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There wasn't much a homeless teen could do for money, it was either sell drugs or sell your body. Theo didn't like either of those choices but not having much of an opinion he decided to seek out a connection to a drug dealer. It didn't take him long to find someone who knew one, it was a bit shocking that it was Stiles, but thinking about it with his father being the sheriff it wasn't too shocking. What was more shocking was that the old sheriff didn't realize his son was high most of the time. Theo figured that since Stiles's school wasn't suffering his dad didn't care.
It took a while for Stiles to introduce him to his dealer, but when he did he was told right away that the man he was going to be working for didn't take things lightly. The dealer introduced himself as Big D, or D for short. D was an apposing man scaring even Theo. He expected his cut every Friday and took his payment one of three ways; by cash, by giving back the unsold drugs, or he'd take it from their ass. That last one didn't sit right with Theo but he just had to make sure he didn't need to do that and he'd be fine.
For the first few weeks, Theo was making more money than he'd ever before. He was even able to get a motel room from time to time and sleep on a bed, instead of inside his truck, or take a hot shower. There were some great benefits to it too, like he was occasionally offered sex in exchange for what he was selling. It was usually blowjobs but it was still a lot more than he'd be offered before. When he'd take them up on it he'd just charge a little more the next time someone was going to pay. It hadn't been a problem since he was usually able to get people to pay, but then he screwed up and was short.
Theo constipated just ditching town instead of facing D but he knew that eventually that would catch up with him. He decided to suck it up and see if his boss could be persuaded to let being short slide the one time.
Going to D's hideout to face the music, he brought all the money he was able to get. Once inside, he saw a bunch of other dealers handing out and getting ready to hit the streets. Some of them Theo knew either from school or being introduced while working. His classmates nodded at him in greeting while most of the others completely ignored him. Getting to D's office, he hesitantly knocked on the door. He was told to go in by D's gruff voice. Entering, he saw D sitting at his desk, counting and binding stacks of money.
"Hey, Theo." Off to the side was Stiles, rolling a joint for later
Theo vaguely acknowledged him as he walked past. D looked up, a smirk on his lips as he saw one of his newest dealers.
"I'm guessing you're coming here to give me my weekly amount," D said, pushing a few stacks out of the way.
"Um... most of it," the homeless teen mumbled.
Stiles stopped what he was doing, his eyes darting back and forth from D to Theo.
"I see. So what are we going to do about that?"
"I...um...was hoping you'd forgive me just this once and I could pay you back later?"
D sat there, looking down at a nervous Theo, the room was tense as he accepted his fate.
"Ok," D simply said.
Theo stood there stunned. "Ok?"
"I'll forgive it for now, but you will be paying me back later. Give me what you have, and why don't you have some fun tonight? I'm sure Stiles can show you a good time out."
"Really?" Stiles and Theo asked at the same time.
"Thank you," Theo immediately said after. "You won't regret it, sir."
"I know I won't," D smirked. "Stiles, show Theo a good time tonight. Show him our VIP room."
"Ok," Stiles grinned, getting up and going to Theo. When he was next to his classmate, he threw his arm around Theo's shoulders. "I'm going to show you a night you won't forget."
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The club was nothing like anything Theo had ever experienced. He was amazed how loud the music was, how easily he was able to get drinks, and how many people wanted to dance with him. Not that he was able to since Stiles kept him close, saying he didn't want to get in trouble with Big D. Throughout the night, Stiles would hand Theo drinks, not too many but enough to loosen the dealer up. By the time Theo was starting to stumble over his own feet, Stiles dragged him to the back of the club and pulled out a key to open a nondescript door. Being guided in, the drunk boy didn't know where he was or what was going on, but he felt incredible. Stiles pushed him onto a sofa before closing the door, but not locking it.
"You having a good time?" Stiles asked, sitting next to the drunk boy. Theo nodded. "Wanna smoke a bit?"
"I... don't..." He slurred.
"I know you don't usually but we're having fun."
Theo tried to shake his head but more flopped from side to side. Stiles wasn't paying attention to him and pulled out a joint from his shirt pocket. He lit it and took a big drag, holding the smoke in his mouth. Forcing Theo's face towards him, Stiles blew a steady stream of smoke into Theo's face. The smoke didn't effect him at first, just smelled the usual scent of weed, but with each new puff to his face, Theo was starting to get high. Being both drunk and high was the perfect combination for Stiles to carry out Big D's plan.
"You're probably feeling pretty relaxed," Stiles remarked, climbing on top of Theo. "I bet you're feeling pretty hot right about now." He started to pull up Theo's shirt, his fingertips traced along the exposed skin and then pulled it off. "Are you still hot?" Theo's head bobbed a bit.
Stiles skillfully slid down to his knees and started to undo Theo's pants, pulling them completely down. His pants were stopped by his shoes, that Stiles easily slipped off, pulling off the pants leaving Theo in his ratty boxers. Theo's dick head was poking out of the fly, his body too stoned and drunk to even think about getting hard. Still on his knees, Stiles got close to Theo's flaccid dick like he was going to suck it but with surprising strength grabbed his legs and pushed them upwards. While in that position, the sober boy worked the back of the boxers up to expose his ass.
"You're going to be grateful for this later," Stiles said before licking up Theo's crack.
Theo never had anyone do that, it felt good in his doped mind but Stiles didn't do it for long. His friend moved away, but his legs didn't go back down, still being held in place. Giving a confused noise, he noticed the big hands gripping his ankles. Looking down at Theo, with a evil glint in his eyes, was a shirtless Big D.
"Thank you, Stiles, for getting him ready."
"No problem, Derek. And since I did such a good job, can I watch?"
Big D smirked. "Of course." Stiles rushed over to the other end of the sofa, unbuckling his pants for the upcoming show. D turned his attention back to the helpless Theo. "I told you I only accept three types of payment," He pushed the legs farther back and exposed even more of Theo's ass. "Cash, grass, or ass. And you failed to give me two of those options." D pushed them so they were practically on either side of Theo's head. "So I guess I have to go with opinion number three."
Theo was incredibly confused, what was D talking about? His vision was hazy as he watched his boss tear open his buttonfly jeans and let his huge cock spill out of them. In that moment, Theo finally realized what D had meant about taking it out of his ass. He fruitlessly tried to struggle out of the hold, it didn't do anything other shake his ass. With only drying spit as the lube, D pressed into the struggling boy. Theo immediately screamed, the pain of something so big in his tight hole was too much, but his mouth was quickly covered by one of Big D's hands. He was pressed all the way in and didn't need to hold Theo's legs open anymore since they didn't have anywhere to go. D didn't take his time, rabbit fucking his useless employee, Theo sobbing as he was violated. Looking over, Theo vaguely saw Stiles clearly jerking off, enjoying his reward of betraying his classmate. When Stiles was close, he got up and walked closer, keeping a hand on his pants so they didn't fall, and finished on top of Theo's tear streaked face. By then, he wasn't screaming anymore, his mind shut down to try and protect itself. It didn't take long for D to finish himself, slamming in one last time before groaning as he unloaded into Theo. Without any regard to his victim, Big D pulled out, grabbing one of Theo's discarded clothes and wiped himself off before buttoning his pants again.
"I think you'd work out better spreading your legs then selling drugs. What do you think, Stiles?"
"You know you'll get your money," the boy smirked.
They laughed while Theo laid there, broken and hurt, knowing his life would never be the same.