Pretty Boy: Dean Winchester x...

By TurnTechCosplayer

6.9K 194 23

(Y/n) needs a night off after almost being jumped by two vampires so she heads to the closest bar. She meets... More

Chapter 1:
Chapter 2:
Chapter 4:
Chapter 5:
Chapter 6:
Chapter 7:
Chapter 8:
Chapter 9:
Chapter 10:
Chapter 11:
Chapter 12:
Chapter 13:
Chapter 14:
Chapter 15:
Chapter 16:
Chapter 17:
Chapter 18:
Chapter 19:
Chapter 20:
Chapter 21:
Chapter 22:
Chapter 23:
Chapter 24:
Chapter 25:
Chapter 26:
Chapter 27:

Chapter 3:

446 11 4
By TurnTechCosplayer


Dean's P.O.V.

We waited anxiously in the waiting room for any news on (Y/n). I'm pretty sure she was in shock, so when the giant oaf of a vampire fell on her she didn't feel much, thank god. Honestly, I don't know how she stood up. We hadn't noticed it before when we were looking at her tooth, but I'm pretty sure she had a punctured lung from that oaf's claws, or maybe a broken rib that punctured it. She was severely fucked up. None of the nurses had told us anything, but we had some experience. One of the nurses came out of the back and hurried over to us. Sam and I moved to the edge of our seats, expecting to hear something about (Y/n).

"Sir, come with me, your cheek and forehead need stitches." She said to Sam. He reluctantly followed her after looking down at me. I got up, heading to the snack machine, getting myself a chocolate bar. I sat back in the waiting room just in time for a nurse to head over to me, she handed me a shit ton of paperwork.

"You came with (Y/n)?" She asked.

"Yeah, but we just met." I said, looking up at her.

"Just fill out what you know." She said, hurrying away. I skimmed the document. I filled out the basic stuff, name, age, sex. Allergies? The only allergy we talked about was the one we had in common, cats. Nothing important though. I felt horrible not knowing anything about her and not being able to do anything about it. When we got out of here I swore to myself that I would learn everything about her. The first thing I noticed about her was her voice then, obviously, the Metallica shirt. But her voice was beautiful. I could talk to her for hours, and I did. But I didn't know enough to fill out this damn form. I handed the nurse the form after filling out what I knew and by that time, Sam was going back to the waiting room. We plopped down next to each other and I opened my candy bar. Sam broke off a piece, eating it.

(Y/n)'s P.O.V.

I woke up, looking around. I could feel a bandage tight on my nose and a cast on my leg. I tried to wiggle my toes only to see that I couldn't. I must have a nerve block. I took a deep breath and my chest ached. I looked on either side of me. On my left was Sam, asleep in an armchair. On my right was Dean, holding my hand and watching the TV. I squeezed his hand gently and he immediately looked up at me.

"(Y/n)..." He murmured.

"Hi." I murmured. He stood, pressing a gentle kiss into my forehead. I smiled and Dean smiled back at me. I moved my tongue, finding a hole. I gasped and looked up at Dean, "M-my tooth!" I said.

"The nurse said that they couldn't fix it and that you needed to go to a dental specialist." Sam said, now awake. All I could do was laugh. The boys chuckled with me.

"Don't worry, you're still the most beautiful girl around." Dean murmured. I smiled softly and he leaned down to kiss me. His lips touched mine gently, making sure not to hurt me.

"What all happened?" I asked.

"Punctured lung, broken rib, broken ankle, broken nose and fucked up tooth." Sam said. I flipped him off with my other hand.

"So when am I getting out of here, and when am I getting to the dentist?" I asked.

"You're getting discharged today and we'll get you to a Dentist sometime soon." Dean said.

"Do you want to go with us?" Sam asked.

"And get better moving from trashy hotel room to trashy hotel room? No thanks."

"Well where else would you go?" Dean asked.

"My house." I said.

"Your house?" Dean asked.

"Yeah, my house is in Tennessee." I answered, looking up at him.

"I knew I heard a slight accent." Dean said with a smile. I rolled my eyes.

"That's really far from here, though." Sam said, looking at Dean, "We're closer to South Dakota." He murmured. I looked up at Dean, confused.

"Would you be willing to stay with our friend, Bobby?" Dean said, looking down at me.

"Singer? Hell no, that guy hates me." I said.

"I'll call him." Sam said, heading out of the room. I groaned and looked back up at Dean.

"Bobby? Really?" I asked.

