Chapter Text
Dean Winchester.
A boy who had to grow up too fast.
A boy who's father never cared for.
A weak, pathetic child.
These are all things he thought. Of course he wanted his father to love him, and he tried to convince him he did, but deep down, Dean knew he didn't. John would never love him.
They never had enough money to eat full meals. Healthy ones, at least. They would go to diners and fast-food places, but they could never buy extravagant food. It was a very rare occurrence they had a good lasagna.
John never paid either of his kids for anything. They either had to take money from John's wallet, find money, or steal it. Occasionally, Dean could do some work around whatever neighborhood they were at, and he would get some money that way. But there's only so much a young teenager could do for money. It doesn't help that John would take any money he could find in their belongings for beer, bets, or both. Neither Sam nor Dean could count how many times they've had to steal just for a bad hot dog.
John was out. He had planned to be gone for a few hours, but knowing him, Dean knew that he most likely wouldn't be back until morning. They were running extremely low on food, with only a few free ketchup packets and small bags of less than ten pretzels. Sam was taking a nap and Dean was stressing over what to do for dinner, because he knew Sam had to eat, and as much as he hated to admit it, he had to as well.
He was standing over the sink, looking down at the two crumpled dollars he had in his hand. At most, he could buy a chocolate bar for him and Sam to share. He had already turned the motel room upside down for any money he could find, and all he found was an oxidized penny, and an old pair of unfamiliar boxers under the armchair.
He looked at himself in the mirror and tried to think.
He looked tired. So tired. He had barely slept all week.
He put the money in his pocket and washed his face with water, trying to clear his head from all his racing thoughts. He leaned over the sink, resting on his elbows as the water kept running. He stared down the drain, looking at the seemingly endless void and he thought of something. Something terrible. Something he shouldn't have even thought of. He grimaced, but genuinely thought about it. He had already exhausted all the jobs he could in the area, and he had seen a few prostitutes already on the sidewalk late at night. He looked at Sammy sleeping on one of the beds. He couldn't let him starve.
He exited the bathroom and made sure the windows were salted. He left a note on the door in case Sam woke up, reading, "Rise and shine Sammy. I went out to get food. Should be back soon."
He left the room quietly and salted the bottom of the door. He walked down the stairs and felt a chill. He shouldn't be doing this. He should just go back and suck on a ketchup packet. He should turn around as soon as possible. But he didn't. He kept walking. He was trying to act tough, but his hands were trembling a bit. He had flirted with countless girls before, and he'd gotten to third base a quite a few times, but when it came to fourth... he'd done it once or twice. His dad hired a prostitute for him a year ago to "make Dean a man," and Dean was on the fence about how he felt about it. It felt good. Of course it did. And the woman was beautiful. But his father had lied about Dean's age, and Dean had only been fifteen. The woman thought he was eighteen, so legal at least, but John just wanted Dean to suck it up and know what it really meant to be a real man. Whatever that meant. He had sex with one other girl after that, and she was his age. They both consented and fairly enjoyed it, but they didn't talk after that. She had pulled Dean aside to kiss him a few times, but no words were spoken. He had only flirted since then.
Dean made it to a dark street corner and stood there awkwardly. There was a woman smoking in a skimpy purple dress with fishnets and messy makeup a few feet away, and he looked her over. He watched how she carried herself, how she dressed, how she reacted when a car drove by. He started acting the same. He copied a few mannerisms and leaned against the brick wall behind him. What he didn't think about, was how long it would take for a car to stop and ask for either of them.
Dean's breath was uneven, even when he tried to stop thinking about the situation. No matter how much time passed, his shaky breath and slightly trembling hands never seized. After what felt like hours, a car slowed down. Not it front of the woman, but in front of him.
It was a fairly nice car, and there was a man inside that looked like he was in his late forties and had a cushy job. The man cranked down the window and smiled.
"Hey, pretty boy. What's got you out here this late?"
Dean hesitated. He slowly walked toward the car and leaned forward to look at the man. "Just waiting for someone like you." Dean said. He masked his nerves pretty well. The man grinned wider. "Is that right? Well, come on in. You look a little cold." Dean hesitated again before stepping into the car and sitting down. The man looked him up and down before looking back at his face again. "You can relax, baby. I won't bite." Dean carefully lowered his shoulders and looked at the man. "So... what's your plan with me?"
"Getting straight to the point, huh? I like it. Well, it's up to you. Do you want to... take this to a motel, or have me drive to an abandoned parking lot and, uh... have fun in the back of this puppy?" The man winked.
"Um... car." He didn't want to risk getting driven back to the motel where Sammy was sleeping. "You got it." The man started driving again and it was only a matter of minutes before the pulled into the parking lot at the back of an abandoned store.
"Hop in the back."
Dean steps out and gets in the back of the car, followed by the man who was clearly getting excited. "Do you have any experience, or is this an opportunity to... get something new in my pocket?"
Dean stuttered a bit. "I have a bit of experience, but none with a guy." The man's hand went to Dean's thigh and rubbed it. "How thrilling. Don't worry, baby. I won't hurt you." His hand fiddled with Dean's jean button. Dean pushed his hips forward a bit. The man's hand unzipped Dean's zipper and slid into the front of his pants. He palmed Dean through the fabric of his boxers. "Damn. You've got a good one on ya." He gripped it a bit. Dean gasped a bit and balled his fists while grabbing handfuls of his jacket sleeves.
"Call me Jay, by the way. What's your name?"
"D-Dean..."
The man nodded and hooked his fingers under the waistband of Dean's boxers. He took him in his hand. "How old are you?"
