Chapter Summary: After receiving some advice from Dean, Y/N makes her own interpretations of it and makes a bold decision.
Chapter Warnings: Fluff and Crack. Mostly Crack.
Disclaimer: Not my gif.
A/N: It’s Week 11 for @supernatural-jackles‘ SPN Weekly Writing Challenge, and I am so happy with this one! Personally I think this is hilarious, but you be the judge. I used both prompts: 1) “Sorry, I thought I was alone...” and 2) “What do you mean you’re sold out?” Which they will be in bold. This chapter was so much fun to write! Hope you guys like it! And Jen, thank you for hosting this weekly challenge! If it wasn’t for this challenge, I wouldn’t have started writing this series :) xx
Ever since the ordeal with Jess, things between you and Sam has been nothing but “cherry pies and blue skies” as Dean had called it. In fact, it was the elder Winchester’s pep talk to you that helped with you to make this decision.
“Look at it this way, Y/N. You and Sam just beat the one of the big bads in any relationship – trust. And now more than ever, you trust him and he trusts you. You guys are on the same page. If you ask me, it’s all cherry pies and and blue skies right now. Things are good. Take it from there and do what feels right. Just like how it used to be.”
Do what feels right he said. What feels… right… Okay. Here goes nothing…
“Hey Sam… I’m ready.”
Sam looked at you quizzically before noticing the seriousness in your stare. Mid sipping on his glass of orange juice, Sam spat the contents out of his mouth, the spray littering all over the table.
“S-seriously?” Sam sputtered, wiping his mouth with the back of his hand. “Are you sure about this?”
“I am,” you smiled. You had never been so sure.
“U-uh… okay. W-wh-when, where, now?” Sam was a mess, face heating up and turning red as he spoke.
“Well, Dean’s at work and won’t be home till late, so we’ve got the place to ourselves, so why not?” You giggled noticing the effects you were having on him.
“Yeah— Yeah! Let’s – yeah,” Sam jumped out of his seat, stumbling over his long legs. “Y-you meet me in the room and—and I’m gonna go get the—the stuff.” And in the blink of an eye, he was gone.
You giggled to yourself, running into his room, jumping on the bed with pure joy and excitement. This was going to be the day. This was going to be your first time ever… and it was going to be with Sam. You couldn’t help the smile stretching across your face. Maybe the two of you would do it more than once? It’s a good thing Dean has more than enough protection.
Sam ran into Dean’s room, shuffling through his drawers in search of what he needed most. When he found nothing, he groaned in frustration. Dean had said they were in his drawer, so where the hell was it now? Sam shifted over to Dean’s underwear drawer, shirts, and closet and couldn’t find anything.
“Where the hell are the condoms?!” Sam growled, his frustrations only adding to his sexual desperation.
“Hey, everything okay in here?” You asked, standing by the door in nothing but his shirt. He could see your nipples sticking through.
Sam gulped, his eyes fixated on you. He knew you were naked under that shirt, ready for him to have you for the first time. If he did this, he’d be taking your virginity. It felt like an honor, and he didn’t want to lose the opportunity. He had never felt this way about any girl before.
“Uh—yeah. I mean… no. Dean’s out,” Sam stated.
“Oh…” that’s okay.
“B—but, I—I’ll just go buy some. The convenience store isn’t that far. I’ll be back.”
“Sam, it’s—”
“Don’t worry. I’ll be quick!” he cut you off.
“But—”
“Don’t go anywhere! I’ll be back!”
Before you could get another word in, he was gone. The roar of his motorcycle filling your ears. You let out a deep sigh, opening your hand and staring at the square foil package in your hand. “I have one,” you mumbled to yourself.
Sam weaved through the road, dodging cars and cutting lanes, when he saw a Gas-n-Sip. He was sure that they would have some on hand. He parked his motorcycle, rushing in. At the front desk was an old guy, so Sam walked up to him. “Hi, umm… do you have any condoms.”
The older man lazily looked up at Sam from the newspaper he was reading before answering. “Sorry kid, we’re all sold out.”
“What do you mean you’re all sold out?”
“It’s exactly what it means. Whataya want me to do? I just work here!” The old man started to get snippy. “Is that all you young folks think about? Having sex? Back in my day, we had to wait till we were married!”
“Sorry,” Sam sighed, before leaving, not wanting to hear the old man go on and on about the olden days.
Hopping back on his bike, Sam headed towards his initial destination. When he arrived, he practically zoomed in, making a bee line to where he would find them. Quickly grabbing the XL package, he hurried to the check out stands, standing in line impatiently.
“Hey Sam!” The cashier greeted. His eyes widened when he saw Charlie. His scholastics teammate and one of your best friends. He had completely forgotten that she worked here. “What are you up to? Where’s Y/N?” She asked with a wide smile.
“Uh…” Sam hesitated. Charlie’s eyes fell to his hand, noticing the pack of condoms clutched within them.
“Oh,” she smirked knowingly. Her grin obviously giving off a teasing tone. In more ways that one, she kind of reminded him of his brother. She was definitely going to tease him about it at school if he didn’t come up with a believable excuse.
“Uh… this isn’t what you think,” Sam laughed nervously, “y-you see… this is for my brother. He—he ran out so… uh... I’m just… he told me to buy these.”
“So you’re telling me, you used all of his so you’re buying the replacements?” She instigated, amused by Sam’s terrible lies.
