Sam lay in bed, waiting for Dean's breathing to even out before sliding out of bed and pulling on his 'work clothes'. They were in Nebraska hunting a possible werewolf and they were running low on cash. They'd both sent out several credit card applications but nothing had come in yet and Dean's hustling was bringing in some money but it hadn't been enough to buy anything but a few items in a convenience store and that had been a few days ago. Sam knew that they had to do something pretty quick since it sounded like Dean was getting a cold and the last thing they needed was to start sleeping in the Impala again since winter was coming fast. So he was gonna go to the local strip club and see if he could make a little extra money. He was hoping to be able to earn it on the stage rather than an alley but he dressed to attract just in case. Once he was satisfied with his appearance, he grabbed his wallet and slipped out the front door, not seeing Dean's eyes popping open.
Dean had long suspected that Sam was up to something. Even doped up on painkillers, he knew that there was no way that they could afford a nice room and the food that Sam brought back a couple of times a week when they'd been in South Carolina after Dean's accident. Sam wasn't any good at hustling pool or darts and Dean knew enough to know that owners of nice hotels didn't let guests work off their tabs but he hadn't been in any position to insist that they leave since they really didn't have anywhere to go and he was still in too much pain to stand a long car ride, so he'd waited, watching his little brother for anything that would give him an idea of what Sam was up to and the only thing he came up with was that it was something that Sam took long showers for, which could be a lot of things but it also meant that it was something that Sam wanted to hide the scent of. He had a bad feeling that he knew what Sam was doing but tried to tell himself that he was being ridiculous, Sam was a smart kid and wouldn't do something like…THAT. That was the one thing that Winchesters wouldn't do, no matter how bad things got. But the more he observed, the more he began to think that Sam had broken that family taboo. Sam went out after he thought Dean was asleep, would be gone for a few hours, come back and head straight for the showers and be in there for a long time before coming back out and collapsing into bed.
Sliding out of bed, Dean walked over to Sam's suitcase and began rummaging through the few articles of clothing before he found what he was looking for, tucked inside a pocket was a large roll of money and a large box of condoms with several missing. There were also several wife-beaters that Dean had never seen his brother wear before and a pair of jeans that looked way tighter than what his brother would ever wear.
Dean felt vaguely ill as he took in the evidence of Sam's nightly activities, the thought of his baby brother going out every night and doing God-only-knows-what for money to support them made him want to find someone and pound the living crap out of them or finding his little brother and dragging him out of whatever rat hole he was in and beat his ass black and blue before shoving him into the Impala and leaving this shithole town behind.
Except that running away wouldn't solve anything. Judging from the amount of money, Sam had been doing this for awhile, so just leaving wasn't going to work. No, he and Sam were going to have to talk about this.
He quickly put Sam's things back in his suitcase and sat on his own bed and waited for his little brother to come back though he wasn't sure what was going to happen when he did.
As the hours passed and Sam hadn't come back, Dean's anger gave way to concern; Sam always came back around 2am after the bars closed. As the sky began to lighten, Dean grabbed his jacket and prepared to go looking for his wayward brother, he wasn't sure what he'd do if he caught Sam in the middle of something but he knew it wouldn't be pretty. He'd just climbed into the Impala when his cellphone rang.
"Dean?" Dean's big brother radar immediately picked up the fearful tone to his little brother's voice and that Sam sounded like he was hurt.
"Sam? Where the hell are you? Are you okay?"
There was a long pause before Sam spoke, "I'm at the hospital and they won't let me go unless someone comes pick me up."
Dean frowned, "What're you doing in the hospital?" How could Sam have ended up in the hospital and he was only now being called?
Sam sighed, "It's a long story. Could you come pick me up?"
Dean sighed, having a nasty feeling about how Sam had ended up in the hospital but pushed back his rage to the far back of his mind. Getting mad and yelling at Sam for being so stupid wouldn't get him anywhere, he'd learned that by watching Dad and Sam interact. "I'll be there in a few minutes."
The trip to the hospital was fairly uneventful and after talking to the doctor, he'd gotten Sam's prescriptions and helped his battered little brother out to the car and called Bobby to let him know that they were on their way. As he headed for South Dakota, Dean vowed that once Sam was feeling better, they were going to have a long talk about what Dean had found in his suitcase. Dean could only hope that what had happened to Sam the night before would be enough to help convince his brother to give up what he was doing.
******Two Weeks Later******
Something was wrong between the Winchester brothers, Bobby knew it as clearly as he knew how a V6 engine worked. To the normal person, nothing seemed out of the ordinary; Sam had gotten the shit beat out of him and Dean was taking care of him like he always did when Sam was hurt, but Bobby had known the Winchesters since they were small and he could sense that there was something else going on. Sam refused to say just how he'd gotten beaten up so badly and there were times Bobby would see a look of anger on Dean's face when he'd look at Sam when Sam was sleeping or just not paying attention.
Finally, Bobby's curiosity got the better of him and he finally cornered Dean one day, "What the hell's going on with you boys? You've both been acting weird since you showed up." When he saw Dean bite his lip, he pressed further, "Does this have something to do with Sam getting hurt?" At Dean's surprised look, he smirked, "I know you boys too well."
Dean sighed and slumped into a chair, "I found out how Sam was earning money for the first couple of weeks after I broke my leg."
Bobby felt his gut clench at Dean's words; surely Sam hadn't gone back to that. He'd swore to Bobby that he wouldn't do that shit again. He forced his features to stay neutral, "What was he doing?"
