Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/4999972.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Teen_Wolf_(TV)
  Relationship:
      Theo_Raeken/Stiles_Stilinski
  Character:
      Theo_Raeken, Stiles_Stilinski, Sheriff_Stilinski, Theo's_mother
  Additional Tags:
      Loss_of_Virginity, Anal_Sex, Pseudo-Incest, Step-Brothers, Boys_Being
      Boys, Silly, POV_Stiles, Plot_What_Plot/Porn_Without_Plot, Bad_Sex, Good
      Sex, Sexual_Experimentation, Bottom_Stiles_Stilinski, Top_Theo_Raeken
  Stats:
      Published: 2015-10-14 Words: 3835
****** Occasional misbehavior ******
by Minyron
Summary
     Stiles wants to try out something new but Theo is suspiciously
     oblivious.
Notes
     More PWP that wanted to get out, though some feels and stuff crept
     in, my bad :p. Enjoy.
See the end of the work for more notes
"Take care, kiddo", the Sheriff told Stiles as he gave him a bear hug, crushing
the air out of his lungs.
He nodded at Theo when they broke apart. His step-son nodded back at him
politely, while his mother was already getting into the car.
"Have some bonding time with your brother, honey. And behave, both of you", she
said, as Theo waved the married couple goodbye.
"Yeah, be good, Stiles", his father warned, as he closed the driver's door.
"Bye, da-", Stiles responded, but the sound was suffocated by the roar of the
engine.
He kept waving until the car turned around the corner, losing steam quickly,
and felt a bit upset afterwards. His shoulders slumped and he let out a sigh,
sad that his dad was ever skeptical of him.
"You heard the man, be good", Theo repeated unhelpfully, hitting his shoulder
playfully.
Stiles side-eyed him, scoffing, and turned around to go back inside the house,
"Very funny."
"Not as much as this", Theo said, and tackled him to the ground, tickling him.
They rolled over in the grass, and Stiles tried to squirm away from the weight
of the body over him.
"Get off, get off", he said, helpless to avoid the chuckles that escaped his
throat.
Leaving them alone for the weekend was a terrible idea.
*
It wasn't planned, really. Stiles and Theo played sometimes. Theo initiated,
mostly; he had the first time. Stiles... he played along. What they did felt
good to him, and they weren't hurting anybody, so Stiles found not so much a
reason to stop as a reason to keep fucking quiet. It's not that Theo wasn't
silent, in fact, he may have more of the problem there, but Theo was dropping
subtle hints all day around to make him uncomfortable. Stiles thought it was a
miracle his dad hadn't picked up on it yet, but then again he and Theo jerking
each other was probably the last thing that crossed the Sheriff's mind.
So what if yesterday Theo had come to his room, late at night, and slipped into
bed with him? What if he'd given him a teasing handjob beneath the sheets? That
was a secret between him and the washing machine.
And what if that morning he'd felt a bit generous and had blown Theo awake,
startling him to great satisfaction. If he'd stealthily gotten under the
sheets, from the end of the bed, and bobbed his head up and down his brother's
morning wood like he'd been doing elsewhere for some months. So what? He was
going pro at this rate. Theo had been a bit rough on his throat at first, but
he could handle it.
Theo had also given him head, and it had been the point of no return for
Stiles. Even standing Theo's smugness and general obnoxiousness was a fair
price to pay for that.
But the thing was, Stiles was still nervous. He was anticipating the... ass
stuff. Theo had mentioned it way early, Stiles had just shut him off, and since
then Theo didn't bring it up as much (well, since then and since regular oral
sex was a thing). Just occasionally. Stiles may've been waiting for Theo to
bring it up again, because bringing it up himself was too embarrassing, and
Theo would never let him live it down. But yeah, he'd sort of decided that next
time Theo brought it up, Stiles would go along smoothly. Heh. Smooth like-
nevermind. He'd say yes, would try at least, it was a perfect plan. The pitfall
was that Theo hadn't brought it up in forever, maybe even more than a week.
They were watching TV in the living room, on opposite ends of the sofa and
markedly not looking at each other. The TV filled the room with its monotone
dialogues.
