u/flirty-mind

Chapter 1

Chapter 8

Hello! My apologies for the long wait between posts. Since it's been so long, I'm posting the next two chapters here together. Enjoy ;)

(All characters are consenting adults)

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Chapter 9 - The Roommate

Preston Roberts was caught.

Dressed in his new uniform and locked in a chastity cage, he had just been spotted by his roommate.

Preston tries not to panic. He knew it would happen eventually, but he had no excuses prepared.

Max steps into the hallway, eyeing Preston up and down. Max was about 5’11’’, with olive skin and green eyes. His hair clung to his face in a short brown buzz cut. He was no bodybuilder, but he was much bulkier than Preston. He wore jeans, sneakers, and a red football jersey.

“What are you supposed to be? Some kind of slutty schoolboy? I knew you were into some freaky shit, but THIS… this is wild even for you”. Max laughed.

“I… I can explain”, Preston stammered. He wasn’t sure if he could explain.

“Save it”, Max replied. “You texted me an address last night. We both know what that means.”

Preston had nothing to say. His social life was ruined.

Max began to pull his phone from the front pocket of his baggy jeans. “My friends are gonna love this”, he laughed. 

Preston and Max had been friends since freshman year, when they were paired up as random roommates. They had seen each other naked plenty of times, and they knew almost everything about each other, but this was too far.

Preston knew he had to act quickly. He put down the garment bags and sank to his knees.

“Please don’t! I’ll explain everything… I’ll do anything you want”, Preston begged. His fists were clasped together and he was on the verge of tears. 

Max paused, considering his pathetic roommate’s plea. Tears were welling up in Preston’s eyes.

After a tense moment, Max smirked. “Did you say… you’ll do anything?”

“Yes! Max, I'll do whatever you want!” Preston answered too quickly, tears streaming down his cheeks.

A mischievous look crossed Max’s face. “Get up, faggot. We’re gonna have some fun.”

Stunned, Preston struggled to his feet. He had always thought of Max as straight. He had girls over all the time. Preston wanted to ask, but it wasn’t worth pushing his luck. Max was usually pretty chill, but seeing Preston like this brought out a new side of him.

As Preston followed Max towards the living room, he remembered that time sophomore year. They were both drunk, but Preston sucked Max’s cock after both boys failed to score at a party that night. It was a one time thing, and they hadn’t spoken about it since.
They walked into the living room, with a big sofa and a coffee table on a carpeted floor in front of a flat screen tv. Max pushed the coffee out from in front of the couch, clearing space on the carpet, as Preston stood watching.

Without a word, Max got behind Preston, bending to kiss his roommate’s neck. Preston let out a loud moan, and Max laughed.

“I bet you’ve always wanted this… Haven’t you, faggot?”

“Y- Y- Yes Sir” Preston stammered between moans. Maybe getting caught by his roommate would have some benefits. 

Max grinned. “Sir? I like the sound of that, bitchboy.”

The wet spot in his tighty whities was growing. By now, precum was staining the crotch of his uniform shorts. 

Max looked down over Preston’s shoulder, noticing the wet spot. “Wow, looks like you’re really enjoying this huh?”

Preston hardly had time to react as his “straight” roommate reached one hand towards his crotch. 

Max groped at Preston’s bulge, and a look of surprise crossed his face as he made contact with the plastic. “What the fuck is this?”

Preston’s face turned red. This won’t end well. “I- I can explain”, he stuttered.

Max laughed. “Well well well… Let’s find out what we’re working with here.”

Max pushed Preston backwards, and he stumbled into a seated position on the couch. Preston had a look of terror on his face as he stared up toward his roommate. Max was enjoying tormenting him.

“Show me”, Max said, calmly.

Preston gulped. “What?”

“I said… show me”, Max repeated, forcefully. “Or I’ll tell everyone we know about the weird shit you’re into.”

Preston shuddered. He didn’t think Max would actually do that to him, but he didn’t want to risk calling his bluff.

