Pretty Boy: Dean Winchester x...

By TurnTechCosplayer

6.8K 192 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 3:
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 22:
Chapter 23:
Chapter 24:
Chapter 25:
Chapter 26:
Chapter 27:

Chapter 21:

122 3 0
By TurnTechCosplayer

Dean's P.O.V.

(Y/n) opened the passenger side door, joining me in her car. I flashed her a sweet smile, but she seemed to be too lost in her own thoughts to notice it. I hoped everything was okay with her mother. She was nice, like I remembered her to be, she looked like (Y/n). They had the same eyes, the same light- though her mother's was a bit dimmer. They spoke the same- and their mannerisms tended to mirror each other. Her mother had the same classic beauty that (Y/n) did, though if I'm being honest she couldn't hold a candle to her daughter's beauty.

"You don't look better." I murmured, starting the car.

"I think it's just my anxiety leaving." She assured me. I didn't believe her, but I didn't push it. I pulled out of the driveway and out onto the road. I glanced over at her a few times, seeing her staring blankly down at the floorboard.

"What are you thinking about?" I asked her.

"What?" She asked, looking over at me.

"The only reason you stop yapping for 5 minutes is because you're thinking about something, so what is it?" I asked. I noticed a smile cross her beautiful pink lips.

"I- I don't know, I think we should talk..." She murmured, turning to stare out the window. I pulled onto the road her house sat on and looked over at her.

"... About?" I asked.

"About us..." She murmured. I pulled into her driveway and parked, looking over at her.

"Okay, go ahead." I said, assuming she thought we were moving too fast... I readied myself for the possibility that she wanted to backtrack. From the way Will referred to me as a boytoy, I assumed the word boyfriend might have made her uncomfortable.

"I think we should talk inside." She murmured, getting out of the car. I got out of the car too and headed up to the door, unlocking it for her and placing her keys on the end table. I peeled off my coat and hung it on the coat hanger and she did the same. I turned to her, looking down and meeting her eyes. "Dean..." She murmured, looking up at me.

"Yes?" I asked. I saw her face go paler than it was before. She parted her lips slowly.

"I- I think we should break up..." She looked genuine. She wouldn't joke about something like this... I felt my heart break into a million pieces as my eyes searched her face.

"What?" I asked. I was at a loss for words... This wasn't happening... this couldn't be happening.

"I- I'm sorry, I just- I don't think I can do this... anymore..." She murmured. I felt a sharp pain in my chest.

"You don't want to be with me?" I asked.

"I- I- Of course I do! I just-" Tears streamed down her face and I felt tears welling up in my own eyes. She looked away from me and I looked down at the floor. Without a second thought, I got down on my knees, gazing up into her beautiful eyes.

"You asked me before if I would kneel for you and I told you the answer was yes..." I said, staring up at her. I took her hand in mine and she bit her lip staring down at me. "I love you more than anyone else." I murmured.

"Dean, please don't do this..." She said, squeezing my hand.

"I'm sorry if I did anything-"

"Dean, stop." She pleaded, "Please..." I bowed my head and stood, looking down into her beautiful eyes. She placed her hand on my cheek gently. Her hand was soft. "I'm so sorry..." She added, I felt tears fall from my eyes. I leaned down, pressing my lips to hers one last time. Our tears tasted salty... I felt her pull back, and lean her forehead on mine.

"I should uh- I should call Sam. He'll come pick me up after he and Bobby finish up their case." I murmured. She nodded. I stalked off to her guest room, leaving her standing in the living room. My heart ached dully as I slammed the bedroom door. What I said was true... I did love her... She was my perfect match... and she had left me... I sat on the bed, pulling out my phone. Maybe I shouldn't call Sam. Maybe I could fix this. I laid back on the bed, staring up at the ceiling. I heard the door to (Y/n)'s bedroom door close and I heard her immediately burst into loud sobs. I wanted to go in and console her, but that wasn't my place anymore... I stood up off the bed, heading to the living room. I paused momentarily in the doorway, looking at her coat on top of mine on the coat hangers. I sat on the couch, propping my feet on the coffee table. I flicked on the TV, going to the news channel. I watched as the reporter talked about a death in the area. They explained how the victim died from blood loss and wounds to the neck. That sounded familiar. I immediately clocked it as a vampire attack. I remembered seeing something about a vamp nest upstairs. I turned off the TV, standing and heading over to the attic opening. I pulled it down and climbed up, looking around at the mess we made the last time we were up here. Notebooks and pens were strewn across the floor. I looked around until I found an old note pinned to the cork board. The handwriting wasn't (Y/n)'s. I looked at it. It gave an address and below it it said 'vamp nest'... well that was simple enough. It looked old, I briefly wondered why no one had done anything about it. I took a picture of the note and headed back down. I closed up the attic and headed to (Y/n)'s door. I knocked on it, but got no answer.

