Dean One Shots

What If? (smut, plus size reader)

"You getting all dolled up for your date with Dean?"

You turn and scowl at your best friend, who pretends not to notice. She perches on the edge of the tub and watches you apply your makeup. "Don't wing your eyeliner; you'll look like you're trying too hard."

"I am trying too hard. Ugh, does dating have to be so difficult?" You mumble, deciding a small wing would be okay and Liz could bite you if she didn't like it. You smooth your hair, debating between two different shades of lipsticks before deciding on the softer, pinker one.

"It's not hard at all. You're just overthinking it again. Typical Y/N." She teases, but there's no malice in her words. "Do you think he's gonna ask you to be official tonight? This is what, your third date?"

"Something like that, and no, probably not gonna make it official. We haven't even kissed yet." You mutter.

"Prude." Liz feigns disgust, wrinkling her nose up at you.

You roll your eyes and tug on the hem of your dress, wondering if you need to change into something less revealing. You wanted to impress him, not display every curve you had to the entire world.

"You don't need to change again." Liz pipes up, easily able to read your thoughts after a lifetime of friendship. "You look amazing. Super hot. He'll be blown away."

"Yeah, or he'll think I look like a busted can of biscuits. I'm telling you, this dress is too tight. I have a muffin top, and a muffin everything else, too." You whine, pulling at the hemline in hopes of magically creating an extra inch of wiggle room.

The was snug in all the right places, but in all the wrong ones, too. You could hear your mother's voice in the back of your mind: Overweight girls shouldn't wear tight clothing. Overweight girls shouldn't wear a lot of make-up. Overweight girls shouldn't hold out for Mr. Right.

"Dude, your mom's a bitch." Liz supplies helpfully, tossing back her long blonde tendrils.

"Okay, I love you, but it's creepy how you do that sometimes." You frown at her, then turn back to the sink to adjust your dress once more.

"I'm serious, though. You're all up in your head right now. Take a chill pill. Stop worrying about what you can't control." She says gently, coming to stand behind you. "Look at that chick in the mirror. She's hot. She's fearless. She's not gonna let her insecurities rule her life, right?"

You sigh. "Right. I like him, Liz, I really do, but there are too many things that could go wrong with this scenario. I'm giving him the chance to really fuck me up, ya know? This is the kind of guy that could destroy me if he wanted to. I could give this relationship a chance and he could wreck me."

"He's not like your ex. He's sweet and kind. Maybe a little dangerous, but hey, you don't want to be dating another pussy, do you?" She elbows you in the ribs and you giggle, thinking about the first time you and your ex-boyfriend had come face-to-face with a werewolf and he'd run away screaming. So much for all the hunting stories he'd told you.

"No, definitely not. I just don't wanna get hurt again, Liz. I'm already halfway in love with him. It's not gonna take much more to make me fall for Dean completely."

"Yeah, I'd say seven or eight inches, and you'll fall for him, alright." She kids, winking at your reflection. You shove her playfully. "Seriously, Y/N, he's a good dude, and you're an amazing girl. Stop worrying and let yourself be happy for a while. You've had a crush on the dude for, like, ever. He's clearly into you, too. Do something about it."

"I hear what you're saying, but it means nothing." You tease. "I'm just gonna continue to freak out until he gets annoyed and stops calling and everything goes back to normal."