"Stop moving", Theo chided him, eyeing Stiles like he was insane, "you're way
too annoying".
Stiles huffed, but it was true he was fidgeting. He stilled his leg, stopped
biting his nails and swallowed.
"Sorry."
Theo didn't say anything else, and after a minute or two the pent-up energy
within Stiles was too strong for him to remain still any longer. He looked at
his watch, got up and looked again, because he'd already forgotten the time,
and saw it was only 3pm.
"Eh... I'm bored. I think I'm gonna take a nap", Stiles said casually, hoping
Theo would take the hint.
Theo looked at him briefly and just nodded, like he was humoring Stiles just
for paying attention to him.
Stiles bit his lip, not breaking eye contact but not knowing what to say to
make his intention more obvious.
"Soo... yup, I shall go now", he finally said, doing a little twirl as he left
the living room and went upstairs.
He made a grimace as soon as he got out of Theo's sight, cursing internally for
being so awkward.
If the hint hadn't been enough, he'd also leave his bedroom's door open. Theo
would have to come up eventually, to pee or shower or something, right?
*
Stiles spent an eternity on his bed, lying on his stomach with his head resting
over crossed arms. He was dressed in comfy pajama pants, with his batman socks
on, and had a white T-shirt on whose sleeves he was chewing lazily.
His muscles tensed when he noticed Theo was just leaving the bathroom. He was
particularly aware of his own buttocks that evening, for no reason. He felt a
pang on his stomach as he heard the footsteps coming closer, slowing down,
until he finally heard a knock on the door.
Fucking damn time.
"Hey", Theo said, clearing his throat, "So, what are you doing? You're not
sleeping."
Stiles looked back at him, grinding involuntarily against the bed, feeling hot
at the realization he already was half-hard. If he also wriggled his ass a bit
with the motion, he wasn't guilty for it, okay? It's not like he was presenting
himself for moving, Jesus Christ.
"Um", Stiles said, pushing stupid thoughts away, so not too eloquent, "I'm...
not sleeping, I guess?", he said, raising his eyebrows at Theo.
"No shit", Theo said, coming inside and caressing th door handle absent-
mindedly.
"So, anyway, I'm bored now too", he said, "Want me to um... close the door?",
Theo said, checking the corridor on instinct, even though they were alone.
"I... don't see why not", Stiles said, nodding and turning around, to bury his
face between his arms. Even if it couldn't make him feel less exposed, at least
the pillow was soft and fluffy.
Theo coughed, and he felt the bed dip when he sat on it. He peeked below his
arm, saw Theo tapping his fingers against the fabric of his shorts, and just
wished.
"Stiles, you know, it doesn't always have to be me to suggest stuff", Theo
provided, and surprised Stiles, "If you want something, you should say so", he
said, placing a hand on his shoulder.
Stiles thought Theo was going to point out how quiet Stiles had been and that
he knew there was something he wasn't sayying.
"I", he coughed, "I promise I won't make fun of you."
Stiles turned around, the unexpected turn of events perhaps his perfect chance,
and sat cross-legged besides Theo. He held the pillow to his chest, thankful
for the kindness. It made him more reassured. Moments like that made him almost
like Theo. He wasn't nice exactly, and maybe he was a bit too rough with him at
times, but he also knew how to handle the important stuff appropriately.
"Well", Stiles said, "now that you mention it, I may have thought about trying
something new, actually".
He felt the heat in his cheeks, and tried not to look away.
Theo frowned, oblivious. "New as in what exactly?", he asked.
Stiles was going to have to spell it out, wasn't he. He may've gone a little
overboard in praising Theo preemptively, even if it was all inside his head.
"Well", he said, for once in his life out of words, "This thing", he swallowed,
"you know, the", he tried again, tangled up in his own shame.
Theo looked at him amused, obviously at the verge of laughing by the faces he
was making.
"The stupid lubricant you bought, dammit", Stiles said, "I want to try stuff",
he said, "on my ass"
Theo raised an eyebrow, letting out a laugh as he placed his hand again on
Stiles's shoulder. Stiles hadn't noticed he was shaking a bit, just a subtle
tremor, but Theo's hand grounded him.