I listened, hearing light snoring inside. I left her alone and headed to the kitchen, jotting down a note. I looked at the picture on my phone, looking up the address. It was close to here. I pulled on my coat and slipped my gun into my waistband and grabbed my machete. I headed outside and glanced at the car, but decided against using it, as I didn't want to leave (Y/n) here without a car in case she needed something. I knew the house was close from the directions.

I headed out, taking a shortcut through the woods to the right of (Y/n)'s house. After walking for about 20 minutes I saw the silhouette of a large mansion in the distance. As soon as I caught sight of it, I heard a snarl behind me. I turned, seeing a vamp coming out from behind a tree. I ran at it, taking off his head in one foul swoop. Suddenly, I felt arms wrap around me, wrestling me to the ground. I reached back, slipping my gun out of my waistband, shooting the thing over my shoulder. It let go in surprise and I whirled around, slicing the vamp's head off. I headed closer to the mansion, taking out every vamp I saw. I looked up at the front porch, taking a deep breath before stepping up on the front step. All of a sudden I felt a sharp pain in my shoulder and I fell backwards. Someone caught me and I felt my arms being cuffed above my head. I felt blood flowing out of my shoulder wound as I was hit in the head and dragged into the mansion. I blacked out and when I came to, I saw that I was in what looked to be a dark basement. A woman was standing in front of me, wearing a gown and holding a metal pipe.

"Why are you here?" She questioned.

"I saw a vamp kill on the news." I answered.

"Who are you?" She asked. I stayed silent. She whacked me in the knee and it let out a sickening crack and I groaned.

"Fuck!"

"WHO ARE YOU?" She repeated.

"I'm your worst fucking nightmare!" I yelled back. She let out a posh chuckle.

"Really? Because from where I'm standing, you look like you're all bark and no bite." She answered, as a smile crossed her face. "If you promise to leave at once, we will let you go." She added. I felt rage course through my body.

"We both know that's not going to happen." I said back. She gave a swift whack to my knee again. I screamed and kicked at her. At that moment my mind started to wander. I walked into this blind... (Y/n) was asleep, and she had no idea where I was. I was screwed.

"I can assure you, we deal with our own around here." The woman said. I clenched my eyes shut, breathing deeply. "I tried to let you out of here the easy way..." She grumbled, raising the pipe, "But now we're doing it my way." She hit me in the ankle.

"Why don't you just bite my damn throat out?!" I asked, grimacing.

"Oh, honey, we don't feed on humans." I felt her hit me again. I screamed out in pain. "But I think this is more fun." The blows came over and over and I felt myself slowly lose consciousness. It felt like forever until I heard someone call out over the blood rushing through my ears.

"Aleda!" A familiar voice yelled. I blinked away the grogginess and looked up, seeing the woman look away from me and up the steps. I felt my throat go hoarse, but I couldn't hear myself scream. I followed the woman's line of vision.There I saw (Y/n) climbing down into the basement. I briefly questioned how she got through the other vamps outside before I realised I didn't care. The woman I loved was here to save me. My brain felt foggy and I could feel my vision dim. I felt my wrists being cut down, but I didn't have the strength to stand. I fell onto the ground as (Y/n) and the woman- I'm guessing her name was Aleda- exchanged words. "Can you walk?" (Y/n) asked. I stared up into her beautiful eyes.

"My leg- I can't." I murmured.

