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Pretty Now

Summary:

Driven to sell himself once more on the streets of Chicago, Dean finds a client who keeps him.

Notes:

Characters from SPN are not mine.

Apologies for any non-American English, I tend to forget and you may see honour rather than honor, etc.

This is a dark fic. Really. So if you don't like that sort of thing, you have been warned.

Chapter 1: One night in South Chicago

Chapter Text

SOUTH CHICAGO – April 1994

Dad hadn’t checked in since Monday, when he said he had a lead on a second black dog.

He had been due back on Wednesday. He wasn’t answering his cell phone.

It was 4pm on Thursday.

Dean knew what he should do. He had a slip of paper with Jim Murphy’s phone number on it.

If he rang Jim and got him to drive seven hours to Chicago, only to have the Impala arrive before him; Dad would not be pleased to put it lightly.

He could wait another couple of days.

If Dad wasn’t back on Sunday afternoon he would act. Jim’s church duties would be done by lunch time and Dean could phone him. Dean set his lips in a determined line at his decision.

Dean stuffed the scrap of paper in his pocket. He carefully opened the broken door of the food cupboard and looked at the single packet of dried chicken noodles; the half can of alphabetti spaghetti and three cookies.

He got a brown paper bag and wrapped the cookies. Then he put a pot of water on for the noodles.

He heard a bus pull up and looked out the window to the busy street below. There was Sam and his school buddy Henry jumping onto the sidewalk.

As he waited for Sam to come barrelling up the stairs, full of excitement at the unexpected bonus of still being in Chicago for the school sleepover at the museum, Dean checked the overnight bag he had packed for his little brother and stuffed the cookies down the side. He gave a smile at the thought of Sammy finding them when he unpacked later.

After their Wal-mart run on Sunday, there had been $25 left in the coffee jar.

Dean had spent $5 on milk and bread. $4 on a box of lucky charms for Sam. $1 each day for Sammy’s lunch. $10 this morning with a forged parental slip for the museum trip.

There was $5 in the jar.

$1 for Sammy’s lunch tomorrow to be handed over to Sam this evening, as the pupils would go straight to school from the museum.
$4 left..... He could get lucky charms, but not milk... or... he could buy new eyeliner and earn some money.

Dean hadn’t eaten since Tuesday morning.

“De, Dee!”

Sam must be extra buzzed if he was calling his brother Dee.

Dean put four notes in his jeans pocket and left one on the counter for Sam, and moved to unlock the deadbolt. The locks were the only things that worked in the crap apartment.

Sam nearly burst as he drew Dean in with his excitement at sleeping under actual dinosaurs and how Henry’s Mom, Mrs Hernandez was bringing a feast, and actual Puerto Rican feast, and Mrs Kawonowski was bringing a real actual Polish cake, that Aggie Kawonowski said she only made for actual Polish weddings, and that they had a spare sleeping bag for him so he wouldn’t have to bring the one from their bed, so Dean would have something to sleep under, wasn’t it great?

Dean’s mouth watered as he listened to the babbling speech. He was tempted to steal back the cookies, but it was important that Sam had something to offer back to Aggie and Henry or whoever. He tipped the noodles into a bowl and added the boiling water, stirring until they were soft, as Sam told him that he had scored an actual one hundred percent on his spelling test.

“That’s great, Sammy. Always say you are the brainiac. I’m proud of you. Now eat your noodles, it will be hours until your feast.” Dean rubbed his brother’s unruly mop as Sam took a stool at the counter.

“Where are your noodles, Dee?”

“I ate earlier, while you were lounging about in school.” Deflect from not eating.

“Why aren’t you going to school?” Deflection. Check. Score one for Dean.

“You know. I had the flu the week we arrived here, and Dad was gone before he could register me.”

“That’s crap Dean. You missed three weeks when we were in Louisiana too.”

“Doesn’t matter, Sammy. Come on finish up and have a shower, you don’t want the United Colours of South Chicago thinking that Winchesters stink. I’ve laid out clean threads for you and your bag is packed. You might want to add a book or something. There is a dollar next to you for tomorrow’s lunch. The bottle of water is holy water and there is a small pack of salt at the bottom of the bag. OK?”

“OK? We got any dessert. I could do a bowl of charms?”

“Nah. I must do groceries later.”

Sam gave him a bitchface. Dean sighed and pointed at the bathroom.

