Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/13878429.
  Rating:
      Explicit
  Archive Warning:
      Underage, Rape/Non-Con
  Category:
      M/M
  Fandom:
      おそ松さん_|_Osomatsu-san_(Anime)
  Relationship:
      Matsuno_Osomatsu/Matsuno_Todomatsu
  Character:
      Matsuno_Osomatsu, Matsuno_Todomatsu
  Additional Tags:
      Teacher-Student_Relationship, Crossdressing, Semi-Public_Sex, Car_Sex,
      Creampie, Stalking, Pedophilia, Underage_Sex, Age_Difference, Possessive
      Behavior, Obsessive_Behavior, School_Uniforms, Loss_of_Virginity,
      Todomatsu_POV, Rough_Sex, Extremely_Dubious_Consent, Anal_Sex, Anal
      Fingering
  Stats:
      Published: 2018-03-05 Words: 3676
****** Temptation, Frustration, So Bad It Makes Him Cry ******
by OfficialKaramatsuGirls
Summary
     When an opportunity arises, he does what needs to be done, and he'll
     be damned if he lets his morality hold him back. His dream come true
     stood in front of him, and without thinking he began to approach his
     prey.
Notes
     so, the police is a good band.
See the end of the work for more notes
The name sits heavy on his tongue, like a young child who wants to swear but is
hesitant because he knows of the repercussions. It's so goddamn tempting, and
no matter what he does about it, it haunts him. Five syllables that burn the
longer they stay in his mouth, desperate to be heard. They sit bitterly on his
mind, scratching at his skull to relieve the pressure and to just exit and be
spoken, the forbidden name that he keeps caged in a dirty fantasy.
All the thoughts, the dreams, the sad and lonely orgasms to the photographs
he's sneaked cannot compare to the desire, the urge, the need for the real
thing. The hours he's wasted thinking of ways to approach everything in a
respective manner, because the last thing he wants is to get too eager and
aggressive, fucking things up for the two of them. If he inflicts pain, he
doesn't know what he'd have to do to get out of the hole he's dug himself in.
One he's been in for a while now, and every day his shovel continues to dig,
every time he hears the bell and sees a specific pair of legs sit in a specific
desk for a single period.
When an opportunity arises, he does what needs to be done, and he'll be damned
if he lets his morality hold him back. His dream come true stood in front of
him, and without thinking he began to approach his prey.
===============================================================================
 
"Osomatsu-chan!" At the mention of his name, Osomatsu looks up, pocketing his
phone back into his skirt.
"Todomatsu-sensei!" The student laughs, waving with his free hand, jostling the
umbrella a little bit. 
"Aren't you cold?"
"I could ask the same of you," the boy quirks back, flashing a grin and
pointing at the teacher. "Where's your umbrella?" With wide eyes, Todomatsu
holds his hand out and watches the steady raindrops hit his skin. He doesn't
even feel it, but has to acknowledge Osomatsu's comment nonetheless.
"I guess I forgot it," he chuckles, brushing his bangs back so they don't mat
in an unattractive manner against his skin. The sweat he feels bead on his
forehead won't be as noticeable now, he supposes. "Have you been here long?"
"Yeah," Osomatsu sighs, taking his phone back out and checking the time.
Todomatsu knew for a fact that the boy had been standing in the rain for 17
minutes, and he missed the bus when it came by 22 minutes ago. The next bus
wouldn't be around for a while, and he couldn't just leave the boy to wait in
the chilly rain. "I think I missed the bus."
"Did you?" With a nod, Osomatsu slides his phone back in his pocket, though his
fingers slip and the device clatters loudly on the wet cement.
"Shit," he swears, squatting on his ankles to pick it up and inspect it. White
panties with blue ribbon accents. Todomatsu had been trying to hide an erection
since he exited his car and has to advert his eyes before his situation gets
worse and more obvious, potentially scaring the young boy away. Trying to shift
his thighs in a very subtle manner seems to go unnoticed, Osomatsu patting down
his skirt when he stands again.
"Is something wrong?" 
"Yeah," Osomatsu pouts, putting his phone in his pocket with much more care and
alertness, securing it inside his skirt and looking up at the teacher. "I can't
get a hold of anyone and it's too cold."
"You'll catch a cold if you're out here much longer." With a sad nod, Osomatsu
faces back towards the direction of the school, then back to Todomatsu, who
tries to put on the most casual and reassuring smile he can. "I could drive you
home, if you'd like."
