reggie11: (Default)


This is Part Two of Firsts 'verse dealing with first sexual encounters. This chapter deals with Sam's first time. The first was Dean's and the third will be Wincest but each fic is stand-alone.

Rating:
NC17
Genre: PWP
Characters: Sam/OFCs, Sam/OMC
Word Count: 4,260
Spoilers: None. Pre-series.
Warnings: Adult Het sex. A brief mention of M/M sex act which in some parts of the world may be considered underage - Sam is sixteen.
Disclaimer: None of the characters belong to me - I'm just borrowing them. No copyright infringement intended.
Author’s Notes: This story is mainly het, there is just a wee dash of M/M.

Link to Firsts Part One - Dean

Sam Winchester was quite unlike his older brother. He didn’t have the same confidence Dean had with the opposite sex or with anything in general that wasn’t related to schoolwork. He knew Dean had started messing around with girls from a very young age because his older brother always had to brag about his conquests even when Sam was still very young and the thought of kissing girls let alone anything else just grossed him out. He even knew when Dean had lost his virginity because, to ten year old Sam’s horror, he’d lost it in Sam’s bed while he was at a sleepover.

Sam’s first kiss was with a girl in his class named Stephanie and after that very chaste peck on the lips she told all of her friends at McKinley that he was her boyfriend. He thought that was pretty cool even though she kinda scared him sometimes. Stephanie had just turned twelve and was always touching him and Sam at eleven didn’t quite know what, if anything, he was supposed to do with that. To his horror, she had even grabbed his thigh under the table when he was eating Thanksgiving dinner with her family right under the noses of her mom and dad. Before they had left town, he and Stephanie kissed a few times (no tongue because that was just eeuw) and she put her hand on his crotch. He ran almost all the way home after that with his heart hammering in his chest and his pre-pubescent dick hard in his pants.

Sam’s first proper kiss didn’t happen until he was fifteen. She was pretty and smart and just as Sam’s luck would have it – and this was something that would repeat itself on and off even throughout his adult life – she was one of the monsters they were trained to hunt and kill. Her name was Amy and she was a Kitsune. Amy knew what it was like to have to move around and not fit in and she was the first person who told him that being a freak made him more interesting and in her he saw a kindred spirit. When her mother found him in their house and tried to kill him, Amy saved his life by stabbing her own mom to death. When she asked Sam to run away to make a new life together a small part of him wanted to because he was so sick of the hunting life – sick of his father dragging him and Dean all over the country and sick of the fear that one day his brother or his father would end up dead – but he couldn’t do it. He couldn’t leave Dean. Even though Amy wasn’t human it didn’t stop him from replaying that delicious kiss over and over and wondering if she was safe wherever it was she had run to.

As traumatic as the circumstances surrounding that first kiss were it had opened up Sam’s confidence a little. Now he knew how good kissing could be he wanted to do it again...and again.

The first girl to let him do more than kiss was Monica Richardson. They had been living in Kenosha for four months – a long time by Winchester standards – and he had actually made some pretty good friends. Both he and Monica were fifteen and spent much of their time in the library. She had a shy smile, a honey blonde bob and glasses that kept sliding down her cute little freckled nose. It took him two weeks to build up the courage to ask her to go get a soda with him after school and another week to kiss her. What Dean had told him about how ‘it's the quiet ones that'll surprise you' seemed to apply to Monica. After he worked up the nerve to kiss her, Monica couldn’t keep her hands off him. He'd go to her house after school to study but most of the time it ended up being long make-out sessions and very little actual studying. Monica gave him his first hand-job and she let him touch her too. Sam was heartbroken when they left town because he thought he maybe loved Monica a little. He hated his dad for making them leave and after that he and his dad went from butting heads to fighting constantly.

Sam's first blow job wasn't even from a girl. He and Rick Mason were on the soccer team together and when Rick had asked Sam to tutor him in algebra he really hadn’t thought it was anything other than the boy needing help with math. Rick was tall and lean with dark  blonde hair, bright blue eyes and a killer smile and Sam thought he was cute which had really confused him. He'd never had a crush on a boy before (other than his hero-worship of Dean) and he hadn’t been sure he was normal. In fact, he was pretty sure he had never been normal. He had nobody to ask about these things because there was no way in hell he was ever going to tell Dean that he thought he might be into guys as well as girls. Most people in the schools he went to already called him a freak, he would never take the risk that the person he loved more than anyone in the whole world would think he was as well. He knew that his brother wasn't homophobic but he wasn’t sure Dean might be so open if he found out his little brother might be bisexual.

