasmed and clutched at his
tongue every time he pulled it back into his mouth, but that didn’t last long.
Her fingers were in his hair and gently pulling him upwards soon after. 
"On my clit please," she said, and Jackson was too into resuming his former
position that he didn’t notice her use of the word please. She sighed against
him in a way that Jackson felt through his whole body, and she added, "If you
want to be inside me you can use your fingers, though." 
Jackson complied easily, releasing one of her legs from his grip and sliding
them into her wetness while he teased her clit with his mouth. She didn’t last
long after that. 
Lydia tensed up with barely a warning and snagged his head in a vice grip with
her thighs. She clutched tightly at his fingers, and Jackson didn’t trust his
teeth not to get involved if he tried to move his mouth away from her, so he
went slack against her body and waited for her to come down. It wasn’t a bad
place to be, he thought, even if her skirt was sort of stiff and uncomfortable
against his forehead. 
She eventually released him with a pleased giggle, and her hands slid down his
neck bonelessly until she found purchase on Jackson’s shoulder blades. 
Damn right—he was fucking good. His lips were numb and his mouth tasted like
Lydia, but she was satisfied and he felt good.
Lydia pulled him up by his shirt, though she was so satisfied Jackson was doing
most of the work, and slid a hand into his pants. It was barely two strokes
before he was shooting, and he realized with startling clarity: he fucking
loved going down on someone. 
===============================================================================
                                      Two
===============================================================================
Stiles’ breath was strained and quiet, like he was trying not to breathe on the
glass that separated them from Lydia. It was more than likely that he was
trying not to cry in reality, but Jackson didn’t bring attention to it; he was
feeling the same way anyway, seeing Lydia injured on the hospital bed. 
He was warm and still beside Jackson, and he could feel Stiles’ heat roll off
into Jackson’s arm, but it did nothing to ease the tension. Fucking nothing
could probably ease the tension, the fear he felt. Adrenaline coursed through
his body, and he didn’t have an outlet for it.
"Do you—" Jackson began, and startled when Stiles whipped his head around to
meet Jackson's, his eyes misty and red-rimmed. He nearly scared himself too—he
didn’t exactly plan to talk, especially not to ask what he had running through
his head at that moment. "Do you wanna blow job?" he finished, his voice
tight. 
Jackson prepped himself for Stiles’ likely cutting sarcastic remark, gripping
the wooden edges of the glass in front of him for stability, but it never came.
Instead, Stiles stared hard into Jackson’s eyes until Jackson couldn’t take it
and looked away, and then Jackson watched him trail his eyes down Jackson’s
body in his reflection in the glass. When Jackson finally got the courage to
turn back to face him, Stiles was biting his lips and looking heavily at
Jackson’s mouth. 
Shit. 
He hadn’t intended it as anything, not really. Yeah he liked going down on
people, and yeah, he really needed to get his mind off Lydia in…in that room,
but shit, this was Stilinski. He was so undersexed he’d probably agree to a
beej from an alien with six rows of teeth. But all the same, heat pooled deep
in Jackson’s stomach.
Stiles licked his lips and Jackson echoed the movement.
"Actually," Stiles choked out. "Actually, yeah. I do." 
Jackson swallowed, his mouth suddenly dry. “Okay.” 
He turned abruptly and started walking towards the exit, hoping they could do
this in the car in the parking lot or something, but Stiles mumbled a quick
“Jesus Christ,” behind him and grabbed his wrist to drag him into a room in the
opposite direction. Jackson reflexively shut the door behind him, and Stiles
let go of his wrist to turn the lights on. 
A bathroom. They were in a single room bathroom. 
"Lock the door dumb-ass," Stiles said, turning to face Jackson without looking
him in the eye. 
Jackson sneered, but reached a hand behind himself to turn the latch digging
into his back. It locked with a click, and Stiles finally looked at him. 
"I used to jerk off in here when I was younger," Stiles offered needlessly, and
Jackson’s pants went a little tighter.