"It's going to be okay, sweetheart." (Y/n) said. Her words made me feel warm and I knew I was going to be okay. I felt her slice through the rope that bound my hands. "Stand up on the good foot." (Y/n) said, I tried to do as she said, as she pulled on my arm, but I let out a loud cry, feeling the pain from the gunshot wound radiating through my body. I felt (Y/n) run her warm hand up my arm, pulling down my shirt. She saw where I had been shot and I saw her grimace. "Fuck, this is going to hurt." She murmured. I felt her pick me up, holding me on her shoulders. I wondered how that was possible, but I soon found myself unconscious again. When I came to, I felt as if I could only focus on one sense at a time. Once when I woke up I could smell her hair. It was damp, like she had just washed it. It smelled sweet and the scent made me feel warm inside. The rest of the way to the hospital was a blur. My brain was still fuzzy when I woke up to see (Y/n) sitting beside my bed.

"(Y/n)?" I asked. She looked up at me.

"Hey, there he is." She murmured softly, "Sam's on his way."

"The last thing I remember is leaving that mansion." I said, meeting her pretty eyes.

"Yeah, you got your ass handed to you." She said with a small laugh, "You're going to have to have surgery." I nodded and glanced up at the TV, it was on the Western channel.

"Westerns?" I asked.

"You like them." She murmured, flashing me a sweet smile. I heard a knock at the door and I looked over. A woman with long dark hair came in.

"Hey." She said, waving and coming in, "We need to set your ankle." I nodded and a few nurses came in after her. (Y/n) held out her hand and I met her eyes. I knew she meant it as a platonic gesture, but it made my heart ache a bit. Even so, I took it anyway. Her hands were soft and warm and I couldn't help but to let my mind wander- remembering how her hands felt roaming my body... her fingers running through my hair... her warm, wet mouth pleasing me- making me feel... so... Fuck! I gripped (Y/n)'s hand harder as the nurses set my ankle. That shit hurt more than I thought it would. Finally, the nurses finished the torture, but I made no moves to let go of (Y/n)'s hand. She didn't either. I looked over at her and she met my eyes.

"This- this doesn't-"

"I know." I murmured, cutting her off. We both settled in and looked back at the TV. "Do you know when Sam's going to be here?"

"Probably in about-" She looked at the clock on the wall, "six hours?" She looked back over at me and I nodded, sighing. "Is your phone broken?" She asked.

