An Archive of Our Own, a project of the Organization for Transformative Works
Umm did someone request a second chapter?
Wednesday and Tyler are forced to complete an English Assignment together, two students that had nothing in common. After Tyler refused to allow Wednesday to write it herself they find themselves working well. Until her distracting fidgeting gets in the way.
An idea for the 'first time' hit me like a fucking storm. I'm not sure yet if it will be a oneshot or end up a series..
But here's what I need from you.
I NEED A LIST OF FIRSTS, AND AGES FOR THEM TO HAPPEN AT.
The general idea, is Reader grows up next to the Winchesters. So I need everything from sweet firsts (first kiss, maybe a first date, as examples), to potentionally kinky ones. It is KINK bingo after all.
I want this to be fluffy, and smutty. Maybe a touch of angst.
Go fucking wild, okay? I want stuff to span a lifetime. YOU CAN NOT POSSIBLY SEND ME TOO MANY FIRSTS. Don't hold back, don't get scared. I want them.
You can comment here, send me an ask, or hit me up on IM. I'll happily give you credit for helping me in the A/N if I use your idea (if you'd rather not, just say no credit, or send an anon ask.)
A/N: So this is part two of the mini series guys! There will be a few bingo squares featuring in the series too. Thank you to my lovely beta as always @negans-lucille-tblr, I really hope you guys all enjoy part two! :) Let me know! If I have missed you off the taglist please let me know and if you wanted to be added to any of my taglists they’re open too :)
Kofi - https://ko-fi.com/mummybear
Part 1 Series Masterlist
After Dean drives away, you take a shaky breath and finally head inside. This definitely wasn’t something you’d expected to happen today, but now he’s all that you can think about. His kisses had been like a drug, your head was still swimming from the effect they’d had on you, and your lips are still tingling.
Unlocking your front door you head inside, still in somewhat of a daze as you walk upstairs and make your way into the bathroom. Hoping that maybe a nice hot shower can clear your mind a little. You quickly strip out of your clothes and climb into the hot stream of water, sighing in relief when the water finally hits your skin. Yet your thoughts are still going back to the time you’d spent in Dean’s car, the way that he’d held you close with those big strong arms, big capable hands that wouldn’t leave your skin, and you swear that you can still feel his touch everywhere; warm, firm and desperate to keep you close. You force yourself to ignore the flutter between your thighs at the mere memory of Dean and his touch, and quickly finish washing up. You step out of the shower on slightly shaking legs, you’re not sure if it’s from the heat of the shower or from the sheer arousal being caused by your racing thoughts.
You wrap yourself in your towel, and head to your room to start getting dressed. You’ve barely managed to get your underwear on when you hear the ping from your phone, telling you that you’ve just received a text. You finish towel drying your hair and toss the towel into the dirty hamper, before going to check your phone.
You’re a little surprised to find a text from Dean - you hadn’t expected one this soon, but that doesn’t stop you from smiling like an idiot at your phone. You open the new message feed, chewing on your bottom lip as you read the messages.
> Hey sweetheart, just thought I’d let you know I finally made it to my hell for the night, so feel free to keep me company😉
You bite your lip as you consider what Dean Winchester’s hell might look like, especially considering that he hadn’t mentioned any plans before he’d left. But you’re glad he’s texted so that you can keep him company, because the last thing on your mind right now is concentrating on any assignments, even though that’s probably what you should be doing. You briefly consider your reply before you type it out.
< Hey Dean, I wasn’t expecting to hear from you so soon… someone is keen 😜 Well what exactly does your hell look like?
You hit send and lay down on your bed, doing your best to get comfortable as you wait for a reply, all thoughts of getting dressed further had been pushed to the back of your mind. You grin to yourself when you receive his reply.
> I am very keen sweetheart 😉 I don’t think that’s exactly been a secret though has it?
> I won’t bore you with details, but I’ve been dragged to some stupid party by a friend of mine. How about you? What are you doing right now?
