Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/2207016.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Teen_Wolf_(TV)
  Relationship:
      Derek_Hale/Stiles_Stilinski
  Character:
      Derek_Hale, Stiles_Stilinski, Sheriff_Stilinski
  Additional Tags:
      Deputy_Derek_Hale, Underage_Sex, Blow_Jobs, Anal_Fingering, Rimming, Anal
      Sex, Ass_to_Mouth, Barebacking, Humiliation, Praise_Kink, Dubious
      Consent, because_like_always_Stiles_is_a_minor, and_also_he_cries_once_or
      twice, Dom/sub_Undertones, Dirty_Talk, Spanking
  Series:
      Part 3 of My_Baby
  Stats:
      Published: 2014-08-29 Words: 8084
****** My Baby's First Time ******
by msemmyjones
Summary
     Stiles Stilinski turned twelve on a Wednesday.
     On Thursday Derek Hale made him a man.
Notes
     All the usual warnings. Please check the tags, and as always this is
     unbeta-ed, so sorry for any and all mistakes.
     Also, I take back what I said about Stiles' age being vague. Seeing
     as this installment includes his twelfth birthday, I guess it's not
     so vague anymore.
     And lastly, I suddenly feel I need to make the disclaimer that
     obviously this is not behavior I would condone in real life. Derek
     should super be going to jail in real life.....
See the end of the work for more notes
"But Da-ad!"
"Stiles, we talked about this. You're old enough to stay home by yourself. I
trust you. And I can't let everyone else work the night shift for me forever.
Everyone's gotta do their part including you and me."
"I know, it's just...it's my birthday this week and I..."
"Hey!" Sheriff Stilinski interrupted his son before he could really wind
himself up. "Stiles, I took the whole day off for your birthday. We're going to
have a whole day of just you and me. And I'm not even going in the next
morning."
"Yeah, just the next night," Stiles muttered darkly. He crossed his arms over
his chest and pouted, turning his face away. Stiles knew he was being childish
and unfair. His father was doing the best he could, and Stiles really was
appreciative of the time they would spend together on his birthday. It was
just...Stiles didn't like spending time at the house alone, especially at
night. It was too empty and quiet now that his mother was dead, and Stiles
didn't like spending time with her ghost.
Sheriff Stilinski sighed heavily and rubbed his tired face with his hands.
Before he could reply to his son, a beep from outside the office grabbed his
attention. "Go pick up that fax for me, Son?" he asked instead.
As he picked up the file in front of him and took another slurp of his coffee -
gone cold during his argument with Stiles - a knock came from his door. "Open!"
he said, and looked up to see Deputy Hale slide through.
Deputy Hale was one of Sheriff Stilinski's favorites, though if you asked him
about it his only response would be "this is a police station, not a damned
popularity contest." Hale was a bit of a loner. No family - they had all died
in a fire when the Deputy was a teenager. He was diligent and hardworking,
patient and kind, but he was quiet and gruff with most people which could
detract from his more positive attributes. Stilinski liked to tease Hale about
a few of the ladies' (and more than one gentleman's) opinions that his face
made up for his prickly personality and see his ears turn red as he glowered
back at him. But what really endeared Deputy Hale to the Sheriff was his
friendship with Stiles. Stiles was one to chatter on incessantly, and where
most people would cut him off Derek listened. Really listened. And, the Sheriff
noted, he even became a bit more chatty and relaxed himself when Stiles was
around.  Sheriff Stilinski knew they spent time together outside of simply
taking care of Hale's dog. Stiles had regaled him with stories of movies and
hikes and time spent at the park. He knew both were a little lonely and was
glad they had begun to curb that loneliness with each other. It might have been
unorthodox, his not-quite twelve-year-old son's friendship with his twenty-six-
year-old Deputy, but damned if Stilinski would discourage it.
"What can I do for you, Deputy?"
"This may be a bit presumptuous, Sheriff, but I couldn't help but overhear your
talk with Stiles just now."
Stilinski sighed. "When your son's mouth is as loud as mine, you get used to
everyone hearing everything. The guys in the holding cell overheard our talk
just now. What about it?"
"Well, I just thought I'd offer...I mean, since he's over all the time anyway
to hang out with Peter...if staying home alone makes Stiles that uncomfortable,
he can always stay with me. I'm working early mornings all this week so I'd
have to slip out before 5, but he'd be able to wake up to Peter."
"That's awfully generous of you, Hale."
"Seriously, it's no problem. I've got a guest room. If you're comfortable with
it, it's all his."
"Well thank you. I mean it, I really appreciate this. He's old enough now, it's
just ever since his mother...well. I'll talk to him and let you know." Deputy
Hale nodded at the dismissal and saw himself out.
A few minutes later Stiles returned, fax in hand. "Oh my God, Dad, that
seriously took forever. Are they sending you the next Great American Novel?"
 
Deputy Hale had only been back at his desk for about five minutes when he felt
a pair of thin gangly arms throw themselves around his neck. "Thank you!" a
voice behind him cried. With a smile, Hale turned in his chair and returned
Stiles' hug.
"I got big plans for you, Birthday Boy."
 
Stiles Stilinski turned twelve on a Wednesday.
The Sheriff let his son sleep late, then took him out for a breakfast of bacon
and waffles. They went shopping for new books and video games, and Stiles
screamed when he was presented with his very own laptop. The two went hiking in
Beacon Hills Preserve, tossed a baseball around at the park, and ended the day
with grilled steak, birthday cake, and Star Wars.
Stiles Stilinski turned twelve on a Wednesday.
On Thursday, Derek Hale made him a man.
