30+ Days of Team Free Will Imagines

Day Twenty-Four

Prompt: Imagine Dean's reaction seeing you in a dress when you two have to go undercover as a couple to a fancy event.

Tags: Dean Winchester/Reader, Female!Reader, Self-conscious!Reader

......

You look ridiculous.

You self-consciously smooth your dress for the hundredth time, staring at yourself in the mirror. Sure, the color suits you and the fit is nice, but you've never liked the way you look in dresses. This one is a floor length sheath in a rich, deep purple. It's gorgeous, but not on you.

Sadly, though, neither of the boys can pass of as women and they would rather not pretend to be a couple for the evening. Which leaves you the task of being Dean's date, a job you wouldn't have a problem with if not for the dress code for the event.

You sigh, double checking your hair, and step out of the motel bathroom.

"Well?" you force out, spreading your arms. "How do I look?"

Dean is sitting on the edge of the bed tying his shoes. He finishes up and stands, and you're pretty sure you've died and gone to heaven. Except your Heaven definitely wouldn't involve you wearing a dress.

The tux fits like a glove, emphasising the lean curves of his body and the broad sweep of his shoulders. His eyes look even more green than usual as they sweep over you and his jaw drops.

Your stomach sinks. He hates it. You knew he would. "I know, it's awful on me. I would change if I-"

"What are you talking about?" he says. "Y/N, you look absolutely stunning." He lays his hands on your hips. "It's taking all of my self control to not tear this off of you right here, right now."

"You do realize I'm still in the room," Sam announces from his spot at the motel room table.

"Technicalities, Sam. You're ruining the moment."

You giggle at that, feeling the knots in your gut untwist. "You really like it?"

"I love it. You should wear dresses more often." He kisses you softly. "Someone's going to have to get a different room tonight, because I don't think I'm going to be able to help myself after the party."

"Yeah, yeah, I can take a hint," Sam grumbles. "You two had better get going. Otherwise you're going to be late."

"Shall we, my lady?" Dean says with a sly grin, offering his arm.

You happily loop your arm through his. "We shall."

After tonight, you may in fact wear dresses more often.