"You have a car?" Eyebrows raised, Osomatsu beams when Todomatsu nods. "Really?
Cool!" 
"Would that be all right?" Todomatsu asks, trying to steady his breath as
Osomatsu considers it. "It's not too far from here, right, Osomatsu-chan?"
"Not really," hoisting his back higher on his shoulder, Osomatsu looks at his
teacher. "Are you okay with taking me home?" Phrasing, Todomatsu bites the
inside of his cheek. 
"I'm asking you."
"Yeah, that'd be fun! Taking the bus is always so loud." Trying to change
position of the umbrella, Todomatsu quickly takes off his jacket, and switches
Osomatsu objects. With a moment's pause, Osomatsu slides his young, slender
arms inside the man's jacket while Todomatsu holds the umbrella above his
head. 
"It's warm!" He giggles, rolling up the sleeves a little and holding his bag
within his fist. "Where are you parked?"
"Around the corner." Where I can see you safely. "Are you ready?" With a nod
and a toothy smile, Osomatsu starts, Todomatsu holding the umbrella high to
keep the boy as dry as possible. 
The black car sits around the corner, parked and still warm from how long he
had been sitting and watching. Some papers are strewn across the passenger's
seat, to which Osomatsu picks up and sets on the dashboard as he gets into the
car.
As soon as he sits inside, however, Osomatsu begins to play with the vents,
angling them around and flicking them open and closed. With the door open, rain
begins to drip inside the car, to which Todomatsu sighs. Without really
thinking around it, he reaches across Osomatsu, pulling the door shut and
sitting back into his seat.
He smells just like his shoes. Sweeter, even. I bet he tastes good.
"Is this new?" Osomatsu's curiosity reminds Todomatsu he is not alone, but with
the object of his desires, who looks at him with a patient smile on his sweet,
sweet face. 
"It's foreign," he informs the other, whose mouth opens a little in a gasp.
"It's very cool, sensei! I want a car like this when I'm able to."
"Maybe one day you can have this very car," the teacher jokes, to which
Osomatsu's eyes go wide in disbelief. 
"Really?" He gasps, then kicks his legs and laughs. "Wouldn't that be great!"
"Mmhmm." The youth's legs cease, and he begins to straighten out his skirt,
opening his mouth with a small smile.
"Don't tell anyone else," Osomatsu whispers, "but you've always been my
favorite teacher. You're so nice, sensei!" His brown eyes are so genuinely
sweet, choking Todomatu up and he falls into a fit of coughs, trying to wave
Osomatsu away when his smile falls into a frown of concern. 
"I'm fine," he croaks out, but that doesn't stop the student from rummaging
through his bag and producing a water bottle, uncapping it and holding it out.
"I-It's okay!"
"Nuh-uh, take a sip, you'll feel better." Getting on his knees, Osomatsu gets
closer, waving the bottle with a slightly more aggressive look on his
face. Stop looking so damn sexy, Todomatsu groans, taking the bottle and
holding it to his lips, taking a hesitant sip. As the coughing stops, he takes
a few deep breaths, trying to settle himself. With another sip, Todomatsu runs
his tongue along the rim of the bottle, making sure to taste any saliva
Osomatsu would've left.
"Better?"
"Yes, thank you." A much smaller hand reaches out for the bottle, cupping his
fingers around the back of Todomatsu's hand when he passes it over. For a
second, he smiles, then takes a sip of the bottle himself, then places the cap
back on and puts it in its place inside his bag. "Where are we headed?" The
ignition turns on with a hum, Todomatsu waiting for Osomatsu's instructions. 
Sitting for a while, Osomatsu tries to explain the area he lives in, though
he's unsure how to get there from their current location. He was so used to the
bus' route that he isn't sure how to get back to his house. Perfect.
"I'm sure we can figure it out," Todomatsu smiles, changing gears and inching
to the intersection. With a left turn, the car falls silence as Osomatsu
ponders the route. Opting for silence, Todomatsu would much rather listen to
Osomatsu mumble under his breath and furrow his eyebrows as he mentally maps
out the area. 
As they drive, the rain pours heavier, Osomatsu ceasing with his mumbling and
watching the rain hit the windows, only to be quickly pushed away with the
windshield wipers. With a click, the car signal of the car turns on, far before
the red light. Slowing to a stop, Todomatsu pulls into an alley, then stops
entirely once he's hidden between the two buildings.
