Don't Go Out Tonight, Supernatural, NC-17
Fandom: Supernatural
Title: Don't Go Out Tonight
Pairing/Characters: Dean, Sam, Dean/Sam (sorta), Sam/OMC
Rating: NC-17
Word Count: 3978
Summary: John disappeared and Dean is left to take care of Sam. When Dean gets himself into big trouble with a bad guy, it's up to Sam to bail him out.
A/Ns & Warnings: This is Hooker!fic. Dean is hooking to make money for him and Sam to live on. This is pimp!fic, in that Dean has to give Sam to the guy who he owes money. It is underage (Sam is 17). But it is consensual. There is also cross-dressing. For those of you who read my other journal, this is the Sam in a skirt fic I was blathering about on Friday.
“Dean?”
“I’m fine.”
“That doesn’t look fine.”
Dean held a hand over his eye. “Just had a little accident.”
“You have accidents a lot lately.” Sam crossed to where Dean was shutting the door of the cheap apartment. “I’m seventeen. Not stupid.”
“Mind your own business, Sam. I’ll handle it.” Dean crossed to the small fridge and got some ice.
Sam crossed to the kitchen space and put his hands on his hips. “This to do with Mosely?”
Dean looked at him sharply. “What do you know about Mosely?”
“I know he stopped me on my way home from school today, told me you owed him a lot of money and that if I didn’t want to be scraping you off the pavement I should help you pay it back.”
Dean kicked the chair. “I told him to keep you out of it. Fuck.”
“Why do you owe him? What do you owe him?”
Dean tried to push past him. “I’ll handle it.”
“Right, because you’re not already beat to shit and you can just pull money out of your ass. Oh, wait…you can pull money out of your ass, after your trick stuffs it up there.”
Dean didn’t mean to do it, but he swung at him, missed and landed on the bed. Dean yelled as his bruised ribs hit the mattress. Mosely’s guys had worked him over pretty good.
Sam sighed and came to the bed, yanking on Dean’s shirt. “Let me see.”
“I said I was fine.”
“Yeah, black eyes and bruised ribs are my definition of fine too.” Sam pulled the shirt up over his head and squatted, pushing Dean’s left arm up over his shoulder, his fingers skimming over the skin. “At least one of these is broken. We should get you to the hospital.”
“Can’t afford it. Mosely took everything I had.” Dean looked away, ashamed.
“How much?”
Dean shook his head. “Doesn’t matter. I’ll get it.”
“Dean.”
He put his arm down and stood up. “I’ll get it.”
Sam sighed and grabbed his arm as he tried to walk away. “He said you had until tomorrow. Then he’ll find other ways to get it out of you.”
“I can’t get it by tomorrow. Not all of it.”
“I have some saved.” Sam headed for the dresser.
“I’m not taking your money.”
“Yes, you are.” Sam rummaged around in the drawer and came up with a sock. He pulled a wad of bills out and tossed it to Dean. “It’s not much.”
Dean rifled through the bills, calculating in his head. “There’s gotta be $300 here.”
Sam shrugged. “Tips from the job you made me quit.”
“Dad would kill me if he knew you were working a place like that.”
“I was just waiting tables.”
Dean shook his head and tossed the wad back. “Isn’t enough anyway. Keep it.”
“Damn it Dean. I’m not a baby.”
“We’ll just leave. We can be gone before midnight.” Dean paced away. “It’s not like we haven’t done it before.”
“What about Dad?”
Dean froze. He’d been gone a long time. They hadn’t heard a thing from him. “He’ll call.”
Going on a year they’d been squatting where he’d left them. Dean hustled pool at first, burned the credit cards they had. Sitting in one place wasn’t too conducive to credit card fraud though and once they’d maxed the cards and he was too well known to hustle well, he’d been forced to other ways of making money.
He’d stripped. Worked a sleazy club. It wasn’t enough. His desperation must have shown. The club’s owner pulled him aside and offered him extra money if he’d give a private show for some big spenders. The catch was this private show meant touching.
It wasn’t a long fall from there to turning tricks. He only did it when they were desperate. At first. He hid it from Sam. Or he thought he did. Of course, he should have known better. Sam confronted him over it a few months before. He hadn’t reacted well, but it seemed like he adjusted.
“He’ll call and we’ll hook up with him wherever.” Dean head for the bathroom, but Sam stopped him.
“We can’t run. Mosely will keep looking. Three hundred dollars isn’t going to get us far. Dad has the car.”
“What do you suggest then Sam?”
This time it was Sam who turned away, his face flushing. “He…suggested a solution.”
“No.” Anything a man like Mosely Aims suggested was no solution Dean was willing to consider. “You don’t even have to tell me what it is, the answer is no. “
“Why don’t you let me help you?”
“I don’t need my baby brother bailing me out. Okay?”
“Maybe you do.” Sam turned back to face him. “I know it’s more than a thousand Dean. That’s a lot of money. He says I can fix it. He said he would let me fix it.”
Dean closed his eyes. “God, Sam. No. Just. You have no idea what he’s asking.”
Sam nodded slowly. “I do. He wants to fuck me.”
Dean covered his ears. He didn’t want to hear Sam talk that way. “I can do it Dean. You do it.”
