Title: The First Time
Author: Kadysn
Beta: The amazing Suz Mc, the wind beneath my wings *humming theme to Beaches*
Pairing(s)/Character(s): Sam/OFC, Dean, (mentions of) John
Rating: NC17 (for teenaged het sexual situations)
Word count:
Disclaimer: This is a work of pure fiction. I don't know the Winchesters *pout* and I surely don't own them, as much as I wish I could. I write for fun, not for money. Period. All OCs are mine.

Warnings: Het. Set pre-series, circa 2000. Sam is sixteen/seventeen.
Spoilers: None.
Summary: Teen!chester Sam is shy, horny, and still a virgin. He's also smitten with a girl from school. Can he find the courage to make her his, and get rid of his cursed virgin status?

The First Time

~Chapter One~

He was not his brother. Never as comfortable around girls like Dean was, Sam was still male, with all the hormones involved, and knowing that Dean had become experienced by the time he was fourteen, Sam wanted some action himself. He just wasn't comfortable with going out and actively looking for it.

Besides, girls flocked around Dean. As yet, they hadn't done the same thing with Sam. They much preferred the charming, James Dean-ish swagger that came off Dean in waves. None of them seemed to be drawn to the gangly, lanky, geeky boy that Sam was, even though he was sixteen and starting to grow into his height, finally!

Dean often teased him about the fact that, embarrassingly, he was still a virgin...and God, how he hated that word. Dean's repeated offers to set him up with friends of the girls he was going out with didn't help matters any. He wanted to find his own dates, thankyouverymuch.

They'd been in the same town for almost two months while Dad was off hunting; long enough for Sam to be enrolled in school for a semester. He was enjoying this time to be able to be around other kids his age, and he even enjoyed the schoolwork. He'd never enjoyed life on the road with Dad and Dean, hunting all the things that, so to speak, went bump in the night. He enjoyed seeing the country, but having to stay in cheap-ass motels or run-down apartments...not so much. He dreamed of the day when he could take off on his own, maybe go to college. It was a dream he'd had for a few years now, and he didn't look forward to the fight he was sure to have with Dad about it.

Dean, when he wasn't out catting around, worked in an auto shop, repairing cars. Sam could tell how much Dean enjoyed the work. He was as good at it as he was at hunting. It was something he and Dad had in common. Sam often thought the only thing he had in common with Dad was his temper. He'd lost track of the number of times Dean had had to come between him and Dad when they'd been getting into each other's faces over something or another. He hated it, but there was no reasoning with Dad when he got an idea in his head about something, and no matter what Sam said or how he tried to get his point across, it was always Dad's way or the highway.

The day would come, Sam vowed, he'd take the highway.


Dad was still out hunting, Dean had a date, so Sam felt free to get together with some friends for an evening of pizza, stealthily acquisitioned beer, and studying. One of the kids in the group turned out to be Holly Jacobs, a girl Sam had been eying since the day he'd walked into first period English two months earlier.

She'd sat right in front of him, and as he walked past her to get to his desk her fragrance wafted up to him, and it pole-axed him. She was beautiful, she smelled delicious, and it made all his underused hormones sit up and take notice.

As he sat down, extending his long legs under her chair, she turned around and smiled at him. Her cornflower blue eyes glistened and her lips, soft and pearlescent pink, curved upwards, making her dimples pop out. Sam wanted to reach out and take a long skein of her platinum blonde hair into his hands and caress it. Instead, he smiled back at her shyly, and was embarrassed to feel his cheeks warm. When she turned back around to face the front, Sam ran a shaky hand through the long hair hanging over his eyes and called himself an idiot.

When Sam walked into his friend Brad's house, there were already several kids there. The aroma of pizza already filled the room, and Sam felt his stomach rumble appreciatively. He waved at the group and said "Hey!" as he found a place on the sectional couch. After exchanging greetings with some of the guys, he looked up when he heard some of the girls entering the room from the kitchen. Holly was one of them.

Sam felt his stomach twist nervously, and he rubbed at it as he watched Holly cross the room toward him. She took the empty seat next to him, and when she smiled and said softly, "Hi, Sam!" he nodded, but he couldn't get a reply to come out. All he managed was a grunt. He cringed as she turned to speak to another girl on the other side of her.

Smoothe operator you're not, Winchester he blasted himself. Find your balls and use what Dean's taught you. Talk to her already.

Easier said than done.

Sam reached into his backpack and drew out his notebook. He'd already finished all his homework; he hadn't needed to join in this study group but had come anyway just to hang out. He'd also been hoping Holly would be there. Just to be in the same room with her, to be able to look at her and watch her as she laughed and chatted with their friends was enough to get his motor revving.

Under the long fall of hair over his eyes, he studied her. The lilac sweater she wore skimmed her curves, making Sam itch to run his hands over her. Her jeans were snug, and worn in places Sam ached to investigate. Her scent...God, her scent...was soft and warm and a little musky and it made his mouth water wanting to explore every inch of her and discover places where he could make her hot and wet.