The first time he went to Rick’s to tutor him, the boy told him straight out that he thought Sam was hot and that he was pretty sure Sam felt the same way about him. As he walked across the room toward Sam he said he’d seen the way Sam had looked at him in the locker room after soccer practice, then he stepped into Sam’s personal space and pressed his hand to Sam’s crotch. When Sam whined at the contact, Rick had wasted no time dropping to his knees making all the blood from Sam’s brain go rushing to his rapidly hardening erection which the boy licked from root to tip. When Rick closed his mouth over the swollen cock and began to suck in earnest, Sam had almost seen stars and the only thought in his head before his brain shorted out and he came was blow jobs are absolutely, positively, the most amazing thing in the entire universe!

He and Rick traded secret kisses and blow jobs for the next two weeks until his dad had moved them again. He was sixteen years old and it seemed he had no issue with playing for both teams because apart from the awesome blow jobs, he'd really liked Rick a lot. He had wondered for a little while afterward if the reason he’d initially been attracted to Rick was because he’d kind of reminded Sam of Dean – with the same bigger than life, cocky personality. He wondered if maybe his fucked up teenage hormones had misplaced his hero-worshiping crush on his brother into a sexual crush on someone like him.

Sam didn’t lose his virginity until he was seventeen, something his older brother endlessly ragged on him about. He’d had ample opportunities but it just didn’t sit well with him to have sex with someone he barely knew. He wasn’t a love ‘em and leave ‘em kind of guy like Dean – it had to mean something. He wasn’t in love with Emily Burton but there was no doubt whatsoever how much he cared for her – she was really something special. It seemed all he ever did was fight with his dad and whenever he got the chance he took refuge from the bitter words with Emily and at school they spent every moment they weren't in class, together. They’d been dating for almost two months and Sam knew she wanted to take things to the next level but it bothered him that they would be moving on in the next month or so. He knew Emily was a virgin too and it didn’t feel right to take what she was offering knowing that he would have to leave her. It just wasn’t fair. He thought he and Emily could have maybe had a chance at a future if he could only stay. He may have loved his father but sometimes he hated him so damn much for dragging him along on his miserable quest for vengeance.

Even though he could never tell Emily anything close to the real reason the Winchesters moved from place to place, he did tell her how much he hated his family's nomadic lifestyle and she had been helping him with applications for scholarships so that he could go to college – be normal, live a normal life. The night Sam lost his virginity he and John had had the mother of all screaming matches. He’d missed an significant test because he’d been dragged along on a weekend hunt which was supposed to be only two days tops but they didn't get back until Tuesday. It was a test that could affect his grades which in turn could affect his scholarship chances. After both he and his father had yelled themselves hoarse his dad had fallen asleep at the bottom of yet another bottle of whiskey and Dean had gone out to a bar muttering something about being sick of listening to the fighting and why was it Sam always had to goad their dad at every turn. Sam went out through his bedroom window. It never seemed to matter to his father or brother that school was important to him. It made him more determined to continue to get good enough grades so he could escape a life of hunting.

He tapped on Emily’s window and she had no problem letting him in. Her parents were asleep at the opposite end of the house and although they had to be quiet, they didn’t need to be silent. She listened as he poured out his anger and frustration and then kissed him until he was breathless.

“You can stay here tonight as long as you're out before my parents get up. They won’t be awake before seven.”

“You want me to stay all night?”

“Do you really want to go home?”

“No, I’m already going to get my ass kicked when I go home but I don’t want to get you into any trouble.”

Emily looked at him and smiled and then lit a couple of candles on her bedside table and turned off the lamp.

“I really want you to stay with me, Sam," she leaned in and kissed him again, "I want...”  She sat up and nervously pulled her nightgown over her head leaving her naked except for her panties. Sam’s breath caught in his throat and after sweeping his hazel eyes over the expanse of her flesh he raised them to meet her chocolate colored eyes. She looked almost ethereal with her dark hair and pale skin that almost glowed in the low flickering light. She looked so beautiful.

“Em, what are you...are you really sure?”

