Dean's nostrils flared madly as his anticipation grew. He started to push slowly into Y/N. She was so tight and tensed up that Dean grunted with the effort. "If you don't relax, this is going to hurt like a bitch! Take deep breaths, Y/N/N. Relax", Dean murmured, rubbing soothing circles on her hips. Y/N tried to breathe deeply and let it out slowly. She was trembling violently. She closed her eyes and tried to calm herself as Dean continued to rub her hips. The tip of Dean's cock was in her entrance so he could feel her relaxing slightly. He leaned over her and whispered in her ear softly. "Remember when I told you that you'd regret that shot to my balls, Baby Girl?"
"Wha....?" Y/N only just got the word passed her lips when Dean drove into her to the hilt in one massive thrust. All the air was pushed out of her lungs without warning and every muscle in her body seized up at one time. She clenched her jaw to try to hold back her scream, but she was losing that fight quickly. The groan of pleasure Dean uttered made her resolve evaporate.
Sam woke with a start at the blood curdling scream that assaulted his eardrums. He knew full well what was happening. His head felt like it would split open and his brain would ooze out onto the concrete floor. He was certain that he had a severe concussion if not a fractured skull. There was blood running out of his left ear and his vision was blurry around the edges. He shoved his back up against the wall and tried to push up with his legs. Sam got half way up when everything started to spin wildly. The urge to vomit was almost too much. He just stayed still with his back on the wall and his knees bent, trying to breathe past the nausea.
"Shit, you're so tight, Princess!", Dean groaned. Y/N was hyperventilating again. Dean slowly started to withdraw and she thought he would pull out of her and she sighed heavily. When he pulled almost all the way out just to violently snap his hips and thrust back into the hilt again, the pain in her core was too much. The next thing she knew, she was being slapped in the face while Dean fucked her mercilessly. "Hey! Wake up!", Dean yelled breathlessly in her face. "There you are! We wouldn't want you to miss your own party, would we? Sweet 16." She wailed while Dean moaned and grunted, his hot breath on her neck.
Sam pushed himself the rest of the way up the wall and stood up on wobbly knees. He took a step and bile rose up into his throat. He swallowed hard to push it back down. He leaned hard on the wall as he took another step forward. He was desperate to get to Y/N and he could only imagine what she was going through. He had only taken a half dozen steps, but it felt like he was running a marathon. Sweat poured down his face and he was out of breath. His broken arm swung uselessly as he walked. When Sam finally got to Dean's bedroom door, he had to clamp a hand over his mouth and squeeze his eyes shut to stifle a sob. He could hear Y/N wailing as Dean rutted on top of her, grunting and moaning. When he turned the knob, it wouldn't open. Dean had locked the Door.
"OH, FUCK, BABY! I'M GONNA CUM IN THAT TIGHT CUNT!!!", Dean's voice shook as his thrusts became sloppy. 2 more sharp thrusts and he unloaded into her. He nearly screamed through clenched teeth as his orgasm hit him in waves. He had never cum so hard in his life. Y/N wailed out her grief at her best friend doing this to her. Dean had been her rock, her foundation since her family was murdered. Now that foundation had crumbled with one foul thrust. Dean slumped on top of her and moaned in ecstasy. "Damn, girl! That was so fuckin' good!" Dean reached into the nightstand and pulled the cuff key out of the drawer and uncuffed her wrists. He raised himself up to straddle her knees. Y/N tried to sit up, but Dean shoved her back down. He grabbed her shoulders and flipped her onto her stomach.
"What are you doing? STOP!", Y/N screeched in confusion. Dean grabbed her around the waist and yanked her up, shoving a pillow under her hips. "NOOOOOOOOOOO!!!!!!", she screamed. She tried to raise herself up on her hands, but he grabbed the back of her neck and shoved her face back down into the mattress. When she stilled, Dean ran his hand down her spine to rest it on her right cheek.