 
Stiles stopped dead in the middle of his story about his awesome twelfth
birthday. His father was already at work for the night. Stiles and Derek were
just finishing up their dessert (Stiles had brought over leftover birthday
cake), and Peter was already snoozing on his bed.
"I'm sorry, did you just say you've never seen Star Wars?" Stiles looked at
Derek incredulously. How was that possible? Stiles had been convinced that
Deputy Hale was the perfect man, and now that image was crumbling before his
very eyes. "Who hasn't seen Star Wars?"
"Sorry," Derek shrugged. "Just never got that into it." He took their empty
plates over to the dishwasher.
"Oh my God, oh my God, we have to fix this. We're watching Star Wars right
now."
"We could. This is your birthday, so we'll do whatever you want." Derek stood
behind Stiles' chair, threading his fingers through the hair at the nape of the
boy's neck. "But I had something else in mind."
Stiles shuddered at Derek's voice, deep and smooth in his ear, and his cock
instantly perked up in his shorts. It had been over a month since Stiles had
given and received his first blow job, over a month since he begged Deputy Hale
to fuck him. So far, despite all their talk, they had stuck to just hand and
blow jobs. Stiles was pretty sure that was about to change.
"Okay," he whispered. Stiles cleared his throat in an attempt to make his words
sound more confident. "What did you have in mind?"
"I thought you'd like to see my bedroom."
Stiles had been helping Derek take care of his dog Peter for over two months
now, spending a portion of almost every day at Derek's house. It had been
almost that same length of time that Stiles had been getting naked with Derek.
And yet, in all the time, Stiles had never seen the inside of Derek's bedroom.
Heart pounding, Stiles got up from the table and followed Derek from the
kitchen.
Derek's bedroom was clean and comfortable. The walls were painted a soft sage
green, and decorated with art, mostly made from dark woods. He had two full
bookshelves, overflowing with books that looked well loved. The top of the
dresser was strewn with personal ephemera: receipts and change, his keyring, an
expired credit card. In the middle of the mess stood a single framed photo, a
teenaged Derek sticking his tongue out at the camera, surrounded by the smiling
faces of his family. Against the far wall was Derek's bed, made of dark wood
with a comforter and sheets of deep plum. It was an adult's bedroom, and Stiles
halted in the doorway in awe that he was being invited in.
Guiding the boy with hands on his shoulders, Derek slowly walked them into the
room. He could tell Stiles was skittish, a little nervous about what was to
come. "Calm down, Baby," he murmured, running his hands soothingly up and down
Stiles' arms. "Take a deep breath for me. Now, have we done anything so far
that you haven't liked?" Stiles shook his head. "Okay, then there's no need to
worry about this either. Why don't you take off your clothes for me?"
Derek watched the boy strip slowly, his clothes falling haphazard on the floor.
He saw that Stiles was trembling now. "Shh, Baby, shhh," he cooed. "You're
okay." Standing behind him, Derek let his hands gently roam the boy's body:
stroking his soft belly or plucking a nipple. Derek bent down to nose at the
boy's throat, inhaling deeply to capture the sweet smell of his baby. "I'm
going to make you feel so good. My fingers, my tongue - they're going to touch
every inch of you. You're going to feel nothing, nothing, but the most
exquisite pleasure. I'm going to take you apart piece by piece, and then I'm
going to open you up on my cock." Stiles moaned at the filth spewing from
Derek's lips, his little cock now fully chubbed up. Derek loved the picture
they made, himself still fully clothed in shorts and a t-shirt and Stiles bare
naked and hard. "Are you ready, Baby? Ready for your ass to be plugged full of
my cock? Is your little hole thirsty for my cum?"
Stiles could barely breathe, he was so turned on. He couldn't even speak, could
only whine and nod as Derek thumbed both nipples.
"Good boy. Okay, now I want you up on the bed on all fours." Stiles scrambled
to obey, presenting his ass. Derek groaned at the sight of Stiles' creamy pale
skin, stark against the dark bedding. Stroking over his own clothed cock he
continued, "That's right, spread your legs. As wide as they go." Sliding down
onto his elbows, Stiles spread his knees. He was wide open now, face down and
hips just hovering over the blanket.
"Good. Now I want you to hump the bed." Stiles blushed and let out a whimper of
embarrassment, though he eventually did as he was told. "C'mon, you can do
better than that. I know how slutty you really are. Show me you mean it."
Stiles whined and humped down harder. The downy comforter felt so good against
his aching cock, so silky and soft. Stiles was mortified to know Derek was
watching him, but he just couldn't stop. He pressed his body down fully on the
bed, fingers twisting in the blankets by his shoulders, and grunted in time
with each thrust of his hips.
Walking around to the other side of the bed, Derek pulled on Stiles' hair to
lift his face for a kiss. Stiles' hips slowed down as he attacked Derek's
mouth, moaning as his tongue was sucked in. The kiss was messy, tongues and
lips everywhere. Without warning, Derek reached over Stiles' body and spanked
the boy, hard. Stiles let out a squeal of surprise, arms and legs flailing.
Pleased with the response, Derek did it again, raining down spank after spank
on those juicy cheeks as the boy screamed through his nose. He was overwhelmed
with the dual sensations of pleasure and pain, and both pushed back into
Derek's hands and tried to squirm away.
When Derek was finished, Stiles' ass was a sweet rosy color. Derek climbed onto
the bed, kneeling next to the boy. He palmed those warm, pink cheeks, soothing
them with gentle hands. Stiles sighed at the soft treatment, at Derek's
murmured words of comfort, and his hips continued thrusting, slow and syrupy.
As his boy relaxed, Derek ever so gently spread his cheeks apart. "There it is.