“Yeah, c’mon, take these off,” she said as she started to unbutton his jeans, “I want you to make love to me, Sam.”

He felt almost lightheaded, they were going to have sex. It was going to happen. It was really going to happen!

“I want us to be each other's first. I know you said you’ll be moving again soon and I wish you weren’t but at least we can have this. I want this, Sam. I want you.”

Lust and nerves were duelling their way through his consciousness, each taking turns at getting the upper hand. Sam wasn’t very experienced because he wasn’t the type to do casual but he was also a healthy seventeen year old boy that had a mostly naked pretty girl on a bed asking for sex. He was so hard it was almost painful and so on edge he knew he wouldn’t last long. Then he realised something that made disappointment override everything else.

“Damn it. I don’t...um...have anything with me...I left my wallet at home.”

“It doesn't matter.”

With the words Dean had pounded into his brain from the time he was thirteen no glove, no love – rattling around in his head he knew he could never go through with it. They may be virgins and disease free but there was no way he was ready to be a father. Just the thought of that was making his erection wilt. He sighed and shook his head.

“No Sam, you dumbass.” She rolled her eyes and looked at him with fond exasperation, “I have condoms. I bought them after the first time we talked about maybe doing this.”

She dug around in the bottom of her underwear drawer and took out two boxes of Trojan Magnums. “One of these better be the right size. Do you know how embarrassing it was to buy these?” She looked up through her lashes and giggled. “I don’t know much about how they’re sized but I know you’re a big boy.” They may not have had full-on sex before but there had been some serious petting sessions.

Sam flushed a deep red, picked up the box of XLs and said sheepishly, “These ones.” He opened the box and placed a condom on the nightstand. “Are you really sure?”

She grabbed both of Sam’s large hands and placed them on her breasts and Sam let out a soft moan. She leaned forward until their lips were just touching and whispered, “I’m a little scared but I’m really sure.”

Sam pulled her in close with one arm around her waist and he cradled her head in his hand he pressed her down onto the bed and kissed her, biting lightly on her bottom lip and then soothing it with his tongue. He began to kiss down her neck as he ran a hand up her thigh to the firm globe of her ass and then between her legs. He slipped his long fingers in under the elastic of her panties finding her already slick and they both moaned simultaneously when he slid his fingers over the wet warmth of her.

He kissed and licked down to her breast and swirled his tongue around the hard bud of her nipple eliciting a sigh which turned into a whimper as he grazed her clit with his thumb. Although they had done things numerous times before, both of them had been mostly clothed and now with the wonderful sounds she was making and the feel of her naked body against his, Sam was ridiculously close to losing it. He moved back up to kiss her as he circled her clit with his thumb and slid a finger inside of her. She writhed underneath him, hard nipples grazing his chest and her thigh giving constant friction to his aching cock.  When she plunged her hand into his boxers, barely wrapping her hand around his length, his orgasm hit him like a freight train and he cried out softly as he spilled into her hand and onto her thigh.

When he came down from the high of coming so hard, he was mortified. They still had their underwear on, hadn’t even gotten to the good part and he’d come as fast as he had when he’d gotten his first handjob and he’d come before Emily. This would never happen to Dean!

“I’m so sorry.” He had his face buried against her neck and was too embarrassed to look at her.

“Hey, it’s okay.”

“God, I’m such a loser. It’s just...you’re so beautiful ...and you feel so good and...”

“Shh, it really is okay. You think I’m beautiful?”

He raised his head then and looked her in the eye still blushing deeply. “God, yeah,” he breathed. “Emmi, you’re gorgeous.”

She beamed at him and he couldn’t help but smile back, full dimples on display. He was still embarrassed but when she looked at him like that, with such happiness and adoration, things didn't seem so bad after all.

Emily scooted over to the edge of the bed and reached over to grab a towel that was hanging on the back of a chair and wiped off her hand and her leg then gave the towel to Sam. She playfully tugged at the elastic on his boxers until he lifted his hips and she slipped them off him and threw them to the floor followed quickly by her own panties. She pulled him back toward her, wrapped her arms around his neck and whispered in his ear, “Now where were we?”