Max pulled out his phone, reminding Preston just how easy it would be to expose him.

Preston quickly unbuttoned the clasp of his shorts before unzipping the fly, revealing his wet tighty whities. The black plastic cage was completely visible through the soaked white cotton.

“Whoa, are you some kinda sissy? Let me see”, Max said.

“It’s not like that”, Preston whined. 

“Dude, it’s totally like that.” Max gestured with his phone, “come on, show me.”

Preston sighed, taking a breath before pulling down the front of his briefs.

Max laughed, delighted. “Wow, it’s so small. How did you even fit in there?”

Preston had no reply. 

Max stepped forward, bending down to feel Preston's locked cock and balls. “If I knew you were like this, I’d have let you give me more blowjobs.” 

Preston’s face got even redder. He secretly always hoped it would happen again.

Max flopped down next to Preston on the couch, his attitude becoming playful. “Dude, you have to tell me all about this.”

Max put his arm around Preston, like the best of friends.

“So… Last night I met this guy…” Preston began.

“Ooh! What was he like?” Max interrupted.

“You gotta let me tell the story”, Preston replied.

“Anyways… He’s an older guy, real business type, wears suits all the time… His name is Brad. So this guy Brad, He told me he wanted to own me as his submissive, and I guess I’ve secretly always kinda wanted something like that.”

Max stared open mouthed as Preston continued. “So to make a long story short, he locked this thing on my dick, paddled my ass, and forced me to wear this uniform.”

“Wow”, Max said. “And you just let him do all this? You must be really submissive. And I bet your ass is so red.”

Preston stood up, lifted his vest, and took the suspenders off his shoulders. As his shorts came down, Preston kicked off his loafers, stepping out of his shorts and underwear.

Preston held up the back of his sweater and blazer, giving a full view of his sore ass to his roommate.

Max gasped before reaching a hand out to touch Preston’s red butt cheeks. His expression changed, darkening. 

“Oh yeah, we’re gonna have some fun.”

Chapter 10 - Double Trouble

Less than a day ago, Preston Roberts was just like any other college twink. Now he had a chastity cage on his cock, no key, a daily uniform, and two Dominants to serve. 

He hadn’t planned on exposing himself to his roommate Max so quickly, but it happened. Now, Max seemed to enjoy humiliating him. 

Preston’s recently-paddled ass was on display for his roommate. He cringed as Max delivered a smack to his left cheek.

“Come on. I know you like it, faggot”, Max said.

Preston whimpered. He did like it.

Max proceeded to give Preston a brutal hand spanking, playing each cheek like a drum set as the boy continued to whine. Preston’s ass would definitely be bruised tomorrow.

Once his roommate’s ass was sufficiently red, Max grabbed Preston by the tie. “Get on your knees, faggot.”

“Yes Sir”, Preston complied, dropping to his knees on the carpet. Following orders was becoming second-nature for him.

Max took off his belt before unbuckling his jeans, letting them fall to his ankles. He pulled down his boxer shorts, his cock springing out from the waistband.

Max’s hard dick was not quite as large as Brad’s, but still much bigger than Preston’s. It was around 6 inches at full mast, and thankfully not quite as thick.

Pulling on Preston’s tie, Max guided the boy’s mouth to his waiting member. Preston opened his lips, parting to take in the head. 

Preston felt embarrassed. Not even a few hours had passed and he was already on his knees again, doing what faggots do.

Max kept pulling on his tie, guiding him up and down with speed and precision. Max’s cock didn’t taste quite as good as Brad’s, but the scent of sweat made Preston’s cage strain. 

After deepthroating a nine-inch dick last night, Preston had no trouble getting all the way down to the base of Max’s shaft. Max’s moans became higher pitched as Preston kept sucking.

Preston was preparing to swallow another load when the pressure on his neck ceased. He looked up at Max, confusion on his face.

“No… not like this. I’m gonna shoot my load all over your faggot face”, Max declared. 

