Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/54932.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      F/M
  Fandom:
      Supernatural
  Relationship:
      Sam_Winchester/Original_Female_Character
  Character:
      Sam_Winchester, Dean_Winchester
  Additional Tags:
      Femdom, High_School, Crossdressing
  Stats:
      Published: 2010-01-23 Words: 1615
****** Pleather and Plaid ******
by ninhursag
Summary
     Everyone I mentioned it to thought that Sam, his high school
     girlfriend and a mini-skirt would be a worthy concept.
Notes
     Thanks to
     [[info]]
cormallen for the quick and dirty beta at midnight, no less. She is the awesome
♥ All mistakes belong to me. A little under 1600 words

Current mood: [http://l-stat.livejournal.com/img/mood/moonsis/stars/yellow/
              awake_sy.gif] pleased
  Entry tags: supernatural
Warnings: It's porntastic pre-series fic, so the players are underage. Sam/OFC,
hints of Sam/Dean. Light, playful d/s.
 
At sixteen, Amy James was already pushing five ten, the star player on her high
school basketball team, the only sophomore to get a five on the AP bio exam and
absolutely convinced that she was going to be stuck dating short guys for the
rest of her miserable existence.
That was before she met Sam Winchester, the sharpest boy in school, with narrow
shoulders and wide eyes. The tallest real live boy Amy had ever seen in her
life. He smiled like he wanted to show her all his teeth and if that wasn't
true love right there, the fact he tested right into her chemistry class tore
it.
Amy had never been shy, never needed to bother with that. She caught up with
him outside on a Friday afternoon and said, "I've been watching you. Do you
want to be friends?"
He smiled at her, quick and a little shy, pink sliding over his cheeks. "Yeah,"
he said. "Sure."
Amy never went out with a boy like Sam before. He had a wide, easy smile, and
he fit when they tumbled down together in the grass during lunch period or in
his bed after school, his angles matching hers. A mess of limbs and tongues,
slotting into place, like it was meant to be.
She could ask him things. Things she hadn't been sure she was ever supposed to
talk about out loud, things she didn't know if it was okay to want, but when
Sam turned his hazel green eyes on her wanting was all she knew how to do. "Can
I?" she whispered to him, when she put her hands under his shirt.
He smiled and tilted back, let her pull it off. "Yeah," he whispered. "Yes."
And again, "Yes," harsh and bitten off, and so damned open, when she pinched
his nipples and twisted.
"Would you?" she murmured in his ear when she slid in behind him and cupped his
ass in her hands. Soft skin and muscle, the hint of a curve, but nothing like a
girl's ass. Narrow, sharp boyish hips and corded runners thighs. She wanted to
pull him wide and open. "Can I? I want to."
Sam sighed and let his head roll back against her shoulder. "Yes. You can."
 