Sam would never understand, and Dean would make sure that he didn’t have to.

By the time Sam was showered and had chosen a book to add to his overnight bag. It was time to go.
Mrs Hernandez was at the door.

“Well you must be Dean? Where is your father? I want to reassure him that Sam will be fine with us. Henry said he only gave his permission this morning.”

Dean put on his best game face for the supersized Mom. “Hi Mrs Hernandez. Dad is working late. Its fine for Sam to go, I packed his bag for him.”

“Well aren’t you a darling? I am sorry to have missed your father.” She gave Dean a mildly suspicious look. He wondered what Sam had been telling Henry. Sam knew better than to draw unwanted attention on them, but he was only ten years old. Dean knew kids could be reckless. He had nearly gotten Sam killed by a striga when he wasn’t much younger than Sam. He would need to have a talk with his little brother the next evening about keeping it zipped.

Sam threw an arm around Dean’s waist and said goodnight, then followed Mrs Hernandez out the door.

Dean locked the door behind his brother and leaned against the wall. He was kind of lightheaded and wished he could go to sleep for a few hours.

Instead he cleaned up Sam’s dishes and the pot and gave the cracked linoleum floor a mop.

A marine always keeps his quarters and his boots polished.

He had the germ of a plan.

The pharmacy on the corner was open until seven.

The Salvation Army soup kitchen opened at eight. It was a twenty block walk.

Ten blocks back to the bus station and the tight hidden alley that he had scouted yesterday when the hunger was getting harder to ignore. Bus stations were always good spots.

Dean wrote a note for Dad and left it on the counter.

You never know, the man might show up. He explained where Sam was and how to get to the museum, how Sam had holy water, salt and his knife, how he was sorry there was no food in the apartment and that he had gone to get some.

Dean pulled his almost empty duffel out from under the bed. He changed into his working clothes. He had a white shirt that was a tight fit for him now and the top buttons were missing. He had the grey goodwill hoodie that Sam refused to wear because it had the wrong soccer team logo on it. It wouldn’t meet in the middle and was glued to his arms but it looked right. He used some of the hair gel that Dad had left behind to spike up his hair, which was overdue a trip to the barbers. The jeans he had on were fine, tight with a rip above the knee. He removed his underwear and put the jeans back on. He had no choice of footwear. He laced up his boots and was ready to go.

In Charleston a man had offered him $250 for the whole night. He had refused. He had to get back to Sammy and he had never let....

Tonight Sam was safe and $250 would set them up for weeks, if Dad failed to show.

If he got three clients (Cherry in Houston had told him to call them clients, he couldn’t call them John) at $25 a blow, then he could do a big grocery shop at the late night Wal-Mart and have a greasy slap up meal at the all night diner. If he let one client spank him and call him baby boy, he might get $100.

Cherry had taken care of him in Houston. She was eighteen, she said. She wanted to know what such a cute thirteen year old was doing on the streets. It was February so he wasn’t still fourteen, for fucksake, he was fifteen, two years older than she thought and he wasn’t on the streets. He had a motel room and a hungry brother. For one week he had worked the corner of 3rd and Brooker with Cherry, two hours per night after Sammy fell asleep. He supposed that Cherry had pimped for him, but she had her own handler. Cherry made sure her pimp never saw Dean. She seemed scared of the man. It was good with Cherry. She laid down the rules. Mouth only and the clients obeyed. Dean kept $15 dollars each time and gave Cherry $10. She gave Dean half her fries. She gave Dean half her joints. She gave Dean the best hand job in history, as she laughed at his small teenage dick, and Dean cringed in humiliation as he came hard against a parking meter. He regretted not being able to say goodbye to Cherry as Dad swept back into the city and bundled them off to Louisiana.

In the pharmacy he struck gold. He could get eyeliner and a lip gloss for a $3.50 deal. Dark green eyeliner (Cherry’s recommendation) and clear gloss. He bought a fifty cent pack of mints at the counter, his last dime to ensure his breath was fresh for each client.

The middle-aged portly man at the counter looked over his head at the next customer. Dean cleared his throat.

“You need something else, son?”

“I need a pack of the free condoms.” God bless Chicago.

“What age are you boy?” Concern not anger. Dean could work with that.

“Sixteen. Thought there was no age restriction.”

