decided to write the boys a little vacay :) even tho i hv like 5 other imagines planned i need to do first but wE doNt tAlk abOUt tHaT. also im sorry if writing parts is annoying pls lmk if they are.

Dean and Sam have never been to the beach, which was odd to you since you mostly grew up in Florida before Bobby took you in when you were ten, and you practically lived on the beach. Finding some free time between cases you decided to book a fancy hotel for the four of you, including Cas. The angel was hanging around the bunker, not really knowing what to do with himself so he mostly helped with cases. You found a nice hotel with a pool and bar and the whole deal in Miami, which had it's own private beach. You spent some time reading all the reviews and making sure everything was included in your stay, meaning free drinks and food and not to mention, parking. Finally deciding on this hotel, you booked two rooms, one for you and Dean, and the other for Sam and Cas. Their room has two rooms, a bed in each room and of course a bathroom, while yours and Dean had a king sized bed and an overly fancy bathroom. You smiled to yourself, glad to be treating the boys to a much needed vacation. You paid for all this with real money, money that your rich parents left you when they died. You mostly saved it for emergencies like hospital visits and such, but you were sure a couple thousand wouldn't be missed. After booking the hotel for three nights and four days. you moved on to shopping sites, were you were planning on buying swimsuits for yourself and the boys, along with other much nicer dinner attire. Dean walked in on you laying stomach down on the bed, shopping for clothes.

"Whatcha up to?" Dean said, putting some laundry away in his drawers.

"Nothing much." You replied smiling. You found a cute pair of swim trunks for Dean and moved your laptop to show him.

"Do you like these?" You asked him making his raise his eyebrows.

"Black ones would be nicer but why ask?" He said, sitting on the bed besides you.

"Whats your brothers pant size?" You asked him, ignoring his question. Dean leaned down to kiss your neck before pulling away to look at the screen.

"Why do you need to know?" He asked, his eyes scanning the screen until they landed on the open tab of the hotel.

"Venture Hotel? Are you planning some getaway or something?" Dean asked, seriously curious now.

"Maybe." You said, sitting up and grabbing your laptop to place it on your lap.

"Y/n, what are you planning?" Dean asked you placing his hand over yours, which was scrolling through Calvin Kleins mens swimwear.

"A vacation." You said with a wide smile, clicking on a pair of twin trunks, showing them to Dean.

"Your kidding right?" He said, slightly angry.

"Your mad?" Y/n could tell from his tone and she shut her laptop.

"Y/n people like us don't get a vacation. Sam found us a new case we were going to leave tomorrow. We have to save people." Dean said calming his tone when he saw the sad expression on Y/n's face.

"Dean, it's only three days. Please, we need this." You begged him, putting your hand on his thigh while poking up at him with puppy eyes, making his eyes roll. You were definitely winning this argument.

~

"I can't believe I'm driving the four of us to Miami." Dean said from the drivers seat of the Impala. You smiled widely, the wind whipping through your hair. For once, the trunk of the Impala was packed with bags of clothes and vacation necessities instead of weapons. You had convinced Dean to this a few nights ago, which actually resulted him in being secretly very happy. Sam, Dean, Cas and you spent the rest of the night blowing through your parents money, buying anything you wanted. No limits you had told the boys.

"C'mon man, we need this." Sam told his older brother, smile evident on his face. Dean chuckled before turning on the radio and singing along to a rock song, to which you and Sam joined.

~

Arriving at the grand hotel, a worker approached you, helping you unload your bags from the trunk. He even complimented Baby, which was already putting Dean in a good mood. On the way in Dean grabbed an overly excessive amount of mints, showing them into his jacket pocket. You told them to wait while you checked them all in, Sam ended up coming to your side to check up on everything since it was taking quite a while. You told him it was nothing, and moments later you were presented with four key cards, two for you and Dean to your room, and two for Cas and Sam.