Dean crossed the room, grabbed Sam by the shoulders and shook him. “Stop. Just stop.”
“He’ll just keep coming Dean. He’ll keep coming until your dead, and then what will I do? How will I tell Dad?”
Dean dropped his hands. “How will I ever face Dad knowing you…that I let you…?”
“He doesn’t ever have to know.” Sam took his hand and drew him back to the table. “Sit down. Let’s get you taped up.”
“Your brother know you’re here?”
Sam nodded tightly. “He won’t tell me how much he owes you.”
“Does it matter?”
Sam crossed his arms. He wouldn’t cross into the office, not alone. He stood in the doorway. “If I’m negotiating for the payoff, I think I should know.”
Mosely nodded. He stood. He was a big guy, more than 6’5”, broad at the shoulders, with a bald head and a goatee. He was almost handsome, if he weren’t such a dangerous guy. His black skin gleamed in the neon light from the beer signs on his wall.
“His original debt was two thousand. That was three months ago. He paid back five hundred. Interest since his last payment brings it back to eighteen hundred.”
“That’s a lot of interest.” Sam said.
Mosely leaned against his desk. “He knew the terms.” He crossed his mammoth arms. “I’ll tell you what though Sam. I’ll offer you a deal. I’ll knock off the interest, and take another two hundred off the total, if you pay off the debt yourself.” He grinned slow and easy. “To my satisfaction.”
Sam didn’t really like the sound of that. “What does that mean?”
“Are we getting specific?”
“Might as well, right?” Sam straightened up. “I mean, obviously you want something.”
His grin got bigger as his eyes swept over Sam. “Yeah. I want something.” He stood up and came a few steps closer. “Let’s be clear. A sum of money like this is not going to be resolved with a single act. I’m thinking three is a good number. Three. In seven days.”
Sam nodded tightly. Mosely came closer. “First time is tomorrow night. In the morning I’ll drop off your…costume for the evening. You’ll arrive dressed and ready. Your brother brings you. He stays silent. He’ll witness everything.”
Sam swallowed hard. Mosely was nearly in his face now. “Any prep you want, you do yourself. I’ll expect you ready.”
He licked his lips, not entirely sure what that meant. “Three times. And when it’s over, Dean’s free.”
“Completely.”
Sam exhaled slowly. “Then I guess I’ll see you tomorrow night.”
There was a bag in front of the apartment the next morning. Dean brought it in and put it on the table. They both looked at it, looked away from it. They didn’t talk about it.
When Dean went in to take a shower, Sam pulled the bag over to the bed and opened it. There was a note with an address and a time and reminders about the conditions. There were clothes in the bag.
For the first time Sam wasn’t sure he could go through with it. He pulled the skirt out first. It was pink and white, pleated…like something the cheerleaders in his school wore. Under that was a pink half shirt that would be tight over his chest.
At the bottom of the bag was a small make up bag filled with blush and mascara and lipstick and frilly little pony tail things.
Sam shoved it all back in the bag and put the bag on the dresser as Dean emerged from the bathroom. “So…I thought we could go catch a movie or something. My treat.”
Dean nodded, not really saying anything.
Sam got up and met him half way to the dresser. “It’s going to be okay.”
Dean shook his head. “I don’t…let’s not talk about it.”
“Yeah, okay. Get dressed.”
If Sam was nervous, or anxious or afraid, he didn’t show any signs of it. They caught a movie, had an early dinner and headed home. Dean couldn’t let himself think about it, but it sort of had this feeling like he was taking Sam through his last day.
When they got home they had about two hours before they had to be at the address Mosely had given Sam.
“I guess I should…start…” Sam chewed on his lower lip, the first sign that his confidence was wavering.
Dean grabbed his hand. “Sam…I don’t want to do this. I don’t want you to do this. It should be me.”
“Mosely was pretty specific, Dean.”
“No…I mean, it’s my problem.”
Sam sighed and shook his head. “It’s our problem.” He went to the bed to grab the bag and disappeared into the bathroom. He heard the shower come on.
Dean paced around the room, grabbed a beer from the fridge and dropped onto the bed, turning on the tiny black and white television so he wouldn’t have to think. He was about to pimp out his brother to save his own hide.
It was wrong. Mosely was doing it because he knew what it would do to Dean. He was the whore in this family. Sam was…well, he wasn’t innocent, but he wasn’t…this.
If Dean were stronger…if he were a better brother, Sam wouldn’t be forced to this. He flipped the channels, then turned the television off, getting up to go back to his pacing.
His father would kill him if he ever found out. Assuming his father wasn’t lying dead somewhere.
The bathroom door stayed shut for a long time. Dean wasn’t sure what to make of it. Then it opened and he couldn’t think, couldn’t breathe. “God no.” Dean groaned.
All Sam’s confidence and bluster was gone. He wouldn’t look up as he stepped out of the bathroom, the now empty bag in his hands along with something else that he was trying to keep hidden.
His long legs were bare, all the way up to where the skirt started. It barely covered his ass. His feet were shoved into his sneakers. His stomach was bare. The halter top barely fit him. His face was made up with pink blush and lipstick, his eyes clumsily darkened with mascara.
His hair was maybe the hardest to look at. He’d pulled it up into sloppy, short pony tails, held with pink elastic and ribbons that dangled down along his neck.
