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 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 10:

256 10 0
By TurnTechCosplayer

"Don't you need to change?" Dean asked.

"No, I've got somewhere to be." I said.

"Where are you going?" Dean asked.

"Back to Tennessee." I answered.

"Mind if I tag along? I've been itching to see where you're from." Dean murmured, coming over to me and placing his hands on my hips, halting my packing process. I thought about it for a moment. It would be nice to bring my emotional outlet with me, especially since it was my mother.

"Sure." I said, flashing him a smile. It's not like we would be staying in my mother's house. Thank god I had my own place we could crash at. "Do you have a shirt?" I asked, "I've already packed all my shirts away." I said.

"Yep." He said, tossing me a t-shirt.

"What happened to my bra?" I asked.

"Here it is." Sam said, grabbing it off the bed and tossing it to me. Dean unzipped my dress for me and I pulled on the shirt, shimmying the dress off underneath, as Bobby was packing up in the bathroom, stealing the tiny soaps. Dean took my dress packing it and my bra away in his bag where he had space. I tucked my heel into my bag, pulling on a sock and one of my comfy sneakers.

"You ready?" Dean asked, standing in front of me.

"Yeah." I said, shouldering my bag.

"Bye!" Sam said. I headed over to him.

"Bye! I'll call you when we get there." I said back, pulling him into a hug. Sam hugged me back. He smelled great. You would've never guessed he had just been in a life or death situation.

"Bye." Bobby said, holding his bag in the bathroom doorway. I headed over, pecking his cheek before heading towards the door where Dean was waiting.

"Bye Bobby!" I waved, Dean took my hand and we headed down to my car, tossing our bags in the trunk.

"Can I kiss you now?" He asked. I chuckled and nodded. He leaned down, capturing my lips in a sweet, heart-stopping kiss. I guess I didn't realise how much I was missing his touch. His hands ran down my sides to my butt. My hands were on his cheeks. I leaned back, leaning my forehead on his.

"I knew it!" I heard someone yell. I looked over, it was Emily. I laughed as she came over. She held out a knife that she had borrowed.

"I wanted to give this back." She said with a smile.

"Thanks." I said, taking it from her, she pulled me into a hug and we said our goodbyes. I turned back to Dean.

"She knew?" He asked.

"She profiled us." I said, handing him the knife. He rolled his eyes and shoved it into his bag.

"Do we have time for a quickie in your car?" He asked, opening the passenger door for me.

"Absolutely not." I said, taking a seat and handing him my keys. Dean got in the driver's seat, begrudgingly. He pulled out of the parking lot. "How was it driving your car?" I asked, already pretty sure I knew the answer.

"Oh my god, it was great, I love my baby. Sammy's been taking good care of her, because he knows I would kill him if he didn't." Dean answered, merging onto the highway. We fell into silence. I reached over, turning on some music. Dean placed his hand on my thigh, gripping it mindlessly. His fingers felt amazing on my inner thighs.

"Deany..." I murmured.

"Hmm?" He hummed, glancing over at me.

"Have you ever gotten road-head?" I asked, biting my lip.

"Hmm... I can't say I have." He answered, looking over at me. I tied my hair up in a ponytail, leaning over his lap. I unbuttoned and unzipped his pants, tugging his boxers down. His cock sprang forward. I licked his tip before taking him into my mouth. I bobbed my head, "Fuck, (Y/n), yes!" He groaned. I could feel the car speeding up. I loved this. I loved the rush. I bobbed my head, swiping my tongue out as I got to his tip. He placed one hand on my head, showing me how fast he wanted it. I moved at his pace and I felt the car speed up more. "Shit, baby!" Dean moaned. Suddenly our ears were met with the sounds of sirens behind us. "Dammit!" Dean said. I pulled away, looking him in the eyes as he pulled to the side of the road.

"How much do you want to bet I can make you cum before he comes up here?"

"Fifty bucks." He answered.

"You're on." I said with a smirk. I leaned back down, taking him back into my mouth. I bobbed my head up and down, quickly, licking his tip when I got to the top and licking his balls when I got to his base.

"Fuck! Fuck! Fuck, baby, yes! Yeah! Yeah! Oh! Oh fuck, I'm gonna cum!" He moaned. I kept pumping up and down and I felt him cum in my mouth. I pulled back, covering him with his shirt as excess cum dribbled out of the corner of my mouth. Just then, there was a knock on the Driver's side window. Our heads shot up, it was the cop. Dean rolled down the window.

"Agents?" The officer asked.

"Yeah." Dean answered him as I wiped my mouth, swallowing.

"Sorry, I didn't recognise your car... You two have a nice day." He said with a wink. Dean and I shared an awkward glance as he walked away before bursting into laughter.