"Lets look at the rooms!" You said excitedly, heading into Sams and Cas's room first. They had a nice hotel room, with two separate bedrooms and a main room. They also had a balcony which had a view of the ocean.

"This is very nice, thank you Y/n." Cas said, smiling while he watched the waves crash onto the beach.

"Don't thank me yet. Do you guys wanna check out our room?" You asked them, while Dean toyed with the swan shaped towel.

"No I think I'll just settle in, Cas?." Sam said, putting his bag down on the floor in one of the bedrooms.

"Me too." Cas told you and you nodded.

"Since dinner is soon, let's all meet at eight by the fountain outside. Dress nicely." You told them before taking Deans hand and leaving their room.

"You've been awfully quiet, is something wrong?" You asked Dean while you two entered the elevator.

"Do you wanna go for a swim at the beach after dinner?" Dean asked smiling, pulling you in by the waist.

"Sure, do you want Sam an-."

"Just us." Dean said lowly and the elevator doors opened. The two of you waled to your room and you opened it, welcomed with the fresh ocean breeze from the open balcony also with a view to the beach. The bed was big and soft and a couple of towel laid there.

"Maybe we should redecorate the bunker to look a little- fresher." Dean admitted, running his hand along the white walls.

"Or maybe we should just go on vacation more often." You said, walking up to him and wrapping your arms around his neck. He dipped his head to kiss you.

"I love this." He said against your lips after pulling away a bit.

"I love you." You said making his eyes light up.

"I love you too." He said back to you before pulling you into a deep hug and inhaling the scent of your hair.

"Dean, we should probably shower before we go out." You said into his hair.

"Together?" He asked, making you roll your eyes and pull away.

"I have to shave." You told him before walking to your bag to get all your shower products.

"I'll help." Dean said, trailing after you.

"You'll only distract me." You said louder before grabbing a towel and walking into the bathroom.

~

"Dean, just wear the suit please." You begged him, holding it out for him.

"I'm not making you wear that dress you cant make me wear the suit." You huffed before sitting on the bed in your tight dress. Your curled hair fell over your shoulder and the heels you had put on already stared to make your feet hurt.

"All I wear is a suit on the job, and this burgundy tie is ridiculous." He said pushing it to the side. The tie had matched your dress and for once you wanted to go out as a couple.

"So you're gonna wear your stupid flannel." You said, slightly upset.

"Just jeans and a nice shirt."

"Dean that's not fancy Italian dinner clothes. Please just wear it." You said, the hurt clearly in your voice. All you wanted was to look good with him and seem normal to others.

"Y/n..."

"Fine whatever, we're not going." You said, taking your gold earrings off and throwing your heels aside. It was just a suit, why didn't he just want to wear it.

"No, no, no wait I'll wear it I'm sorry." He said, taking the suit in his hands. You rolled your eyes and laid on the bed, slightly stressed you were going to miss the dinner reservation.

~

Finally, Dean got his act together and cleaned up quite nicely. The two of you left the hotel room and you slipped the card into your black purse that matched your black strappy heels. Your burgundy dress was backless and had a low front plunge too but it covered your arms all the way. It went down until mid thigh and this was probably the most scandalous thing you've ever worn.

"You look stunning." Dean told you while the two of you stood in the elevator going all the way to the lobby. He held your hand when you two walked out of the hotel going to stand next to the fountain outside, where Sam and Dean already were. Cas wore a suit that looked much crisper as usual, but still wearing his trench coat. Sam had a suit on with a bowtie and his hair looked neater then usual.

"Y/n you look beautiful." Sam told you, smiling at you and Dean.

"You don't look too bad yourself Sammy." You told him, jokingly slapping his arm. Dean protectively wrapped his arm around your waist before you walked to the Italian restaurant on the hotel of the property, but you had to pay unlike the buffet that was free.

~

Sitting around the round table, Dean was on your left, Sam on your right and Cas across you. Everyone had their noses buried in the menu's and you smiled, seeing as everyone was relaxed for once.