Max stood up, towering over Preston, and began jerking his cock. He pushed Preston backwards, and the boy fell into a seated position.  

Preston wanted to move, afraid of staining his clothes, but Max grabbed his tie. To his horror, Preston was pinned in place as Max ground his tie into the couch.

Before Preston could think to loosen his tie, Max let out a loud groan. 

“Aww yeah, sit there and take it, faggot”, Max moaned. 

In seconds, Max was shooting rope after rope of cum as Preston squirmed. The first rope landed squarely in the center of Preston’s face, another landed his tie, and more squirts landed on his blazer and vest. 

Once Max was finished cumming, Preston’s face was covered in cum, and his uniform was practically ruined.

Max smirked, pulling out his phone without releasing his grip on Preston’s tie. He proceeds to snap multiple pictures of Preston on his knees covered in cum.

“Hey! Why did you do that?” Preston panics.

“Relax… it’s just some insurance so you’ll keep doing what I want”, Max said.

Max turned the phone, showing the pictures to Preston. His cum-covered face, disheveled uniform, knee socks, and straining chastity cage were all visible.

“Please please please don’t show those to anybody”, Preston begged. He was genuinely distressed at this point, but his caged cock pulsed knowing Max had so much power over him.

Max threw his hands up in mock surrender. “Hey! I promise I won’t show them to anyone. It’s just something for me to jerk off with later… if you don’t wanna help me out.”

“Yes Sir”, Preston said with a resigned sigh. He had no choice now.

Preston stayed seated on the floor, cum drying on his face, as Max picked up the tv remote and turned on a football game.

After a few minutes without speaking, Max breaks the tension. “Dude, are you ok?” 

Preston sighed. “It’s fine… the last day or so have just been a lot for me, and that was intense.”

“Aww man, I’m sorry. I didn’t mean to hurt you or anything. I just thought you liked being dominated, and I gotta admit, you look sexy in that outfit with that thing on your dick”. 

Preston smiled. “Thanks.”
“Aren’t you forgetting something?” Max wisecracked.

Preston rolled his eyes. “Thanks… Sir.”

“That’s more like it”, Max chuckled.

“You know…” Max started. “You don’t have to wear that outfit if that Brad guy isn’t around. It looks great on you, but nobody will stop you if you wanna take it off.”

“You’re right”, Preston said.

Preston cleaned the cum off his face with a towel and tried his best to wipe the stains for his clothes, before taking the uniform off and walking towards his room to get some clean clothes.

“Hey, why don’t you come here for a bit?” Max called from the living room.

Preston turned and walked towards Max, joining his roommate on the couch in nothing but his socks and his chastity cage. Preston leaned his head on Max’s shoulder, and the two boys cuddled. 

“What’s that thing on your dick called anyway?” Max asked.

“It’s a chastity cage. It’s supposed to help me learn discipline or something when I can’t cum”, Preston replied.

“Can’t you just take it off and wank?” Max questioned. 

Preston laughed. “Nope! I don’t have the key.”

“Dude, that sucks. I guess maybe I’ll have to help you out”, Max offered.

“You wish!” 

The two boys broke out into raucous laughter before settling back into their cuddle.

They spent the rest of the day like that, lazing around the house, Max watched some TV, with Preston taking breaks from cuddling to fetch his roommate snacks and drinks. After a while, Preston fell asleep on Max’s shoulder.

Max picked up a sleeping Preston, carrying the boy to his bedroom. Max tucked Preston in, admiring how peaceful he looked in his sleep.

Chapter 1

Chapter 7

(All characters are consenting adults)

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Chapter 8 - The Next Morning

Preston wakes up a few times throughout the night from the pressure of his cock straining in its chastity cage. Laying on Brad’s chest, he doesn’t mind the pain so much. He knows this new normal will be an adjustment, but he’s willing to give it a try.