He fucked her for the first time on her own bed, under the shelf of her
basketball trophies and science fair ribbons. She spread his thighs wide and he
looked up at her, wide eyed and soft, like she was the biggest thing in the
world.
"Amy," he said. "Come on." And he grinned at her when she climbed on top,
straddling his thighs.
"I want to," she said.
"You can," he whispered. He let her press his hands down against the pillows
over his head, let her climb on. She was sloppy wet, so much she could smell it
and she ached from the inside, wanting. There was no questions about his yes.
It hurt; it burned, pushing him inside, but no worse than a sprain. Better.
"Come on, Sam," she hissed, and he smiled at her and nodded, like he wasn't
sweating, like he wasn't hard and there, inside her.
"Okay," he said and raised his hands, cupping her breasts with them, fingertips
pressing into her nipples. "Anything you want." His smile was sweet and wide
and he moved so fast it left her gasping when he turned them over and around so
that he was on top.
"Sam," she growled and he licked her, rough and wet, a swipe of tongue from
breast to collarbone. The muscles in his arms flexed as he moved on top of her.
It was hard to think, it was hard to do anything but be when he moved, when he
twisted and arched, but she didn't think this was his first time at all.
When she came over to his house on a Saturday, with a school project and
something else in her book bag, she was practically tingling with excitement.
She barely even noticed that he wasn't home alone; after all, it was just his
older brother, not his parents or anything. Amy nodded a hello, but was too
distracted to notice if Dean said anything back.
Sam just grinned at her, that same wide open smile and when they were safe in
his bedroom. If Sam didn't close the door particularly tightly, Amy didn't
notice or care. Instead, she showed him what was in her bag; he just watched
her face for a long second and then lit right back up with that bright, burning
grin.
"Yeah. Okay," he said. He let her unzip his jeans and pull them off him, let
her lift his feet and tug them down like he was a little boy. His cock was
anything but little when she bared it, already glistening across the slit, like
he was more than ready to be ready for her.
She pulled out the skirt, a new one, all pleather and plaid, and too big on
her, but she hadn't bought it for herself. It was just loose enough that she
could slide it over his lanky hips, snug as she'd imagined it would be. They
both sighed when it dragged over his cock, made it jump, made him whimper and
tip back his throat.
"You're so pretty," she said and kissed him, kissed his pink, smiling mouth
until he parted his lips for her and took what she wanted to give him. "You're
so pretty, Sam. I want you to be my girlfriend."
He laughed, warm and low in her ear, his lips swollen and red. "Yes," he said.
"I will. I will be."
"Come on, then." Amy pushed at him and he went down, easy and loose, pliant. He
let her pose him like a doll, spread eagled, wide open on his own bed. The
sheets smelled of him, cheap detergent, semen and new sweat. The skirt tented
up and she could see a spreading, darkening damp spot where fabric met
pleather. She took a deep breath, almost tasting it. "On your stomach," she
told him and his head bobbed once, agreeing.
He rolled over and went up when she urged him, on all fours. She pulled the
skirt up, exposing his ass, bare long muscles, and pale unmarked skin. "Gonna
spank me?" he asked, low and serious. He craned his neck to look at her over
his shoulder. His eyes were dark, blown until they were almost all pupil.
"No," she said, even though she shivered, even though she thought about it.
"Not today." Instead she shook out the remaining contents of her bag. A tube of
lube, the expensive kind. A condom. A sparkly red henna pen and an even
sparklier red dildo, long and narrow.
The pen was what she reached for. "Can I?" she asked, even though she was more
than sure of the answer. "Can I, Sam?" she demanded.
 
It was worth asking for the way he looked at her and the way he said, "Yeah,
yes. Please."
"Please," Amy whispered back. She wrote the word in her loopy, messy
handwriting, pressing it into his slippery sweaty back, right below where the
skirt flopped down. 'Please', she wrote. 'Mine'. Then she paused for a second,
thinking.
"You have to hold still," she muttered and smacked him lightly across the ass
when he craned his neck to see what she was doing. He rolled his eyes, but
turned his head compliantly forward.
The lube was cold on her fingers when she spread it over the dildo, thick and
generous. She didn't know whether it was the cold or the burn of it that made
Sam gasp, made him quiver when she pressed it against him. "Let me," she
whispered. "Open up for me. I want to. I want to."
He whimpered. She could see the fine tremors in his spine, in his limbs, while
he tried to do what she said. She could see the moment when his body stopped
resisting it, when he went loose again, with a low, easy whine.
It went in smoother after that, until just the base was still outside of him.
"Shhh," Amy said and rubbed her hand down his spine, slow and easy. Then she
turned the black knob and settled back on her heels to watch as it started to
vibrate. Sam's whimper was almost lost under the low hum of the toy.
"No touching," she said and smacked him smartly over the knuckles with the
henna pen when he reached for himself. She could see the shudder run through
him and wondered if he could come like this, if she could make him. It made her
whimper, too, made her itch between her legs.
She uncapped the pen. 'Amy James', she wrote, in long broad strokes, right
under the spot she'd written 'mine'. She stared down at the letters as they
appeared, almost enraptured.
So caught up she didn't hear the squeak of the door until it was open all the
way. She raised her head, startled, and caught a flash of Dean Winchester's
narrow green eyes. Just a flash, but enough to know that he might have been
peeping, but that he hadn't been looking at her.
 
All his attention was on one place. When she turned back to Sam he was craning
his neck and staring at the door too, wide eyed and shaking. For the first time
since Amy had met him, there wasn't a hint of his smile.
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