< Very true Dean, you’ve got me there. Subtly is not exactly your strong suit 😂
< Aww you poor baby! I told you, you should’ve stayed here… As it happens I just had a nice hot shower and now I’m laying in bed texting you 😏
You can’t help but giggle to yourself as you hit send, and you almost immediately see those little three dots appear on your screen to tell you he’s replying. He wanted you to distract him, you’re pretty sure that did the trick.
> You’re such a little tease sweetheart. And not to be that guy but… what are you wearing?😏
< Oh wow 😲 I am shocked! Such a pervert Dean! 😜
> Don’t pretend you don’t love it and there is no way you’re surprised by that!
> And you didn’t answer the question princess…
You look down your body and smile to yourself, feeling a blush burning it’s way across your skin as a thought comes to mind. You’re interested to see just how far you can push him, before he snaps and decides to do something about your teasing. There’s this strange pull you’ve always felt towards him, even if you’d tried to deny it. But since the two of you had kissed that feeling is so much stronger, and dare you admit that you have feelings for a man you can never really have. Soon enough he’ll be leaving your life to take over a business, he’s already told you this can only last a limited time, so why are you so disappointed? You try to ignore the uneasy feeling and decide to lose yourself in the moment, and quickly type out your next message.
< Hmm, I guess I didn’t answer… But I’m sure you’d be terribly bored looking at me right now. After all, I'm only wearing these red lacy panties and matching bra, all alone in bed. It’s very boring 😋
> Fuck sweetheart. Are you a constant tease?
> Can I at least get a sneak peak? You gonna show me what I’m missing?
You bite your lip and squeeze your thighs together. You’d never done anything like this, you’d especially never sent anyone a picture of you like this before. But you don’t want to tell him that. You don’t want Dean to think that he is pushing you in any way, because the truth is you’re tempted to send him what he wants and so much more.
< Hmm… maybe you could try and persuade me to show you. But what do I get in return?
You’re a little nervous as you hit send, but to your surprise his reply is almost instant.
> I’m sure I can find somewhere private to show you just what you do to me sweetheart. 😉 I’m just betting that the real thing looks even better than what I’m imagining right now. Haven’t stopped thinking about that perfect little mouth of yours since I dropped you off, I was hard as a damn rock driving here.
Swallowing thickly as you reread the message for the third time, you can’t help but whimper as the thought of him between your legs rushes through your mind.
> Mmm you’re thinking about it right now aren’t you? Getting yourself all wet and worked up? All I could think about was dragging you into my lap and making you squirm 😉
“Shit,” you whisper aloud to yourself, feeling the blush rising in your cheeks, as you see exactly what he’s describing playing out in your mind, almost mixing with your real memories in that front seat. Chewing your bottom lip, you shakily type out your reply.
< I haven’t stopped thinking about it. Almost had to touch myself in the shower because I was thinking about what we could’ve gotten up to, about what I wish would’ve happened.
< I bet you’d love to know just how wet I am right now? 😏 Well so you know… I think it’s safe to say these panties are ruined now 😏
> Fuck baby. Come on, show me. What I wouldn’t give to have you in my lap right now, need a bit of help to hide just how fucking hard you make me. Instead I’m improvising. I’ll bet you could give me something to focus on, not that it would make my current situation any less obvious 😉
You wish you were with him right now too, just thinking about the fact that he’s hard because he’s thinking about you, and that has your mind running a mile a minute. What was he thinking about? How was he imagining you? What would his reply be to a sexy picture from you? How hard could he make you come?
Nerves grip you tightly as you change onto your camera app. You adjust yourself slightly in bed, wiping your sweaty palms on the duvet as you do. You decide you want to keep your pose as simple as possible, since this is your first time. You find the best angle to take the photo, laying on your back slightly off to the side, you snap several photos and then decide to go through them. Surprisingly you manage to find one you’re happy with. You can see your lingerie perfectly, every one of your curves accentuated just right, and the photo starts at your clamped together thighs, where you can see your thumb tucked into the waistband of your panties, pulling down the edge teasingly, and goes no further than you biting your lip. So at least your face isn’t visible, you don’t need this photo coming back to bite you in the ass if the worst comes of it.