Your little virgin hole. It's so pretty, Baby, so pink and sweet." Stiles
squirmed slightly at the praise, embarrassed at just how exposed he felt. He
sighed as he felt Derek trace the rim with the tip of one finger. The touch was
soft and light as he rubbed over the hole. "It's going to look even better when
it's stretched out on my cock." Drawing the finger back, Derek tapped lightly
directly on the hole, three times in quick succession. He delighted at Stiles'
little jump and keen, and watched as the rose winked just slightly open at each
tap. So beautiful, Baby. I just have to taste it."
Before he even had time to process the meaning of those words, Stiles felt
something wet, warm, and pulsing press against his hole. Stiles moaned long and
loud as he realized it was Derek's tongue. Derek was still holding open Stiles'
rosy cheeks, and using his tongue to lick long, fat stripes down the crack and
over Stiles' hole. It felt good, it felt so good.
Pulling back, Derek ran two fingers more incessantly over the hole. He grinned
as he drank in Stiles' throaty whines and groans, watched him pushing his ass
back into Derek's hands searching for more. "You like my tongue, huh Baby?"
Stiles squealed in response as Derek surprised him with another quick spanking
before gently dragging his tongue back over Stiles' hole.
"Do me a favor, Baby, okay?" Derek's lips tickled against Stiles' hole. "I want
you to relax your hole, can you do that?" Counter-productively, Stiles' whole
ass instinctively clenched at the words. "You can do it, Baby, just relax and
let me see your little hole open for me." Stiles took a big breath in and Derek
could see his ass muscles clenching. But then Stiles slowly, slowly, let the
breath out, and with a ripple along his body completely relaxed, his little
hold gently unfurling.
With a laugh, Derek dove down to kiss the hole, and when he pulled back saw the
little starburst tightly furled again. Taking two fingers, Derek brushed
lightly up and down the area below the hole, gently tickling Stiles' taint.
With a whine, Stiles canted his hips up, searching for more of Derek's tongue.
Instead Derek reached between Stiles' legs to pull his cock through, stroking
it a few times before bending down to suckle the head.
"Please," Stiles moaned, unsure exactly what he was begging for, just knowing
he needed more. Derek's only response was to tongue the slit - savoring the
bitter taste of Stiles' precum - and reach out to squeeze Stiles' little full
sac. He rolled the balls in his palm, jiggling and squeezing them, listening to
Stiles' increasingly desperate moans.
"You're doing so well for me," Derek crooned. Reaching up, Derek tugged his t-
shirt over his head, leaving his shorts on for the time being. Two fingers
trailed down Stiles' crack to again come to his hole. As he rubbed against the
hole steadily - up and over, around the rim, a gentle press in - Derek leaned
over to pepper Stiles' face and shoulders with kisses. He mouthed wetly at the
boy's throat as Stiles let out thick, shuddery pants.
"Did you know your ass would taste so good?" Derek asked, lips brushing over
the ridges of Stiles' ear. "I did. I was sure of it. A pretty boy like you had
to have the sweetest ass." Stiles bit his lip to stifle a groan. "No don't,
Baby. I love your noises, love hearing how good I make you feel. Do you like my
tongue on your little hole?"
Moaning, Stiles nodded.
"You're in luck, Baby, because I'm not done with your whorehole yet." At this,
Derek swung a leg over the boy, basically straddling Stiles' shoulders. Leaning
forward, Derek again pried open the boy's cheeks, rolling them in his hands.
Pulling his hands back, Derek let loose a series of sharp, quick spanks,
marveling at the juicy cheeks' jiggling and Stiles' pained "uh...uh...uh..."
timed with each hit.
"Get your hips up, Baby." Stiles struggled to hold his hips up higher, weighted
down with Derek's body on top of him. Pulling the lifted cheeks apart one more
time, Derek dove in, this time with no reservations. Stiles shrieked as Derek's
tongue didn't just lick over his hole but pushed its way in. Using his lips as
much as his tongue, Derek kissed and sucked Stiles' hole. His tongue fucked in
deeper and deeper, wet and wriggling, his stubble prickling the sensitive skin.
Pulling back to catch his breath, Derek ran his hands down the boy's calves to
his ankles. His thumbs made soothing circles on the balls of Stiles' feet as he
pulled them together in a frog-like pose. Raising up slightly and leaning even
more forward, Derek brought one foot to his mouth. He kissed over the arch and
sucked a few toes into his mouth, wetting the webbing with his tongue. "God,
Baby, even your little feet are beautiful."
Stiles whimpered piteously. His head was spinning with arousal. He needed to
cum so badly. And Derek's mouth felt so good on him. Everywhere. Stiles was
pretty sure he might be able to cum just from Derek sucking on his toes. He
didn't think something like that would have felt so good, but it did. Just
soft, gentle sucking and a warm tongue squirming between his toes. It was a
nice respite from the intense pleasure of Derek's tongue in his ass.
That respite didn't last long, however, as Derek was soon once again buried in
Stiles' ass. This time he held nothing back, nipping around the rim, pushing
his tongue in deep before pulling out for quick dips in. He growled deep in his
chest, wrapping his arms around Stiles' waist to haul the boy's hips up higher.
Saliva leaked out of Stiles' hole, dripping down his taint and balls. Derek
pushed his tongue deep into the hole, as deep as he could go, pulsating in the
heat and wiggling like it was alive. Stiles gripped onto Derek's ankles where
they were bracketing his head. Stiles thought he was going to come apart. This
was too much, the pleasure was too intense. He didn't think he could take
anymore. With one last spank, Stiles howled beneath Derek as he came on the
blankets below.