"He's your best bet." Dean said, kissing me gently.

"You're pretty." I said, looking up at him. I reached up, placing my hand on his cheek.

"You're pretty." He said back. I ran my fingers through Dean's hair as he sat next to me on the hospital bed.

"Are you guys done with your sappy shit?" Sam asked, leaning in the doorway. I chuckled as Dean's face reddened slightly. Sam came in and a nurse followed.

"I'm here to discharge you." The nurse said, flashing me a pretty smile. Her hair was long and dark and she was beautiful. I think Dean saw the sparkle in my eye when I looked at her. Dean cocked his eyebrow at me as I signed the paperwork. The nurse left and I sat up, immediately in pain. I landed back on the pillows.

"I need to get dressed." I murmured.

"I'll go get the car." Sam said, leaving Dean and I alone.

"So her?" Dean asked. "I didn't know you liked women." Dean said, pulling the hospital gown over my head. My nipples hardened immediately after they were exposed to the cold hospital air. "Damn... didn't see those yesterday..." Dean murmured. I smiled faintly, covering my breasts as he handed me my bra. I shrugged it on and Dean clipped it for me. I adjusted it and Dean helped me into my tank top and then moved the blankets off of me. He helped me into my underwear, stretching them over my cast. I stood up on my good foot and Dean pulled them all the way up as I held onto his arms for support. My leg had been cut out of my jeans. I sat back on the bed and Dean pulled my pants on. I stood back up and he pulled them on the rest of the way. He buckled them and zipped them up. Dean wheeled over a wheelchair and I sat down in it. Dean wheeled me out of the hospital and to my waiting car. He and Sam helped me into the backseat and I relaxed into it. My car smelled amazing. Like fresh coffee, that wasn't its normal state. I looked down to the cupholder. I had the cupholders installed, custom. All the hardware inside the car was gold. The seats were dark blue leather. In the cup holder was a Starbucks cup.

"You told me last night that your favourite coffee was an iced caramel macchiato, so I had Sam get one in the lobby." Dean said, looking back at me. I smiled as he handed me the drink.

"Thank you." I said, taking it and having a sip.

"Okay, so the plan is, we go back to the motel, pack our shit, and Dean drives you to Bobby's while I take our car to Bobby's." Sam said, looking back at me as they climbed in.

"Got it." I said, flashing them a smile. They drove us back to the hotel and they left me in the car while they gathered up my stuff. They hurried back out, putting it in my trunk.

"Did you get my makeup?" I called.

"Yeah." Dean said back.

"Hand it to me, you can't put it in the trunk. I don't want it to melt." I said. I could almost hear Dean roll his eyes. "Dick." I scoffed

"Bite me." Dean answered, poking his head in the door and handing me my makeup bag.

"Oh I will." I said, winking at him.

"Yeah and I'm gonna have little snaggletooth bite marks all over me." Dean said, hopping in the front seat.

"Not funny!" I said with a small chuckle, hitting his shoulder lightly. I could see Dean smiling in the rearview mirror. "You're pretty." I murmured. He looked in the mirror, meeting my eyes.

"You're pretty." He said with a sweet smile.

"I wanna kiss you, but I can't move." I murmured back.

"Sorry, Snagglepuss, we gotta get you to Bobby's." He said, "Then you're gonna get some more happy pills." That must be why I was feeling so weird. Dean pulled out of the parking lot and onto the road. He drove for about 20 minutes until I realised I had to use the bathroom.

"I gotta pee." I murmured. Dean let out a groan.

"Piss your pants." He said.

"Fuck you, just find a rest stop." I said, shoving his shoulder again. Dean did as he was told, pulling into the nearest rest stop. He opened my trunk, pulling something out that I didn't even know he had. It was a wheelchair from the hospital. "You stole that?" I asked as he helped me out of the car.

"You needed it." He said, flashing me a smile. He locked my car and wheeled me into the service station. The bathroom was a single bathroom thank god. Dean wheeled me into the bathroom.

"I think I've got it from here, turn around." I said. Dean did as he was told and I locked the wheelchair's wheels, standing on my good leg. I heard someone knocking on the door.

"It's Sam." Sam said through the door. I unzipped and unbuckled my pants

"Don't let him in." I said to Dean.

"Obviously." Dean muttered as I did my business.

"Everything okay in there?" Sam asked.

"Yeah." Dean said, "(Y/n) had to pee."

"I'm gonna get you guys some food." Sam said.