The man passed him the slim white cellophane box of ten condoms, “You don’t look more than fourteen. You sure I can’t call someone for you. A family member?”

Dean was out the door before the man could think of any other help he might try.

On the walk to the Salvation Army, Dean indulged in six mints, one every three blocks. By the time he reached the soup kitchen his breath was awesome and his stomach doing rumble sound checks. The doors were open and the queue moving slowly. The guy in front of him stank of urine and beer. He had cooties in his hair. Dean tried to keep a step between them.

Behind him an old woman dressed in a goodwill store of coats limped along. She looked at Dean’s half open shirt and tiny hoodie.

“Hey Sonny-Jim, you wanna coat?”

“That’s very kind of you Ma’m. But I’m good.”

“OK, you just reminded me of my daughter, is all. She was all blond lashes and pretty lips.”

Dean didn’t know what to say. The woman was batshit crazy, one minute he was Sonny-Jim, the next she thought he was a girl. He didn’t even have his face made up yet.

They got into the kitchen and the smell of stew and bread made Dean’s knees go weak.

He took a tray and his eyes drank in the steaming bowl of stew, the square bread roll and the slice of goddamned apple pie that were added as he made his way down the line.

He found an empty spot at the end of a table and got a cup of water.

Dean didn’t register any of the other diners. He was focused on his food. Closing his eyes in pleasure as the warm stew filled his stomach. Screw Sam and his multinational feast, the Salvation Army could cook!

As he ate the last two bites of his pie he leaned back satisfied. He took a moment to admire the scenery. Most of the diners were down on their luck, on the tramp side of homeless. There was a table with two women and a number of kids. They all looked clean but anxious. The only other people who looked different were two guys in their late teens in leather jackets near the exit. As Dean took a better look at them he saw a tall brown haired man in an expensive suit approach the guys. One of the volunteers moved to intercept him, but the suit just jerked a thumb at the door and the two teenagers followed him out. Dean wondered if they were trade, or maybe the kids were delinquents who had been taking advantage of the charity.

Putting his tray on the rack provided, Dean got bible-thumped. Always a risk with the Salvos.

“Have you found Jesus?”

Don’t say is he on a taco, don’t say is he on a taco.

“Ahem, he..." Don’t say is Jesus missing? Don’t say is he missing?

“The Lord forgives all sins. Mary Magdalene is our guide here at the centre.”

“OK, look I gotta go. Thanks for the food and all. It was great.”

The man put a hand on Dean’s arm.

“We are not just a soup kitchen, son. We have a safe hostel, back to education programs, stay clean meetings...”

“Hey man. I’m not on drugs.” Dean shook off the hand. This was why the Salvos were the last resort. Fucking interfering God Whollapers.

“Alright, son, when you are ready we are here. If you are not ready to receive the Lord into your heart. Pray to your guardian angel, he will watch over you.”

It took all of Dean’s restraint not to stab the man with his concealed knife. What the fuck? Angels. Where were the angels his Mom had prayed to when she was burned alive on the ceiling? Where were the angels now?

He escaped into the restroom. His hand shook with temper as he used the urinal. As he tucked himself back into his jeans he got himself back under control.

Okay time to go to work.

Dean made a clean firm sweep of eyeliner on his lower lids and then carefully traced the line on his upper ones. He blinked. His eyes did look bigger. A quick squirt of gloss and he was ready.

Ten blocks to the bus station. Dean relaxed into the walk. His stomach was full and his mood lightened.

A large black sedan with darkened windows drew up alongside and matched Dean’s pace.

Huh? Dean didn’t think he was in a red light area but he was dressed the part and must have drawn a client. Well, this might save a walk. Maybe the John, the client, would drop him at the bus station after.

Dean made his way to the driver’s door as the window glided down, electronic action.

There was a big guy with a broken nose, squashed face, forties, asking Dean how much. The dude was Fugly with a capital F, but beggars can’t be choosers.

“$25 to blow or a hand job, $40 for both, extra for any kinky stuff.” Dean tried to sound confident and not desperate.

“How much to bareback?”

“Sorry man,” Dean pulled back from the window. “I don’t. Find another guy.”

He took another step back and landed against a hard muscled body. Arms came around his upper ones pinning him. To scream or not to scream?

“Hey sweetheart. Don’t panic now. I’m going to take care of you. OK Pretty?”

