Requested by: Ashlyn_upchurch imagine it's your first date and your brothers go to the extreme.

You've been waiting for this moment ever since you were 6. Getting dressed up, wearing fancy clothes, and going on your first date with a guy you actually like. In the past your date was either a trap set up by your brothers, or the guy turned out the be an absolute pig.

This time you were determined to live out the first date fantasy. You stare at yourself in the body mirror loving yourself for once. You smile as you push a curl over your shoulder and add lip gloss as the final touch. You sit on your bed taking out your favorite pair of heels and putting them on.

You stand back up giving yourself a last glance over before walking out. You hear your heals clatter as you walk down the hallway towards the main room. Your brothers stare at you as you spin around in your dress smiling.

"Wow," Sam smiles giving you an approval nod.

"Oh no go change; it's too revealing," Dean crosses his arms like a judgmental grandma.

"It's fine Dean he's going to be here any minute," you roll your eyes grabbing a juice from the fridge.

"He's coming here," Sam straightens a slight of panic rising in his voice.

"No silly I'm meeting him at the motel up the road. It's kind of hard explaining why you live in what seems like a sewerage entrance," I grab my set of keys unlocking the door.

"You need us to drop you off," Dean asks taking a step from the counter.

"No! I'm good you guys stay here," you emphasize on the stay.

Dean sighs leaning against the wall. You save goodbye and walk outside.

You grab your bike taking off your heels placing them in the basket. You make your way to the motel thanking God it's not raining.

~~~~~~~~~~~~~~~~~~~~~

You sit in the booth facing C/N (crush's name. If you don't have a crush make up a name).

"You look beautiful tonight," he speaks up breaking the comfortable silence.

"Thank you. You don't look bad yourself," you reply hating the words that came out of your mouth.

Your not good at this whole flirting thing and didn't know where to start. This would be a great time to have a mom to help you out with this situation.

"So what do you plan on getting," He asks holding up his menu looking at the bunch of choices.

"Probably a bacon cheese burger or some ribs,"
You reply shrugging your shoulders.

He looks at you raising an eyebrow surprised.

"Oh uhm I mean a salad," you mumble pulling the menu in front of your face embarrassed.

He chuckles lightly pushing the menu back down so he sees your red face.

"I like a girl who isn't afraid of being herself," he leans back in his chair smiling.

You chuckle taking a sip of your lemon water.

"Okay you love birds ready to order," you hear the waitress say.

You look to see Dean dressed as a girl with a whole bunch of makeup on his face. He blinks at you innocently getting his pen ready. You sigh mentally face palming.

"Yeah I'll have the chicken breast with a side of a baked potato please," He hands Dean the menu giving him a friendly smile.

"Sounds good and for you ma'am," He looks at you shifting his weight back and forth.

"She'll have the bacon cheeseburger with a side of curly fries," C/N cuts in before you could mumble out your order.

You look at him smiling and he hands your menu to Dean.

"Sounds delightful your order will be out soon," he flips his wig out of his face and goes to walk away.

He stumbles a little in his heels but manages to walk in the kitchen.

"Well she's an odd one," C/N chuckles grabbing your hand which directs your attention back to him.

"Very odd," you grin staring in his E/C eyes loving this moment with him.

"You know I have to be honest with you Y/N; I've never felt like this with anyone before I don't know how to handle it," he chuckles holding your hand tighter.

"I feel the same way," you admit leaning in closer to him.

He leans in closer smiling and closing his eyes. This is it, you're about to have your first real kiss and nothing else mattered in the world.

"Would you like to have some butter with your lobster," you hear a high pitch voice ask interrupting your special moment.

You look to see now a Sam dressed as a woman patting his eyes holding out some melted butter.

"We didn't order any lobster," you smile with gritted teeth.

"Oops wrong table my bad," he chuckles walking away almost falling over his own feet.

You let out a breath turning back to C/N.

"Sorry," you laugh pushing a strand of hair behind your ear.

"You have nothing to be sorry for," he puts his hand on the side of your face and pulls you closer.

Inches away from his lips you hear someone clear their throat. You were in the mood to murder your brothers. You lean back in your chair watching as Dean places the food in front of you guys.

"Anything else," he claps his hands together looking at the both of you.

"We're all good here," C/N smiles looking at Dean.

"Okie dokie," He turns walking back into the kitchen ignoring the other customers request.

You dig into your food not saying much to each other.

~~~~~~~~~~~~~~~~~~~~~

After the meal and everything gets paid C/N takes your hand as you both walk out of the restaurant.

"Want to take a stroll through the park," He asks.

"Sure," you reply as you both get ready to cross the street.

You guys talk about everything as you walk around the park. He stops you under the light post pulling you closer to him. You smile wrapping your arms around his neck leaning into kiss him.

This was worth the wait, kissing under the stars is all you ever wanted. He leans in and finally without no interruptions your lips touch and sparks go through your whole body. You smile kissing him deeply and passionately.

He picks you up spinning you around and setting you back down. You laugh breaking apart from each other.

"I have wanted to do that with you ever since I met you," he admits pushing a strand of hair behind your ear.

"I-," you get cut off my Dean yelling your name from behind.

You turn to see your brothers in the car staring at you.

"I'll text you," you step backwards smiling at him.

"I'll be waiting," he smiles back letting go of your hand.

You turn away biting your lip and walk to the car. You take a quick peak behind to see him pumping his fist in the hair like he's celebrating. You chuckle to yourself getting in the back of the car.

"How was your date," Dean asks still having some left over lipstick on his lips.

"Like you wouldn't know," you tried sounding angry but you were too happy to care.

"I have no idea what you mean," he pulls away heading back home.

"You still have left over lipstick," you chuckle looking back at the your now favorite park.

Sam laughs and Dean smudges the lipstick even more. As you travel home you can't help but wonder how long this relationship would last.