14, 18, 22 - Stiles Stilinski (Smut)
Author: @harringtonstilinski Characters: Stiles Stilinski x Reader Word Count: 3,796 Warnings: tiniest bit of angst, fluff, Smut: no | yes; virginity loss, protected piv, Requested: Yes. I hope this meets your expectations! A/N: Hi, friends! It's been a while!! I hope you like this! If you do, please do not hesitate to reblog and give some feedback, whether it be in the reblogs, comments, or my inbox. As always, read at your own risk and enjoy 😊
You and Stiles made a pact when the two of you were 11 years old that if you hadn’t had any “firsts” by a certain age, you’d be each other's first. At first, you both thought it was silly that you were making this list of firsts, but as you sat on your bedroom floor looking at the list of neat and sloppy handwriting at the age of 14, you smiled a little to yourself.
Your bedroom door opening had your head snapping up to see why in the hell someone would bust into your room. The answer came in the form of your best friend, Stiles, practically falling onto your floor.
In between breaths, he said, “Guess… who finally… said hey to me.”
Pretending to think about it, you put your index finger against your jaw, humming in thought. “Let me see,” you said, quietly, tapping where your finger rested. Pointing up while widening your eyes, you said, “Oh! I got it! Scott!”
“Ha ha, very funny,” he deadpanned. “No, I’m serious.”
Sighing, you go back to looking at the piece of paper from three years ago. “Let me guess; Lydia?”
Spazzing out, he said, “Yes! I was walking by her locker and she said hey.”
Looking up confused, you said, “Yeah, she wasn’t talking to you.”
“Ya’know, you don’t have to ruin my moment here,” he said, without missing a beat.
You giggled, still looking at the paper. Stiles sat next to you, looking at the paper as well.
“Oh, wow,” he whispered. “I forgot we wrote this.”
“Yeah,” you whispered back. “I found it last night shoved in the back of my nightstand.” You looked over your shoulder at him, his nose almost touching yours. Hesitantly, you asked, “Have you had your first kiss?”
Stiles shook his head, his eyes locked on yours. “No.” Before either of you knew it, he had leaned forward, pressing his lips against yours. It took you a moment before you kissed him back.
The two of you stayed like that for a moment before you pulled away at the same time. Keeping your eyes closed, you quietly asked, “Why’d you do that?”
“Because you haven’t had your first kiss yet,” he responded just as quietly.
~~~
Graduation day. The day you leave high school… forever. You’re excited about it because that means no more waking up at the ass crack of dawn, no more listening to teachers bitch about students not doing their part, no more fashion contests or popularity contests. Just… no more… for three months.
Stiles turned 18 a few weeks before you and your friends walked across the stage. Everyone wanted to have a joint graduation party at Lydia’s lake house… until a stupid supernatural creature ruined it.
A week had passed between graduation and the party, and while everyone was sitting around the campfire talking about their firsts, all you could do was cast your eyes downward, picking a spot on the ground to stare at as you tried your best to block out the voices.
Once you heard Stiles’ voice, you stood up, tears in your eyes as you walked into the lake house, hearing your name being called from behind you. Making your way up the stairs, you wiped a tear from your cheek that had fallen. Once you made it to the top of the landing, a hand grabbed your arm, gently turning you around.
“What’s wrong?”
Sniffling, you rested your forehead on Stiles’ chest, letting out a quiet sob. “I couldn’t take it anymore.”
Wrapping his arms around you, Stiles sighed and rested his chin on your head. “Couldn’t take what?”
“Hearing you all talk about your firsts,” you whispered.
Stiles put a curved index finger under your chin, lifting your head to look into your tear filled eyes. “You haven’t had your first?”
Shaking your head, you closed your eyes, letting the tears fall. “No. I almost did, but… he wasn’t the right person.” You reached into your back pocket, pulling out a folded piece of paper, holding it up.
Stiles looked at it, a small smile starting to form on his lips. “You carry it with you?”
Nodding, you closed your eyes again to let the tears fall before opening your eyes back up, Stiles’ eyes already on you as you said, “Ever since I found it.”
Without thinking it through, Stiles placed his lips on yours, a sigh coming from your nose. He cupped your cheeks in his hands, carefully walking you backwards into the nearest room, which happened to be the room both your stuff was in.
You made quick work to take off Stiles’ shirt, the two of you breaking apart for a moment to pull the shirt over his head before your lips were back on each other’s only to break apart again for a moment for your shirt to come off.
Stiles looked down at the tops of your breasts that weren't covered by your bra. He looked back up, your eyes locking before he leaned forward, connecting your lips again in heated kiss, his arms circling around your back to hold you to him, your bare stomachs touching.
You hummed at the feeling, wrapping your arms around his neck. Pulling back, you looked at him with a shocked expression, feeling your bra loosen around your chest. “I didn’t even feel you unclasp it.”
