By Cowjam40

Todd stomped up the stairs of the cottage, his head narrowly missing a wooden beam on the way up. The ceilings were low enough to be a hazard. There was a small, cold dilapidated bathroom, and two bedrooms.

“In here.” Dan gestured by swinging his arm into the smaller bedroom.

It was basic. Vinyl grey floor, beige walls, and little furniture – just a single metal framed bed, wooden chair, and empty bookcase. The sloping roof and wooden beams reduced the headroom and while there was some natural light, it came from a small, draughty window at waist height.

Todd scanned the room. IT. WAS. FUCKING. CRAMPED.

“Yeah, I know, lad. It’s small. But you’re only sleeping here.” He walked over to the bed where he’d left some folded sheets, a towel, and toiletries – things like a razor, toothbrush, soap. He emptied the prison bag on the mattress. “Is this everything?”

Todd’s face fell. “Yeah.” He said slowly.

“Well lad, you travel light don’t you?”

One corner of Todd’s mouth stretched a smirk. He turned away, embarrassed at his own reaction. He didn’t want anyone to know he could be manipulated like that.

A few unbranded clothes, some paperwork, a battered mobile phone, a Tupperware box filled with a few notes, coins, and pocket fillers – there was nothing of value.

“The mobile’s useless, we don’t get signal here.” Todd’s wasn’t impressed. “You’ve got nothing to wear for work.” That was true. “And I was expecting a girlie mag.” He looked closely for a reaction – the smile widened, at least Todd had a sense of humour.

Dan disappeared into the bathroom and the shower began gushing. “Right then, shower next. The towel’s there. Don’t let the water get cold.” Dan disappeared downstairs.

Todd was looking forward to some clean clothes. He stood in the bath under the shower and allowed the water to wash away the grubbiness. He rarely got enough time in the prison showers, so this was a luxury. He allowed himself to relax. Todd was toned but not muscular, neither smooth but not particularly hairy, he was mostly average – except he was gifted with a firm, beautifully rounded arse.

“Nice stripes.”

Todd jumped in surprise, turning to see Dan leaning against the door frame. He wondered how long he’d been inspecting him.

Dan pointed at Todd’s arse – the caning he’d given had left stripes on his cheeks. Todd re-lived that humiliation in his mind and lowered his head.

Dan continued pointing, his finger made a circle. “I’ve seen this all before, lad. Carry on.”

Todd did, but still felt exposed.

“So here are some more of my rules.” He spoke sternly and loudly to be heard above the shower. “To be a professional, you need to look like one. That means a shower and shave before you start work, brushed teeth, clean clothes.”

“Yes boss.” SHIT. WHY. DID. I. SAY. THAT. He called prison officers “boss,” but that was an accident.

“You got that right, lad, I am your boss.” Dan smiled. “And there will be a daily inspection to check you’re up to standard.”

REALLY? FUCK. WHAT. ELSE.

“No drugs, and no booze. This is a dry house.”

Todd spun around. “No beer? Why?”

Dan’s faced dropped. “That’s the way it is.” He was annoyed at the question. “Get used to it.”

There was something else deeper, nagging at Dan, but he wasn’t given the opportunity to investigate further.

“Turn it off.” He said irritably. “Time to get a trim. You look like a clown.”

“What’s wrong with my hair?”

“It’s a mess.”

“Why can’t I…”

“…because you can’t.”

“I wanna have…”

“I didn’t ask what you want.” Dan called out casually, as he went downstairs. Something scraped against the floor, followed by heavy footsteps. He reappeared at the bathroom carrying one of the bar-backed kitchen chairs. “Sit.”

“What’s the problem with my hair?”

“Get here. And sit.” He said firmly, pointing at the chair.

Todd scowled.

“Give me hassle lad. Go on, I dare you.” This was not about hair, it was about testing Todd’s obedience.

Todd could see he meant it. He recalled his caning. This wasn’t worth a fight. He got out the bath, towelled himself down, put his boxers back on, and slumped in the chair in a huff.