He’d always known she was great but he couldn’t believe how cool she was being. He didn’t expect her to laugh but he had expected her to look disappointed. Instead, she looked...well...pleased. He rolled her onto her back and kissed her languidly. He had to admit that now the urgency was gone it was actually better. He was relieved he could take more time to make it as good for Emily as he could. He was pretty nervous about it being her first time, knowing he was larger than average even when he wasn’t hard. He’d been given the nickname ‘tripod’ by some of the guys in his gym class who had seen him in the showers at his last school which had embarrassed the hell out of him when it spread through the small school like wildfire. And to his utter humiliation, the name had somehow even gotten back to Dean who had spent weeks teasing him mercilessly by bringing it up in the most inappropriate places just to watch him squirm and blush.

He kissed his way down Emily’s body stopping to suckle at her nipples while he teased and stroked up her inner thighs without actually touching where she wanted him to be. He continued covering her torso and stomach with open mouth kisses, circling his tongue around her navel before lightly blowing over the damp thatch of curls between her legs.

“Please, Sam.”

She sounded so wanton and he felt his cock starting to thicken again when she parted her legs allowing him to settle between them. With the first touch of his tongue to her clit she let out a delicious moan and grabbed at his hair. He loved this. He absolutely loved going down on her and making her quiver. He loved her scent and her taste and the pretty noises she made when she was nearing climax. Of all of the things that they had done so far this was his favourite although he felt that was probably going to change once he sank himself inside of her.

He took his time sucking and licking at her clit like he was worshiping it. When he slid two fingers into her, that was all it took and he felt her body stiffen and tremble as her walls fluttered around his fingers and he moaned as lapped at the sudden gush from her orgasm. He was rock hard again as he kissed his way back up her body loving the little trembles of her aftershocks.

“Are you ready?”

She smiled up at him, her pupils blown so that he couldn't really see the brown anymore and nodded, “Just...um...just go slow okay.”

“You can tell me to stop and I will. I don’t want to hurt you.”

“It’s going to hurt, Sam, but I still want this.”

His nerves were back in full force again as he reached over and picked up the condom wrapper and his hands shook so much he dropped it twice. Emily took the little packet and tore it open and gave the condom to him. He was so nervous he had trouble rolling it on and he would have laughed if it wasn’t for the fact that he was both incredibly horny and totally terrified.

When he settled himself above her, he kissed both of her eyelids and then her nose. He thought he should tell her that he loved her but those were words he knew he could never use unless he really meant them. He liked her so very much so instead he said, “You’re so beautiful, Emmi” and she leaned up to kiss him. When he broke the kiss he lined himself up and gently started to push his way inside. He had to grab the base of his cock to stave off coming at the first feeling of that incredibly tight warmth. He had to fight to keep his eyes open as he was overwhelmed by the sensation of feeling himself slowly pushing in because he needed to see if he was hurting her. He felt resistance and Emily’s breaths were coming in short pants, her brow furrowed from the discomfort.

Jesus, he was close to coming. The tightness of her was overpowering but when he felt a sudden give and Emily cried out softly from pain, dug her fingernails into his back and screwed up her face it brought him back from the brink quickly. He stilled even though the urge to push was monumentally strong. “God, Em, are you...should I stop?”

A tear fell from the corner of one of her tightly closed eyes and she shook her head and replied, “Just give me a sec, I’m okay.” She pulled in a deep breath, opened her eyes and saw Sam’s hazel eyes looking at her with such worry she smiled and then urged him to move.
As he pressed in as far as she could take him he was torn between concern that he had hurt her and the delicious feeling of Godyessofuckinggood. She couldn’t take his full length but it didn’t matter because being inside of her felt so amazing. He pulled back and pushed in again slowly finding his rhythm and then kissed her deeply, their tongues tangling as she started to match his thrusts with presses of her hips. He could tell she was still uncomfortable so he reached his hand between them and began to rub her clit soft and fast. He raised his head and bit his lip trying desperately not to come until she did but he felt the familiar coil of heat and his balls started to tighten. He lost all rhythm and threw his head back as his orgasm ripped out of him and tried not to cry out and wake Emily's parents.

With labored breathing he dropped forward and kissed her and, then with great difficulty, resumed his attention on her clit while fighting to hold himself above her on one very shaking elbow. She began a litany of “oh, oh, oh” and he felt her contracting around his cock as Emily came shaking beneath him. He worked her through it and then gently eased his slowly softening cock out of her holding the base of the condom tightly.