Stiles smirked, a cocky one. “I’ve had some practice.”
Your face fell at his words, the confidence you were gaining crumbling to the ground. Stiles noticed and quickly tried to reassure you, “That wasn’t a dig, I’m sorry. It was just–”
His words stopped when you crashed your lips to his again, getting lost in his lips. You didn’t register your bra completely coming off as you made work to unbutton and unzip his jeans.
Slightly pulling away, you kept your lips close to his as you took your bra the rest of the way off, breathlessly saying, “You gotta stop doing that.”
“Doing what?” he chuckled.
“Doing things without me feeling it.”
Laughing lightly, Stiles undid the button and zipper on your shorts as you started to push his jeans down his legs.
Looking at him with an almost serious look that was more laced with humor, you said, “It’s hot as hell, quit.”
Another kiss as he backed you up to the mattress, the backs of your legs meeting it before you fell back on it, crawling backwards on the bed to lay comfortably, your hair splaying out around you. Stiles crawled on top of you, pressing his lips to your stomach every so often before his lips were wrapping around one of your nipples, a moan sounding from your throat.
“Mmmmmm, Stiles,” you moaned, threading your hands through his hair. You looked down at the same exact time Stiles released the bud, only to make his tongue visible as he licked at it. “Fuck, that’s hot.”
Chuckling, Stiles’ forehead met your breast as he laughed at your words. “Let me finish.”
“Then let me continue,” he said, looking up at you. As you nodded, he pushed himself up towards your lips once more, pressing his lips to yours before pulling back, giving your other nipple the same attention.
What you had failed to realize as he kissed his way down your stomach was the fact that your shorts were in a pile on the floor. “Wait, wait.” Stiles lifted his head, eyes swimming with a small bit of fear. Shaking your head, you took a breath. “It’s not bad, just a question.”
He nodded his head, readjusting his hands on the mattress. “Yeah?” “When did my shorts come off?”
He laughed at that, looking down at your stomach. Lifting his head to look back at you, he replied, “When you fell on the bed.”
Your eyes danced around the air above him before you tilted your head to the side a little. “Fair enough.” Looking back at him, you said, “Continue.”
Shaking his head, he looked back down at your stomach, placing a kiss on it. Your nerves started to come up as you watched him wrap his fingers on the top of your panties, anticipating what was going to happen next.
You watched porn before so you knew what to expect, but for it to actually be happening to you was… surreal. The moment that Stiles pulled the top of your panties down a little to place his lips there, you sucked in a breath, the anticipation killing you.
Stiles knew exactly what he was doing. He was fully aware he was taking his time and ultimately teasing you, but he wanted to make this moment with you last as long as he possibly could. Truth be told, he never wanted Malia as his first. She was just there for him in Eichen when Nogitsune possessed him.
He hooked his fingers in the sides of your panties, slowly pulling them down, a quiet “Lift” sounding from his mouth. If you hadn’t been staring at his mouth, you wouldn’t have heard him say it, your body on autopilot as you complied, doing what he asked.
After he dropped your panties to the floor, Stiles placed a kiss to the top of your slit, your breath hitching as he lowered himself, spreading your legs apart, revealing your core to him, your arousal shining. “Damn,” he whispered. He looked up at you, his signature smirk on his lips. “This for me?”
Nodding, you bit your bottom lip, anxious of his next movements.
Stiles looked back down at your core, using his thumbs to spread your lips apart, revealing more of your arousal to him. He moved his eyes to your clit, staring at it for a moment before placing a kiss to it, a hiss coming from your lips.
“Stiles.” It came out in a half moan, half whine. “Do somethi–” A gasp sounded from you as Stiles wrapped his lips around your clit, sucking gently, your back arching off the bed a couple inches. Dropping back down, you moved your head to the side to look at him. “Fuuuuuck.”
He released your clit to lick a long stripe up your core, gathering a little bit of your arousal. “Damn, you taste like heaven.” He licked another stripe before stopping at your clit again, using his tongue to flick at your sensitive bud.
You all but screamed when you felt one of his fingers enter your pussy, a moan sounding out as he slowly pumped his finger in and out before slowly adding another one. Feeling your climax building, you threaded your fingers through his hair, resting your hand on the top of his head.
“Please don’t stop,” you breathed, eyes closing at the pleasure he was giving you. It was way more than you expected. It almost seemed too much. But just as you were about to release all over his fingers, it all suddenly stopped. You looked down at him, shock laced all over your features. “Wha–” The answer that you received from Stiles wasn’t words, but his lips on yours, a promise of what’s to come through the kiss.
He pulled away from the kiss, standing by the edge of the mattress, bending down to retrieve his jeans that you had pushed down his legs earlier. Grabbing his wallet, Stiles looked at you, eyes roaming over your body.