"Okay." Dean answered. I finished my business quickly but I couldn't get my pants buttoned and zipped.

"Dean..." I said.

"Yes?" He asked.

"I need help." I murmured.

"Can I turn around?" He asked.

"Mhm." Dean zipped and buttoned my pants for me and helped me back into the wheelchair. I washed my hands and Dean wheeled me out. Sam was paying for snacks at the front counter. Dean wheeled me over to Sam and I kicked him in the shin with my good leg.

"Ow! Pegleg Pete!" Sam said. I laughed as I looked through the snacks. He got my favourites, beef jerky and a Toblerone. I smiled and took my food after Sam paid.

"I'll pay you back." I said. Sam smiled as he handed Dean a piece of pie that he bought. Dean took me out to the car, helping me in. Sam got in their car and got back on the road as Dean loaded the wheelchair in the back of the car. He got in and I gnawed on my beef jerky. Dean started back out on the road again and we began talking like we did the night we met. Our conversation was one of those conversations that seem like they could last forever. His voice was gravelly and I liked when he looked at me in the rear view mirror. We talked about our work, our families, our friends.

"What's one thing you want to get off your bucket list this year?" I asked.

"I don't have a bucket list, baby, I live every day like it's my last." He said with a smile. "What about you?" He asked.

"I want to get stronger and faster." I said, "Fast enough to take on six vampires at once." I said.

"Oh yeah, I'll just pencil that in after the recovery." Dean said with a laugh. "Okay, my turn to ask a question." Dean murmured.

"Go for it, pretty boy." I said, chomping down on a triangle of my Toblerone.

"Okay, what do you think?" He asked.

"Of what?" I questioned.

"About everything, about all of this, about this life, about me?" He asked.

"Truthfully?" I questioned, "Totally transparent?"

"Yeah." Dean confirmed.

"I enjoy my life, I know it's not a conventional one and it gets hard sometimes, but I like it." I said, placing my hand on his muscular shoulder.

"And me?" Dean asked, grimacing slightly as he spoke, almost as if he didn't want to know the answer.

"Honestly, I really like you..." I said, catching his eyes in the rear view mirror. His shirt was soft. "What about me?" I asked.

"I- I like you too..." Dean said.

"Maybe we should stay together for a while, see where this goes?" I asked.

"I like that idea." Dean said. We both quieted for a moment before Dean looked back at me. "What tapes do you have in here?" He asked, opening up my glove box. He pulled out my gun and laid it on the seat before searching around more, being sure to keep his eyes mostly on the road. He pulled out one of my tapes. "Mötley Crüe?" He asked, glancing back at me

"Hell yeah!" I said.

"No." Dean said back. I frowned and he reached back into the glove box, pulling out a pack of pop tarts. He looked back at me in the mirror.

"For emergencies." I said, he smiled and put the pop tarts back in the seat. He reached back in the glove box and pulled out more tapes, going through them.

"Alice Cooper, Avenged Sevenfold, AC/DC, Nine Inch Nails, Rob Zombie, Ozzy Osbourne, Van Halen, Metallica. Dean leaned in pulling the last tape out. I blushed as he read it. "BRITNEY SPEARS?!" He asked, looking back at me. He cackled as I blushed.

"Well, which one do you want to listen to?" I asked. Dean looked up at me in the mirror, cocking his eyebrow.

"Do you even know me?" He asked, scoffing. He shoved in the Metallica tape and Battery started playing. "Oh fuck yeah!" He said, tapping the steering wheel as the song started to pick up. We arrived at Bobby's in no time and Dean drove my car up his Driveway. Bobby came out waving his gun.

"I'd know that car anywhere! (Y/n) get the hell out of here!"

"Woah, woah, woah, Bobby, it's me!" Dean said, opening the car door.

"What are you doing in (Y/n)'s car?" Bobby asked.

"We need your help..." Dean said, heading to the back of the car. I gave Bobby a little wave as he passed my window, but he couldn't see my injuries.

"Why the hell do you have a wheelchair?" Bobby asked as Dean pulled it out of the trunk. Sam parked behind us and got out, coming up to my driver's side door and helping me out. "Jesus Christ!" Bobby said, looking me up and down, "What the hell happened."

"A vampire fell on me." I said, looking up at him. I could tell he was holding back a laugh.

"She needs to stay with you." Dean said. Bobby's face fell.

"Balls!" Bobby said, I laughed at him. "Come on in." 

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