30+ Days of Team Free Will Imagines

Day Twenty

Prompt: Imagine losing a bet so Castiel has to pick out your wardrobe for a week and he gets you a trench coat and suit to match his + Imagine having a laundry day with Castiel and having him strip down to his boxers because those are the only thing that's clean.

Tags: Female!Reader, Castiel/Reader, TWF in their boxers.

......

"Hey, Cas, I bet you can't hit that target from here."

You and Cas are in the gun range in the Bunker's basement, where you have been teaching him to throw knives. He's picked it up surprisingly quick.

"The far one?" your boyfriend inquires. "What do I get if I win."

You think for a moment. "How about this. If you win, you get to pick my outfits for a whole week. If I win, I get to pick your outfits. Deal?"

"Deal."

X X X X X X

"Wait, you bet him what exactly?"

"I bet he couldn't hit the furthest target with a knife."

"And you lost."

"He hit it dead center, so yeah, I'd say I lost."

"And now he gets to pick your clothes for you."

"Yes."

Dean snorts. Sam's lips twitch, but he manages to suppress his smile.

"I'm sure it won't be that bed," the younger brother assures you, patting your arm.

"Probably not, but the suspense is killing me."

"Suspense?"

You startle, having not heard Cas come into the kitchen, and whirl.

"I have laid out your clothes in your bed," he says. "If you would like to go change."

You nod and make your way to your room. You shut and lock the door behind you, and then turn to see what Cas has chosen.

Your breath catches in your throat.

Laid out on the bed in Cas' very precise manner are a white bra and panties set, a white button-up blouse, black slacks and a matching suit coat- both designed for women- and a female version of Castiel's old tan trench coat.

X X X X X X

You change quickly and turn to look at yourself in the mirror. You have to say, you look pretty good. The clothes all fit perfectly and you're beginning to realize why Cas wears the same thing every day. The outfit is actually quite comfortable.

You grab your shoes- sensible, yet still fashionable black slip-ons with the smallest amount of heel possible. Cute, comfortable, and still great for kicking ass. You dab on some makeup and whip your hair up in a cute, professional messy bun. Once you're satisfied with your appearance, you return to the kitchen.

The Winchesters bust out laughing when they see you, but Cas immediately breaks into a huge smile.

"Well," you say, ignoring the two doofuses you call your best friends in favor of your boyfriend. You hold your arms out. "How do I look?"

Cas gets up and wraps a strong arm around your waist, pulling you in for a kiss. "You look stunning," he says, fixing the lapel of your trench coat. "You're not mad? I was worried I had overstepped a boundary."

"I'm not mad," you assure him. "Far from it. I think you're the sweetest boyfriend a girl could ever ask for. I like dressing like you. Beside, this is actually very comfortable. I can see why you're so fond of it."

Sam gets ahold of himself first. He wipes his eyes, still grinning. "You two are so cute it's gross."

"Shut up, Sam. You're just jealous," you tease back.

That only serves to Dean, who had just started to calm down, to bust a gut all over again.

X X X X X X

Dressing like Cas is actually quite fun. Even once the week is up, you keep the clothes and wear them on occasion. It always makes Cas happy.

A few weeks after your week of dressing like him, Sam finds a case. You grab your duffel, the one you always keep packed, and throw together a second bag just in case, including your suit and trenchcoat.

The case, a simple salt and burn, is followed by a series of cases of varying difficulties. Before you know it, you've been away from the Bunker almost a month.

You find yourself, accompanied by the Winchesters and Cas, at a 24/7 laundromat. Lucky for you, the clothes you're wearing are clean. You really don't feel like stripping down to your underwear in front of the Winchesters tonight. It wouldn't be the first time and it certainly wouldn't be the last. You wouldn't mind all that much, except that once the last old lady leaves, the Winchesters begin stripping. They toss their clothes into the washers and pull themselves up onto them. You stare, a little stunned, as the brothers, clad only in their boxers, whip out a pack of cards and begin a game of poker. That's not something you've ever seen before. Obviously Cas doesn't mind, as he just continues what he's doing.

Speaking of Cas.

Your boyfriend is also stripping. You stick the required quarters in your washer and turn to admire the Angel as he undresses. You can't help comparing him to the Winchesters.

Sam is built like a moose and, had you not grown up with him and were he not more like a brother than anything else in your eyes, you would definitely be attracted to him. You take in the miles of tan muscles, strong jaw, and silky locks, and realize that Sam is incredibly handsome.

Dean, on the other hand, is softer in places then Sam. His immense love of burgers and pie, and lack of a regular workout routine- Sam is an intense workout partner- have made him a little softer around the middle than his brother. Still, the older man has powerful thighs and massive biceps, and is in no way unhealthy. Not to mention his brilliant green eyes, chiseled jaw, and plump, very kissable lips. Where Sam in undeniably a sexy beast, Dean can only be described as gorgeous in every way.

Then there's Cas. The Angel is down to white boxers now, seeing as they're his only clean item of clothing, and you feel a stirring in your gut. You pointedly ignore it in favor of admiring your boyfriend. Where Sam is huge and Dean is soft, Cas is all lean, tan muscles. Jimmy Novak, before he was the vessel for an Angel, was a runner. A marathon runner, Cas told you once. You take in the lean runner's legs and golden skin. He rolls his shoulders and a shiver of pleasure runs through you at the way the muscles on his back ripple.

He steps over to where the boys are playing poker and they deal him in. You lean casually against the washer, taking in the sight before you. It's a very pleasing sight, you have to admit. The three of them make quite the trio. Any girl with less self control wouldn't be able to resist. Luckily, you're not just any girl.

"Enjoying the show?" Dean says in a teasing voice.

"Oh, yeah," you respond, moving to wrap your arms around Cas from behind. "This show specifically. You guys? Not so much."

"Hey!" Dean protests, faking offense. "I'll have you know the ladies consider me quite the catch. Sam, on the other hand..." he shoots you a wink.

Sam rolls his eyes. "Stop flirting with Cas' girlfriend and take your turn."

"Yes, Mom."