“What? No. I don’t need to be taken care of. Just let me go.” If he could get to his knife, he could jam it into the man’s thigh and run.

“Now now, shush, what is a baby like you doing trying to run your own gig on my patch?” The man spun Dean around but kept a tight hold on him as he pushed him out to arms length and examined his clothes and face. The driver got out of the car and pressed up against Dean’s back, sandwiching him between them. It was the guy in the suit from the soup kitchen. He was taller than Dean recalled, almost as tall as Dad. He had a straight nose and blue piercing eyes. There was the thin white line of a scar bisecting his right eyebrow. His dark black/brown hair had an expensive cut with a few stray bangs at the side.

“I’m sorry,” Dean wasn’t but he knew he was in the shit here. “I’ll go. I didn’t know.”

“Naw, baby boy, you don’t have to go. You came to the right place. You just went about it the wrong way. What age are you?”

“Sevent...” Dean began. There was a crack and blossoming pain. The man had slapped him across the cheek.

“I’m sorry Pretty, but I don’t condone lying. Let’s start again. What age are you?”

“Fifteen.” Dean lowered his head.

The man put two fingers under Dean’s chin and lifted his face back up.

“Look at me” an order with menace.

Dean nodded the little amount he could with the fingers still there. He understood orders. “Yes sir.”

Maybe if he played along. Let them threaten him, rough him up a little, they would throw him into a dumpster or something and he could
make his way home.

“Good boy. Now come along.” The man was pulling him towards the car. Big guy was pushing. No. He was not getting in the car. He was not ending up with bullet in his head. He struggled, kicking out, but it was useless. Big guy caught his legs and the man had him under the shoulders, and he was in the back seat before you could blink.

Dean slid across the seat and tried the opposite door. It was locked. Dean bundled himself up by the window, keeping his knees up. The man was sitting calmly beside him. Ignoring Dean he pulled out his cell phone and when his call was answered, the man just said, “One to book in. I want Cahill to stay and get Sylvester and Chico at the door.”

When the man had his phone back in his pocket he turned to Dean.

“Open your mouth.”

“Where are we going?” Dean asked.

“Open your mouth Pretty.”

“You want me to blow you for free? Can I go if I do it?”

“Open your mouth.” The man repeated patiently.

Dean sighed and seeing no other way out of it, dropped his jaw. The man moved across and pulled out a pen flashlight.

Dean went to close his mouth but the man held it open with one hand and peered in with the light.

“You have real nice teeth, Pretty, and no signs of thrush or sores.” The man patted his knee and sat back.

“My name is De...”

“Pretty.” The man interrupted.

“No.” Dean was starting to think the guy was a sandwich short of a picnic. “My name...”

The man held up a hand to stop Dean from speaking, “I don’t care if your name is Bill Fucking Clinton, Pretty. You get me?”

“Yeah.” Dean muttered.

“What did you say?” The grip on his kneecap hardened and the man’s fingertips dug under the cartilage.

“Yes sir.” Dean flushed. He had had freaks who wanted to call him baby boy, or son, or some guy’s name, but being called Pretty was fucking embarrassing.

“Good boy. You and I are going to get along just fine. Now, Pretty, you said you don’t bareback? Have you ever? Don’t lie to me.”

“No, sir. I’ve never done it, even with a rubber. I blow or get blown, or I give a hand, or sometimes I get spanked.”

“You never had a John go further than you agreed? Never had a John take more than you offered. Remember Pretty, no lies.”

Dean squirmed. He didn’t like to think of Fort Worth.

“Come on now. You can tell me. I have heard everything. I mean everything. You ever tell anyone else? Your pimp?”

“No. Don’t usually have a pimp. I move around a lot.” Why was he telling this creep?

The man increased the pressure on his knee.

“Once only. My second time, I was thirteen. I blew a guy. Motel clerk, so we could stay another night when our paid stay had ended. I thought ‘cause it wasn’t on the street like my first time, it would be safer, stupid kid I guess. He had a ruler and gave me a few stripes, nothing I couldn’t handle, you know?” God it did feel good to finally tell this to someone else.

The man nodded and started to run his hand up and down Dean’s shin.

“So I thought I was finished and he pushed me down on the carpet, hard, pressing my face into the pile. My pants were down, for the ruler, you know?”

The man nodded again and moved a little closer.