“I…need to…um.” His hands fluttered and the bag fell, revealing the bottle of lube in his hands. “I got this…but I don’t…”
He looked up fleetingly and Dean had to look away. “Jesus Christ Sam.”
“He said….I should…you know…prepare.”
Dean covered his face. He couldn’t do this. He couldn’t. “We’re not doing this. Get that shit off.”
“No.” Sam moved awkwardly away from the bathroom door where he’d stopped. “I’m okay…I just…don’t really…I don’t know what to do.”
Dean’s eyes locked on his hands, watching them slide up and down over the bottle of lube. Mosely told him to prepare. Like Sam would understand what that meant. Watching him standing there, looking to Dean for assurance, for support, Dean cracked a little and went to him taking the bottle of lube out of his hand.
“He’s a big guy. You need to loosen up, or he’s going to hurt you.”
Sam nodded, but Dean could see he wasn’t getting through. “Okay…put your hands on the table and lean over. I’ll…well…”
Sam did as he was told, still not really sure…not that Dean was either. He poured some lube onto his fingers and warmed it. “Lift…lift the skirt.”
His hands shook as he did. Dean’s hands shook as he moved closer. “I’m going to touch you now. Okay?”
Sam’s nod was jerky and Dean had to swallow a lump of disgust and hurt before he could actually bringing himself to do it. He started with a single finger. Sam jumped and pulled away. “Easy, Sammy…it’s just me…it’s okay.” Sam’s head bobbed up and down and Dean watched him try to relax. He slipped the finger in and out gently, pressing against him, easing him open.
“Okay…second finger.” Sam tensed a little, shifted his feet. Dean slipped a second finger in and worked him open a little more. “You okay?”
He closed his eyes, because nothing about this was okay. He was sticking his fingers into his brother. His in stroke pressed against the nub of nerves that was Sam’s prostate and Sam stiffened.
“Dean.” His voice was strained. His left hand left the table and went to his groin.
Dean licked his lips and scissored his fingers open before plunging them back in and caressing over the spot.
“Fuck, Dean.” His face was red, making the pink lipstick look pale and strange. “I’m…I’m hard.”
Dean nodded. “It’s okay Sam. Just go with it.” Maybe it would be easier if the kid got off before…before Dean gave him over to be fucked like a cheap whore. “Third finger.” He worked another one in, opening Sam’s ass. Mosely wouldn’t care if he hurt Sam. If he tore his ass in the process of getting what he wanted.
“Dean.” Sam’s hand was up under the skirt, pulling on his cock in time to Dean’s stroking into him.
“That’s it Sammy…relax and let it happen.”
“I’m gonna…” And he did, groaning as he came onto the floor under him.
Dean eased his hand out and away, reaching for the roll of paper towels on the counter to clean up. Sam’s face was flushed and he turned away, reaching for a jacket.
“We…we should go.”
Dean nodded and grabbed his own coat. Sam clutched the jacket closed over his ridiculous clothes, but it only reached his knees, leaving his legs exposed. Of course, everyone was going to know exactly where Sam was going and why.
“Here.” Dean pulled his collar up and put a baseball hat on over the ribbons. “Keep your head down. I’ll get you there.”
The address was only a few blocks away…one of the apartment buildings where Mosely put up his whores. Dean guided Sam through the cat calls and staring junkies, flunkies and hustlers, up the stairs to the apartment. He knocked on the door and one of Mosely’s boy’s opened it.
Mosely sat in the middle of a couch with two of his girls. Several of his flunkies filled out the rest of the room. “Well, I was beginning to think you were going to be late.”
The rules said Dean couldn’t talk. Not a sound or he’d kill the whole deal. Sam lifted his head, his eyes skating around the room. “We’re not late.”
“Lose the coat and hat. I want to see my girl.”
Sam’s jaw clenched, but he shrugged off the coat and pulled the hat off.
“Turn around.”
Sam did as he was told. Dean seethed.
“The rest of you get out. I got me some business.”
It was obvious from where Dean stood that he was ready for his business too. His dress pants were already tented. The girls pouted, but did as they were told and the guys followed them out.
For a long minute, Mosely just sat staring. “Been thinking about this all day. How I want it…where…” He stood, adjusting himself. “How hot and tight it’s going to be.” He tossed off the dregs of some drink on the coffee table. “Come on over here.”
Sam took a deep breath, squeezed Dean’s hand and went to where Mosely was standing. Mosely ran a finger over his face, down the neckline of the top. “You ready for me?”
Sam’s nod was shaky, and he tensed when Mosely leaned in to lick over his neck. Mosely’s hands slipped over his waist, around the top of his skirt, then slid down, under, cupping Sam’s ass.
It took everything Dean had not to punch him. His thick fingers kneaded Sam’s ass, pressed in toward his crack. Sam lurched into him when his fingers found his hole. “Mmm…see you got started. Hot.”
Mosely’s eyes met Dean’s. “Did big brother help you? Did you let him touch you?”
Sam jerked back. “Can we just…you know?”
Mosely’s grin was amused. “You want me to fuck you, little girl?”
“How…where?” Sam’s voice was quivering and Dean wanted to grab him and run…just run and never stop.
“Table. Facing the mirror.”