Sam rummaged in his pockets desperately hoping he had what he needed. He frantically searched all his pockets and finally came out with his lock pick kit. Kneeling down he picked at the knob with his tools trying to listen for that magic sound. That click of the lock. Eventually, the tumbler turned over and the lock clicked open. Sam slowly turned the knob and opened the door a crack. He wanted to have the element of surprise, hoping to catch him off guard. He saw a very naked Dean straddling Y/N's legs. He couldn't see her but he knew she was face down on the bed.
"Shh, Baby. I'll be gentle this time. I promise", Dean murmured to her, rubbing circles on both cheeks. He started to stroke himself again as he squeezed her ass cheek with his other hand. Just as he was lining himself up for the grand finale, Dean felt himself being violently yanked backwards with an arm around his throat. He went flying head over heels off the foot of the bed, landing on his stomach with the wind knocked out of him. He wheezed and tried to suck in a breath. He was up on his hands and knees trying to breathe.
"Stay down, Dean!", Sam growled at his older brother. Sam moved around the bed and saw the knife on Dean's pants. That wasn't just any hunting knife on his belt. It was the Demon blade. Sam grabbed it and gripped it tightly as Dean raised up on his knees in front of him. "What have you done, Dean?", Sam asked trying to stay calm.
"I popped me a cherry. I was about to get me some ass when you so rudely interrupted", Dean shrugged. Sam's nostrils flared as he tried to control his anger. Dean winked and shot him a wicked grin. Sam lost it and shoved the blade up under Dean's chin. Dean chuckled at the disgusted look on Sam's face. "Do it", Dean purred.
Sam was trying to hold back the tears threatening to break free. Dean started to push against the blade. "Come on, Sammy. Or don't you have the balls?", Dean snickered. Sam's gaze only shifted away for an instant, but it was long enough. Dean lunged at his brother, wrapping both hands around Sam's throat. The blade flew backwards over Sam's head, landing near the door. Dean sneered down at his brother and growled at him. "Ya know Sammy, I always knew that when it came right down to it, you were a coward". Dean started to squeeze oh so slowly. He was having fun and wanted to draw it out as long as possible.
"DEAN!", Sam wheezed. His eyes started to roll back into his head as his air was cut off. Sam saw black spots start to appear in his field of vision and the hand that was trying to pull Dean's off his throat started to feel heavy. Just as Sam was about to pass out, a lamp came whizzing through the air and connected with Dean's head. Dean slumped over on top of Sam. Sam gasped for air and looked up. to see Y/N standing over Dean with a broken lamp clutched in her hands, panting and sobbing miserably.
"Y/N?", Sam croaked. "Are you alright?" She just shook her head, backing away as she continued to wail. Sam shoved Dean off of him and struggled to get to his feet. He walked slowly toward her, trying not to frighten her anymore than she already was. He stepped in front of her with his good hand raised, showing her he meant her no harm. He slowly put his hand on her shoulder. She dropped the lamp and threw herself at him wrapping her arms around his waist and sobbing into his chest. Sam hugged her tight, placing a gentle kiss on the top of her head. His palm on her bare back brought back the realization of what happened to her and he cringed. He led her over to the bed and grabbed a sheet from it to wrap around her shoulders. Sam sat her down on the edge of the bed and stood up.
"WAIT! PLEASE DON'T LEAVE ME!", Y/N wailed hysterically, grabbing Sam's wrist. She started to hyperventilate and Sam hugged her tight to him again.
"I'm not leaving you, Y/N/N. I have to get the demon cuffs from Dean's duffel". She nodded and Sam stood back up and moved to the other side of the room. Finding Dean's bag, Sam got the cuffs and moved back over to where Dean still lay face up on the floor. Sam rolled Dean over on his stomach and not so gently cuffed his hands behind his back. He sat down hard on his brother's butt and heaved a heavy sigh. He sat there with his elbow on his knee and his head in his hand. After a few hard breaths, Sam reached into his pocket, pulled out his phone, and dialed. "Hey, Bobby? It's Sam. I need you to come to the bunker. Yeah, right now. No, I can't say right now", Sam whispered into the phone, shooting a pained glance over at Y/N with that last sentence.