Slowly, gently, almost reverently, Derek leaned back and pulled Stiles up and
out from under him. He cradled the boy to his chest, running soothing hands up
Stiles' arms. Stiles was trembling, overwhelmed by the immense pleasure he had
just experienced. Derek ducked his head and softly kissed his lips. He peppered
the boy's face with kisses - his cheeks, his nose, and eyelids covered with
soft kisses - all while murmuring in his ear. "You were beautiful, Baby. So
good. I'm so proud of you. I was going to reach around and jerk your little
cock off but I didn't have to. You came right on my tongue."
When he was finally able to speak, Stiles looked up and said, "You didn't fuck
me."
Derek laughed. "Not yet, Baby. But there's still time. I needed you loose
before I plugged you up with my cock. Needed you to cum first."
"Oh." Stiles let his body melt against Derek's as the man sucked gently on his
neck. "Mmmm..." he sighed, happily relaxed. "So you're still gonna fuck me?"
"Only if you want, Sweetheart. It's your birthday, right? I meant for us to,
but I didn't mean to get so carried away making you cum first. Your ass was
just too sweet. I couldn't help myself!"
"Okay." Stiles closed his eyes and rubbed his face against Derek's hard chest.
"Give me a minute? I think I still want you to fuck me."
"Anything for you, Baby." Derek tilted Stiles' face up and kissed him again,
deep and slow. These kisses were sleepy and sloppy, wet lips lazing against
each other. Derek offered Stiles his tongue, and he took it fully, letting it
fill his mouth and his senses. He sucked on it hungrily.
Still kneeling, Derek lowered his body down to be resting fully on the backs of
his legs. Without ever letting their lips part, he pulled Stiles so the boy was
fully in his lap. Derek groaned as Stiles shifted, his ass rubbing against
Derek's still clothes cock, hard and wet in his shorts. Grabbing onto Stiles'
ass for balance, he bucked his hips up, grinding their bodies together. Stiles
wrapped his arms around Derek's neck and let his body be used, losing himself
in Derek's kisses.
Slowly - so slowly Stiles didn't realize it was happening - one long finger
snaked down between his cheeks and came to rest right on the rim of his hole.
With movements so miniscule and gentle, the finger circled the hole. Stiles
sighed into Derek's mouth, relaxing subconsciously at the finger's
ministrations. Then slowly, still so slowly, Derek's finger began to push in.
With a noise of surprise, Stiles broke the kiss and pulled back to stare at
Derek, wide-eyed. Derek himself said nothing, just held Stiles' gaze until his
middle finger was fully buried inside his boy. Then, just as slowly, he pulled
his finger back out again. In. And out. In. And out.
"You're inside me," Stiles finally whispered.
"I am." Derek leaned forward for another kiss. "Your little hole opened right
up for me. It's a slutty hole, just like I thought." Derek had actually
expected there to be more resistance at this first breach. But Stiles' ass was
still so wet from their previous activities, not to mention loose and relaxed
from his earlier orgasm and their current makeout session, that Derek's finger
was able to slide in easily.
Derek continued the slow glide of his finger, but at the moment didn't add
anymore. While Stiles admitted to himself that the feeling of the finger inside
him was a little weird, he also realized how much he liked the rhythmic pushing
and pulling on his sensitive rim. And he appreciated knowing it was Derek
inside of him, Derek touching his insides. Stiles glowed with that knowledge,
and canted his hips back slightly wanting to be filled with more of Derek. He
whined when instead the finger was removed.
Derek was pretty sure he was going to cry if he didn't get some relief for his
dick soon, so none too gently he wrestled Stiles back onto the bed. Flat on his
back, arms above his head and held together by the wrists in Derek's hand as he
hovered over him, legs spread - Stiles made a mouth-watering picture of
corrupted innocence. Derek lowered himself down onto the boy whose legs
instinctively wrapped around his waist, little cock - hard again from the
fingering - grinding against his own. But it wasn't enough. Derek reared back
and quickly, finally, shucked his own pants.
Now fully naked, Derek attacked his boy like an animal. Stiles moaned as Derek
grinded their hips together, his body fully covering the boy's. He sucked
bruises onto his smooth, pale chest and shoulders and bit down on little,
sensitive nipples.
"God, you're so fucking sexy, Baby. I can't wait to bury my cock in you. You're
going to feel so good on my dick, so wet and tight." Stiles writhed under
Derek's assault, unable to do anything but surrender himself to the pleasure of
Derek's body on his.
Pulling himself off, Derek grabbed Stiles' ass and hauled his hips up, bending
the boy nearly in half - ass in the air, knees back by his ears. "Derek...oh my
God, oh my God, Derek!" Stiles wailed as Derek sunk his tongue back into his
still sloppy, wet hole.
With one last hard kiss to that juicy hole, Derek pulled off and sat back on
his haunches, letting Stiles' body drop unceremoniously down to the bed. "Come
here, Sweetheart. Crawl over here and get my dick wet."
Clumsily, Stiles clamored up onto his hands and knees and crawled over to
Derek. From his position he looked up, mewling meekly, and head butted Derek's
hip, nosing into his groin. Derek grinned at the boy's kitten-like affection.
Lowering himself to his elbows, Stiles got to work sloppily mouthing at Derek's
cock, licking and kissing at the shaft and balls below. Eyes closed and head
back with pleasure, Derek breathed deeply. "Good, Baby. So good to do what
you're told." Stiles' whole body wriggled at the praise, so pleased to make
Derek so happy.