Mosely was still watching Dean as Sam moved into the kitchen alcove. He moved a chair out of the way and took a stance not unlike the one he’d taken for Dean to open him up.
“Ready.”
Mosely and Dean looked at the same time. Sam already looked debauched, his lips all slick and swollen, leaning forward so the skirt inched up. He was looking back at them, one hand on the table, one dangling down his leg. Dean inhaled sharply.
“Come along big brother. I want you to see this.”
Dean yanked his arm away when Mosely reached for him, but went willingly enough to Sam’s side. Mosely took up position behind Sam and unzipped his pants, letting them drop to the ground. His cock sprang up hard and dark. He hissed and cracked his neck.
He positioned Sam’s head so that he was looking in the mirror, then turned to Dean. “Give him to me.”
Dean licked his lips, closed his eyes. Dean touched Sam’s back in apology, let his hand slide down until it was on the skirt. Slowly he pulled it up until Sam’s ass was exposed. He looked at Mosely, but it was obvious he wanted more.
Sam met his eyes in the mirror. He raised an eyebrow, and Dean nodded minutely. If Sam could do this, Dean could. He kept his eyes on Sam and reached to gently separate his ass cheeks, exposing his hole.
“See, now that’s what I’m talking about.” Mosely said with a grin. He guided his cock closer.
Sam’s body tensed, his eyes closed and Dean willed him to open them, to look at him. Mosely groaned and Dean couldn’t help but look as he pressed into Sam. He pressed in incessantly, not giving Sam any time to adjust.
Sam gasped, his hands tightening their grip on the table. Dean looked back to the mirror, to Sam’s eyes. They seemed to say that he was okay. That he could handle it.
The table rocked as Mosely fucked into him, eventually pushing Dean’s hands away so that he could grab Sam’s hips. Dean never let his eyes leave Sam’s.
Sam’s eyes closed, opened, watered, but always came back to Dean’s in the mirror. Mosely’s hand grabbed Sam by one ponytail, pulling him back onto his cock. “Fuck that’s it.”
His rhythm increased, the table creaking and rocking. The sound of flesh slapping into flesh joined the mix along with Mosely’s moaning in pleasure. “Fuck.” He slammed in, pressing Sam down and into the table. His body jerked and he hissed, pulling out before his cock was done spewing, covering Sam’s ass.
He backed off a step. Sam didn’t move for a long minute. Dean found his hand petting over Sam’s back until Sam reached out to stop him. “I’m okay,” he said softly.
He straightened up, flipped the skirt down so it was covering his ass.
“Clean me up.” Mosely said, holding his come slick cock with one hand.
Sam looked to Dean, obviously uncertain. Dean looked to Mosely, then back at Sam, raising one hand to his lips. “Oh.” Sam looked shocked, but turned to the big man. He went to one knee hesitantly. His tongue was tentative and Mosely’s hand fisted in his hair to guide him.
When his cock was spit polished, Mosely pushed him away. “Not bad for a first time. I’ll be in touch.”
Dean helped Sam up and went for his coat.
“Wait.” Sam froze. Mosely smiled at Dean. “Bend over. I want to see.” Sam looked at Dean, then slowly did as he was told, exposing his ass with come oozing out of the red ring of his hole. “Nice.”
Dean slung the coat around his shoulders and guided him out. Sam huddled into the coat and into himself. Neither of them spoke the whole way home.
When the door was safely shut, Sam shuddered and dropped the coat. “Gonna shower.”
Dean just nodded. His first time he’d reacted the same way. Showered six or seven times in two hours. His stomach hurt. When the bathroom door shut Dean collapsed onto the bed. He wasn’t sure what disgusted him more, the thought that he’d given Sam to that fucking bastard, or that he’d gotten hard watching.
The tears spilled hot and silent and he rolled face down into the pillow to hide them. The water kept running and Dean’s cock hurt. He unzipped and wrapped his fist around it. The look on Sam’s face. The sight of that big black cock banging into Sam’s white ass.
It was twisted and wrong and Dean just wanted to forget it all. Instead he jacked off into his fist and got up to wash his hand in the kitchen sink and break out the bottle of whiskey they kept on hand for dealing with pain.
This certainly qualified. He poured two shots and waited for Sam to come out of the bathroom. When he finally did, his skin was red from the hot water and he was dressed in sweats.
Dean handed him the shot and Sam took it without question, downing it, then making a face. The silence was awkward and strange and Dean dealt with it by downing two more shots.
“You should sleep.” Dean said finally when Sam was just standing and staring at the table.
Sam nodded absently and put his glass on the table. He went to the bed, but stopped before laying down. “Don’t go out tonight.”
Dean couldn’t look at him, not when his voice was so shaky and young. “Sam…”
“Just. Just tonight? Stay with me?”
Dean downed one more shot and nodded. He went and checked the lock on the door, cleaned up the salt line and turned off the light. In the small light from the bedside lamp, Sam looked so young. He pulled down the blanket and crawled in, then held up the blankets for Dean.
He slipped into bed and let Sam move closer. They weren’t touching, but there was barely air between them. Sam turned off the light. Dean doubted either one of them would actually sleep.
He wanted to say something…but there weren’t any words for what Sam had done.
Sam’s hand found his and squeezed. Dean squeezed back. Then they both rolled back to back and pretended to sleep.