"It's okay. That's great", he said, "You know I thought we should give it a
try. I'll go get it, then", he added, moving up to leave the room at the speed
of thunder.
Stiles appreciated the reassurance, because it meant a lot coming from Theo. He
faked a smile until he had left. After he was out of the room, Stiles bit his
lip, suddenly feeling a bit overwhelmed. All the muscles in his body tensed at
the thought of the unknown.
*
"So what exactly do you wanna do?", Theo asked, de-capping the bottle of lube
with his thumb and placing the top on Stiles's desk.
It was on the other side of the room, so he then walked straight towards Stiles
before hopping up on the bed. They settled on it, sitting cross-legged again
and facing each other.
Theo was smirking. Stiles was sure by now he'd planned it all so that Stiles
would be the one to ask. What a jerk.
"Whatever comes up? It's no big deal", Stiles said, shrugging, "I dunno. We
could start with... fingers and see where it goes?"
"Can do", Theo said, and gestured for Stiles to lie down on his stomach, like
he'd been before Theo arrived.
If they could get along like they did when fooling around, their parents would
be much happier. And their lives would be easier, Stiles thought, but it was a
lost cause.
"Why don't you roll...", he instructed, pointing at the desk, as Stiles turned
to face it and that side of the room. He gave his back to the wall and Theo.
"Yeah, that", Theo continued, shifting and moving to lie behind his brother,
between him and the wall. That way they were in a more adequate position.
A more adequate position for Theo to put his fingers inside Stiles's ass, or
something along those lines.
Stiles took a deep breath, not quite believing that this was happening. His
stomach was twisted in a tight knot.
Theo placed a hand over Stiles's hip, and it felt comforting. "Relax, it will
be okay."
He nodded, and Stiles couldn't help but shudder when Theo pulled down his
pants, all the way down to his ankles.
Theo's breath ghosted over his nape, and his mouth felt a bit too dry. He was
very aware of his body and his functions, consciously breathing and swallowing,
trying not to get more nervous.
It didn't work, because soon one of Theo's hands was on his ass cheek, and he
felt totally exposed to him. Theo split them to reveal his crack.
"Are you-", Theo started to say, and Stiles responded on instinct,
"I had a shower before lunch, I think I'm clean", he explained hastily.
"I was gonna ask if you were sure", Theo said, resting his chin over Stiles's
shoulder, and slapping his ass cheek, "you're a bit tense, see? Are you
scared?"

Stiles yelped indignantly, elbowing Theo's stomach and turning around to look
at him. He frowned.
"I'm sure. Just get to it already, you're taking forever. I don't think it's
that hard to put the finger in the hole!", he said.
"Fine", Theo said with a sigh, rolling his eyes, and pushed Stiles over.
He straddled him as he lay on his stomach. Stiles closed his eyes and took
another deep breath, clinging to the edges of the pillow. He could hear the
slick sound of Theo coating his fingers with lube, his presence hovering above
him.
"Here we go", Theo said, and Stiles braced himself.
Then he felt it. It was weird, kind of cold and intrusive. The ring of his ass
clenched around Theo's finger on reflex, and his step-brother tugged on the rim
with his thumb. It didn't feel bad, almost ticklish.
"How does that feel?", Theo asked curiously, voice resonating from above
Stiles's head.
"Okay, I guess?", Stiles said, "But that's just one. One finger is nothing, get
going", Stiles urged, impatient.
Theo chuckled and removed his finger, returning with two and stretching the
rim, giving him the same fealing but more intense. It was kind of pleasant, but
then Theo pushed much deeper all of a sudden and something
gave. Everything Stiles had been aware of faded in favor of a very acute pain.
"Aw, aw, aaaaw", Stiles said, clenching viciously around Theo's fingers, though
his brother withdrew them forcefully, "fuck", he cursed, feeling beads of cold
sweat build on his temples.
"Sorry, did I hurt you?", Theo said, rolling Stiles over again, so he was lying
on his back.
Stiles was grimacing, breathing sharply, and looked at him. He fisted the
sheets, trying to recover, but the pain was definitely still there.
"What the hell do you th- think?", he said, between gritted teeth.
Theo smiled nervously, moving back a bit.
