Dean tried to escape on the third night.
His reasoning for this came from an old story of his dad's. Back when he was in Vietnam, he and a couple of his buddies were found scouting the enemy camp... in civilian clothes. In order to prevent being shot by the guards as spies, they told the soldiers they were deserters, interested in joining the other side. His dad had told the story to the eight year old Dean, and with a serious look on his face, turned it into a lesson. He said to Dean, "If you are ever captured by an enemy, sometimes the best thing to do is pretend to join up. Don't stay with them, but make a plan. They'll expect you to run on the first night if they think you're an idiot. If they think you're clever, they'll be waiting for you on the second night. By night three, they should be starting to trust you. Plan to escape that night, stockpiling and hiding rations if need be. Be convincing, and you won't have any trouble getting away. It worked in 'Nam, and it should work for you if you ever find yourself in a similar situation."
He had eaten the bare minimum each day for breakfast, lunch, and supper, stuffing the extra food in his shirt and pockets when he was absolutely positive nobody was looking. It's not like he wasn't used to eating stingily, so it was no problem. The food was placed under a board in the room he shared with five other boys. Once he heard the sound of their breathing even out, he loosened the board and placed his loot under it. Both nights he heard Sonny come in to check on them around 12:00, so Dean planned to leave after midnight.
There was only one window in the house that would allow him to leave without walking by Sonny's room. It was in the bathroom in the hall. Unfortunately, Dean hadn't planned on a squeaky door.
The muffled thumps coming from the bedroom across the hall gave Dean all of the incentive he needed to start moving into action. He quickly opened the window, clambered up onto the 'sill, and onto the roof, quickly and efficiently lowering the window without making a sound. Now he just had to get onto the ground. Using the fence and the edge of the roof, he swung onto the wet grass, crouching down to reduce noise and visibility. He melted into the shadows cast by the trees along the yard, moving quickly but surely to the road. Once he reached the road, he started running at a steady pace, eager to reach the town and Sammy.
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There's a reason that the police trust Sonny with troubled kids. He's responsible, well-mannered, and due to his time in prison, craftier than any teenager. That is, until Dean Winchester came around. As soon as he heard the bathroom door squeak, Sonny knew the kid was trying to escape. For one thing, there's a bathroom in the boy's room. For another, his breathing hadn't been deep and even when Sonny had checked on him earlier in the night. When he rushed into the bathroom, he cursed himself when he found it empty. The hint of smoke gave him some idea of where Dean had gone. See, they had been burning the firewood that had gotten damp all day, so the air still smelled kind of smoky. The smell in the bathroom could only be a result of an open window. Sonny rushed downstairs and out the door, wondering how the kid could have gotten outside so fast and fumbling for his keys as he went to his truck. There was no way he could let another kid give him the slip, not after Jimmy Slater had left without a trace half a year ago.
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Dean, being no beginner, had stuck to the fields and pastures instead of the road. Whenever a car drove by, he would dive into the grass to avoid detection. Slowly, but steadily, he reached town and headed for the motel where he and Sam had been staying. Undoubtedly, Dad would eventually call Bobby to check on Sam, but he was busy with a hunt so it might not be the most important thing on his mind right now. Just like Dean obviously wasn't. When he reached their room, he used his secret knock to let Sammy know it was safe to let him in. He waited a few minutes before he pulled out the paperclip that he had stuck in his boot. Maybe he did get something out of staying at Sonny's: You didn't have to use a lock pick to be able to pick a lock.
He slowly eased the door open and peeked inside. The room looked clean, obviously Bobby had already come to pick up Sam. He went over to his bed and picked up the one thing that marred the emptiness of the room: his duffel. Apparently, Bobby and Sam left it there in the hope that he returned. Dean picked it up and turned around to walk out the door, when a pair of headlights practically blinded him. He froze for a moment, caught in the glare, and then bolted. Sonny's yelling echoed after him as he darted across the parking lot and into the woods that edged the motel.
Running through the forest at night ain't exactly the smartest thing a person could do. Yet somehow Dean always ends up doing it. At least this time it was just a regular human chasing him. Not like it's a wendigo or a werewolf. In fact, it was starting to be downright pleasurable. That is until he was tackled from behind by a 190 pound man on a mission. As Dean grunted in pain and tried to get up, Sonny clenched his hands together and said, "Let's get on home and have a good talk." Dean grimaced and tried to pull away from Sonny, but his grip tightened, and the bruises that were just starting to heal were irritated. Turns out a werewolf can sometimes be preferable than an angry ex-con.
They sat in the truck in icy silence on the way home, the doors locked and Dean's hands cuffed together by the same cuffs he had just gotten out of three days ago. When they reached the house, Sonny manhandled Dean back inside and dragged him to his room, delaying the talk for the morning. As he was handcuffed to the bed to prevent further escape, Dean realized that perhaps he should have listened closer to Dad's story. Maybe the fourth night was the best night to escape.
The next morning, Dean woke up sore and tired. Turns out, being cuffed to a piece of furniture after being tackled doesn't really do any wonders for a person's back. When Sonny came into the room to wake up the other boys, he backed up in apprehension, afraid of the consequences of his little escapade. Sonny leaned down and unlocked the cuffs before he woke up the other boys and told them to do their chores before breakfast. When all of the boys were gone, Sonny looked at Dean and sat down to discuss the previous night. Dean hung his head and waited for the yelling to start.
"I'm disappointed in you." These words brought his head up in surprise. Sonny saw the shock looked at him sadly, "I'm not going to yell at you if that's what you're expecting. The boys who I invite into my home are often misjudged, living every day in fear of the wrath of a parent or the flippancy of a teacher. You are safe here." Dean scoffed at this and said, "My dad isn't like those other parents. He keeps me safe." Sonny shrugged, looked Dean and the eye and said, "Maybe so. But I don't want to let you go back to a father who turns his back on his own son when he makes a mistake." Dean looked down at his hands and remained silent. He was too afraid of the truth of that statement to acknowledge it. "I'll make you a deal," Sonny said. "Stay with me until your dad comes to pick you up. If your mind changes about leaving by then, you'll be free to go. But until then, you abide by my rules, and that means no more trying to escape."
Dean hesitated before nodding his head in agreement. He didn't really want to be tackled anymore and this guy was starting to be interesting. Sammy would be safe with Bobby. Maybe it was time to try and be as close to normal as he could get, even if it's only for a little while. Who knows what other chances he'll get?