When he disposed of the condom he wrapped himself around Emily and asked if she was okay. She answered by kissing him long and sweet.

“Was it...did I...”

“It was perfect, Sam. It hurt for a bit but then it felt good although I’ll probably be sore tomorrow...but good sore.”

He winced but she smiled at him and they wrapped themselves together in a sweaty tangle of limbs and kissed until they fell asleep.
He woke just before dawn and he kissed Emily awake and told her how much the night had meant to him. He snuck back out of her window as the sun was coming up over the horizon. When he got back home his father was waiting and he was beyond furious, launching into a tirade as soon as Sam walked in the door. Within minutes, the shouting brought Dean into the room ready to join his father at yelling at Sam for worrying them. When he saw Sam’s face it stopped him short. His stubborn, defiant little brother wasn’t yelling back and there was none of the usual fury – in fact he had kind of a dopey look on his face.

When John stormed out of the house slamming the door in his wake and Sam went to go to his room, Dean raised an eyebrow in question.

“What?”

“You know you’re gonna be paying big time for staying out all night with the training from hell and any other God awful punishment dad can think up for the foreseeable future.”

Sam sighed and then shrugged, “Yeah, I know.”

“So was it worth it?” Dean asked with a smirk.

Sam smiled sheepishly,“Yeah, it really was.”

Dean threw his arm around his not so little brother’s neck and pulled him down for a noogie.

“Aw, our little boy’s all grown up.”

“Shut up.” Sam blushed furiously but couldn’t keep the grin off his face.

“Go take a shower, princess. Dad's gonna be back with the punishment from hell as soon as he's calmed down and because I’m such an awesome big brother, I’ll take you out for breakfast to celebrate your deflowering before he kills you.”

Sam rolled his eyes and flipped Dean the finger, smiling all the way as he walked out of the room. When he was in the shower Dean snuck into the bathroom and said, “Hurry up, bitch,” as he flushed the toilet. He ran out of the room laughing as Sam screeched, “Oh, you jerk!” when he was hit by ice cold water.

Fin
reggie11: (Default)
This is Part One of Firsts 'verse dealing with first sexual encounters. This chapter deals with Dean's first time. The second will be Sam's and the third will be Wincest but each fic is stand-alone.

Rating:
NC17
Genre: PWP
Characters: Dean, OFC
Word Count: 3240
Spoilers: None. Pre-series.
Warnings: Graphic Het sex. Underage (Dean is fifteen)
Disclaimer: None of the characters belong to me - I'm just borrowing them. No copyright infringement intended.
Author’s Notes: This is my first time writing porn and it's a little nerve wracking. I hope it's not disappointing. This first story is purely het, the second will be het with just a dash of M/M and the third will be pure slash. If you don't like Wincest you only need avoid the third story.


Dean had known he was attractive before he had even hit puberty because people constantly said so. From the time he stopped thinking girls were gross, he realized that he could have them eating out of the palm of his hand with his smile and swagger and he used it to full advantage. He was always confident – with the way they lived and the things he’s seen and done, he’d always seemed older than his age. Whatever school he landed in, he’d smile and wink and the girls just ate it up. Even at thirteen he had that whole rebel without a cause thing going so he really had no problem fitting in wherever he went. The girls wanted him and the guys wanted to be like him. He didn’t have much free time though because he had to look after Sammy. Not that he minded – he adored his little brother and Sammy worshiped the ground he walked on.

His first proper kiss was with Sally Kingston when they were living in a trailer park in Oregon. He was not long gone thirteen and she was fifteen and she taught him the fine art of French kissing in the laundry room and let him get to second base that same day. During week two she jerked him off and taught him how to bring her off with his fingers.  It was awesome! On his fourteenth birthday he convinced Rachel McCarthy to give him his first blow job behind the science block at school. By that age he could pretty much get any girl he wanted and he was even getting hit on by guys. He learned quickly that he could flirt with just about anyone to get anything he wanted.

Two weeks after Dean’s fifteenth birthday Sam had asked if he could spend the night at his new friend’s house. Dean knew his father wouldn’t approve but he wasn’t going to be back for a few more days. Sam always found moving around and not having permanent friends really hard so he couldn’t bring himself to say no to those pleading eyes but made him promise to keep it their secret. If dad found out he’d have Dean’s balls.