"You're too impatient", he said, a bit bitterly, and then looked away for a
moment.
Theo's expression became a bit regretful and unsure. "Do you want to stop?", he
said, looking back at Stiles.
Stiles stopped wincing, and opened his eyes wide.
"No, no", he reassured Theo, trying to sit up, "you're right, it was my
fault..."
"You don't have to apologize, it's normal", Theo said, looking at him with a
soft expression.
"How do you know that?", Stiles asked, curious, "Have you done his with someone
else?"
The worst of the pain had already subsided. Theo looked genuinely surprised at
the question, and looked thoughtful before responding.
"No, not really. I've... I've only been with girls", he said.
Stiles bit his lip, feeling self-conscious that he was the only virgin left in
the family.
"Do you want to stop?", Stiles said, and felt strangely unwanted even though he
knew Theo had been after this for long.
For some reason, he felt bad. It's not like he had to prove anything, and he
didn't need to please his brother, this was as much for himself. But it had
just hurt a lot, so much it had killed his boner.
"I'm into it if you are", Theo said, reassuring him quickly for once, "I don't
care that you're a virgin, Stiles, it's okay to go slow the first time. And you
know, we're just trying okay? It's not an obligation or anything", he offered.
It pulled Stiles a bit from his spiral of insecurities. He felt much better
after hearing those words from him, even though he already knew all of that. It
just helped to know Theo understood, because at times, when they weren't
fooling around, they argued. And then it felt like Theo didn't care for him at
all, and that hurt too.
"How about we do something else and try again later, when you're up for it?",
Theo spoke again, raising his eyebrows in invitation.
Stiles nodded vigorously. "Okay, that sounds good."
He did want to try again, because he knew he'd gone too quickly and that Theo
was probably right. His step-brother smiled wolfishly and finished peeling off
Stiles's pants and underwear, discarding his socks too. Bare but more
comfortable, Stiles took Theo's instructions and laid back, trying to relax.
Theo massaged his thigh a bit before paying attention to Stiles's dick. He was
hard again soon enough, and in minutes Theo was giving him a blowjob that had
his chest heaving.
He stopped for a minute, earning a whine from Stiles, but then he saw that Theo
was picking up the lube. Theo looked at him questioningly, and he nodded. The
older boy poured some of the fluid on Stiles's dick, wrapped the slick hand
around and returned to the slow motions that had Stiles arching his back the
slightest. With the other hand, Theo spread Stiles's legs a bit. He came down
to lick at his balls, and kept traveling down the midline.
Stiles's eyes widened when Theo's tongue met the most sensitive skin, tongue
circling but not quite touching the ring of muscle. He spread Stiles's cheeks
with his hand, the position surprisingly appropriate, and pressed a finger
inside. When it was up to the second nuckle, Theo crooked it.
"Oh", Stiles said unwillingly, a completely different sensation coming to life
inside him, "do that"
Theo's laugh vibrated around his crotch, raising the heat that was pooling
inside him.
He added another finger, carefully, just pushing against his wall from below.
At the same time, he came up and replaced his hand on Stiles's cock with his
mouth, taking him in one go. Everything felt so much more intense, the pressure
against the spot just giving everything an extra spark, and that was a lot to
say when he was almost short-circuiting from Theo's wet mouch around his cock.
"Fuck, fuck", Stiles mumbled, unable to help the aborted little thrusts his
hips made.
He didn't have much room of maneuver, with one of Theo's hands in his ass
below, and Theo's mouth on his dick, the other hand grounding his thigh.
"Hmmm", Theo hummed around Stiles's cock, moving his hand appreciatively over
his skin. His thumb pressed on the softness of Stiles's belly, just above the
bony ridge of his hip.
"Theo, I'm gonna coooo- aahh", Stiles moaned more than said, climax imminent.
Theo didn't slow down. Stiles came inside his mouth, stilling when Theo pressed
his hand over Stiles's body more firmly. He swallowed through his brother's
orgasm, and kept his fingers pressed deep inside Stiles, milking his prostate.
Stiles did last for longer than usual, pumping more and more come and feeling
tingly all over.