Dan saw there was a risk he might try to use his fists again. “You will not be giving me any hassle.” He pulled handcuffs from his overalls, which he’d used on Todd before. They were rigid speedcuffs, the ones used by police. They had a large black plastic grip in the centre and metal hinged cuffs either side. “Do not struggle, or these will hurt.”

The chair had a low back so Todd’s arms could droop comfortably. He could hear the ratcheting noise as the cuffs tightened around his wrists, the cold metal pressing against his skin. His position made it very difficult to lift himself out of the chair.

“I only know one cut, and you’re getting this one.” Dan pointed at his own head. The style was high and tight, with a fade on the back and sides. He threw a sheet over Todd, grabbed clippers from the bathroom cabinet, and began slowly and methodically gliding front to back over his scalp. Dan circled around the chair, his hands roughly grasping and clasping Todd’s head.

A buzzcut wouldn’t have been Todd’s choice, but he didn’t have a choice. It was strange being restrained and submitting to a cut. Curls of hair fell all around. Each stroke of the clippers, gradually stripped away part of him, revealing something clean cut and new underneath.

“All done.” He smoothed his hand over Todd’s head, rubbed it with a towel to remove the debris, then leaned in close to inspect his work.

Todd’s new look was striking. Tidy, sharp, clean lines. It was an overwhelming transformation. An intense pride surged through his body, a feeling which left him embarrassed as his cock stirred in his boxers.

“Looks better. Doesn’t it?” He noticed Todd’s red face, hot and sweaty.

“Yeah, boss.” He was genuinely grateful. Calling him “boss” seemed fair. He was developing respect for him, starting to trust him, beginning to even like him.

Dan knelt down, removed the sheet, and released the cuffs. He noticed the bulge in Todd’s boxers and smiled. His new lad was horny, cocky and complex, but he was confident he could be transformed into an obedient worker – just like his other apprentices.

“Ok, lad.” He looked at his watch. “We’re going to get you kitted out.” Todd looked confused. “If you’re going to work with me, you need some new gear.”

They’d been in the Dan’s van for more than an hour. Todd could hear tools constantly clanking in the back. It was a stomach-churning journey sat in the front, Dan’s driving was unforgiving on the uneven twisting roads. They parked up next to an army surplus warehouse on an industrial estate.

Inside it was crammed with old and new military and workwear. It was a mess, but Dan was familiar with the layout and dived into rails, pulling out kit in various sizes. He had a plan.

Todd would only be getting workwear, Dan decided that would help shape his mindset. There were army green lightweights built for comfort and strength; quick-drying ripstop camouflage combats; orange hi-viz polo and trousers with reflective stripes; and hardwearing grey cargos with hanging pockets and black panels at the knee. Then warm jackets, fleeces, combat shorts, wet-weather gear, a selection of polos, sweatshirts, t-shirts, in army greens and navy blues. They all formed a huge pile he dumped on the floor next to a curtained off cubicle in the far corner.

“Try them on. In you go.”

“What? All of these?”

“I’m not buying anything that doesn’t fit. And I’m not coming back.”

Todd would have been ok with sweatpants and a football shirt. He picked up the grey cargos, entered the changing cubicle, and drew the curtain.

“We don’t have time.” Dan said, parting the curtain again, and entering the cubicle with him. Todd stumbled in the legs of the trousers and grabbed Dan for balance. “Are you drunk, lad?” There was banter, they were relaxed each other, and Todd was ok with Dan taking full charge.

“Comfortable?”

“Yeah, boss.”

They quickly circulated through all the gear. Dan would get up close to check the fit – pinching and pulling at the material – the inspection was thorough. But he wasn’t just inspecting the clothes. There were very few times when Todd could remember someone making so much effort on him, taking an interest in his appearance, even spending money on him.