Title: Don't Go Out Tonight
Pairing/Characters: Dean, Sam, Dean/Sam (sorta), Sam/OMC
Rating: NC-17
Word Count: 3978
Summary: John disappeared and Dean is left to take care of Sam. When Dean gets himself into big trouble with a bad guy, it's up to Sam to bail him out.
A/Ns & Warnings: This is Hooker!fic. Dean is hooking to make money for him and Sam to live on. This is pimp!fic, in that Dean has to give Sam to the guy who he owes money. It is underage (Sam is 17). But it is consensual. There is also cross-dressing. For those of you who read my other journal, this is the Sam in a skirt fic I was blathering about on Friday.
“Dean?”
“I’m fine.”
“That doesn’t look fine.”
Dean held a hand over his eye. “Just had a little accident.”
“You have accidents a lot lately.” Sam crossed to where Dean was shutting the door of the cheap apartment. “I’m seventeen. Not stupid.”
“Mind your own business, Sam. I’ll handle it.” Dean crossed to the small fridge and got some ice.
Sam crossed to the kitchen space and put his hands on his hips. “This to do with Mosely?”
Dean looked at him sharply. “What do you know about Mosely?”
“I know he stopped me on my way home from school today, told me you owed him a lot of money and that if I didn’t want to be scraping you off the pavement I should help you pay it back.”
Dean kicked the chair. “I told him to keep you out of it. Fuck.”
“Why do you owe him? What do you owe him?”
Dean tried to push past him. “I’ll handle it.”
“Right, because you’re not already beat to shit and you can just pull money out of your ass. Oh, wait…you can pull money out of your ass, after your trick stuffs it up there.”
Dean didn’t mean to do it, but he swung at him, missed and landed on the bed. Dean yelled as his bruised ribs hit the mattress. Mosely’s guys had worked him over pretty good.
Sam sighed and came to the bed, yanking on Dean’s shirt. “Let me see.”
“I said I was fine.”
“Yeah, black eyes and bruised ribs are my definition of fine too.” Sam pulled the shirt up over his head and squatted, pushing Dean’s left arm up over his shoulder, his fingers skimming over the skin. “At least one of these is broken. We should get you to the hospital.”
“Can’t afford it. Mosely took everything I had.” Dean looked away, ashamed.
“How much?”
Dean shook his head. “Doesn’t matter. I’ll get it.”
“Dean.”
He put his arm down and stood up. “I’ll get it.”
Sam sighed and grabbed his arm as he tried to walk away. “He said you had until tomorrow. Then he’ll find other ways to get it out of you.”
“I can’t get it by tomorrow. Not all of it.”
“I have some saved.” Sam headed for the dresser.
“I’m not taking your money.”
“Yes, you are.” Sam rummaged around in the drawer and came up with a sock. He pulled a wad of bills out and tossed it to Dean. “It’s not much.”
Dean rifled through the bills, calculating in his head. “There’s gotta be $300 here.”
Sam shrugged. “Tips from the job you made me quit.”
“Dad would kill me if he knew you were working a place like that.”
“I was just waiting tables.”
Dean shook his head and tossed the wad back. “Isn’t enough anyway. Keep it.”
“Damn it Dean. I’m not a baby.”
“We’ll just leave. We can be gone before midnight.” Dean paced away. “It’s not like we haven’t done it before.”
“What about Dad?”
Dean froze. He’d been gone a long time. They hadn’t heard a thing from him. “He’ll call.”
Going on a year they’d been squatting where he’d left them. Dean hustled pool at first, burned the credit cards they had. Sitting in one place wasn’t too conducive to credit card fraud though and once they’d maxed the cards and he was too well known to hustle well, he’d been forced to other ways of making money.
He’d stripped. Worked a sleazy club. It wasn’t enough. His desperation must have shown. The club’s owner pulled him aside and offered him extra money if he’d give a private show for some big spenders. The catch was this private show meant touching.
It wasn’t a long fall from there to turning tricks. He only did it when they were desperate. At first. He hid it from Sam. Or he thought he did. Of course, he should have known better. Sam confronted him over it a few months before. He hadn’t reacted well, but it seemed like he adjusted.
“He’ll call and we’ll hook up with him wherever.” Dean head for the bathroom, but Sam stopped him.
“We can’t run. Mosely will keep looking. Three hundred dollars isn’t going to get us far. Dad has the car.”
“What do you suggest then Sam?”
This time it was Sam who turned away, his face flushing. “He…suggested a solution.”
“No.” Anything a man like Mosely Aims suggested was no solution Dean was willing to consider. “You don’t even have to tell me what it is, the answer is no. “
“Why don’t you let me help you?”
“I don’t need my baby brother bailing me out. Okay?”
“Maybe you do.” Sam turned back to face him. “I know it’s more than a thousand Dean. That’s a lot of money. He says I can fix it. He said he would let me fix it.”
Dean closed his eyes. “God, Sam. No. Just. You have no idea what he’s asking.”
Sam nodded slowly. “I do. He wants to fuck me.”
Dean covered his ears. He didn’t want to hear Sam talk that way. “I can do it Dean. You do it.”
Dean crossed the room, grabbed Sam by the shoulders and shook him. “Stop. Just stop.”