Without Stiles noticing, Derek reached back under the pillows and retrieved the
lube he'd stored there earlier, coating his fingers. Stiles' face was buried in
Derek's crotch, making happy slurping noises, and his ass waved high in the
air. With Stiles happily distracted with his cock, Derek brought one slick
finger back to the boy's hole. Stiles froze, then let out a long, low moan as
the finger pushed in, only stopping when it was fully hilted.
"You like that, Dirty Boy?" Derek asked, grinning wickedly as he began to pump
his finger in and out.
"Yes, yes, yes," Stiles panted into Derek's stomach, one hand reaching up to
take over for his mouth. He jerked Derek off in time to his finger, moaning
constantly.
Without warning, Derek fed a second finger into Stiles' hole, the clench
tighter but the glide still smooth and easy. "Oh God, oh God, yes!" Stiles
canted his hips up, trying desperately to get those fingers deeper. While the
first finger may have felt weird, two was like Heaven. Derek was stroking his
insides and they were on fire for more. Stiles knew he needed to be filled,
knew two fingers was not going to be enough. He needed them deeper, he needed
them thicker, he needed Derek's cock.
Though it wasn't where he needed it, Stiles took hold of the thick shaft and
sunk his mouth down, moaning anf drooling down Derek's cock.
"Need it bad, don't you, Baby? Your slutty ass is just begging for my cock,
begging me to split you open and fill you up."
Derek tangled the fingers of his free hand in Stiles' hair and held him steady,
allowing the boy to calm down; two fingertips just breaching his hole and only
the cockhead for him to suckle. Once the boy was still, Derek slowly fed him
his cock, the head just entering his throat. They'd spent the summer working on
Stiles' deep-throating techniques, and while he still couldn't take it all, he
was making big improvements. He could feel the boy swallowing around him.
Keeping his eyes locked on Stiles' eyes, glassy with desperation and lust,
Derek slowly pushed in a third finger.
Stiles screamed around the cock in his mouth. He could feel his hole stretching
to accommodate the three big fingers forcing their way inside. It was harder
this time, so much harder to get all three to fit, and it burned. But Stiles
felt so good. He was full on both ends, stuffed with Derek's cock and his
fingers, and he didn't think anything could ever feel better than this. And
then Derek twisted his fingers just so and Stiles knew he's been wrong.
White hot pleasure coursed through Stiles' body and he jolted like a live-wire.
Derek's cock pulled free of his mouth with a wet squelch and Stiles wailed at
the loss while simultaneously humping back onto Derek's fingers.
"Pleeeeease!" he begged. "Again, again, again, please. I'll be good, I'll be so
good. Please let me be your good boy, just touchmetouchmetouchme!"
Instead, Derek pulled his fingers out. Stiles moaned unhappily, hips searching
for anything to fill him. "Please," he sobbed.
"Shhh..." Derek cooed, pulling his boy up to wrap his arms around Derek's neck.
Stiles sagged against him, trembling with need. Derek's big hand soothed over
his boy's body, thumbs gently rubbing his nipples. "Don't worry, Baby. I still
have to fuck you." Stiles shivered with anticipation.
Holding the boy close, Derek kissed him sweetly. "But first," he said, "I need
you to do something for me. I need you to look at me and tell me how you feel."
Stiles stared as his mind raced to answer the question. How did he feel? He
felt good, he felt horny. He felt empty, missing Derek's fingers and cock. He
felt guilty because this relationship had gone was passed the initial plan and
he was sure his father would disapprove. He felt special and cared for and
safe. He felt overwhelmed with both pleasure and his emotions. He felt scared.
He felt dirty. He felt cherished. He felt...
"I love you."
Derek's eyes widened in surprise. He had only asked to check in with Stiles,
make sure he was doing okay. And he liked listening to the boy talking through
his discovery of his sexuality. He was not expecting a declaration of love. He
looked back at Stiles, eyes wide and trusting. A crackle of electricity rushed
through Derek's body and he felt warm and light. He smiled.
"I love you too, Baby."
Gently, Derek lowered Stiles to the bed. He positioned himself between the
boy's legs and sank his mouth down on his cock, sucking gently. Stiles arched
his body with a sigh of relief as he was once again filled with three big
fingers.
When his fingers could glide easily, scissored apart or not, Derek pulled out
again. Pushing back on Stiles' knees, he raised that juicy ass in the air.
Without being prompted, Stiles grabbed his own legs and held them there, spread
wide. Reverently, Derek licked over the hole.
"Please," Stiles whined. "Please."
Derek lowered him down again and crawled over him, covering Stiles with his
body. He kissed him deeply and gently dragged their cocks together. Resting his
forehead against his boy's he asked, "Are you ready for me?"
Stiles nodded.
Pulling himself back up to his knees, Derek quickly slicked his cock. He took a
firm hold of it in one hand and raised Stiles' leg up to his shoulder with the
other, Stiles' other leg wrapped loosely around Derek's waist. He let his lubed
cock kiss the hole a few times teasingly, just a gentle press and release.
Finally, in response to Stiles' impatient whine, he pushed in.
Stiles' body spasmed at the breach. His arms jolted and flailed at his sides as
if unsure what to do, fingers clenching and unclenching in the blankets. His
eyes were wide and looked shocked by what was happening to him, tears welling
up at the stretch. His mouth had fallen open in a silent cry, to overwhelmed to
make any actual noise.
If Derek Hale was a better man, the sight of those tears would have stayed his
hand. He would have stopped, would have pulled out. But Derek Hale was not a
better man and Stiles Stilinski was beautiful with tears on his face. Slowly
and steadily, the glide smooth and tight, Derek pushed until he was buried in
Stiles' heat, hips flush with Stiles' ass.
"I'm in, Baby. How does it feel?"