Those thoughts alone made his jeans tighten in embarrassing ways. He covered his lap with his notebook, and hid his face, hoping no one noticed the wood he was sporting.

When Holly raised a longneck and took a sip of beer, Sam felt a shudder run through him. The way Holly's lips covered the mouth of the bottle made him imagine what it would look like if she took his dick between those lips. The mental image made him squirm.

Holly turned back toward him and sent him a soft glance and a sweet smile. "Hey, Sam. What are you working on tonight? Did you get the report for Mrs. Talbert's class finished?"

Sam nodded and managed to croak, "Yeah. I, um, finished it during study hall. You?"

Holly shook her head. "Not yet, but I'm close. I still have to look up some stuff. What'd you bring to work on tonight?" she asked as she leaned forward to put her beer on the coffee table in front of them. Sam's gaze locked on her chest; the v-neck of her sweater revealed the curves of her cleavage as the knitted fabric fell forward enough to give him a peek of her lightly freckled skin and just the tiniest hint of the lacey bra that cupped her breasts.

His face flushed, Sam admitted, "I didn't, actually. I just came to hang out. You know...free pizza and beer. Always a good thing."

Holly's giggle warmed him. "I get that. Since you're not working on anything, would you be able to help me with my history? The test we have tomorrow's freaking me out. I'm nowhere near ready. Run some dates by me?"

Sam nodded and accepted the note cards Holly handed him. Clearing his throat, he looked at the first card in the stack and read the words on it out loud....


After that night, Sam and Holly started to meet each other in the hallways at school: at her locker between classes, eating together at lunch, and finally, at her house. Sam was still a little nervous around her, but over time it got easier for him to talk to her and to do so without his hormones overloading every time. He still jonesed for her; that was a constant, but he didn't get instantly hard every time he was in her presence for longer than a minute.

Dealing with Dean, on the other hand...yeah, that was a joy.

Sam walked into the run-down apartment he and Dean were living in while Dad was away. For once, Dean was there ahead of him. It was close to midnight, and Sam had expected to be home and in bed long before Dean dragged in, only to find his brother kicked back on the ratty couch, beer in one hand and TV remote in the other.

"Hey, bro." Dean looked back at him with a tired smile.

"Hey, Dean. No date?" Sam asked as he tossed his backpack on the floor next to the door and ambled across the open room to the couch where Dean was sprawled out. He thumped on his brother's feet until Dean moved them, then Sam sat beside him and sighed loudly.

"Date's over. Chick had to get home early."

"Dude, I assume she has a name. Didn't you care enough to remember it?" Sam gave Dean a look that he knew would be ignored.

"Um, well...yeah, she has a name. Sara...Shelly—" Dean caught the look Sam gave him, then shrugged. "Ok, it's an S name. Sue me." he grinned lasciviously, then added, "Fuck, she was hot. Yeah..."

Sam shook his head. Typical Dean. The epitome of 'Wham, bam, thank y' ma'am.' Fuck 'em and leave 'em, but at least he left them with a smile on their faces. Sam would give at least that much to his older brother. He was curious about something, though, so he turned to look at Dean and asked, "Have you ever been in love?"

Dean rolled his eyes and snorted, "Dude, where'd that come from? What? You wake up this morning with girl parts, or something?"

Sam knew he should have expected Dean to smirk and avoid the question, but he wanted the answer, so he persisted. "Dean, I'm serious. Have you ever been in love? Have you ever loved a girl, and not just been in it for the sex?"

Dean shifted on the couch, turning so he could look at Sam full on. "What's this about, Sam? What brought this on? Seriously. Don't tell me..." He tipped his head down so he could look into Sam's eyes under the fringe of hair covering them. "Do you have a girlfriend? Dude...you do!" He grinned hugely at Sam and reached out to thump him on the knee.

Sam felt his face flush. He didn't respond to Dean's assumption, no matter if it was right or wrong. He knew no matter what he said, Dean would get mileage out of it, and he didn't want to give him any satisfaction.

Dean could read his brother like a book. "Sam, I'm not going to shovel shit at you. Answer me seriously. Do you have a girlfriend?"

For a few moments, Sam considered just walking off and not continuing the interrogation, but he wanted answers of his own so he decided he'd be honest with Dean. It was only fair, he supposed. "Not exactly."

"What do you mean 'not exactly?' Either you do or you don't. It's not a hard question."

Sam sighed then looked up at Dean and said, "No, but I want her to be."

"What's her name, Sammy? Why haven't you mentioned her before?" Dean asked, giving his shy brother an encouraging grin.

"Because I knew I'd catch crap from you and I wasn't in the mood for it. Besides—" he paused to gather his thoughts.

"What? C'mon, Sam, this is your chance. Talk to me. I promise I won't tease you--" Dean reached out and placed a hand on Sam's shoulder and squeezed it a moment, "—much." He smirked, but when he saw how Sam started to back down, he backpedaled, and added, his voice low and serious, "Just kidding, Sam. C'mon, tell me about her. I wanna know."