“He’ll just keep coming Dean. He’ll keep coming until your dead, and then what will I do? How will I tell Dad?”
Dean dropped his hands. “How will I ever face Dad knowing you…that I let you…?”
“He doesn’t ever have to know.” Sam took his hand and drew him back to the table. “Sit down. Let’s get you taped up.”
“Your brother know you’re here?”
Sam nodded tightly. “He won’t tell me how much he owes you.”
“Does it matter?”
Sam crossed his arms. He wouldn’t cross into the office, not alone. He stood in the doorway. “If I’m negotiating for the payoff, I think I should know.”
Mosely nodded. He stood. He was a big guy, more than 6’5”, broad at the shoulders, with a bald head and a goatee. He was almost handsome, if he weren’t such a dangerous guy. His black skin gleamed in the neon light from the beer signs on his wall.
“His original debt was two thousand. That was three months ago. He paid back five hundred. Interest since his last payment brings it back to eighteen hundred.”
“That’s a lot of interest.” Sam said.
Mosely leaned against his desk. “He knew the terms.” He crossed his mammoth arms. “I’ll tell you what though Sam. I’ll offer you a deal. I’ll knock off the interest, and take another two hundred off the total, if you pay off the debt yourself.” He grinned slow and easy. “To my satisfaction.”
Sam didn’t really like the sound of that. “What does that mean?”
“Are we getting specific?”
“Might as well, right?” Sam straightened up. “I mean, obviously you want something.”
His grin got bigger as his eyes swept over Sam. “Yeah. I want something.” He stood up and came a few steps closer. “Let’s be clear. A sum of money like this is not going to be resolved with a single act. I’m thinking three is a good number. Three. In seven days.”
Sam nodded tightly. Mosely came closer. “First time is tomorrow night. In the morning I’ll drop off your…costume for the evening. You’ll arrive dressed and ready. Your brother brings you. He stays silent. He’ll witness everything.”
Sam swallowed hard. Mosely was nearly in his face now. “Any prep you want, you do yourself. I’ll expect you ready.”
He licked his lips, not entirely sure what that meant. “Three times. And when it’s over, Dean’s free.”
“Completely.”
Sam exhaled slowly. “Then I guess I’ll see you tomorrow night.”
There was a bag in front of the apartment the next morning. Dean brought it in and put it on the table. They both looked at it, looked away from it. They didn’t talk about it.
When Dean went in to take a shower, Sam pulled the bag over to the bed and opened it. There was a note with an address and a time and reminders about the conditions. There were clothes in the bag.
For the first time Sam wasn’t sure he could go through with it. He pulled the skirt out first. It was pink and white, pleated…like something the cheerleaders in his school wore. Under that was a pink half shirt that would be tight over his chest.
At the bottom of the bag was a small make up bag filled with blush and mascara and lipstick and frilly little pony tail things.
Sam shoved it all back in the bag and put the bag on the dresser as Dean emerged from the bathroom. “So…I thought we could go catch a movie or something. My treat.”
Dean nodded, not really saying anything.
Sam got up and met him half way to the dresser. “It’s going to be okay.”
Dean shook his head. “I don’t…let’s not talk about it.”
“Yeah, okay. Get dressed.”
If Sam was nervous, or anxious or afraid, he didn’t show any signs of it. They caught a movie, had an early dinner and headed home. Dean couldn’t let himself think about it, but it sort of had this feeling like he was taking Sam through his last day.
When they got home they had about two hours before they had to be at the address Mosely had given Sam.
“I guess I should…start…” Sam chewed on his lower lip, the first sign that his confidence was wavering.
Dean grabbed his hand. “Sam…I don’t want to do this. I don’t want you to do this. It should be me.”
“Mosely was pretty specific, Dean.”
“No…I mean, it’s my problem.”
Sam sighed and shook his head. “It’s our problem.” He went to the bed to grab the bag and disappeared into the bathroom. He heard the shower come on.
Dean paced around the room, grabbed a beer from the fridge and dropped onto the bed, turning on the tiny black and white television so he wouldn’t have to think. He was about to pimp out his brother to save his own hide.
It was wrong. Mosely was doing it because he knew what it would do to Dean. He was the whore in this family. Sam was…well, he wasn’t innocent, but he wasn’t…this.
If Dean were stronger…if he were a better brother, Sam wouldn’t be forced to this. He flipped the channels, then turned the television off, getting up to go back to his pacing.
His father would kill him if he ever found out. Assuming his father wasn’t lying dead somewhere.
The bathroom door stayed shut for a long time. Dean wasn’t sure what to make of it. Then it opened and he couldn’t think, couldn’t breathe. “God no.” Dean groaned.
All Sam’s confidence and bluster was gone. He wouldn’t look up as he stepped out of the bathroom, the now empty bag in his hands along with something else that he was trying to keep hidden.
His long legs were bare, all the way up to where the skirt started. It barely covered his ass. His feet were shoved into his sneakers. His stomach was bare. The halter top barely fit him. His face was made up with pink blush and lipstick, his eyes clumsily darkened with mascara.
His hair was maybe the hardest to look at. He’d pulled it up into sloppy, short pony tails, held with pink elastic and ribbons that dangled down along his neck.
