Male/Ftm Reader x random

Dean x male!reader

A/n: not proofread. I hope you enjoy anyway!

(Y/n's POV)
I was sitting in the shitty motel room we had rented reading my book. The boys said I want allowed to go on this hunt because I was injured. It was just some stupid broken arm. I could have at least been back up but I understand their concern. Cass has been MIA for a long while and so they couldn't risk me getting more hurt than this. I was mostly just disappointed because it was Valentine's Day and Dean wasn't here with me, I  just missed him.
I was getting pulled back into my book just as there was a knock on the door. I pull out my knife and move the Curtains ever so slightly with the knife to see what it was. It was Dean and, he was holding something.
I holster my blade then open the door. He was holding a small bouquet of flowers and smiling at me.
"Happy Valentine's Day!" He said with a big goofy grin on his face. "I hope you didn't think I forgot." He said when he saw the look of surprise on my face.
"Well, I did think so, just a little.
But thank you for proving me wrong!"
I took the bouquet from him and smelled them. It was wonderful, almost as sweet as candy.
"Thank you Dean darling." I kid his cheek gently then put the flowers on the table. I stand aside and he comes inside. Sam also gets out of the car and comes inside. Dean walks up to me and puts his hands on my hips.
"How's about a date handsome?" He asks, between soft kisses.
I blush a little and nod. I pull him into somewhat of a side hug being careful of my arm.
He hugs me back then as he slides away, he grabs my hand and his keys.
"Bye Sammie, see you tonight, maybe." He says winking at him.
Sam rolls his eyes and picks up the book I was reading, and closes the door behind us. I slide into the impala and Dean starts her up. I smile at him and put my hand on his leg. He shoots me a sly grin then holds my hand in his.
"So, where are we going Love?" I ask him leaning back to get comfortable.
"Someplace special!" He answers with enthusiasm.
Once we start to drive, I pop in a tape and start to sing along to some Lead Zeppelin song I vaguely know. I can feel Dean watching me but I don't care at all.
When Dean shuts off the car we are in front of an antique book store. I smile really wide, teeth and all and look over at Dean. He is smiling watching me. I lean over and to hug him but I hit arm on the seat and pull back in pain.
"Come on Disaster, let's get you inside." He jokes as he gets out and walks to my side to help me out.
Once I am out of the car and into the store Dean practically loses sight of me. Not that he minds too much, he knows I'll emerge when I'm finished.
Meanwhile, I am carefully scanning all of the books until I find a beautiful, hardback copy of Oscar Wilde's "The Picture of Dorian Gray"
I pull it down gently and open it. The spine cracks with age and the pages are edged with yellow. I close it and put it under my arm. As I start to wander again, I find another ornately bound book with the words "Poems by Emily Dickinson" embossed on the spine. I pick up this book and without even looking at it put it under my arm. I walk around a bit more but can't find another book that strikes me so I walk up to the counter and find dean reading a car magazine, some things never change.
I put the books on the counter and reach back for my wallet when Dean steps in and puts his hand on mine.
"I got it." He says and hands the lady some cash. She gives him his change and I pick the books back up again. I smile as Dean holds the door open for me. I walk out and we both slide into the car. I put my books in the back then look to Dean.
"Now what?"
"Now It's dinner time. And I know this isn't the fanciest restaurant and I am sorry for that but I hope it works."
"Dean, I'm sure that you could take me absolutely anywhere and make it a romantic dinner. Remember that dinner back in Tupelo?"
He chuckles and rolls his eyes.
"How could I forget a place like that? And this place is nothing like that, I say it in the way back from the hunt and thought it would be perfect."
Once again, he puts the car in drive and off we go.
After about a half an hour of driving, we pull up to a small Italian restaurant. We both get out and walk inside, a waiter leads us to a table and we sit down.
Dean and I talk about the hunt and where we have to go next. Apparently they have a lead somewhere in Arizona, great, the lands of poisonous bugs and crippling heat. (Sorry Arizona people)
Then our dinner is served and we eat and continue to talk. Once dinner is over we have a bit of dessert, pay, then leave.
On the ride back to the motel I fall asleep as Dean drives. When we pull up to the room he gets out then comes over to my side. He wakes me up and holds my hand as we walk inside. We both start getting ready for bed and he helps me because it's kind of hard to get dressed and undressed your arm in a sling.
Anyway once that is finished we both climb into our bed and hold each other close.
"I know it's not much, but I hope you had a good day." He says tracing my lips with his eyes.
"Oh Dean, it was amazing, thank you so much! We both needed a break and that helped a lot."
"I'm glad you had a good time."
"I love you Dean darling."
"I love you too (y/n)."

___________________________
A/n: day #3. I love dean so much, he is really caring despite what people think. Anyway, I hope you enjoyed and if you have any requests, you can comment them on any of my stories, or dm me!