"That’s nice," Jackson said, managing to school his voice into sounding bored.
 
Stiles stepped forward and licked his lips, and Jackson knew what was coming
before Stiles’ face came close enough for their mouths to touch. He turned his
head at the last second so Stiles’ lips pressed on Jackson’s jawline. 
"This is a blowjob, not a romantic encounter, Stilinski." 
Stiles made a frustrated noise, and Jackson’s hand slid up between them to
shove Stiles away from him. He left his hand resting on Stiles’ chest, fingers
spread and creating odd wrinkles in Stiles’ formerly white dress shirt. 
The bathroom was fairly clean for a bathroom, though that was probably to do
with the whole hospital thing. Jackson had initially planned to make Stiles
stand in front of the toilet while Jackson sat on it, but the floor didn’t look
bad; he wouldn’t mind going on his knees for the short time it would take for
Stiles to go off. 
He directed Stiles to the wall furthest away from the door and the toilet with
the hand on his chest, though really it wasn’t much of a difference, and
dropped to his knees without warning. 
"Holy God,” Stiles said, and his head fell back against the wall with a solid
thunk that echoed through the bathroom. 
Jackson undid Stiles’ pants with ease and pulled the thick material down to mid
thigh, where Stiles’ trembling hands kept it from going any further. Stiles was
thick, and from what Jackson could tell, almost entirely hard underneath his
ridiculous blue boxer shorts with some sort of cartoon character that Jackson
didn’t recognize on them. He was fucking easy. 
Jackson didn’t expect Stiles to last long—there was no way the guy wasn’t a
virgin—but he still felt the need to show off his tricks. Stiles wasn’t the
first guy Jackson had had, no way in hell, and definitely not the first guy
he’d blown. Towards the middle of his and Lydia’s fuck buddy arrangement,
before feelings had started getting involved, they’d had a couple of threesomes
because Lydia had figured out just how much Jackson liked giving oral sex. 
Jackson mouthed at the head of Stiles’ dick through his boxers, and Stiles’
hands immediately slid into his hair. Jackson was surprised at the size of
them; Stiles was Scott’s loser friend, not anyone with any kind of sex appeal,
but Jackson would bet Stiles would be fucking amazing at fingering, and
Jackson’s dick twitched just thinking about it. 
Stiles’ eyes were sort of hazy and unfocused, but Jackson didn’t care. He could
picture whoever the fuck he wanted on his dick; he just needed to realize that
after it was all done, it was Jackson’s skills that made him blow his load. 
He slid his fingers up the side of Stiles’ boxer shorts, the side he was
hanging, and pulled his dick out through leg hole. The fabric would make things
a little bit more of a hassle, but he didn’t feel like dealing with pubic hair
up his nose when he got to the deep throating portion of his system. 
Stiles was a good size, a little thin at the top and curved slightly to the
left, but a good dick all the same. It’d probably be the sort of dick Lydia
would like to ride, if she had the choice, but that didn’t matter to Jackson.
They all sort of felt the same in his mouth, anyway. 
Jackson sucked the head into his mouth and tongued at Stiles’ slit, and Stiles
let out a sinful moan and threw his head back into the wall. The fucker was
going to give himself a concussion. His hips were already starting to thrust
forward in small shaky little twitches that Jackson knew Stiles was trying to
control, but trying wasn’t nearly enough, so Jackson grabbed the base of
Stiles’ dick and pushed Stiles’ hips against the wall with his forearm. 
With that part done, Jackson pulled back and sucked him back in, his cheeks
hollowing. Stiles was louder than Lydia, louder than a lot of the guys Jackson
had blown before actually, and Jackson fought off the urge to pull off and tell
him to shut the hell up. They were in a bathroom in the hospital—quiet was
probably ideal—but every moan, every hitch of breath, fueled Jackson’s ego. 