You almost felt insecure with the way he was looking at you. Watching as Stiles grabbed a condom out of his wallet, you sat up, reaching for his cock, beginning to stroke him a little to help keep his erection in place.
Groaning at the pleasure coursing through his body, he closed his eyes, relishing in the feel of your hand on him. What shocked Stiles was the fact that you had slid down the side of the mattress, wrapping your lips around the head of his cock.
Moaning your name, Stiles threw his head back with his eyes closed, not wanting this moment to end. When you hit a certain spot on his cock, he bucked his hips, immediately regretting it when you whined and pulled back.
He looked down at you, making quick movements to help you stand up as your hand was at your mouth. “I’m so sorry,” he whispered, hands on your upper arms.
You shook your head, closing your eyes for just a moment. “It’s okay.”
Stiles moved the both of you to sit on the edge of the bed, hand on your back. Truth be told, when he bucked, the tip of his cock hit the back of your throat, almost setting off your gag reflex. Looking at Stiles, you softened your eyes even more than what they already were. “It’s okay, Stiles. Really.”
He stood, starting to pace, mumbling to himself about how he lost control and that he regretted it. You couldn’t help but chuckle at him, his erection still ever present. Standing, you moved in front of him, grabbing him by the shoulders to stop his pacing, a smile on your face.
When his eyes connected with yours, your smile was still on your face. “It’s okay. I promise. I’m fine. Feeling passed just as quickly as it came.” Looking down at his hands, you grabbed the foil from him, tearing the packaging open to carefully pull the condom from the foil.
Remembering what your sex ed teacher taught you, you carefully rolled the condom onto his shaft before grabbing his hands, pulling him with you back to the bed. “Now, forget about all that and take me.”
Crawling back on the bed, you got into your previous position as Stiles crawled over you, hands on either side of your head to brace himself. He placed his lips on yours, giving you a sweet kiss before pulling away and looking down at your core.
You lightly moaned, closing your eyes, the feeling of Stiles’ fingers back on you like pure heaven. Opening your eyes, you watched as Stiles lined himself up with your entrance, gathering the arousal that had formed during both of his touches.
“Stiles,” you moaned, breathlessly.
He locked eyes with you, softness lacing his caramel colored orbs. “It’s gonna hurt.”
You nodded. “I know.” Carding your fingers through the side of his hair, you sighed. “I trust you.”
He mimicked your nod, giving a chaste kiss to your lips before looking back at the spot where the two of you were about to become one. Sighing in anticipation, you closed your eyes, groaning at the feeling of Stiles entering you for the very first time.
Tears formed at your waterline, the pain almost becoming too much. You hadn’t realized you held your breath upon Stiles entering your core until you felt his hand cup your cheek, his thumb smoothing over your cheek.
What you loved in this moment was the fact that Stiles was letting you take all the time you needed to adjust to his size. He didn’t want to pressure you into telling him to move and that it was okay for him to move.
After a moment, Stiles heard you sigh. “You okay?” he asked.
You looked at him, a tear falling from the corner of your eye to your ear, Stiles making a quick movement to catch it with his thumb. Nodding, you kissed the tip of his nose. “Yes. It hurt at first, but it doesn’t anymore.” Cupping his cheeks, you looked him deep in his eyes. “You can move now.”
“Okay,” he whispered. “I’ll start slow and then you can tell me if you want–”
Chuckling, you said, “Stiles, I know, and I will.”
He breathed a quick laugh, his breath fanning over your face. “Okay. Here I go.” Pulling out slow, the both of you hissed at the feeling before he slowly pushed back in. He kept the pace, listening for your cue’s on whether or not you were in pain.
Once your breathing evened out, your moans turned from almost strained and painful to soft and pleasurable. Stiles moved to rest his forearms by your head, almost cupping the top of your head with his hands.
“Stiles,” you lightly moaned. “You can go a little faster, maybe a tad harder.”
He breathed the word fuck, doing as you asked. He respected you so much, happy that you allowed him this moment with you.
As pleasure coursed through you, your moans grew louder, letting Stiles know that what he was doing was the right move, the right thing. You moved your hands from his cheeks to wrap your arms around his neck, Stiles instantly wrapping you in his arms the best he could.
“Stiles,” you moaned, loudly. “Gonna cum.” Stiles’ pubic hair was rubbing against your clit, sending immense pleasure through you. “Don’t stop.”
“Don’t plan on it,” he whispered. “Let go, babe. I’m so close.”
“Stiles!!” You breathed in deep, your release shattering through you, Stiles instantly releasing with you. Neither of you moved for what felt like hours, but it was only a couple minutes as you both regained your breathing.
Stiles leaned up a little, looking into your eyes. “Are you okay?”
Nodding with a small smile, you carded your fingers through his hair. “I’m perfect. Thank you.”