"Sensei?" The student asks, looking at the adult with a questioning gaze.
"Something wrong?"
"Osomatsu-chan," he murmurs, turning the car off. "Can I ask you a question?"
"Of course!" Despite the shady situation, Osomatsu doesn't fail to have a smile
on his face, though it's quickly covered by Todomatsu's lips on his own. "Sen--
" the man's hands cup both of Osomatsu's cheeks, pulling in close for a kiss he
refuses to let go of. Pulling apart to breathe, the questions are meaningless
to the buzzing in his ears as he leans forward again. Their second kiss has
Todomatsu wanting more. He's always wanted so much more of Osomatsu, and he
doesn't want to waste time. His tongue darts out to taste Osomatsu's lips,
licking his teeth and trying to get into the boy's mouth. 
When Osomatsu's jaw opens more does Todomatsu moan, pressing Osomatsu against
the passenger door. His head hits the window, furrowing his eyebrows in pain,
groaning slightly into their kiss. 
"Sensei, wait!" Osomatsu all but yells, Todomatsu pulls back from their kiss in
fear. He's fucked up, he's truly fucked up. When Osomatsu's hand scrambles for
the door, the color in Todomatsu's face drains. 
The young hand takes hold of the door handle, but quickly digs deeper and once
he finds it, he reclines the seat back until he's all but flat on his back.
Without saying anything, Osomatsu waits patiently for Todomatsu to kiss him
again, which he does with a scramble and tries not to hurt the boy when he
crawls over. Pushing the seat backwards to get more room, he straddles Osomatsu
and places his lips on the boy's exposed neck, holding both of his wrists high
above his head. 
"Fuck," he whispers, angling his head higher in order to give his teacher more
flesh to mark with his kisses. Todomatsu's palm roughly pats down Osomatsu's
side, trying to feel his body. His hand settles on his stomach, pushing his top
up until it stretches across his collarbones, exposing his pretty pink nipples,
which harden as they're exposed to the cool air. 
Before he can think about it, Todomatsu's mouth is sucking on the boy's teat,
biting at the bud. In response, Osomatsu's hips rise, grinding against the
chest of the other, trying to push his torso more against the warm tongue that
tastes his skin. 
"Sensei," with a whine, Osomatsu tries to free his hands, to which Todomatsu
grants him the right. A young boy's fingers are short, carding through
Todomatsu's wet hair, tugging lightly when Todomatsu did something that he
picked up as pleasurable for the student. 
One of his legs hooks the best it can across Todomatsu's body, to which his
erection is very apparent as it presses against Todomatsu's torso from beneath
his skirt, through the panties. Trying to move smoothly, Todomatsu manages to
reach beneath Osomatsu's skirt, cupping the boy's dick, where they both moan at
the feeling. Opening his mouth to mumble something, Osomatsu's mouth is
occupied once more with the man's desperate tongue, eager to drink in all of
the moans, cries and whimpers he can coax out of the boy. 
"-ck me."
"What was that?" Todomatsu whispers against his skin, pressing kisses along his
neck. 
"I..." swallowing, Osomatsu finds it hard to repeat something he said in such a
passionate and lustful rush. "I want you t-to..."
"To what, Osomatsu-chan? I'll only do what you're okay with me doing."
"... To fuck me," he whispers, words barely audible, but Todomatsu's own cock
convulses so hard, he's pretty sure he just came at that alone. 
"W-What was that?" His voice cracks, sitting up slightly to look Osomatsu in
the eyes. The boy can barely make eye contact, face red with embarrassment and
anxiety.
"Fuck me, sensei," mumbling into his shoulder, he looks up at his teacher
through the corner of his eye, Todomatsu watching him intently to make sure
that's what he wants. "I'm... I'm okay with th-tha-that," he stutters and moans
when Todomatsu dips his hand under the elastic band of the panties, holding his
small, hot cock within his hands and feeling it pulse under his touch. I've
waited so long for this.
Sitting back as much as he can, Todomatsu helps the boy tug down his underwear,
leaving it hanging off his right ankle, then briefly admiring the sight before
him.