"Big," Stiles moaned. "It's so big." He was right. Derek's fingers were nothing
compared to his fat cock. Fully sheathed, Derek stayed still, giving the boy
time to adjust to the intrusion. Stiles gritted his teeth and breathed deeply
as he continued to moan, "So big, it's so big, so big in me."
Stiles' whole body was buzzing. It was as if every nerve had rewired itself to
be directly linked to his ass - specifically his hole which was now stretched
wide. It hurt. It burned. His tears were a testament to just how much he was
stretched. But at the same time, it felt so good. He was filled, stuffed full,
with Derek inside him. As the two lay still, Derek looked at Stiles with such
tender affection that it actually helped ease the hurt to a dull ache. Soon,
Stiles relaxed and was able to breathe a sigh of relief.
During this time, Stiles own little cock never flagged. Derek reached out to
give it a squeeze, a reward for taking Derek so well. Stiles let out a wet moan
at the contact, and Derek took that as his cue to start moving. Slowly, he
pulled out and pushed back in. Over and over he pulled out and pushed back in -
long, steady strokes. Stiles himself could do nothing but moan continuously,
his entire being reduced to nothing more than his hole, clinging to Derek's
cock.
Derek, for his part, was much more vocal. Using his free hand to grab Stiles'
leg from around his hip, he spread the boy wide and let loose a litany of
filth.
"God, Baby, look at your little hole taking my cock. You're split so wide. Your
little ass is just gobbling me up. I knew you'd be a hungry boy. Knew your ass
would be just as slutty as the rest of you. And God, you're so tight. So tight.
Little hole just squeezing around me, trying to milk my cum out, aren't you?"
Finally able to speak again, Stiles moaned out the words Derek was hoping to
hear. "Oh God...so good!"
That admission of pleasure was all Derek needed. Lowering himself down to cover
his boy and kiss him soundly, Derek snapped his hips and began pounding into
Stiles at a punishing pace. Stiles wrapped his arms and legs around Derek and
buried his face in his shoulder, wailing, overwhelmed at the feeling of
fullness.
Derek was in Heaven. He'd never been in an ass this tight. He could feel it
stretching to accommodate his impressive size - could feel the glide getting
smoother as the boy relaxed and welcomed him in. Stiles was hot and silky and
he could feel the rim cling to his cock every time he pulled out, like it
couldn't stand not being filled.
"I'm so proud of you," Derek panted. "Doing so good, Baby. You feel so good
around my cock." With wild abandon, he devoured Stiles' body: petting his face
and throat, peppering his chest with kisses, teasing a pebbled nipple in his
teeth. He traced the boy's moles with his tongue, relishing the taste of salty
sweat-slicked skin. Stiles arched into his touch, his body responding of its
own accord to Derek's worshiping.
With a deep kiss, Derek slowed his frantic thrusting. Burying his himself deep
in Stiles' ass, he grinded his hips as Stiles relaxed around him. Derek's
tongue filled the small mouth below him as he re-angled his cock, searching for
Stiles' prostate. He grinned when Stiles' howl of pleasure let him know he'd
found the right spot. Kneeling up to grab hold of the boy's hips, Derek
rabbited into that one spot, hitting it over and over again.
"Yesssss...yesyesyes. Oh my God, yes. So good. So good, so good, yes!"
 Abruptly, Derek pulled out. Stiles keened high and loud, body writhing into
the covers at the unwelcome feeling off emptiness. Laying himself down on his
back, Derek pulled Stiles up and over him. The boy squatted down and fed
Derek's cock back into his hole, but it wasn't enough. The angle was all wrong,
he couldn't go very deep, and Stiles was uncoordinated at the best of times.
Stiles whined high in his throat, hips working desperately to get Derek's cock
buried back inside of him.
"Please," he begged. "I need it! Please, Derek, please!"
"What do you need, Baby?" Derek teased.
"Need your cock. Need it in me, I'm so empty now!"
Derek could not believe some of the words that would come out of his dirty
baby's mouth. His little virgin was a natural. He pulled the boy down to lay on
top of him, knees on either side of his hips, and fucked up into him, deep and
slow. Stiles moaned his relief at being filled once more.
"There you go, Baby. There's my fat cock filling your little hole."
"Thank you," Stiles whispered. He panted into Derek's neck as he let the
pleasure of Derek's cock filling his ass wash over him.
Eventually, Derek's hips slowed, and Stiles whined unhappily when they stopped
altogether.
"C'mon, Baby," Derek cooed. I can't do all the work, can I? You wanna be
fucked, I wanna see you earn it. Fuck yourself back on my cock, Baby, let's see
your slutty ass work for it."
Stiles hauled himself up only shaky arms and tentatively pushed his hips back.
"Mmm..." Derek groaned. "I know a cock-hungry whore can do better than that.
You're not getting anything else until you prove you're a good cockslut."
Whining high in his throat, Stiles picked up speed until he was slamming
himself back on Derek's cock. His head hung down between his shoulders, sweat
glistening on his brow. Stiles was desperate for Derek's cock to fill him, to
keep filling him, to touch all those mystery places inside him. He rolled his
hips, little hole sucking Derek in deeper, and Derek marveled at how beautiful
he looked.
The current angle was just now enough. He needed more. Pulling himself fully up
onto his knees, Stiles sank all the way down, impaling him fully on Derek's
cock with a cry of relief. His thighs trembled as he clumsily worked himself
into a rhythm.
Derek threw his head back and groaned. "Yes, Dirty Boy, ride me. I wanna see
you bounce up and down on my cock. Are you all filled up now?"
"Yesyesyesyes," Stiles cried. "So full. Please, please I'm a good boy. I'm a
good boy, I need it. Please fuck me!"