"I think I'll take you up on that quickie." I said. Dean pulled back onto the road, looking for a secluded spot to park. I climbed into the back, pulling off my shirt as Dean pulled into a back road, parking under some trees.

"It's so nice to cum after ganking something." Dean said, meeting my eyes in the mirror. I slipped off my panties, throwing them in the front seat. Dean climbed in the back with me. "I can't wait to have sex somewhere that lets me have my full range of motion again." Dean joked. I laughed, moving to sit on his lap. Dean guided his cock into me and I balanced on my knees on either side of his legs. I started bouncing quickly, and Dean attached his lips to my neck, kissing it and biting it. I threw my head back

"Fuck! Fuck! Fuck!" I moaned out as Dean thrusted up into me.

"Yes, babe! Shit, you feel so fucking good!" Dean moaned into my neck.

"Yes, Dean! Fuck!" I moaned, moving my hips forward slightly in my bounces. My walls clenched around him as my orgasm approached quickly. I buried my head in his neck as I felt him twitching inside me. He reached down, letting his fingers circle my clit, getting me closer. I pressed my chest to his. He held my hip with his other hand. I let out a loud moan as I came hard. I felt Dean cum inside me and he looked up into my eyes worriedly.

"Please tell me you're on birth control." He murmured. A grin crossed my face.

"I am, but we should probably grab a plan b just in case." I said, pecking his lips. He smiled up at me. I moved to get off of him, but he pulled my hips back down, roughly.

"One more round?" He asked.

"Absolutely." I answered, I leaned in, pressing my lips to his. He opened his mouth and I did the same. Our tongues met, circling around each other. He gripped both my hips, raking them backwards and forwards slowly. He was still inside me, giving me some much needed friction, "Fuck." I murmured.

"I was right before, you're fucking perfect." He murmured. He pushed me beside him on the seat. I laid down, and he started pumping in and out of me at a slow pace, sitting up straight so he could watch himself go in and out of me. I reached down, pleasuring my clit, biting my lip and looking up at him, meeting his eyes.

"Pretty boy..." I whispered.

"Why do you call me that?" Dean asked, referencing our conversation the night we had sex for the first time.

"Because you are very..." He pushed into me, deep, "very..." He pushed into me again, meeting with my words, "very pretty..." I finished as he pushed into me again. He pulled up his shirt slightly, revealing his abs, and giving himself a perfect view of us meeting over and over again. I circled my fingers around my clit.

"You're so fucking gorgeous..." Dean groaned, reverting to his regular pace. I looked up at him, moaning as he fucked me hard and fast.

"Shit! I'm gonna cum again." I moaned.

"Cum, babygirl." Dean groaned, pulling my hips to meet his over and over again. I came again, clenching around him hard. I felt Dean cum in me again, "Fuck, I love cumming in you." Dean panted, pulling out of me, leaving me laying on the back seat as he pulled up his pants and boxers, buttoning them and zipping them before climbing back into the front seat. I breathed deeply.

"Fuck..." I whispered, staring up at the ceiling.

"You good babe?" Dean asked, placing his hand on my inner thigh.

"Better than good, Deany." I murmured, "Fuck, you're amazing."

"I can't take all the credit, beautiful." Dean said, "You ready to go?"

"Yeah." I murmured, stretching and taking my hair down. Dean pulled back out onto the road. I sat up, massaging his shoulders.

"You're so fucking perfect." Dean groaned. He pulled up to a CVS, getting out and heading inside. He came back out, taking the pill out of the packaging and pulling a blue cream soda out of the bag, handing them both to me.

"Awe! Thank you!" I said, kissing his cheek before taking the pill.

"You are very welcome." Dean answered. I stood up, leaning into the front seat and grabbing my panties. I grabbed them, pulling them on and climbing back in the front with Dean.

"Why are you going now?" Dean asked, looking over at me, "Sam mentioned something about this being your first time home in three and and a half years." I looked out my window.

"Well, when I left to be a hunter, my mom told me to never come back." I answered, sipping my blue cream soda.

"I thought you came from a family of hunters." Dean said, placing his hand on my knee.

"I did, my mom and my dad were raised hunters, my mom's sister too, they raised us in it. My dad died in the life years ago after my sister had her second kid. She hadn't hunted in years, but she needed to blow off some steam so she left alone. Whatever she was after followed her home and killed her husband and her two kids... ripped them to shreds... She couldn't stand the guilt so she locked herself up in a psychiatric care facility." I murmured, "I wanted to see if I could find what it was but my mom told me that if I left to hunt, I was never allowed to come back..."

"I- I'm so sorry..." Dean murmured, "Why are you going back now?" He asked. I coughed, wiping my eyes as Dean gripped my knee.