Sam frowned, unsure if he wanted to continue, but seeing the earnest look in his brother's eyes, he exhaled loudly, then admitted, "Her name is Holly. Holly Jacobs. She's one of my friends at school."

Dean smiled and nodded. "And?"

"And...we've been hanging out a lot." Sam looked over at Dean and after a brief pause, decided to go for broke. "She's so beautiful, Dean. So nice. I—"

"Have you kissed her yet?"


"It was another simple question, Sammy. Have you kissed her?" Dean dipped his head to look up into Sam's eyes, hidden behind that long fringe of his hair.

Sam blushed. "Not yet."

"So what's stopping you, dude? Where's your 'nads, man?"


Thinking back on the conversation he'd had with Dean made Sam blush all over again. He hated it, and it made him feel weak and girly, and the fact that he'd actually sat through 'the talk' with his brother just added misery to the embarrassment that made his stomach ache. It wasn't the 'birds and the bees' conversation, thank God. That had happened years ago when he'd woken up one morning sporting wood, and Dad had noticed it. That had been bad enough, but Dean had too, and had made sly comments until Dad had growled at Dean and sent him outside to detail the 'Pala.

After Dean said, "Yes, Sir," and slipped out of the room, Dad sat on the edge of Sam's bed and, his tone crisp and matter of fact, went into a spiel that had Sam cringing.

The talk he'd had with Dean was just as mortifying, and Sam wanted to forget it, but then again, he knew that the advice Dean gave him was worth remembering. Dean had the experience to back up his words, so Sam mentally shrugged and decided to keep the advice in mind for when he needed it...just in case.

Just the word 'condoms' out of Dean's mouth was enough to bring a hint of pink to Sam's face, but when Dean said, with his patented wise-ass smirk, "You won't need the extra large like I do," Sam wanted to slug him. He had to fight back the urge even stronger when Dean then asked, "Do you need me to show you how to put it on like I did for your socks?" By the time Dean advised, as he pulled out an obscenely large box of condoms and handed them to Sam, "Forget about the neon ones. That's just too gay," Sam thought he'd had just about enough of his brother's smart-ass attitude. Just holding the huge box of rubbers made Sam realize how much of a man-slut his brother really was.

He sucked it up, though, and settled in to listen to Dean's advice, especially when Dean's expression grew more serious, and surprisingly enough for Sam, almost flustered. He rarely saw that from Dean, so Sam listened quietly as Dean began considering what techniques he thought Sam should use when he finally got around to hooking up with Holly.

"Maybe you should do...wait, no. I know! You should try...wait, you'd hurt yourself." As Dean went from one idea to another, and not being happy with any of them, Sam put his face in his hands and groaned. Then Dean said, "Be gentle, but not so gentle she'll think you're scared or gay. Oh, and don't forget foreplay because girls love that shit. Besides, give her the O before you're even inside her and she won't even know you're a virgin."

Sam, embarrassed by the whole idea, still needed to ask. "Shouldn't I just tell her?"

"Fuck, no! You wanna make her think you've banged everything from Miami to San Fran!"

When Dean continued, going into the mechanics of the old 'in and out', Sam had finally had his fill of his brother's coarse, but well-intentioned, advice. Disgusted, he yelled, "Enough!" Leaving Dean on the couch, Sam thrust himself up and crossed the room and into his bedroom, slamming the door behind him.

Later that night, when all was quiet and he knew Dean had gone to his own room, he vaguely heard his brother's snores through the wall between their rooms. Sam lay in his bed, thinking of what Dean had shared with him. Just the thought of doing with Holly what Dean talked about...kissing and caressing, tasting, baring himself and her to each other...Sam groaned as he felt his dick expand, tenting the crotch of his boxers. He pressed a hand over the mound and rubbed at it, craving relief from the ache.

Feeling glad that, at least in this instance, he had privacy and a room to himself rather than having to share sleeping space with Dean, Sam slipped his hand under the waistband of his shorts and clasped it around his dick. He gave it a few strokes, and thumbed the tip, drawing the pre-cum down the length until it was lubricated and slid easily within his grasp. As he jerked off, arching into his hand, he imagined having sex with Holly, and the giving and receiving of pleasure they would share, until, with a guttural moan he came, the warmth of his release shooting out over his hand and stomach.

Sam met Holly at her locker the next morning, and it was all he could do to look her in the eye as he thought about jacking off to thoughts of her the night before. He leaned against the locker next to hers as she pulled her first period books from within. She smiled up at him and asked, her voice soft and silky on his ear, "Save us a table at lunch?"

Sam nodded and just then, the bell rang, signaling the students that first period was just about to start. To his surprise, Holly stretched up on her toes and kissed him on the cheek, then slammed her locker shut and moved past him toward class. Flummoxed, Sam stood there a moment then with a grin, he turned and followed her into the classroom.