With nobody to make dinner for he thought he’d take the opportunity to see if Luke was home. Luke was always bragging that his parents would stay out ‘til all hours on a Friday night and he and his older brother would get drunk. Dad was on a hunt and Sammy wasn’t going to be home until lunch time tomorrow so hell yeah, that sounded like fun. As luck would have it Luke wasn’t home. Dean found himself sitting on a bench at the park trying to figure if he could stretch their meager funds enough to go see a movie when he saw her. She was sitting under a tree flicking through a magazine. She had long brown hair tucked behind her ear and she was wearing a skin tight, low cut t-shirt that barely contained her ample breasts. He couldn’t stop staring – man she was hot. She looked up and caught him watching her and even though she was obviously a lot older than him he was cocky enough to flash her his best smile. When she grinned back he sauntered over, “Hey.”

“Hey yourself” She bent forward to retrieve a pack of cigarettes from her bag and he spied a tattoo of a butterfly peeking out from her jeans on her lower back.

“Cool tatt”

“Thanks, ya wanna smoke?”

“Yeah, thanks.”

“I’m Jasmine”

“Dean. Pretty name for a pretty girl”

“Well aren’t you a smooth one,” she let out a husky laugh that had his dick twitching and he flashed another smile. “You’re cute, how old are you?”

He knew he looked older than he was, partly from his recent growth spurt, partly from all of his physical training and partly from his self confidence so he thought he’d see if he could get away with it. Plus, by the way she was staring at his lips he knew she liked what she saw, there was no way he was gonna blow this by telling the truth, “Seventeen.”

“Hmmm, seventeen huh? Really?” She gave him a thorough once over looking a little doubtful but if she didn’t believe him, she didn’t say so.

“How old are you?”

She smiled at that and licked her lips. “Nineteen.”

She commented on his Led Zeppelin T-shirt which led to talking about music and he found they both had very similar musical taste. Dean flirted shamelessly and he was a little surprised when Jasmine flirted right back. He never had a problem getting with girls his own age or even a little older but his mind was blown that a hot nineteen year old babe really seemed into him. After an hour or so of talking and smoking and with his heart hammering in his chest, he leaned forward and softly pressed his lips to hers and she kissed him back. He broke the kiss and put his hand to her cheek and looked at her to gauge her reaction. She flicked her half lidded gaze from his eyes to his mouth and back to his eyes again so he kissed her again lightly touching her bottom lip with his tongue. When she let out a small sigh he deepened the kiss. When they came up for air she suggested that maybe they should take this somewhere else. When he told her he had the apartment to himself and she told him to lead the way he couldn’t believe his luck.

As they entered the apartment she said “So, you said your dad is working out of town. He’s not due back tonight is he?” She sat on the sofa.

He took a couple of his dad’s beers from the fridge and handed her one, “Nah, he’ll be gone for a few more days and my little brother is at a sleep over.” He’d ask Luke’s brother to buy replacement beer for him tomorrow before dad got back. He took a pull from the bottle and sat close beside her.

“So...”

“So...”

He leaned in, cupped the back of her head in his hand and sucked her bottom lip into his mouth. When he snaked his tongue into her mouth she met it with her own eagerly. Soon the kisses became hotter, deeper and more urgent. She swung her leg over his lap and straddled him without breaking contact. All of his blood seemed to rush straight to his dick and he rocked up against her.  He started kissing her neck from just below her ear down to her collarbone and she let out a breathy little moan. He had one hand in the middle of her back and ran the other from her waist over her ribs to her breast feeling her nipple go hard under his palm. When her breath hitched he lightly tweaked it. She ran her hands up under his t-shirt and then tugged on the hem and pulled it up. He raised his arms and let her remove it. Thanks to all of their training he had great muscle tone for his age and she seemed to appreciate it.

“Let me see you,” he said and she pulled her own t-shirt off exposing her tanned skin and pink lace bra. “Damn, you’re hot!” She smiled and dove in for another devouring kiss.

“Should we take this to the bedroom?” she asked and Dean thought he was going to come in his pants right then and there.

“Um, er, yeah, just give me a sec would you, I share a room with my little brother and I just want to make sure it’s not too much of a mess.”

When he got into the room he quickly moved the knife he kept under his pillow and took the knife that was tucked into his boot and put them in the drawer with the gun. He quickly shoved his schoolbooks back into his bag so she wouldn’t see his 9th grade textbooks and did a quick scan of the room. All good.