He kissed your nose in response, telling you that he was going to carefully pull out, the both of you hissing as he did. He walked into the bathroom, cleaning himself up before bringing a warm washcloth to you, carefully cleaning you up. He sighed a little to himself, seeing the tiniest bit of blood on the washcloth.
“What?” you asked, sitting up a little.
“You’re bleeding,” he whispered, showing you the cloth.
Sighing lightly, you said, “That’s to be expected, Stiles. It’s fine. I’m fine. I’ll be sore tomorrow, but I’ll be fine. I promise.”
Realizing that you were right, Stiles smirked that smirk that could kill before nodding slightly, moving to dress himself before helping to redress you. He helped you down the stairs, you reassuring him that you’re not fragile and that you’re okay enough to walk on your own.
When the two of you made it back to the fire and sat back down in your original spots, you looked at Scott, the True Alpha werewolf knowing what just happened between you and Stiles, a chuckle sounding out of your throat as you told him, “Shut up.”
~~~
Another graduation day. This time for you graduating from college. You were more than excited to finally be done with school for what will probably be the rest of your life, if you didn’t find something else to go for.
As all the graduation caps flew into the air, you had the biggest smile on your face, remembering all of your friends and family screaming and hollering and celebrating as you walked across the stage after your name was called.
Since all the guests had to wait outside for the graduate, you were practically buzzing to get outside to see everyone. The friends you made during your four years at college will forever be your best friends, but no one will ever hold a candle to your Beacon Hills friends.
Once you made it outside and spotted your family, your smile stretched so wide across your face, you thought you’d permanently become the Joker. You ran to your family, your mom engulfing you in a hug, holding you tightly to her chest. You hugged your dad next, putting your hand on each one of their shoulders, the smile never faltering as you looked them in their eyes, thanking them for everything they’d done for you this far in your life.
The smile on your dads face had you looking over his shoulder, spotting your friends behind him. Moving to squeeze yourself in between your parents, you all but jumped into Scott’s arms, the Alpha giving you a tight, brotherly hug.
Lydia was next, followed by Malia, Liam and Mason. Sheriff was even there! But you couldn’t spot the one person you wanted to hug more than anything; Stiles.
Looking around, you started to get worried as you heard gasps all around you. “Where’s Stiles?” you asked, looking at Scott.
He didn’t say anything for a moment, just smiled at you before he whispered, “Turn around.”
You did as he asked, turning around, but not seeing Stiles… until you looked down, your spazz of a best friend on one knee, a velvet box in his hand. “Stiles,” you whispered, covering your mouth with your hand. “What?”
“We made a promise,” he said. “A promise as kids that we’ve kept.”
Letting out a quick, breathy chuckle, you said, “It was a pact.”
“Same thing,” he said, a smile on his face. “There were a lot of things that I regretted with that pact, but I’m happy I got to be it for you. For all of it.”
“Wait, what?” Malia asked.
Everyone laughed at her question, you turning to face her. “When Stiles and I were eleven years old, we made a pact that if we hadn’t had certain firsts by a certain age, we’d be that first for each other.” Turning back to Stiles, you whispered, “He was my first kiss, and first time.”
“And I’m now hoping I’ll be your first proposal,” he whispered back, to which you nodded.
“Can you get on with it even though we’re not a couple?” you asked, already buzzing with your answer.
“You’ve made me happy since we were kids, and I would love nothing more than to make you happy for the rest of our lives,” he continued. “Yeah, we’re not a couple, but you know everything there is to know about me. Come to think of it…” He trailed off, looking deep in thought. “I don’t think there’s a thing you don’t know about me.”
“Stiles!” everyone exclaimed.
Looking back at you, Stiles shook all thoughts from his head. “Oh, right, sorry.”
“Just ask!”
“Will you marr-”
“Yes!” you all but yelled. “Now get up so I can kiss you!”
Stiles smiled, standing and wrapping you in his arms. “You didn’t see the ring yet.”
“I don’t care,” you said, cupping his cheeks and bringing his lips to yours. The kiss that solidified your love for the boy you absolutely loved since your first kiss at fourteen, your first time at eighteen.
He pulled back, smiling at you before he opened the box, revealing the engagement ring of your dreams. As he took it from the box, you put your hand out, excited to be his. Once he slipped it on your finger, you looked at him once more, cupping his cheeks again to tell him those three words you always wanted to tell him.
“I love you.”
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A/N 2: hi, friends! let me know what you thought about! again, please do not hesitate to reblog and give some feedback, whether it be in the reblogs, comments, or my inbox.
Additional Notes:
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*Please don’t post my writing anywhere else without my consent. The author of this work will always and forever be @harringtonstilinski.
All characters, story lines, and plot aside from y/n and her storyline & plot, are all of the work of Jeff Davis.
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Posted on September 24, 2023