Derek looked up at Stiles who was absolutely writhing on his dick, hole
clenching down with every drag up. He was beautiful: face red and flushed,
mouth open, little cock bobbing wildly between his legs. Derek grabbed hold of
Stiles' wet cock and thumbed the head.
The dual pleasures were too much for Stiles. Overwhelmed, the boy wailed and
burst into tears. He fucked himself down faster on Derek's dick, sobbing,
"Please please please, I'm a good boy, I'm a good boy!"
With hands rubbing soothing circles into his back, Derek pulled Stiles down to
his chest. He wrapped his arms protectively around him, letting the boy snuffle
into his shoulder, and shushed him. Long, deep thrusts of Derek's hips soothed
Stiles, keeping him filled but calming the intensity of his pleasure.
"You're okay, Love." Derek listened as Stiles' shaky breath evened out,
interrupted by the occasional wet hiccup. "You're okay. And you are a good boy.
You're my good boy. I'm so proud of you, Baby. You're doing so good for me. You
just got a little overwhelmed."
"Too much," Stiles agreed. Clinging to Derek, he nuzzled further into the man's
shoulder, relaxing into the steady rhythm of his hips. "Liked it though,"
Stiles continued. "Liked being all filled up."
"I'm glad, Baby. I like making you feel good." Derek turned his head to gently
kiss Stiles' wet face. "And your ass feels so good around me. Like it was made
just for my cock."
Stiles shivered, letting out a little moan as Derek's cockhead brushed gently
passed his prostate. "Just yours," he breathed.
"All mine," Derek agreed. "My good boy."
By this time, Stiles had calmed down considerably, and while he could happily
spend a whole day just being gently filled with Derek's warm cock, his own
little cock really wanted to cum. He began to roll his hips back- tentatively
at first, but then more confidently - meeting each of Derek's deep thrusts.
"Fuck me again, Derek?" he asked meekly. "Please?"
 Derek surged up and attacked Stiles' mouth, kissing him deep and messy. He let
his tongue fill the boy's mouth, capturing his taste. Pulling back, he gave a
playful spank to Stiles' ass and helped him climb out of his lap.
"Nooo!" Stiles whined as Derek slipped out of him. "Back in, back in!"
"Calm down, Babyslut," Derek laughed. "I'll be back in that greedy ass soon
enough. Now get on your knees and present."
Stiles paused, confused. "Do...what?"
"C'mon Little Boy, just like you did when we started, when you moaned so pretty
for my tongue. Hands and knees, face down, ass up, presented to your master!"
Derek smirked teasingly as Stiles blushed at the word.
Grumbling under his breath, "Please, like you could handle all of this. I'm a
handful," Stiles maneuvered himself into position, back arched, ass wiggling
enticingly. After a few seconds of nothing, Stiles started to squirm under
Derek's scrutiny, embarrassed by the shameless position.
Finally Derek reached out and took Stiles' plump cheeks in hand, pulling them
apart and massaging them gently. He took in the sight of Stiles' now well-used
hole. It was red an puffy around the rim from the abuse it had already taken.
Derek groaned thinking of the pounding still to come.
Bending down, Derek licked a soft stripe over the hole, soothing the tender
flesh. He grinned at Stiles' pleased whine and pulled back to blow on the wet
rim watching it twitch excitedly. "Couldn't help but take a taste, Baby."
Kneeling up close behind Stiles, Derek took a firm hold of cock, newly re-
slicked, and smacked the head down against Stiles' hole. Laughing at Stiles'
surprised squeal, he did it a few more times. The hole made a wet squelch as it
tried to suck the head inside.
"What are you doing, dude, put it in! Teasing isn't nice!"
Stiles' words broke off into a long moan as Derek thrust in, bottoming out
without warning. "There you go, Babyslut, that what you wanted?"
"Yesyesyes," Stiles began, but then, "NOOOO!" when Derek pulled out again
completely.
"Not enough?" Derek smirked, pumping his cock in and out once more. Stiles'
hole clenched around nothing, desperately trying to keep that cock inside.
Derek thrust his cock in and out of Stiles' hungry hole a few more times,
alternating with several sharp spanks on the boy's bouncing cheeks, and reveled
in the desperate mewls he heard. Unable to take anymore teasing, Stiles hauled
himself up onto his hands and glared back at Derek. "God dammit, Asshole, I
thought you were going to fuck me. Fuck me!"
A beat of stillness and silence passed between the two until Derek grinned
wickedly. He was on Stiles in an instant, pushing him face-down onto the bed,
and pounding into the boy who could do nothing but wail, blissed out at the
feeling of being fucked hard. Derek was relentless, fucking into Stiles with
suck strength his ass was sure to be bruised in the morning from the pounding
of Derek's hipbones. Their bodies came together with a loud slap, slap, slap.
Derek's full sac swung between his legs, and Stiles could feel it slam against
his taint. Stiles moaned, unable to speak from the animalistic fucking he was
receiving. The wet fullness of his ass, the slick glide of his channel, and the
tight stretch of his hole became his whole world, bathing him in pleasure.
"That's right, Babyslut, take my cock. Just open up for me. You're right where
you belong, ass up and getting fucked." Derek grunted as his hips kept up their
brutal pace. "Made for this, Dirty Boy. Made for my big cock."
Roughly, Derek hauled Stiles up off his arms and back onto his hands. He
grabbed onto Stiles' shoulders for leverage, slamming him back even harder on
his dick. The change in angle caused Stiles to howl as his prostate was hit
with every thrust.
"Little hole is so greedy for it," Derek continued. "And I'm gonna wreck it.