Before you can change your mind, you hit send, and you feel like you’re holding your breath from the moment he receives the message up until you see those little dots appearing. You feel your heart starting to race when those dots appear and disappear several times. Before you can type out another message to ask if everything is okay, you hear your text tone sound repeatedly.
> Son of a bitch! Where the fuck were you hiding all of that?
> You naughty girl 😉😏
> Fuck I always thought you’d look hot in red. Guess that’s my suspicions confirmed. I’d literally kill to bite that lip of yours right now.
> Sorry about the delay. I had to hide in the damn bathroom, you got me fully worked up now. Couldn’t hide this if I damn well tried 😜
You can’t help but giggle at the onslaught of messages, but there’s no denying the blush that stains your cheeks. You weren’t expecting that kind of reaction, not from someone like Dean, who had no doubt seen it all before. Not that there’s any part of you that’s complaining.
< Very glad that you approve, Mr Winchester. Should I be expecting some sort of retaliation then?
> Mmm baby girl, you wanna see what you do to me? How fucking hard my cock is right now… thinking about being anywhere near that sweet pussy of yours.
You whimper at the mere idea of his hard cock being within touching distance, and another wave of arousal washes over you. You’re not sure if you’ve ever been this wet in your entire life.
> Yeah, show me baby, please 😏I want to see what I’m letting myself in for. Wanna see just how bad you’re gonna ruin me for every other man.
Less than a minute later your phone pings, and you open the message immediately, feeling like you’ve swallowed your tongue and lost the ability to breathe, all in the space of ten seconds. His cock is fucking perfect, just like the rest of him. One of his big hands is wrapped around the thickness, and God, it’s thick. You back arches at the mere thought of him being inside you - you’re pretty sure you’ll be able to feel him inside you for weeks after you have him.
< Jesus, Dean! Where the hell have you been hiding that!?
< You’re so big baby, you’re gonna be a tight fit. But I can’t wait to watch my pussy stretch around your thick cock. You gonna be rough with me Dean? Make me scream?
Those dots are back and your heartbeat is in your throat, you can feel the throb between your legs becoming increasingly uncomfortable.
> Such a filthy little mouth. Oh I’ll be rough sweetheart, don’t think I’ll be able to stop myself. Can’t wait to hear you beg for my cock, bet you’re gonna sound so pretty. But I’m not gonna give it to you… not straight away 😏
You quickly force yourself to type a reply, but that’s interrupted when your phone starts to ring in your hand. You hadn’t realised before but your other hand is pressed between your thighs, resting against the thin soaked lace of your panties.
Your breath catches in your throat as you answer the phone and hear his deep breathy voice on the other end.
“Sweetheart? You there?” his voice is ragged, and almost desperate as he speaks.
“Dean, I need you. Come back please? You look like you could use some help with that very big problem,” you moan, barely even recognising your own wrecked voice.
Dean groans deeply, and you hear him moving around on the other end of the phone.
“I can’t baby, I told them I’d stay another few hours. But I promise you the second I get out of here, I’m all yours.”
You sigh and push down the grumble of disappointment.
“It’s okay, I get it, I won’t hold it against you,” you giggle, hearing him sigh in what sounds like relief. “What? Did you think I was gonna throw a bitch fit?”
“Honestly, I wasn’t sure. I wouldn’t blame you if you did, but it didn’t really seem like your style. Thank you for understanding, I promise I’ll be there as soon as I can get away,” he assures you, and you can tell he feels guilty, which of course is madness, he has no reason to feel that way.
“Don’t worry, have fun! Besides it’s not like you’re my real boyfriend, I don’t expect you to ask how high when I say jump,” you laugh, but very quickly you feel like you’ve said the wrong thing.
His laugh is humourless and his reply is very clipped and stiff.
“Yeah, guess you’re right. I’ll see you soon, sweetheart.”
The phone goes dead, and you can’t help but worry as you stare at your phone like it just burned you. You sigh, feeling so many mixed emotions swirl around your head, from lust to disappointment and back again. You pull on your thin lace dressing gown, and head downstairs. You really need a drink to settle you somewhat, especially after all of that excitement. But you can’t help but wonder, had you just fucked up the best thing that had happened to you in months?