Jackson was right; Stiles wouldn’t last long. He’d barely started getting his
hand in the action, and he was maybe ten or so thrusts in when Stiles let out a
noiseless scream and yanked Jackson’s hair so hard that Jackson had to actually
stop himself from biting on reflex. He managed not to choke on Stiles’ cum,
which was an effort all on itself given Jackson’s surprise, and he waited with
a mouthful of it for Stiles’ breathing to calm and his hands to release so
Jackson could pull off his dick. 
He had no plans to swallow, so once he could get free he made his way to the
toilet and spit, wiping off the jizz that had dribbled out with crummy, one-ply
toilet paper.
Jackson could hear Stiles stumble after him, but he didn’t make a big deal out
of it. He just calmly tossed the last of the used toilet paper into the toilet
and flushed before turning around. He wanted to say he wasn’t surprised when
Stiles immediately started kissing him, but he was. Jackson let it happen
though, returning the barest of kisses and letting Stiles stick his tongue in
his mouth when he pushed it forward. It was a fucking awful kiss, but Jackson
wasn’t really into kissing him in the first place. Some guys liked being able
to taste themselves after they were sucked off, and who was Jackson to deny him
that? 
Stiles’ hands grabbed at Jackson’s ass, and Jackson let himself feel their
size, their warmth through his dress pants for a minute. They weren’t there for
long anyway—Stiles slid them along to the front of Jackson’s pants, where he
was still hard, and started to undo them. Jackson leaned back to get away from
Stiles’ mouth, and grabbed Stiles’ wrists to still them. 
"I’ve got this. You can leave." 
Stiles snarled half-assedly, his eyes firmly planted on Jacksons lips, and
Jackson licked them subconsciously. 
"Leave," he repeated, and Stiles jerked out of his grip with a frustrated
noise. 
Once Stiles was out of there, Jackson rubbed one out thinking of Stiles’ hands,
and walked back to the spot he’d been earlier, bumping elbows with Stiles and
staring at Lydia’s unconscious form on the hospital bed. 
===============================================================================
                                     Three
===============================================================================
"If you do this, I’ll blow you." 
The words hung heavy between them, canceling out the noise of the lunchroom
surrounding them, and Jackson jiggled his leg nervously. He didn’t know why he
said that—he had a porsche for God’s sake so it wasn’t like he didn’t have
money—but it slipped out, and he definitely wanted it. 
Boyd tilted his head, and Jackson watched the entire column of his throat shift
as he swallowed. 
"And twenty," Boyd stuttered out, and he turned away to look at one of the
corny posters that lined the edge of the lunchroom. "My price is fifty, so a
blowjob and a twenty." 
Jackson forced his leg to still with a hand on his knee, and said, “Alright.
Twenty and bj.” 
Boyd didn’t turn his face, but his eyes looked at Jackson’s through the
corners. “I won’t do this at school.” 
Jackson nodded his head. So he wasn’t quite as desperate as Stilinski, or as
public as Lydia occasionally wanted to be. He could deal with that. “I can take
you to my place after school.”
Boyd’s eyes turned back to the poster, “The bus usually drops me off a little
after 3:30, so as long as it’s fast.” 
Jackson smirked to himself. “It will be.” 
===============================================================================
Boyd was gentler than Jackson expected, but not in a romantic way. He didn’t
expect kisses or a candlelit dinner or anything, but his hands were soft and
for the short amount of time they had to do this, slow. Jackson could to gentle
though. Sure, his experience was mostly limited to Lydia sensitive on her
period, but he could do gentle.
Jackson ran a hand up Boyd’s stomach, lightly tracing his stretch marks and
pressing into the folds of fat around his hips while his other hand rubbed him
to hardness through his pants. 
Boyd’s grip on Jackson’s shoulders was light, even though Jackson knew he was
in ROTC and likely had enough thick muscle to hold him tighter or force him
where he wanted. It was strange. Even Stilinski and his scrawny arms had tried
to push Jackson down on his dick, so having the freedom to do whatever made him
feel a little uneasy. 
Jackson didn’t let himself dwell on it too much, and he unbuttoned Boyd’s pants
and pulled him out through the fly of his boxers. Time to get to business. 