Dean sighed again, "He was turning tricks, Bobby. If I'm right, that's why he got beat up."
Bobby felt anger rising in him at Sam for breaking his promise and doing something so stupid and dangerous, "Did they tell you that the hospital?"
Dean shook his head, "No, I looked in his suitcase and found condoms, a huge roll of cash and clothes I've never seen him wear." At Bobby's look, he explained, "I knew he was doing something but I wasn't sure what so I decided to investigate. I was going to confront him about it when he got back but then he called from the hospital."
Bobby felt his anger erupt, "Goddamn it! He promised me that he wouldn't do this shit again!"
Dean stared at his friend and surrogate father in shock, "Again?! You mean he's done this before?!" So many questions were racing through his mind; when had Sam done this before, how did Bobby know and why the hell hadn't Bobby told him or Dad? Dean was sure that their dad hadn't known because he would've told Dean. "Did Dad know?! Why the hell didn't you say something before?!"
Bobby sighed, "I promised him I wouldn't, Dean. Hell, threatening to tell you was how I got him to stop in the first place. And your dad didn't know, I thought about telling him a few times but I didn't want to break Sam's trust."
Dean was stunned at the thought that Sam had done this before and Bobby had known about it and hadn't said anything. "How did you find out?"
Bobby shrugged, "I was on a hunt in San Francisco and decided to check up on Sam on my way back and I caught him blowing some guy in an alley a few blocks from the school and he begged me not to say anything and I promised on the grounds that he promise to never do it again. And I checked up on him from time to time to make sure he was keeping his promise."
Dean sighed and ran a hand through his hair, this was worse than he'd imagined; he'd often wondered how Sam had survived in college but had assumed that Sam had done the 'normal' thing and gotten a job, he'd never imagined that Sam had been turning tricks in order to survive. The realization that his baby brother may have been selling himself for money for years made him want to wring Sam's neck and hug him at the same time.
"How am I gonna handle this, Bobby? It was bad enough just thinking that he'd done this, but knowing he's done this before just makes things worse."
Bobby sighed, not sure what to say, "I don't know, son. You're just gonna have to go for it cuz otherwise, Sam'll just keep doing it and next time, he might not be so lucky." With that, he got up and headed outside to talk to a customer that had just pulled in, leaving Dean alone with his thoughts.
Sam knew he was in major trouble when Dean walked into Bobby's library and said 'We need to talk.' He'd known that it was coming ever since Dean had picked him up from the hospital after those asshole rednecks had jumped him outside the strip and stolen his money.
"What do we need to talk about?" He knew it was stupid to play dumb but he didn't want to talk about what had happened in Nebraska.
Dean sighed, "Look Sam, I'm not gonna beat around the bush; I know what you've been doing to make money since I broke my leg."
Sam suddenly felt like he'd been hit in the stomach, "I don't know what you're talking about." He prayed that Dean just thought that Sam had been working in strip clubs.
Dean raised his eyebrows, "So why did I find condoms, a big roll of money and a bunch of clothes that I've never seen you wear except for the night you got beat up." At Sam's surprised look, he sighed, "I got suspicious and looked through your suitcase."
Sam shot off the couch and promptly regretted it when the room spun, Dean grabbed his brother's arm and helped him sit back down, but it didn't stop Sam from glaring at his brother, "You had no right to do that, Dean!"
"The hell, I didn't," Dean growled. "Sam, you've been sneaking out and doing God only knows what for months and now you've been beaten to a pulp and you want to tell that I have no right to be worried about you?!" As he thought about what Sam had been doing, his anger grew. "What the hell is wrong with you, Sam?! Dad and I taught you better than that!"
"How? How did you teach me better?!" Sam yelled back, ignoring the way his head protested the loud noise, "Dad didn't teach us anything that wasn't related to hunting or hustling. I'm not good at hustling pool or darts or playing poker, I'm good at this."
Dean stared at his brother, dumbfounded, "You're good at this?! Good at what, Sam, letting people use you for money? You're better than that, SMARTER than that!"
Sam shrugged, "Fat lot of good being smart is when you're starving and need to pay rent." Realizing he'd said too much, he looked away.
Dean felt all his anger die and be replaced with hurt, "You could've called us, Sammy. We would've sent you money."
Sam scoffed, "And give Dad something to hold over my head for the rest of my life? No thanks. I handled it. And when you got hurt, I handled it again."
Dean shook his head, "Not anymore, Sam. I don't want you doing this shit again. You could've been killed."
Sam frowned, "Dean, I wasn't turning tricks that night. I had gone to the local strip club for Amateur's Night and some asshole and his friends got mad because I beat out his girlfriend and they beat me up and stole the money I'd won."
Dean rolled his eyes, leave it to Sam to nitpick, "I don't care what you were doing that night, Sam, I don't want you doing it anymore. Promise me you won't."
It was on the tip of Sam's to say that he couldn't promise that, that he'd promised himself so many times that he wouldn't sell himself again, only to fall back into the trap again. But this was Dean asking him and he'd always obeyed his big brother. "I promise."
Dean knew that it wasn't going to be that simple, the fact that Sam had gone back to selling himself after promising Bobby that he wouldn't said that this was more than just a safety net in Sam's mind. It was going to take time but Dean was confident that now that it was out in the open and he knew Sam's secret, he could keep his little brother out of that mess. That's what big brothers did.