“W-what? No! No! Me and Y/N… we’ve… we’ve never done it yet.”
“If you say so,” she said, smile still plastered on her pale skin.
After she rang him up, Sam gave his thanks. “Thanks. Uh, Dean will appreciate it.”
Charlie giggled as she watched the lanky teen run off.
You were laying on the couch fiddling with your phone when you heard the rumbling sound of a motor, instantly knowing it was Sam. You smiled with excitement, positioning yourself in a sexy stance. You laid on your side, propping your head up with your hand while the other rested on your hips. You made sure to rise the shirt a little over your hips, and flipped your hair to one side.
As if on cue, the door opened, and in came a shirtless Dean. He was working on his belt when he walked through the door, his pants falling to his ankles before he even noticed you were in the room.
“D-Dean!” You shrieked, sitting up and trying to cover your modesty.
Dean shouted with surprise. “Mother f—Y/N? What the hell are you doing here!” His eyes couldn’t help but wander over your small figure no matter how much he tried to stop himself.
“Dean!” You shouted again, this time in a scolding tone.
“Sorry! Sorry, I thought I was alone... I didn’t see the bike out there,” he finally shut his eyes while pulling up his pants.
“Aren’t you supposed to be at work?” You asked frantically, still flustered.
“I was. But I finished early today. Where’s Sam and what are you wearing?!” Dean was as worse as you. He wasn’t expecting to come home to you wearing absolutely nothing but Sam’s shirt. And the shirt you wore was thin! So… so thin!
Both of you were so lost in your minds and embarrassed that neither of you heard Sam’s arrival. Dean had parked the Impala at the back of the trailer, so Sam didn’t realize his brother was home and came running through the door guns blazing.
“I got the condoms!” He huffed stepping through the door, only to be met with you and Dean. “D-Dean!” Sam yelped in surprise.
Well this was awkward…
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You walked through the halls with a bouquet of flowers consisting of exactly three sunflowers. Hands sweating, heart palpitating irregularly, and with shaky knees you moved closer to Sam Winchester’s locker. He‘d transferred to the school a little over a month ago, at the start of the new semester. Despite being shy and withdrawn, he was the heartthrob of the school, not that he had any idea. This was going to be your strength. You had a few classes with Sam and talked to him quite a few times, which never failed to make butterflies rave in your heart. You knew he had no idea how desirable the rest of the student body found him and you knew he was too shy to ask anyone out. This opened the perfect opportunity. While others waited around for gorgeous, dimpled, eyes like poetry in motion Sam to ask someone out, you were going to strike!
Sam bumped his elbow on the door of his locker. He tightened his jaw absorbing the pain quietly. A few nearby students glanced at him with a sympathetic wince, so he waved awkwardly. You came up behind him with an affectionate smile. It was a private theory of yours that Sam had one hell of a growth spurt as he always seemed to have difficulty measuring distances when he was distracted. Plus, you’d seen some stretch marks on his lower back when he put away his microscope in lab once.
“Hey Sam.” You greeted.
He turned shaking his backpack like Shake n’ Bake to get a thick book that didn’t look like one of your textbooks to settle. Recognition brightened his eyes and he flashed you an earth shattering smile.
“Hi Y/n, what’s up?” His eyes flickered down to the bundle in your hands. “Are you about to meet someone?”
You chuckled shaking your head slowly. You gripped the flowers tighter trying to stop your shaking hands.
“You know, it’s a good thing you’re cute, Sam.” You teased. He tilted his head to the side inquisitively, so you continued with your explanation desperately trying not to notice that people had begun to stop and stare. “These are for you, silly.”
“Wait, what?” His eyebrows lifted, disappearing into his hairline, eye wide. Your heart skipped a beat as he zipped up in backpack and slung it over his shoulder. The air evacuated from your lungs all at once as he reached out for the flowers, an adorable shy smile curling the corners of his lips. His hands paused over yours. He gazed into your eyes searchingly. “Really?”
“Y-yes!” You pushed them into his hands clumsily.
“Wow,” He looked down into the flowers happily. “I’ve never gotten flowers before.”
“Happy Valentine’s Day.” The words jumped from your throat gracelessly.
He grinned, looking out at you from under his bangs as a blush touched the tips of his ears. “Thanks, Y/n. Happy Valentine’s day.”
You sucked in cool air, pushing it past your heart lodged in your throat. “Do you maybe want to do something after school with me? Or later tonight?”
“Sure.”
You blinked. “Sure?”
“Yeah,” he chuckled making your stomach cartwheel and flop, “Let’s go out after school. I’ll find you.”
You gaped. “Oh.”
The first bell rang. Sam passed by you, pausing at your side allowing a whiff of a mix of scents you could never quite place. He touched your upper arm gently, heat rolling off his body.
“Thanks for the flowers, Y/n.” His thumb rubbed your arm, “I’ll see you in class.”
How about the first time Sam had a blowjob? He's at a new high school and the boy who sits next to him in history keeps brushing his leg against Sam's. Friday afternoon after track, the boy leads Sam behind the bleachers and drops to his knees. Sam's confused, but then his dick is being pulled out of his boxers and enveloped by a hot, wet mouth. Sam forgets how to even think for several seconds until he opens his eyes to see Dean standing close by staring at him in shock with burning green eyes.