Dan disappeared briefly and returned with some brown bib overalls, the same brand he was wearing, but new and unfaded. They were a snug fit for Todd. He was given a blue t-shirt to wear underneath. Then came a pair of used heavy, black, workboots – unforgiving blocks of leather with steel toe caps. Todd leaned onto Dan as he wiggled his foot into the battered leather – they needed shining, but it completed the look.

“Now lad, you are ready.” Dan was looking Todd up and down.

Todd turned to check himself out in the full-length mirror. “Yeah.”

They were wearing the same, the look was the same, the hair… it was the same. Todd froze. Dan stood behind him, his warmth breath on the back of his neck. His hands gently rested on his shoulders.

“Now lad, are you’re ready to become my apprentice?”

Todd spun around and faced him. He swallowed nervously. “Yeah.”

“Are you though? Ready? To follow my rules?” It was a test.

“Yeah, boss.” He said softly and nervously. And he did mean it.

Dan sensed something had clicked in Todd’s head. “Right, well you can get changed back and…”

“Can I…” Todd looked at himself in the mirror again. “Might as well keep this on, boss.”

“Sure.”

There was another reason Todd didn’t want to change back. His new uniform had transformed him, given him an intense pride, a new focus. But he was also horny, and keen to hide his rock hard cock.

By the time they returned to the cottage it was late and they were both tired. Dan reheated some leftovers in the fridge for dinner. Then before sleep, there were more rules for Todd.

“The bed is for sleep only, and it needs to be made every day. I want to see your clothes neatly folded on display in the bookcase. Don’t take care of them, and you won’t get any more. And as promised, there’s a morning inspection of you and your room. My alarm’s set for 7am. That’s when you get up too. Questions?”

“No boss.”

“One other thing. I removed the door from your room. Privacy is a luxury for people who earn my trust.”

Todd had crash landed. Todd wanted to prove himself capable, he also realised he’d be forced to make compromises. It was a lot to take in.

“Now get cleaned up and get to bed.”

They took turns in the bathroom, and then Todd settled into bed. IT. WAS. FUCKING. FREEZING.

He could see glimpses of Dan in his bedroom across the landing preparing for bed, stripped to just some classic white Y-fronts. Dan glanced across, and saw Todd leave his bed.

“What’s up?”

“I’m freezing.”

“I’ll get a blanket. Back to bed. And no boxers, lad. Men don’t need them.”

Todd got back under the sheets, naked, and Dan emerged from his bedroom with a thick quilt which he unfurled into the air. He let it fall onto the duvet, tucked it under the mattress and sat on the bed.

“Warmer now?”

“Yeah thanks, boss.”

This was the first time Todd got to see Dan’s body. He was stocky, but in proportion, with a full furry chest, and tattoos on his arms.

He was jealous of his body, his confidence, and his self-belief. He wanted that swirling tattoo design, he wanted those muscles, and to have that thick body hair. He tried not to stare. But Dan had noticed. And seen the outline of his hard cock.

“Are you going to follow my rules lad?”

“Yeah, boss.”

Dan rested his hand on Todd’s chest and leaned slightly in. “And follow all my instructions?”

“Yeah, boss, I will.”

Dan reached out his other hand, and gently massaged the back of Todd’s neck. “Good lad.”

It was intensely comforting. Todd was horny but also too tired to give it much thought. He closed his eyes and remembered all the experiences he had that day, Dan was so engrained in all of them. SO. DAMN. HORNY.

Dan returned to his bedroom, turning out the lights.

Todd left it a few minutes, reached down to his hard cock, and began jerking himself off. The motion started the bed rocking and squeaking loudly. DAMN! He was going to wake Dan.

For the rest of the night he was left frustrated. And when he did manage to drift off, he couldn’t shake Dan from his thoughts.

To be continued …

The next chapter:

Todd’s Transformation: Chapter 3 – The Routine

Todd faces a harsh, disciplined routine, designed to make him more compliant. Now Dan has a real struggle on his hands.