He returned, took her hand and led her down the short hall. He pulled her down onto his bed and was almost dizzy from a combination of lust, fear and awe. Although he’d done a lot more than other boys his age, this was the first girl he’d had in his bed...in any bed. All of his teenage groping thus far had been rushed and mostly clothed in places like laundry rooms and under the bleachers or behind buildings. He leaned over her, kissed her deeply and slid his hand into the cup of her bra, gently kneading her breast and then pulling the lace back he licked at her nipple. She ran her hand down his flank, over his developing abs and slowly unzipped his fly. When she slid her hand into his boxers he let out a moan. With the stimulation and the thought of where this all might be leading, he had to start cataloging car parts in his head to stop himself from coming. He undid the button of her jeans and when she didn’t protest he pulled down her zip and slipped his hand into her panties. When he felt her wetness he moaned again and when he began rubbing small circles on her clit she let out a small whimper.

She took her hand out from his boxers and pushed him back a little and he thought he had pushed too far until she started to wriggle out of her jeans. Now fantasy was becoming reality as he was pretty sure that he actually was about to get laid. “Jesus,” he breathed and was intensely glad that his dad had given him condoms even though he was slightly embarrassed at the time. He peeled off his own jeans and for all of his bravado he was suddenly struck by nerves. He knew the mechanics of sex, hell he’d had his cock sucked plenty of times but knowing and doing were very different and he really didn’t want to embarrass himself.

Although the only light in the room was coming from the streetlight outside, as Dean was removing his jeans Jasmine could see he was shaking a little and she could see both lust and fear fighting for dominance in his expression. She pulled him down beside her and kissed him. “Oh shit, you’ve never done this before have you?”

Damn, he really, really did not want her to freak out because he was some sort of dorky virgin and leave. “Pfft, of course I have.”

“It’s okay if you haven’t...it’s actually kinda hot.”

For just a moment his swagger broke and she could see the vulnerability on his face. “Well, I’ve done all this and other stuff but no, not all that.” He quickly recovered his too cool for school look. “So, it’s hot huh?”

“Yeah, it really is. So I guess I’m driving then,” she grinned. She pushed him flat on his back and straddled him.  She leaned down and started questioning and kissing “So, how far have you gone?” Kiss. She ran her hand over his rock hard cock. “Hand job?” Kiss. He nodded. Kiss. “Have you been sucked?” Kiss. He groaned loudly and once again nodded. Damn it at this rate he was going to come before the main event so he pulled her hand away. That husky laugh was back. “You worried you’re gonna come?” Kiss.  He blushed but before he could answer Jasmine asked, “How about I suck you? If you come now you’ll last longer when we fuck.”

“Jesus. Fuck. Yeah,” he answered with an involuntary buck of the hips. “Please, suck me.”

Jasmine sat back up, unhooked her bra and brought Dean’s hands up to remove it. She hovered above his crotch and even through both sets of underwear he could feel her heat. She guided his hands to cup her breasts and encouraged him to gently squeeze her nipples and panted when he did. She leaned forward and put her nipple in his mouth and he swirled his tongue around the hard bud. “OK Dean, Drivers’ Ed time, that feels great. Now suck it and then really gently use your teeth. Oh. Oh yeah. Just like that. Now the other one. Hot damn, your mouth should be illegal.” He smiled and flicked his tongue out.

She ground down once hard on his cock and her wetness soaked through his boxers making his breath hitch. She laid her body flush with his and started to slide his boxers off. He opened his legs so she could settle between them. “Mmmm, you’re big.” Then she engulfed his cock with her hot, wet mouth. She only sucked a few times until Dean stuttered, “I’m gonna...” She took him as far as she could and he shot hot and fast and he couldn’t believe she let him come in her mouth! He was breathing so hard he thought he might hyperventilate and then she was suddenly kissing him and he could taste his own jizz. He couldn’t believe how hot that was.

“Have you ever gone down on a girl, Dean?” Even though he had only just come, his cock twitched. He shook his head and said cockily, “No but I think I’m about to.”