Turning his back, the teacher hastily grabs for the handle of the glove
compartment, grabbing a bottle of lubricant that has obviously been used. He's
masturbated in here before, watching Osomatsu out with his friends while they
eat outside at a cafe. Or while Osomatsu was in the park, walking his dog,
Todomatsu had been taking pictures with his phone and getting off to them in
the public restrooms because he couldn't make it back to his car like that.
During summer break, Osomatsu spent a lot of time riding his bike around town,
stopping at a kiosk of shaved ice every day at 13:34, after going on his usual
route. Todomatsu couldn't stand to watch the sweat drip down his face, the
relief evident in his expressions as the chill of the ice warms his system,
smiling a very comfortable and relaxed grin that Todomatsu would fuck himself
off to. 
"You keep that here?" Osomatsu giggles, Todomatsu not responding but pouring a
generous amount onto his fingers, lifting Osomatsu's left thigh. "I-I'm a
virgin," he blurts out, causing the man to freeze.
"You are?" He asks quietly, looking at Osomatsu's flushed features. Nodding
shyly, Osomatsu looks out the window and waits for his teacher to laugh at him
for being a virgin at his age. A loud moan flies from his lips when a hand
grasps his hard cock, giving him steady and firm strokes while his other hand
circles the ring of muscle.
"Sensei!" Squealing, Osomatsu looks forward again with half-lidded eyes. "Be
gentle, please."
I want to fuck him raw. I want to destroy him.
"Of course, Osomatsu-chan. I'd never want to hurt you."
I want to fuck him until he can't walk and he'd have to stay at my place, where
I'd fuck him senseless again.
"Promise?"
"I promise."
I want him to crave me, and me alone. He can't live without the feel of my cock
stretching his tight asshole apart. 
A cautious finger positions itself at the entrance, pushing inside, where
Osomatsu tightens at the intrusion. So fucking tight. 
"Are you all right?" With a nod, Todomatsu takes it as a sign to continue,
making sure to stroke his erection in order to ease his mind from the
unfamiliar sensation, but rather putting him in a more blissful state of mind.
Their kisses become more needy, seeking more pleasure as Todomatsu's finger
digs deep inside the boy. Quiet pants fill the air, Osomatsu grabbing at the
collar of Todomatsu's shirt, reaching up and tugging hard at the feel of a
second finger easing him apart. 
"Does it hurt?"
"No, it's just weird."
"Okay. You're so perfect, Osomatsu-chan." After more teasing, a third finger
helps open him up, Todomatsu adding his pinky finger to absolutely make sure he
is stretched apart enough. When he withdraws, Osomatsu lets out such a needy
moan, seeking the full feeling he was suddenly deprived of.
Todomatsu's zipper is undone, and as he fishes himself out of his boxers he can
tell he came twice. He's not sure when the second time was, but all that
matters is how he's ready and how Osomatsu is willing to take the boy's
virginity and fuck his tight asshole so hard on his car seat. 
"I don't have any condoms," Todomatsu says, holding both of Osomatsu's knees
while he runs his cock over the boy's own member.
"That's fine," with a gentle smile, Osomatsu reaches out to touch Todomatsu,
who uses one hand to lace their fingers together, the other aiming his head for
the stretched orifice. 
"Are you ready?" Sucking in his breath, Osomatsu nods, bracing himself for
what's to come next.
As his teacher slowly pushes in, thrusting back out and going a little deeper
the next thrust in, Osomatsu finds it's not as awful as he thought. The
preparing really helped, Todomatsu making sure he was comfortable. 
"How is it?" I want to tear him apart.
"Good." He's so fucking cute.
The deeper he moves, the tighter Osomatsu holds him, trying to pull him down by
the neck into a kiss, but Todomatsu is fixated on watching Osomatsu's tight
walls suck in the teacher's hard cock until his pelvis is flush against his
balls. The cry Todomatsu lets out as he's fully sheathed makes Osomatsu whine
as well, succeeding in bringing the man into a passionate and messy kiss.
"You can move," the words press against his skin, Todomatsu adjusting his
position and moving.
His hips smack hard and fast against Osomatsu, who screams and pulls
Todomatsu's hair so hard his head yanks back at the motion.
"Fuck!" Osomatsu shouts, body tense. "It hurts!"
I'm going to destroy him and make him mine, and only mine. 
"Sensei, sl-slow down!"
"So good," he groans, nails digging into Osomatsu's thighs. "So
fucking tight." 