"Man I just want some chicken." Dean said and you leaned over to look at his menu. You pointed to something you had seen and thought he'd like it.

"I think you'd like this." You said to him and he kissed your cheek as a thank you. Everyone ordered, even Cas ended up getting food although it all just tasted like molecules to him. He ordered spaghetti and meatballs, amused with the shape of it.

"What are the plans for tomorrow?" You asked the boys, wondering what they'd want to do on their first official day of vacation .

"Beach." They all said in unison and you threw your head back laughing. They laughed along too when eventually you settled down when the bottle of wine arrived. The waiter opened it, pouring some into everyones glass. He made eye contact with you for a little too long then you felt was comfortable and you shot Dean a look. He furrowed his eyebrow before placing his hand on your thigh for the waiter to see. Sam and Cas started conversation making the table less quiet and eventually the food came, you all started to eat.

"This is so good." Dean practically moaned while shoving another forkful of his food. You giggled, bringing up another topic to talk about while the four of you ate and drank your wine, genuinely having a good time. The air was filled with laughter and positive energy when you signaled to the waiter for another bottle of wine.

"Do we order dessert?" Cas asked making you smile.

"Pi-." Dean started before you stopped him.

"I swear to god if you say pie." You warned him.

"Tiramisu?" He said carefully, watching for your reaction.

"Better." You said back to him making him sigh as Sam laughed. The dessert menus came and you and Dean ordered tiramisu. He was too scared to get anything that even resembles pie.

"I'm glad we decided to do this." Dean said, raising a wine glass for a toast.

"To us." Sam said, raising his glass.

"And to many more years of us." You added, tasing your glass. Cas raised an eyebrow but did it too and you all clinked your glasses to a toast.

~

You groaned taking your heels off, feeling tired and tipsy from the wine.

"You still up for a swim?" Dean asked, taking his suit off.

"I'd love to Dean, but i'm still exhausted from the road trip." You said, knowing he'd be slightly upset.

"That's okay, truth be told the wine made me drowsy." You yawned right after he said that, making him chuckle. You took your jewelry off, following with your dress which caused you to walk wound the room in your red panties. You bent down to get some clothes and makeup wipes from your bag. You pulled on and oversized t-shirt over your bare body.

"So no hot hotel room sex tonight?" Dean asked jokingly. You smiled at him, taking your makeup off in the mirror.

"As much as I want you to screw my brains out on the balcony, tomorrow." You said, throwing the dirty makeup wipe off and going to use the bathroom. When you were back, Dean was already in bed, checking some things on his laptop. He wasn't wearing a shirt, only his boxers. You pointed at the small lamp on the nightstand and he turned it on before you turned the lights off. You got into bed with Dean, laying your head on his shoulder while he answered some emails.

"Deannnn." You whined when you realized they were emails from hunters that were just filling him in.

"I know I'm sorry but I have to." He said before checking one last email from Garth that was sent a while ago. He had sent Dean a picture of him and his wife with a very long paragraph, probably filling him in on basically everything.

"Looks like Garth is happy." You said reading the email with Dean. He chuckled, glad at least one of our friends was still alive and well.

"We should send him some pictures. And reply to his email." You said to him. Dean nodded, typing up a storm back to Garth.

"Tell him we're all on vacation and we wish he was with us." You ordered Dean, and he did, adding in some more things to say about you such as "I never knew Y/n looked so good in a dress." You laughed at this and so did Dean. Finally he sent the email and shut his laptop putting it on the nightstand. The two of you layed in the same position for a but before he turned around to spoon you.

"Goodnight." He whispered against your hair and you yawned.

"Goodnight Dean."

wc-2400

guys pls lmk if writing parts is annoying or if i should continue bc tbh i dont wanna bore anyone so pls lmk :( dont forget to vote and comment <3

also i edited the red tie on so thats why it looks off

and thank you for 300 reads although half of them are probably my own