He rolled her onto her back and plunged his tongue into her mouth. She guided his head to her breast again and he laved over her nipple, sucking and nibbling like she showed him before. She writhed beneath him and his head was spinning. He was thinking that this was the best night of his whole life! She nudged his head down and he slipped her panties off and settled between her thighs. He looked up at her and her eyes were dark and glittering and he had no clue as to what he should do. He looked at the small dark thatch of curly hair and the shiny wetness and said, “Teach me” and tentatively lapped at the moisture. The lightly musky scent and the salty taste of her making his heart beat impossibly fast and his dick twitch and begin to fill again.

“Mmmm, that’s good” she cooed. He gently and almost reverently parted her lips so he could see her pussy and licked a stripe over the whole surface making Jasmine moan. “Yeah, that’s nice, do what you feel like and then use your tongue like you did with your fingers. Give me your hand.” He looked up at her and stretched his arm out. She took his hand and put his palm to her mouth and made tight little circles and flicking movements over his palm with her tongue and said, “Do that to my clit”. His cock went from half hard to granite hard and he'd never thought it was possible to be this turned on. He licked around her inner lips and pushed his tongue inside her like he was fucking her with it and she gripped his hair and was making sweet little moans so he figured he was doing alright. Then he licked up to where he thinks her clit is and started to move his tongue like she showed him. She moved his head slightly and then gasped and then he knew he’d gotten exactly the right spot.

He flicked his tongue and she asked him to put a finger inside her and when he did he sucked a bit at the same time and she bucked up hard. He had the winning combination now so he just kept it going and pushed a second finger in. She started to pant heavily so he sped up his fingers and flicked his tongue quickly and suddenly she clenched around his fingers, he looked up at her face and she was making a perfect little ‘O’ with her mouth and when she shuddered she gushed her juices all over his chin. She pushed him away a little so he wiped his mouth and chin and crawled up to kiss her. He was achingly hard so when she said, “Have you got a condom?” he almost fell over his own feet to get to his wallet.

He opened the foil pack and remembering everything from health class he rolled it on and looked at Jasmine. She was still breathless from her orgasm and she looked so goddamn hot he hoped he wasn’t going to shoot his load in the first ten seconds. He was past nervousness now and so horny and ready he just wanted to jump her but he leaned forward and kissed her and she smiled and helped guide him inside. It was tight and so warm and he groaned loudly as he pushed in. He started to move slowly, trying not to come and she wrapped her legs around his thighs and he found his rhythm. He was glad she blew him earlier or he would’ve shot his load the moment he entered her. She was moaning and bucking up to meet his thrusts and all of a sudden her body started to stiffen up and she’s dug her nails into his ass cheeks. She held her breath, then shouted “Oh God” and she shuddered again. He could feel her pulsing around his cock as he thrust wildly and then he was coming so hard he thought he might die.

He slumped forward and almost crushed her. She pushed at him and he realized he was squashing her so he rolled off as he grabbed the condom and pulled out. They were both lying there breathing heavy and she whooped, “Wow, you’re a natural Dean. Are you sure you haven’t done that before?” He felt immense pride at the compliment and gave her a big shit-eating grin, “So do you think I’ll get my license to drive now?” They both started to laugh and she rolled onto her side and put her head on his chest, “I think you’re officially off your learner’s permit now”.

When Sam got home the next day he passed Jasmine on her way down the hall. Dean was standing in the doorway in just a pair of jeans.

“What was Jasmine doing here?”

Dean’s eyebrows shot up. “You know her?”

“Yeah, she’s Ryan’s and Melissa’s sitter. You’re not planning on getting her to look after me?” he scowled, “Dad will kill you if you leave me with a babysitter, Dean.”

“Sammy, she wasn't here about you. Jasmine and I were just having a little fun together.”

“What kind of fun?”

Dean smirked and raised one eyebrow.

“Sure, Dean – as if.” He rolled his eyes. “ You're fifteen and she’s in college. You’re so full of it.”

“Whatever you say, Sammy.”

Dean headed into the bathroom for a shower and Sam went into their bedroom to dump his bag and he spied a pair of little pink lacy panties at the end of his messed up bed. Holy cow!

He only knew the basics about sex but it sounded awful and messy and he couldn’t believe Dean had actually done it. Then he screwed up his nose and shouted, “Eeeuw, you’re so gross, Dean! Why did you have to do it in my bed?”

He heard Dean laughing from the bathroom, “Sucks to be you, Sammy!”

Fin

Firsts Part Two - Sam

June 2016

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