Boyd was uncut with a bright pink head that glistened with precum before
Jackson had even gotten his mouth on it. He was responsive and still just as
fucking gentle (who could grab onto Jackson’s hair without pulling? Boyd
apparently), letting out soft breaths and shifting his legs instead of being
noisy and loud. 
Jackson was determined to get a noise out of him though, but didn’t manage
until he sucked Boyd completely down into his throat and swallowed, and Boyd
had shot his load with a half-assed warning. Jackson swallowed, not having much
choice else, and wiped his mouth with the back of his hand. He tucked Boyd’s
tumescent dick back into his pants. 
"We gotta go," Jackson said, his voice a little hoarse, and Boyd nodded his
head, his eyes barely focusing. 
"Keys are in the back of my pants," Boyd said, and Jackson dug around to pull
the ice rink’s keys out.
They made it to Boyd’s house at 3:34, barely beating the bus. 
===============================================================================
                                     Four
===============================================================================
Isaac was fucking Erica from behind, with Jackson underneath them trying to
do something with all of Isaac’s frantic thrusting. 
"I’m going to bite your fucking ballsack if you don’t slow down, or like, pick
up a basic fucking rhythm," Jackson said. Despite the music thrumming through
the bathroom, his voice was loud in the space they shared. 
He once more sucked Isaac’s hairy-ass sack into his mouth, his nose brushing
where Isaac and Erica were joined, and had it ripped from his mouth with a
particularly random movement. 
"Shut up," Isaac panted out. 
"You could fuck me too, if you want," Erica said with way too much innocence in
her voice to be seriously suggesting double penetration. 
"I’m good down here," Jackson said, and he was. The club’s bathroom floor was
nasty as hell, but he didn’t care. 
If Isaac wasn’t going to let him pleasure him, Jackson would do something else,
so he ran his tongue down Isaac’s cock, the distance shortening and lengthening
with each thrust, and managed to catch enough of a ride for his tongue to slide
into Erica too. She let out a long moan, but Isaac didn’t make much of a noise
to acknowledge that he’d felt it too. He probably couldn’t tell much with Erica
and the condom around him.
His tongue couldn’t handle that for long—Isaac’s thrusts were too hard—so he
kept moving until he reached Erica’s clit, and judging my the noise she made,
she really appreciated that. 
Isaac came too early, stiffening over them with a startled moan and filling up
his condom when Erica was only half way there. He didn’t seem to expect it, but
it was alright. Jackson was there to pick up the slack while Isaac pulled his
head back together. 
Erica was different than Lydia—once Isaac had pulled out she’d sat on Jackson’s
face and pulled forward until his tongue was in her rather than on her clit.
She humped his face, and Jackson brought his hands up around her thighs to
brace himself while she fucked herself on his tongue. She didn’t care much for
skill at that point, she just wanted to get off, and Jackson was more than
willing to comply. Especially when he felt Isaac’s hands at his dick. 
He almost wished Isaac hadn’t used a condom, so he could suck his cum out of
Erica and maybe feed it right back to one of them, but he wasn’t in the
position for that and Isaac had used a condom.
Erica came before he did, but he held her over him with a hard grip around her
waist just so he could breathe her in. 
===============================================================================
                                     Five
===============================================================================
For all his experience, Jackson had yet to give an angry blowjob. Lightly
pissed cunnilingus, sure, but not a blowjob. 
Mccall, of course, ended up being the one to change that. 
"You treat everyone like dirt, Jackson," Scott said, waving his finger at
Jackson like he thought he was the voice of reason. He didn’t know shit about
Jackson though, and Jackson wasn’t in the mood, so he turned away from Scott
and busied himself with his locker. 
Scott grabbed his shoulder, a sudden cuff of warmth through his t-shirt, and
turned him. “Listen to me, Jackson. They’re after you, and I’m trying to help
you, but you’re too much of a…a shit to listen to me.” 
Jackson rolled his eyes and crossed his arms in front of his chest. “This may
surprise you, Mccall, but I’m perfectly able to take care of myself.” 