"Well, my mom has cancer and-" I choked back my tears, "and she's really not doing well."

"I'm so sorry." Dean whispered. He pulled over on the side of the road, getting out and coming to my side. He pulled open my door and I climbed out and looked up at him. I wrapped my arms around his neck and Dean ran his hands down my thighs, picking me up. I hugged him tightly, burying my head in his neck. Dean rubbed my back gently. "I'm so so sorry..." He murmured into my ear, "Are you okay?"

"I'm okay." I murmured, wiping my eyes.

"You're not..." He murmured, kissing my forehead. I tangled my fingers in his hair. "Take a nap in the back, I'll drive for a while."

"Thank you." I murmured, leaning my forehead on his, "My house is in Covington."

"Got it, beautiful." Dean murmured, pressing his lips to mine. He was so warm and he smelled so good. Just a kiss from him was enough to make me feel so much better, like I could do anything. Dean placed me down on the ground before pulling his lips away from mine.

"Do you want some pants?" He asked.

"Yeah I'd better put some on, I'd hate for people to see me pantsless." I said with a chuckle, wiping the final tears from my eyes. Dean laughed and headed to the back, pulling out a pair of his pajama pants. He handed them to me and I pulled them on. I climbed in my back seat and Dean closed the passenger door for me. He climbed back into the driver's side. He pulled off his canvas jacket, draping it over me before starting the car and pulling back onto the road. "Hey Dean?" I asked.

"Yeah?" He asked.

"Thank you..." I murmured, "for everything." He had helped me so much. He was willing to help a fellow hunter that he didn't even know, so were Sam and Bobby, but Dean stayed with me, helping me with everything and anything I needed. Then when Bobby told us we'd met before, we became closer, and I hoped I wasn't reaching when I said he was my best friend. It's hard to have friends in the business, so having someone that understood, that was willing to help you and be there for you was just great. Usually I didn't work well with others, but Dean and I were so similar it seemed like I could read his mind in a fight, we fought the same, thought the same, killed the same, it was weird, like I'd met my doppelganger.

From what I'd heard, Dean Didn't exactly work well with others either. Maybe Emily was right, maybe he was 'in love with me' or whatever she said. Even if he was, was that such a bad thing? I never thought I was a relationship person, but that was because of the job. The more time I spent with Dean, the more I learned about him, the longer I wanted to do it. I think I could work with him forever and never get tired of it. Working with others was actually kind of nice, you didn't have to be on guard 24/7, someone always had your back. I couldn't remember the last time I got to take a nap.

Working with Dean obviously meant working with Sam, and I enjoyed his company too. It also meant working with Bobby on occasion. Bobby and I may not be each other's biggest fans, but I could get used to that.

"No problem." I heard Dean murmur. I snuggled into his jacket. It was warm and smelled like him. I felt myself start to drift off to sleep. I soon woke up and glanced at the time. It had been three hours. I sat up, wiping my eyes. "Nice bed head, sleeping beauty." I heard Dean say. He was looking at me in the rear view mirror. I flipped him off.

"Asshole." I murmured with a small smile. I ran my fingers through my hair. Dean had put on Van Halen and he was drumming on the steering wheel. I noticed a bag of pork rinds. I looked at him.

"Really?" I asked.

"Yep." He answered, "I got you this though." He said, pulling out a sucker that he had placed in the cup holder. It was a green apple caramel sucker.

"How did you know I like these?" I asked, taking it from him.

"I saw them in the store and I remembered you liking them when we were kids."

"Thank you." I answered, unpackaging it and popping it into my mouth. "Where are we?" I asked, climbing up in the front seat and moving his pork rinds.

"Kinder, Louisiana." He answered. I grabbed my purse, fishing out my cigarettes. I took one out, lighting it. I rolled down my window, switching between eating my sucker and smoking. Dean held out his hand and I handed him the cigarette, we shared it and he blew it out his window. I turned up the music until it hurt our ears and Dean sped down the highway. We sat like that, just enjoying each other's company for about an hour until I reached over, turning the music down.

"While we're there, do you want to look for a case?" I asked.

"Sure." Dean murmured.

"Do you want to swap out?" I asked.

"Nah, you drove most of the way to texas, I don't want you to have to drive most of the way home too." He answered.

"Do you want to fuck again?" I asked with a small smirk.

"As much as I hate to turn that down, you said you were in a hurry." He said with a chuckle.

"Yeah, I've been on the road so long, I don't even know if I remember what my house looks like." I joked.

"So we should probably get groceries?"

"Yeah." I answered. Dean reached over, placing his hand on my thigh. "You're so hot..." I murmured, looking over at him.

"Maybe we should fuck..." He murmured with a sly smile.

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