"I don't know." I murmured, gesturing towards my pants that were sitting in a pile with my other clothes on a chair. We spoke for a while longer, her telling me about the truce and about her sister. I liked listening to her pretty voice. It made me feel safe and warm.

~~~

I looked around. I was in (Y/n)'s house. I felt so groggy. I looked up and saw Sam wheeling me into her guest room. I could feel my consciousness going in and out. I opened my eyes again, seeing I was in the bed. (Y/n) was standing above me.

"You need to put your pajamas on, Deany." She murmured. I leaned forward, allowing her to remove my shirt. "How does it feel?" She asked.

"Fuckin awesome." I mumbled, smiling. It wasn't a lie, these happy pills made me feel great. She pulled the t-shirt over my head, smoothing it down my body. She stood back up and I took her hand. "I love you, you know?" I asked. I saw a gentle smile spread across her face. She was so beautiful.

"I know..." She murmured back. I wrapped my arms around her, burying my head in her chest. She ran her fingers through my hair.

"Please don't leave me." I begged.

"I'm sorry, Deany." She whispered into my hair.

"Please, (Y/n)..." I said back.

"I'm sorry, Deany." She repeated, pressing a sweet kiss into my hair. I knew begging her not to leave me was pathetic, but she caught me in a moment of weakness. She was all I ever wanted. I wiped my eyes, laying back on the bed. I unbuttoned and unzipped my pants, pulling them down so she could help me into my pajama pants.

"This seems familiar." I joked, attempting to lighten the mood. She chuckled as she pulled up my pajama pants. I raised my hips, making sure not to put pressure on my bad leg.

"You should go to bed," She murmured, " it's been a long day." On a whim, I took her hand, pulling her towards me. She landed on top of me, and her lips met mine. Her lips were soft and perfect against mine. She melted into me, and I jutted out my tongue, swiping it over her bottom lip. I didn't care that we were broken up. It was easy to see that she needed this almost as much as I did...

She opened her mouth allowing my tongue to enter and explore. She threw her leg over me, sitting on my lap softly, almost as if she were afraid of putting her full weight on me. I always loved when she sat on my lap or laid on me, something about having her weight on me was amazing, intoxicating even. I wrapped my arms around her and she tangled her hand in my hair. She pushed her hips into me ever so slightly, almost subconsciously. I doubt she even knew she did it. She let out a low moan against my lips. That sound... I found myself wondering if I would ever get to hear those beautiful sounds again.

"Oh- Jesus, sorry!" I looked behind her as she pulled away quickly. I saw Sam ducking out of the hallway and I cursed him silently. Goddamn cockblock. She looked back at me and placed her hand on my cheek, cupping it lovingly.

"You should probably get some sleep..." She murmured, staring deeply into my eyes.

"I'm sorry." I murmured back. I felt bad that I had let my desire for her overtake me in the moment.

"It's okay." She assured me, standing up from my lap. She headed out the door, leaving me feeling cold and alone once again. I soon found myself falling asleep.

All of a sudden, my eyes snapped open to a loud noise. At first I thought my brain might have been playing tricks on me. I registered my surroundings. I was in (Y/n)'s house. Soon after the loud noise though, my ears were met with a loud yelp. It sounded like (Y/n). I shot straight up in the bed, staring out into the hallway.

"Shit (Y/n) are you okay?!" I heard Sam ask. I heard her say something I couldn't quite hear. If I had to guess I would say (Y/n)'s clumsy ass fell over something.

"What's going on out there?!" I called out, swiping my hand through my hair, hastily.

"I fell off the couch!" (Y/n) called. I wouldn't expect any less. Sam appeared in my doorway with a grimace on his face.

"We need your help." Sam muttered, not meeting my eyes. I wondered briefly why he was averting his gaze when I remembered I didn't care. I groaned and rolled my eyes.

"I can never get a good night's sleep when you're around, Sammy." I muttered. I noticed his cheeks flush and I wondered if I'd phrased it too harshly. Sam came over and I threw an arm over his shoulder. He lifted me up and helped me into the kitchen where my eyes were met with an odd sight. (Y/n) wasn't wearing any pants. "Uh..." I cleared my throat, looking down at the ground.

"My pants were too tight... so I got comfy..." She explained. I nodded, it made sense. She turned and my face dropped to a grimace as I saw her ass covered in blood and shards of glass. Sam and I let out similar breaths. "Is it bad?" She questioned. I had to bite back a laugh, as there was no way it felt better than it looked. I knew it had to hurt like hell.

"Well... it looks like it hurts." I muttered.

"Get on the island." Sam said to (Y/n), pulling out one of the island bar stools for me to sit on. (Y/n) perched her foot on the lower shelf of the island, trying to step up, but she was unable to, letting out a sharp cry as she landed back on the floor. "I'll help you." Sam said, hurriedly lifting her onto the island, carefully. She laid on her stomach. I eyed her ass, sucking my teeth and letting my eyes search down her lower back and thighs. She was such a beautiful woman...

"How much glass is it?" She asked. I didn't even know how to answer.

"Not... all of it?" Sam murmured. I saw blood trickle down her thighs and I saw the outlines of the bruises I had left on her days ago...

"This is going to hurt." I murmured, reaching out tentatively. She gasped as Sam and I began plucking pieces of glass from her soft, but marred, skin. I knew this would leave quite a few scars. Sam scooted a trash can over to us for us to toss the shards into. "How did this even happen?" I asked.

"I-" (Y/n) started, she cut herself off, probably in too much pain to speak at the moment.

"She tried to jump onto the couch and overshot it." Sam said.

"Mhm." I murmured, still finding it rather odd that Sam felt the need to answer for her.

"(Y/n)?" Sam murmured, "You should go get a shower."

"Yeah." She confirmed. I stood.

"I'm going back to bed." I grumbled, heading back to the bedroom, holding onto the wall as I limped, trying to hold myself up. I ducked back into my bedroom, shutting the door behind me as I collapsed on the bed. I wrapped myself up in my blankets, burying my head in my pillow. The bed smelled like her. I guess that made sense, it was her house after all. I felt myself falling asleep quickly and I welcomed the escape.

(A/n): I hope you guys like this chapter!

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