Supernatural Preferences and Imagines

-.- First Time They See You in a Dress-.-

Images as shown above or to the side...

Dean-

You were on a case. There was a man, vampire to be specific, that seduced women in fancy restaurants. The woman would go in alone, come out with a man. You were going in as bait. You had pinpointed the next target restaurant, but it was very high class, there was no way they would let you in unless you were wearing a nice dress.

You hated dresses, skirts, or anything similar. Your fashion was jeans and a tee shirt, yet, that vamp needed his head burned on a stick.

So, you went out and got a dress fitted. It was a flowing and black that went down to your toes with a slit at the side that went towards your middle thigh. You styled your hair in a not-too-casual not-too-fancy way. All you needed was some black heels and you would be vampire bait.

"I just wanted to say be careful- woah." You turned to face Dean to see that he was sizing you up with awe on his face. "Damn, you look beautiful." He smiled softly as he crossed the room. Once he reached you, he gave you a soft kiss.

Sam-

You two were going out on a date for your one year anniversary. You decided to change things up a bit. Most of your dates were'stay at home and watch a movie' or 'go out to a cheap diner and get burgers,' but this time, Sam was taking you somewhere special. Special enough that you saw him putting on a tux.

You went to your room and looked around for a dress. You didn't really own any dresses, you only wore them on an occasion. Neither Winchester had seen you in one yet...

The dress you picked out was a V-neck flowy navy blue dress that didn't quite reach your knees. You gave a wave to your hair and walked to meet Sam.

"Y/n!" Sam stuttered. "You look beautiful."

Castiel-

For a hunt, you and Cas were going to break in to a high class party to stop a demon said to be there. You both had stolen invitations, but you had to look the part. High class party equals overly fancy outfits.

Castiel had no problem wearing a nice tuxedo, but you didn't own any dresses...

Luckily, you sent Sam and Cas out to find one. What they came back with was a beautiful mermaid style gold dress. Since the clock was ticking down to the time of the party, you slipped into the dress and put your hair up into a sleek bun, applying minimal makeup.

You rushed over to the car you were renting for the night and slipped in. Dean, pretending to be your escort, drove you to the party location.

Cas zapped into the car and did a double take on you.

"You look extraordinary. Gold suits you."

Crowley-

"Love, let's go out on a date."

"A date?"

"Yes, I was thinking Madrid, Spain. We could have dinner."

"Love it."

"We'll leave when your ready."

You walked over to your closet and looked over your dress options. You've never worn a dress around Crowley before...

You settled for a strapless, fitting red dress that sat on your thighs. You putting your hair into a bun and walked out to meet Crowley. His eyes widened immediately.

"You look ravishing tonight."

Gabriel-

You and a couple of your friends decided to have a bar night. They thought it would be fun to 'ditch the guys and have some fun!' They also insisted you wear a dress.

You sighed, looking at yourself in the mirror. Your dress was thin strapped, green, and it seem to flow down to your knees.

"Let's get this over with." You groaned and started heading to the door.

"Where are you going, Sweet Thang?"

"Girls Night."

"I see." You turned around to see that Gabriel was faking a pout. "Don't worry, I'll reserve tomorrow for you and I." You winked and turned to the door again.

"Wait!"

"Whaaaat? I'm already late."

"I just wanted to say, you in a dress equals yowzah."

Charlie-

It was your friend's wedding, she wanted you as the matron of honor. The bridesmaid color was electric blue, your friend said that she wanted you to be in a long dress.

So, you went out shopping with Charlie for the perfect bridesmaid outfit.

You found a few dresses with the right color and went to try them on. First one didn't suit you, but the second one... It was a side strapped dress that fit around your chest then flowed past your feet. The back was silver along with a belt under your chest. You knew this was the right one. You walked out to model for Charlie.

"I [don't really] hate to say it, but you may look more beautiful than the bride."

Lucifer-

"Honey, I'm home!" Lucifer called out. 

You smiled and walked over to greet him, then noticed he had a bag in his hand. 

"What's this?" you asked curiously.

"I was wondering if you would like to go out tonight?"

"Sure!"

"And I was also wondering if you would like to wear this." He reached in the bag and pulled out a burgundy cocktail dress with a vintage neckline. 

"Lucifer, this is beautiful," you gushed, then realized that he had never seen you in a dress. 

"You okay leaving in an hour?"

You nodded, then rushed to your room to try it on.

Once you stepped out with black heels and makeup, you saw Lucifer sitting on the couch, already in his suit. You cleared your throat and he turned to you as you walked down the hall.

Immediately, he paled. His eyes went wide as watched you approach.

"Y/n," he gasped. "You look... beautiful. Absolutely gorgeous!"