When he'd come down from the post-orgasmic haze, he realized he was in a
different position. Theo had moved and was pressed firmly against his back,
snuggling close. His head was in the crook of Stiles's neck, and his hard-on
was digging on Stiles's bare ass cheek.
Right, Theo hadn't come yet. Though he looked in no rush to do anything about
it.
"Do you want to fuck me?", Stiles asked, because why not, too uninhibited by
the rush of hormones to stop himself.
Theo was sleepy, but his deep breathing became sharper when he stirred.
"Would you like that?", he asked against Stiles's neck, hopeful.
"Yeah", Stiles whispered, wriggling his ass against Theo's crotch, and
receiving a grunt in response.
"Fuck, Stiles", Theo said, with a shaky voice, "you're all loose now"
He was. After he'd come, and with all the lube, Stiles could take two easily,
and a third had him stretch even more when Theo started fingering him in
earnest. No matter how deep he went, Stiles didn't clench. Stiles felt good
about the control, reassured that it wasn't that hard if done properly.
Even so shortly after coming, Stiles could feel a familiar heat pooling in his
belly again, yet an urgency of some different kind than his usual one. It was
hard to place, but he just had an desire to be stretched more.
"I'm ready. Put your dick inside me, dumbass", Stiles said, though it carried
no heat, and he heard Theo swallow very close to his ear.
Theo was hasteful to take off his clothes, apparently sharing Stiles's feeling
of urgency, which was good. Shirt and shorts came off, and he threw away his
underwear before pressing his erection to Stiles's ass again. Theo lifted one
of Stiles's legs to get an easier access. He slicked himself up with some more
of the lube, hissing in the process. Stiles could feel how worked up he was,
but he didn't blame Theo, because after all his dick had been pretty
neglected for the time being.
"Yeah", Theo whispered, and pressed the tip against Stiles's hole, lining
himself up. Stiles clenched a bit in anticipation, but then relaxed, and it
came naturally enough now.
Theo pushed the head in, going past the rim and letting out a sigh. Stiles took
a deep breath, loving every second of it, and pushed back, making Theo go
deeper inside him. He was being filled with a really hard dick and he didn't
think he could ever get enough. Theo's hips jerked on instinct, and soon he was
balls deep inside Stiles, the slide smooth and easy with all the lube.
"Stiles, you're so hot", Theo confessed, sounding very raw.
Stiles appreciated how it was affecting Theo too, sighing in relief and pushing
back again. Theo responded accordingly, and they got into an easy rhythm.
Theo sped up after a while, his grip over Stiles's knee a bit too painful, and
ran his nose up Stiles's neck until he was close to his ear.
"Can we... can you get on all fours, for me, please?", Theo begged.
It went straight to Stiles's dick, which twitched, and he realized he was hard
again.
He complied, too aroused and distracted by Theo's needy tone to mind. He was
barely aware of what happened after he agreed, still in his dreamy haze; but
soon he was on his knees and hands on the bed, and Theo was kneeling behind
him.
Theo pounded into him from behind, doggy style. From the angle he could hit
that spot inside him even better, with each thrust, and it was too good. Stiles
was leaking soon enough, just from hearing Theo's ragged sounds. He was unable
to avoid stealing glances of his brother's sweaty and careless expression as he
fucked into him. Theo kneaded Stiles's lower back, and grabbed his hips more
forcefully when his pace increased.
It didn't take long for Theo to lose it, snapping his hips erratically and as
deep as he could. He pushed Stiles forwards a few times until he stilled.
Stiles felt Theo's dick twitch inside him when he came, moaning, and his own
orgasm followed unexpectedly. He came intensely too, clenching around Theo's
cock, and another moan escaped his brother with the additional tightness.
Stiles ruined the sheets, white ropes of come landing all over the bed.
*
"Stiles, holy shit, that was so good", Theo said, limp and content. He was
resting over Stiles, covering him like a blanket.
They both were a mess of limbs, tangled with the sticky sheets, but too lazy to
move.
"It was", Stiles said, still basking on the afterglow. He let out a chuckle,
feeling just happy.
"What are you laughing about?", Theo asked, amused, turning his head to look at
Stiles's face.
Stiles looked at him too, a devious smirk on his face.
"I guess this counts as bonding time?"
End Notes
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