“I…need to…um.” His hands fluttered and the bag fell, revealing the bottle of lube in his hands. “I got this…but I don’t…”
He looked up fleetingly and Dean had to look away. “Jesus Christ Sam.”
“He said….I should…you know…prepare.”
Dean covered his face. He couldn’t do this. He couldn’t. “We’re not doing this. Get that shit off.”
“No.” Sam moved awkwardly away from the bathroom door where he’d stopped. “I’m okay…I just…don’t really…I don’t know what to do.”
Dean’s eyes locked on his hands, watching them slide up and down over the bottle of lube. Mosely told him to prepare. Like Sam would understand what that meant. Watching him standing there, looking to Dean for assurance, for support, Dean cracked a little and went to him taking the bottle of lube out of his hand.
“He’s a big guy. You need to loosen up, or he’s going to hurt you.”
Sam nodded, but Dean could see he wasn’t getting through. “Okay…put your hands on the table and lean over. I’ll…well…”
Sam did as he was told, still not really sure…not that Dean was either. He poured some lube onto his fingers and warmed it. “Lift…lift the skirt.”
His hands shook as he did. Dean’s hands shook as he moved closer. “I’m going to touch you now. Okay?”
Sam’s nod was jerky and Dean had to swallow a lump of disgust and hurt before he could actually bringing himself to do it. He started with a single finger. Sam jumped and pulled away. “Easy, Sammy…it’s just me…it’s okay.” Sam’s head bobbed up and down and Dean watched him try to relax. He slipped the finger in and out gently, pressing against him, easing him open.
“Okay…second finger.” Sam tensed a little, shifted his feet. Dean slipped a second finger in and worked him open a little more. “You okay?”
He closed his eyes, because nothing about this was okay. He was sticking his fingers into his brother. His in stroke pressed against the nub of nerves that was Sam’s prostate and Sam stiffened.
“Dean.” His voice was strained. His left hand left the table and went to his groin.
Dean licked his lips and scissored his fingers open before plunging them back in and caressing over the spot.
“Fuck, Dean.” His face was red, making the pink lipstick look pale and strange. “I’m…I’m hard.”
Dean nodded. “It’s okay Sam. Just go with it.” Maybe it would be easier if the kid got off before…before Dean gave him over to be fucked like a cheap whore. “Third finger.” He worked another one in, opening Sam’s ass. Mosely wouldn’t care if he hurt Sam. If he tore his ass in the process of getting what he wanted.
“Dean.” Sam’s hand was up under the skirt, pulling on his cock in time to Dean’s stroking into him.
“That’s it Sammy…relax and let it happen.”
“I’m gonna…” And he did, groaning as he came onto the floor under him.
Dean eased his hand out and away, reaching for the roll of paper towels on the counter to clean up. Sam’s face was flushed and he turned away, reaching for a jacket.
“We…we should go.”
Dean nodded and grabbed his own coat. Sam clutched the jacket closed over his ridiculous clothes, but it only reached his knees, leaving his legs exposed. Of course, everyone was going to know exactly where Sam was going and why.
“Here.” Dean pulled his collar up and put a baseball hat on over the ribbons. “Keep your head down. I’ll get you there.”
The address was only a few blocks away…one of the apartment buildings where Mosely put up his whores. Dean guided Sam through the cat calls and staring junkies, flunkies and hustlers, up the stairs to the apartment. He knocked on the door and one of Mosely’s boy’s opened it.
Mosely sat in the middle of a couch with two of his girls. Several of his flunkies filled out the rest of the room. “Well, I was beginning to think you were going to be late.”
The rules said Dean couldn’t talk. Not a sound or he’d kill the whole deal. Sam lifted his head, his eyes skating around the room. “We’re not late.”
“Lose the coat and hat. I want to see my girl.”
Sam’s jaw clenched, but he shrugged off the coat and pulled the hat off.
“Turn around.”
Sam did as he was told. Dean seethed.
“The rest of you get out. I got me some business.”
It was obvious from where Dean stood that he was ready for his business too. His dress pants were already tented. The girls pouted, but did as they were told and the guys followed them out.
For a long minute, Mosely just sat staring. “Been thinking about this all day. How I want it…where…” He stood, adjusting himself. “How hot and tight it’s going to be.” He tossed off the dregs of some drink on the coffee table. “Come on over here.”
Sam took a deep breath, squeezed Dean’s hand and went to where Mosely was standing. Mosely ran a finger over his face, down the neckline of the top. “You ready for me?”
Sam’s nod was shaky, and he tensed when Mosely leaned in to lick over his neck. Mosely’s hands slipped over his waist, around the top of his skirt, then slid down, under, cupping Sam’s ass.
It took everything Dean had not to punch him. His thick fingers kneaded Sam’s ass, pressed in toward his crack. Sam lurched into him when his fingers found his hole. “Mmm…see you got started. Hot.”
Mosely’s eyes met Dean’s. “Did big brother help you? Did you let him touch you?”
Sam jerked back. “Can we just…you know?”
Mosely’s grin was amused. “You want me to fuck you, little girl?”
“How…where?” Sam’s voice was quivering and Dean wanted to grab him and run…just run and never stop.
“Table. Facing the mirror.”