“So the guy gets some office supplies off the desk. He laughed as he stapled into my ass cheeks.” Dean blushed as he relived the shame and the job he had removing them in the bathroom after.

“You are cute when you blush, Pretty. Go on sweetheart, what happened?”

Dean caught a traitorous tear rolling down his cheek. Dean Winchester, you will not cry like a fucking baby in front of this pervert.
“He had a sharpie. He wrote things on my back and my bottom....”

“Go on, darling, what things?”

“Awful things. I couldn’t remove my shirt in front of my family for weeks. It was the middle of the summer. I couldn’t swim with my little brother...” Fuck. Dean sucked in a breath. Fuck he had mentioned Sammy. He looked at the man, but he still seemed concerned, worried about Dean. He didn’t seem to have noticed Dean’s panic at mentioning his little brother. “When he had finished writing he spat on my hole. Then he got a pencil and he pushed it in.” Dean looked down.

“Head up, Pretty, remember. Come on now.”

Dean looked back at the man. He didn’t look disgusted, just sad. “He got a second pencil and he pushed them in. It burned when he moved them around and around. I did nothing. I just lay there. I don’t know why I did nothing.”

“Mmm, I do, pet. Did he do anything else?”

“The bell rang. He left to go see to the desk and I... I pulled out the pencils and I ran. I thought he would come to the room. I stayed awake all night, but he never came.” Fuck he was a cry baby. The man pulled him over onto his lap, and Dean was so out of it that he didn’t fight him.

The man was stroking his hair and whispering in his ear what a good boy he was. Dean found his hand fisting into the man’s jacket. He smelled nice. Like expensive aftershave.

The car stopped in front of what looked like a block of apartments. The man carried Dean out. “Put your arms around my neck Pretty. I don’t want you to fall and hurt yourself.”

The man kept stroking Dean’s hair and Dean wrapped his arms around his neck.

Why was he doing as the man said? Fuck. Maybe he was a monster or a man-witch. Had he put Dean into a trance? Maybe he had hypnotised him, with the look into my eyes stuff.

Dean shifted a little, uncomfortable now that he had thought of unnatural forces at work. He looked at the man and said “Christo.”

The man chuckled as they walked towards two huge bouncer types in the lobby. “You religious, pet? Found you at the Salvation Army after all?”

“No sir.”

“Good. I can’t abide all the guilt and praying and gnashing of teeth. So Pretty, this is Chico and this is Sylvester.” The man pointed at the two gorillas. Dean couldn’t tell them apart. “Guys, this is Pretty. He is coming upstairs with me. I’m going to take care of him.”
He rubbed circles on Dean’s back, like Dean did for Sammy when he was sick, but no one ever did for Dean. He knew now why Sammy liked it so much.

Gorilla One got in the elevator with them. Dean turned his head into the man’s shoulder. He wondered how to convince the man to let him go home when he was done with him. He had to be back by the time Sammy was out of school.

“So Pretty,” the man talked into the top of his head, “this is my block. The top floor is my space. The lower four floors all have six small but comfortable apartments. Each of my whores has their own apartment.”

Dean stiffened at the word whore, and worried he was about to be dumped into a unit and have the door locked behind him.
The elevator stopped and they exited into a short outer hall facing double doors.

“Calm down darling.” The man began to rub circles again. “Here we are at my home.”

Dean let out a breath. He wasn’t being imprisoned in an apartment to service clients.

“Here Chico, open the door.” The man passed the gorilla set of keys.

When they were through the entrance, Dean could see a big open space like something on 90210. There was a huge wrap around leather sofa in the centre with a guy in scrubs sitting on it watching Roseanne on the largest TV he had ever seen.

“Hello Mr Goodman, sir. Is this the new sub you want me to examine?”

Dean almost giggled that the creep was called Good-man, but then the other words sank in.

“What the fuck?” Dean leaped out of Goodman’s hold and moved for the door but Chico was there. He was crushed to the floor in one move and he flailed against the gorilla as he heard the man berate the doctor for his lack of discretion and the fear filled apology in response.

Then Goodman was kneeling by Dean’s head. “Calm down, sweetheart, I’m sorry you were frightened by Dr Cahill. It’s all good now.” He smoothed the back of his hand over Dean’s forehead, distracting Dean from noticing the doctor approaching his other side.

Dean felt the prick of a needle and his eyes grew heavy.

“Sleep, my Pretty” he heard as he was pulled under.