Tears drip down Osomatsu's flushed face, jaw open wide as he screams and cries
at the burn and stretch of his teacher fucks him so hard he can't think
straight, only moan and sob.
"I'm gonna--" Osomatsu turns his head towards the window, hidden between the
small space as he continues to cry loudly.
"Look at me," Todomatsu orders, taking hold of Osomatsu's chin and facing him
forward. "I want to see your face when you cum by my cock." At the vulgar words
Osomatsu whimpers, opening his eyes when Todomatsu squeezes his cheeks with his
fingers. 
"I'm-- Sensei-- I-I'm-I'm cumming!" He screams at the top of his lungs, raising
his hips as much as he can as his body tenses and shakes, reaching his orgasm
as it rocks his body over. The thin cum is quickly caught within Todomatsu's
hold, then pressed against the man's mouth as he laps every drop up and
swallows it, not stopping and causing Osomatsu to sob louder as the aftermath
of his orgasm makes him sensitive to touch. "It hurts!"
"Close," Todomatsu mumbles, "I'm close. Ju-Just a little more. Please." As
Osomatsu shakes his head and begins to try and fight back, Todomatsu pins his
wrists high over his head and fucks him as hard as he can. 
I'll fill him to the brim. Defile him. Ruin him. Dirty him. Wreck him.
Warmth fills Todomatsu's groin as he feels his orgasm approach, moving to grasp
Osomatsu's cock as it erects back to life, pumping it until it's fully hard and
pulling on it harshly. 
"Don-Don't!" He sobs out, pulling his teacher's hair harshly, no longer with
desire, but out of pain and uncertainty. "Todomatsu! Stop it!!"
"So fucki-ing close, Osomatsu. Shut up. Shut up!" Leaning forward, he takes the
young student's bottom lip between his teeth and bites hard, Osomatsu trying to
hide the moan that is pulled from his throat in guilty pleasure. 
Todomatsu's hands pull Osomatsu's ass apart, stretching him wide as his thrusts
become more shallow, then the muscles in his body tense, forcing himself to
continue his thrusts. Pushing himself to the very base, he holds Osomatsu tight
as he cums inside the boy, who screams as he himself cums once more, his semen
hitting his stomach from where his shirt is still bunched up. With a shuddering
sigh, Todomatsu pulls out, then sets Osomatsu flush on his back, body hot and
sweaty against the leather seats. The cum drips out of his abused asshole,
slipping down his thighs and pooling under him as the student continues to cry,
softer now that he's by himself.
"I'm sorry," pressing gentle kisses to his skin, Todomatsu apologizes. He
didn't intend for it to be that rough, but he's wanted this for so, so long. 
"I want to go home," he whispers. "I want to go home."
"I'll take you home, I promise." A very soft kiss to Osomatsu's forehead,
Todomatsu sits up and tucks his soft penis back into his briefs and takes his
phone out. Making sure to turn it on silent and turn the flash off, he points
it down and takes photos of the reddened asshole that he fucked, the cum
leaking out of him, the bruises to form on his skin. His fingers delicately
lift his thighs up, opening them and taking a closer picture of how badly he
ruined Osomatsu, then gently kisses his inner thigh and sets him back. Taking
tissues from his coat pocket, he cleans the child up, puts his underwear back
on, fixes his uniform and sits him back of.
Having fallen asleep, Osomatsu sighs and snores lightly, pressing his head
against the window as he slumps over. Tears stain his cheek, Todomatsu cleaning
him up as well. 
Turning the car back on, he backs out of the alley and heads towards Osomatsu's
house, where he's lurked outside so many times before. The ride there all he
can think is how he wants to fuck his student once more, bending him over a
desk as the whole school hears his voice while he cums to his teacher's cock.
He shudders and shivers, letting out a sigh as he begins to palm himself at a
stoplight. Now he has so much valuable material to last him until he can do
this again.
End Notes
     i'm going through things in my life right now, and i guess i'm trying
     to vent by changing subjects in my work. sorry if this isn't
     something that's necessarily desired to be read, but thank you for
     reading regardless and i hope you enjoyed.
     i also wrote this in one sitting, and it's almost six in the morning
     so i'm going to post it, sorry for any errors.
     feedback is greatly appreciated, thank you!
Please drop_by_the_archive_and_comment to let the author know if you enjoyed
their work!