Scott made a frustrated noise. “These are werewolves, Jackson.” 
"I got the bite," Jackson said, and he did, he just hadn’t seen anything happen
yet. But it would. It definitely would. The black blood was just a precursor,
and soon he’d be tough and strong and as good as everyone else.
Scott squeezed Jackson’s shoulder hard enough that it hurt and pushed him into
the lockers. “And how’s that going for you?” he muttered darkly, and Jackson
sneered in response. 
He forced his shoulder up and over to dislodge Scott’s hand and send him
backwards away from Jackson, but Scott’s werewolf reflexes were a little too on
point because he grabbed Jackson’s shirt and sent them both onto the locker
room floor. 
"I can take care of myself, Mccall," Jackson shouted, trying to pin Scott to
the ground. But Scott was a quick and slippery one, and he easily rolled them
over. 
"You need my help," Scott snarled, and Jackson managed to hit him in the chin
with his elbow to roll them back over. 
They struggled for a bit on the locker room floor, only stopping when Jackson
got a hand around Scott’s throat and Scott was half shifted. They were close
enough to breathe into each other’s mouths, and Scott was so hot against
Jackson’s body. 
He didn’t know who made the first move, but suddenly they were kissing,
snarling and biting into one another’s mouths in a less dangerous version of
the fight they were having. Scott shifted back to human sometime during it, but
not nearly fast enough because Jackson was pretty sure that was his blood being
pushed between their mouths. 
As all things did between them, it escalated and Jackson blew Scott on the
locker room floor and then ran, shouting that he didn’t need his fucking help.
And he didn’t. His werewolf gene stuff would activate and he’d be even stronger
than Mccall. 
===============================================================================
                                   Plus One
===============================================================================
"Your morning breath smells like ass," Jackson mumbled sleepily into his arm,
trying to decide if he wanted to get up or sleep some more. 
Derek huffed against his neck and burrowed farther into Jackson’s shoulder. He
fucking hated the stubble burn, but it felt too nice to care at the moment. 
"I could make my breath smell like something else," Derek said, and he brought
his arm around to grab Jackson’s morning wood. 
"What? Literal ass?" 
Derek pressed his mouth against Jackson’s shoulder, stifling a smile, and said,
“I was thinking jizz, but I can do literal ass if you’d rather.” 
Jackson opened his eyes and stared at the alarm clock on his bedside table.
“Jizz is good,” he said, and rolled over into Derek’s chest. 
He let Derek steal a kiss, even if his morning breath made Jackson want to
puke, and Derek slid down the bed to pull Jackson out of his boxers. Derek
slept naked and never really understood Jackson’s want to wear boxers in bed,
but he tolerated it, just like Jackson tolerated the stubble burn. 
Derek deep throated him immediately, and Jackson’s back arched in surprise, his
hands grabbing at Derek’s hair and one of his ears. 
"Jesus," Jackson said, and thanked the heavens that Derek didn’t pull off his
dick to say something stupid like, "No, I’m Derek." That was more of
Stilinski’s thing anyway. 
Derek loved to use his hands in a blow job, and Jackson loved that he loved it,
especially since he mostly used his hands to finger Jackson, or play with his
balls. The lube was a little too far away and it’d been a while since Jackson
had taken it up the ass, so outside of a little rubbing around Jackson’s rim
with spit to ease the way, he mostly rolled Jackson’s balls in his hands. 
Derek pulled back a little to play with Jackson’s head, and Jackson whined at
the loss of head and pressure around him. 
"Shut up, you baby," Derek said into his thigh, and then went right back to
Jackson’s cock. 
Even if Derek’s technique was more cut and dry rather than creative, Jackson
got off fast, and Derek left the room to spit in the bathroom sink. 
"C’mere," he said into the space between them, and when Derek leaned over to
kiss Jackson again his breath tasted like toothpaste. Well, it wasn’t jizz, but
Jackson would jerk him off anyway. 
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