Mosely was still watching Dean as Sam moved into the kitchen alcove. He moved a chair out of the way and took a stance not unlike the one he’d taken for Dean to open him up.
“Ready.”
Mosely and Dean looked at the same time. Sam already looked debauched, his lips all slick and swollen, leaning forward so the skirt inched up. He was looking back at them, one hand on the table, one dangling down his leg. Dean inhaled sharply.
“Come along big brother. I want you to see this.”
Dean yanked his arm away when Mosely reached for him, but went willingly enough to Sam’s side. Mosely took up position behind Sam and unzipped his pants, letting them drop to the ground. His cock sprang up hard and dark. He hissed and cracked his neck.
He positioned Sam’s head so that he was looking in the mirror, then turned to Dean. “Give him to me.”
Dean licked his lips, closed his eyes. Dean touched Sam’s back in apology, let his hand slide down until it was on the skirt. Slowly he pulled it up until Sam’s ass was exposed. He looked at Mosely, but it was obvious he wanted more.
Sam met his eyes in the mirror. He raised an eyebrow, and Dean nodded minutely. If Sam could do this, Dean could. He kept his eyes on Sam and reached to gently separate his ass cheeks, exposing his hole.
“See, now that’s what I’m talking about.” Mosely said with a grin. He guided his cock closer.
Sam’s body tensed, his eyes closed and Dean willed him to open them, to look at him. Mosely groaned and Dean couldn’t help but look as he pressed into Sam. He pressed in incessantly, not giving Sam any time to adjust.
Sam gasped, his hands tightening their grip on the table. Dean looked back to the mirror, to Sam’s eyes. They seemed to say that he was okay. That he could handle it.
The table rocked as Mosely fucked into him, eventually pushing Dean’s hands away so that he could grab Sam’s hips. Dean never let his eyes leave Sam’s.
Sam’s eyes closed, opened, watered, but always came back to Dean’s in the mirror. Mosely’s hand grabbed Sam by one ponytail, pulling him back onto his cock. “Fuck that’s it.”
His rhythm increased, the table creaking and rocking. The sound of flesh slapping into flesh joined the mix along with Mosely’s moaning in pleasure. “Fuck.” He slammed in, pressing Sam down and into the table. His body jerked and he hissed, pulling out before his cock was done spewing, covering Sam’s ass.
He backed off a step. Sam didn’t move for a long minute. Dean found his hand petting over Sam’s back until Sam reached out to stop him. “I’m okay,” he said softly.
He straightened up, flipped the skirt down so it was covering his ass.
“Clean me up.” Mosely said, holding his come slick cock with one hand.
Sam looked to Dean, obviously uncertain. Dean looked to Mosely, then back at Sam, raising one hand to his lips. “Oh.” Sam looked shocked, but turned to the big man. He went to one knee hesitantly. His tongue was tentative and Mosely’s hand fisted in his hair to guide him.
When his cock was spit polished, Mosely pushed him away. “Not bad for a first time. I’ll be in touch.”
Dean helped Sam up and went for his coat.
“Wait.” Sam froze. Mosely smiled at Dean. “Bend over. I want to see.” Sam looked at Dean, then slowly did as he was told, exposing his ass with come oozing out of the red ring of his hole. “Nice.”
Dean slung the coat around his shoulders and guided him out. Sam huddled into the coat and into himself. Neither of them spoke the whole way home.
When the door was safely shut, Sam shuddered and dropped the coat. “Gonna shower.”
Dean just nodded. His first time he’d reacted the same way. Showered six or seven times in two hours. His stomach hurt. When the bathroom door shut Dean collapsed onto the bed. He wasn’t sure what disgusted him more, the thought that he’d given Sam to that fucking bastard, or that he’d gotten hard watching.
The tears spilled hot and silent and he rolled face down into the pillow to hide them. The water kept running and Dean’s cock hurt. He unzipped and wrapped his fist around it. The look on Sam’s face. The sight of that big black cock banging into Sam’s white ass.
It was twisted and wrong and Dean just wanted to forget it all. Instead he jacked off into his fist and got up to wash his hand in the kitchen sink and break out the bottle of whiskey they kept on hand for dealing with pain.
This certainly qualified. He poured two shots and waited for Sam to come out of the bathroom. When he finally did, his skin was red from the hot water and he was dressed in sweats.
Dean handed him the shot and Sam took it without question, downing it, then making a face. The silence was awkward and strange and Dean dealt with it by downing two more shots.
“You should sleep.” Dean said finally when Sam was just standing and staring at the table.
Sam nodded absently and put his glass on the table. He went to the bed, but stopped before laying down. “Don’t go out tonight.”
Dean couldn’t look at him, not when his voice was so shaky and young. “Sam…”
“Just. Just tonight? Stay with me?”
Dean downed one more shot and nodded. He went and checked the lock on the door, cleaned up the salt line and turned off the light. In the small light from the bedside lamp, Sam looked so young. He pulled down the blanket and crawled in, then held up the blankets for Dean.
He slipped into bed and let Sam move closer. They weren’t touching, but there was barely air between them. Sam turned off the light. Dean doubted either one of them would actually sleep.
He wanted to say something…but there weren’t any words for what Sam had done.
Sam’s hand found his and squeezed. Dean squeezed back. Then they both rolled back to back and pretended to sleep.