Dean gripped his jacket tighter. "Um... sixteen..." He stared at Jay's hand. Jay smirked. "Young boy like you shouldn't be prostituting. You should be studying for your classes." He rubbed the tip of his thumb against Dean's urethra.
"A-ah..."
Jay chuckled. "You like that?" He pressed down. Dean whimpered, uncomfortable. Jay grinned widely, almost with a predatory glint in his eyes. "I'll take that as a yes. Get on your back, pretty boy." Dean hesitated before shifting onto his back. It was a tight fit on the seats, but Jay didn't seem to mind.
Jay slowly pulled down Dean's pants and boxers, along with taking off Dean's jacket and pulling off his shirt. Jay ran his hands over Dean's body, resting his fingertips on Dean's nipples. He leaned forward and kissed the center of Dean's chest.
Dean didn't have anything to grip onto now. He avoided looking at Jay the best he could, looking at any part of the car he could focus on as Jay groped him.
Jay undid his pants, pulling out his already hard penis. Dean looked down and his eyes widened. He tensed and looked up at the roof of the car. Jay spread Dean's legs and rubbed his fingers along his hole. "So pretty. You're gonna let me do this, right? No complaints?"
Dean nodded quickly. He was nervous and scared but he couldn't admit it.
“For Sammy…this is for Sammy…” He thought.
"Relax, Dean. It'll feel good." Jay pressed one finger in. Dean pushed away from it instinctively. He pushed himself up enough to it and he panted a bit. His eyes were wide and his cheeks were red.
Jay seemed a little frustrated, but he chuckled. "What's wrong?"
Dean wipes his forehead. "I-I can't do this..." He looks at Jay. "Sorry, but I just... I can't..."
"I'll pay you good." He pulls out two hundred dollars. "This is what you want. Right?" Dean looked at the money and thought it over. Being uncomfortable for a little while doesn't compare to seeing Sam happy for a few weeks.
"Lay down, Dean." Jay gave him a pointed look.
"...fine." Dean lays back down carefully and stares at the top of the car. Jay grabs Dean's hips, keeping him exactly where he was, more frustrated than before and spat on his hand. He stroked himself up and down. "You are a tease." He rubbed his tip against Dean's hole. "A slutty, little tease." He slowly pushed in. Dean's eyed widen and opened his mouth but nothing came out. The pain was unbearable as Jay went deeper.
Dean's eyes squeezed shut and his head tilt back. He held his breath and the pain caused tears to prick up by the sides of his eyes. "Agh..! S-stop!"
Jay doesn’t. Instead, he speeds up. Pain coursed through Dean's body and he lets out a involuntary yell. "Stop!" He tried to push Jay away, but Jay grabbed his wrists and dug Dean's hands into the seat.
"I'll stop when I'm done. Now, shut up."
Dean tried to escape, but it was to no avail. He thought his father taught him well. Trained him well. His father... would be so disappointed. He tried to fight with his legs, but Jay persisted. "Stop fighting, bitch!"
The torture felt like hours. It might've been. Dean could barely breathe anymore. He was bleeding. It wasn't the worst bleed he's had, but it was bad. Really, really bad. Pain everywhere and bruises dragged along his arms and neck. Jay came inside Dean, and the pain kept persisting. The hot spurts did not help at all. Jay made Dean cum as well. He didn't want to. God knows he didn't, but Jay wanted him to. Dean felt used more than ever before. More than when his father used him as bait with or without him knowing.
Jay grabbed a napkin from the floor and wiped himself off. Dean was too weak to fight Jay now. Panting, sweating, painful agony, and disassociation. Jay plugged him up with the napkin. "You're welcome. Get dressed."
He hopped out and went to the driver seat. "Hurry up."
Dean put on his underwear and pants, red in the face and trying to focus on anything else. Before he knows it, he's back at the street corner where the prostitute was, sleeping now, leaning against a dumpster with a small jacket covering her legs. "That was nice, Dean. I'll be around for... future occasions. Will you?" He looked at Dean in the rearview mirror. Dean was too on edge to say anything, or tell the truth, so he just nodded. Jay tossed the money to Dean and he quickly got out and stumbled. Pain shot through his legs and he winced. Jay chuckled. "See ya, pretty boy."
Dean watched the headlights slowly disappear down the road. He gripped the brick wall, his fingertips getting scraped as he balled his hand into a fist. He had to walk back to Sammy, and he needed food. He didn't care about himself. He promised Sam he'd come back with food. He walked to a gas station. The closest gas station. Every step felt like knifes. He could feel himself still bleeding, and the napkin getting soaked, but he couldn't remove it or else blood would flow down his legs and probably stain his pants in a way he wouldn't want.
Once he made it to the gas station, he grabbed a large blue slushy and a few hot dogs, keeping a poker face as best as possible. He placed everything on the counter and paid with one of the hundreds.
"Gimme change. Every penny. Also a pack of Menthols."
The clerk rolled their eyes and counted every dollar and cent before handing it back to Dean. "Have a nice day." Dean waved quickly and left with the paper bag his stuff was put in. He limped back to the motel, trying not to think about anything that just happened. Finally, he made it back to the room. To Sammy. He unlocked the door, his eyes meeting a still sleeping Sam on the bed, curled up with the blankets. He sighed and put the bag down, taking out the slushy and hot dogs and throwing away the note he left. He quickly goes to his bag and pulls out the first aid kit. He stumbles to the bathroom and closes the door before collapsing on his knees and falling forward to lay on the ground. It may be dirty, but it felt like the comfiest thing he'd ever lay on.
He brought the first aid to his face, but closed his eyes. He felt tired. So, so... tired...