You want that, Baby?"
"YESYESYESYES!"
Clamoring back down to his elbows, Stiles frantically fucked himself back onto
Derek's cock. His ass was bouncing and meeting Derek's hips thrust for thrust.
Derek could see the boy was getting himself worked up again. Moans were being
pushed out through gritted teeth and movements were becoming more and more
desperate. Without slowing his hips down, Derek spanked those bouncing cheeks.
Hard.
Stiles screamed. Face smooshed into the blankets, flushed red with exertion,
Stiles screamed. His hole clamped down on Derek's cock with every hit. It felt
like Heaven, that velvet vice-grip.
"Please," Stiles sobbed, face again wet with tears. "Please let me cum. Need to
cum, need to cum, pleeeeeeeease."
"Shhh..." Derek said as he pushed Stiles down flat on the bed until on his lush
ass was raised. "You're gonna cum, Baby."
Derek's hips began to slow in an attempt to sooth the boy, but Stiles only
became more hysterical. "Nononono!" he screamed. "More, need more. Fuck me,
make me cum. Pleasepleaseplease!"
"Shhh..." Derek whispered again. He kept his hips moving, steady but slower, as
he kissed over Stiles' back and shoulders. Stiles squirmed at first, desperate
to cum, but he calmed soon enough under Derek's gentle ministrations.
"Good boy," Stiles moaned. "I'm a good slut. Please please please let me cum."
With one final kiss between the shoulders, Derek hauled Stiles upright on his
knees. Stiles sobbed in satisfaction as he sank down on Derek's cock. Derek
wrapped one arm around Stiles chest to keep him upright, tweaking a nipple in
the process, and the other reached down for the boy;s wet cock. Stiles threw
his head back in ecstasy as Derek tugged on it, stroking in time with his
thrusts.
"This what you wanted, my love?" Derek asked.
"Yesssss," Stiles hissed. "Oh God, yes. So good."
Derek bent down to lick the boy's ear. "And what do you say when someone gives
you their cock for a birthday present?"
"Thankyouthankyouthankyou!" Stiles panted. He could feel the tell-tale fire in
his belly. He was so close. "Oh God. Thank you for fucking me. Oh God oh God oh
God. I'm gonna cum!"
"That's right, Babyslut, cum with my cock in your ass."
Stiles shuddered as he felt himself shoot and clamp down hard on Derek's cock.
This was a new feeling. A good feeling. He definitely liked cumming with his
ass filled.
When he felt Stiles sag against him, fully spent, Derek pushed the boy back and
with a roar, took his fill. Stiles moaned and shuddered around him, body
oversensitive but too sated to care. It only took a few minutes of Derek
pounding into Stiles' soft body before he came. Starting out deep inside the
boy, flooding his hot channel, Derek pulled out to paint the swollen hole. He
groaned, milking the final drops out, as he watched his cum cling to the puffy
rim and drip down the empty balls.
Crawling up the bed, Derek raised up Stiles' sleepy face and brought it to his
softening cock. "Clean me up, Babyslut."
Meekly and wordless, Stiles opened his mouth and let Derek feed him his wet
cock. He closed his eyes as he suckled, centering himself on the bitter taste
in his mouth. He whined when Derek gently pulled himself out, wanting more of
the safety and love he felt with that weight on his tongue.
Derek kissed the boy softly before climbing off the bed. He padded into the
adjoining bathroom and returned with a wet washcloth. Stiles let himself be
turned over onto his back and allowed Derek to wipe down his teary face and
sweaty body, but he protested when Derek reached for his ass.
"No," Stiles said. "I want to sleep with you in me."
"Stiles, I'm not just in you, I'm on you. I'm all over you." Derek laughed
gently. "I made a big mess of you. Let me clean you up, you'll be all sticky in
the morning otherwise."
"Then I'll deal with it in the morning," Stiles insisted. "I like it. I like
wearing you, feeling you in me. It makes me feel like I'm yours, even if no one
else knows it."
Derek abandoned his washcloth and climbed back onto the bed, maneuvering Stiles
so they could both be under the covers. Derek reached up to turn the lights
off, and in the darkness pulled his boy close to him.
"You are mine, Baby," Derek whispered as Stiles buried himself more fully into
his embrace. "I didn't mean for it to happen. Shit, I will get into so much
legal trouble if anyone ever find out. But I did. You're mine now. My baby." He
paused, kissing Stiles' hair softly. "And I'm yours too you know, Sweetheart. I
love you."
"Love you too," Stiles yawned. "Go to sleep now. Tomorrow you have to get up
early and go fight bad guys. And then be ready when you come home."
"Be ready? For what? You think your ass can take me again so soon?"
"Nope. We're watching Star Wars."
End Notes
     So that's that, I guess. Stiles is a man now. Sort of.
     That was a lot longer than I originally planned. And fluffier. I'm
     not exactly sure where that declaration of love came from. But I'm
     kind of okay with it. I think. I may have to rethink some of my plans
     for this series. Initially it was going to be a bit darker, with
     Derek being a lot more manipulative. But I think I'll keep with the
     sweetness.
     Also, let me know if there's anything particular you'd like to see. I
     may be keeping it sweet but that doesn't mean I can't dive deeper
     into kinkiness. Maybe the two need to branch out to include more
     people in their shenanigans. Like Derek's new partner Deputy Parish
     or his newly adopted son Isaac. Maybe Peter needs to get in on the
     action (which was the first entry of the series that I wrote which
     will need to be SUPER rewritten before posting). Maybe we need to tie
     Stiles up. I can't guarantee I'll write all of them (or any of them),
     but I'm more than open to suggestions.
     Thanks for reading!
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