Between the hard plastic of the cage, the tie tight around his neck, and the wool socks pulled up on his calves, he’s surprised he can sleep at all. 

At around 6:30 am, the blackout curtains light, and early morning light pours into the room. Brad and Preston awaken, spending a while cuddling, making out, and staring into each other's eyes.

Brad sits up against the headboard of his bed, spreading his legs with his silk robe hanging open. Preston takes his Master’s cue, crawling over to give the man a morning blowjob. 

Preston worships Brad’s cock, sliding his mouth and tongue up and down the shaft. Brad pulls on the boy’s tie, guiding him into position for another face-fuck. 

After just a couple minutes, Brad groans, shooting a load into Preston’s mouth. Preston enjoys the feeling of cum sliding down his throat.

After he is finished, Brad smiles. “Good morning boy”.

“Good morning Sir”, Preston replies.

Brad gets out of bed, warming up the standing glass shower with a waterfall head.

“Join me in the shower?”

Preston nods. Brad undresses Preston before removing his own robe and clothing.

Together, they step into the steamy shower. Emboldened by the warmth, they begin making out again.

After a moment, Preston feels a stream hitting his legs. He opens his eyes and looks down, Brad is peeing.

Preston’s first reaction is disgust, but he’s here to push his limits, isn’t he?

Preston sinks down to his knees, his skin making contact with the wet tiles. He points his face upwards and opens his mouth wide, taking in some of the stream.

Brad groans. “Awww yeahh. That’s my gooood boy.”

Preston didn’t know what he expected, but not this. It was warm, salty, and bitter. He can’t help but spit some of it out. 

After Brad is done urinating, he soaps up Preston’s ass, along with his locked dick and balls, cleaning the boy. 

Brad takes a razor from a holster on the wall, taking his time to shave the boy. First his face and chin, then his chest and arms, followed by his legs.

He also makes sure to remove all of the hair covering the boy’s armpits, surrounding his cage, and even in the crack of his hole. 

After the shower, they dry off. Brad applies lotion all around Preston’s body, soothing the razor irritation. Preston puts his own robe on over his chastity cage, shocked by the smoothness of his own skin.

Brad dresses meticulously in a three piece charcoal suit, combing and slicking his hair. He uses a razor in the mirror to touch up his beard. Every detail is perfect.

Preston takes the time to perfect his own hair, making sure to gel it in place without a single strand sticking up.

At Brad’s direction Preston dresses in white briefs, a white shirt, gray shorts, black socks, and a navy blue tie, complete with a maroon sweater vest, brown loafers, and a monogrammed blazer. The shirt stays are almost visible against the boy’s thighs. 

A female staff member walks in, packing Preston’s clothing and a few sets of uniform components in bags for the boy to take home.

“Thank you, Carissa. You may go”, Brad says. 

She leaves with a nod.

“As you’ll come to know, I’m a very busy man. I have a team of staff that live in their own quarters downstairs. They won’t disturb us unless I ask”, Brad explains.

Preston nods. His new Master must be VERY wealthy.

“I think it’s about time for you to go home, boy. I will give you my phone number, and I expect a timely response whenever I contact you. I’ll be seeing you very soon”, Brad says.

They exchange phone numbers. 

Preston doesn’t want to say goodbye. He doesn’t know if he’ll be disciplined enough to keep up with all his new rules alone.

“You should take the bus home, boy. It will do you some good to get used to being seen in your uniform.”, Brad continues. 

Preston hoped the man would call a car, but he had no choice but to comply. 

“Yes Sir.”

The straight a long embrace and kiss before Preston is on his way home. As Preston’s loafers clack against the sidewalk, he reflects on the events of the past day. 

Here he is with his penis locked in a chastity cage and no access to the key. The key is around the neck of an older man he just met, with no unlock in sight. He knows he should be concerned at his own recklessness, but his dick presses against the bars containing it.

Not only that, but he’s 22 years old, dressed up like a schoolboy at the direction of that same man. Suddenly, he’s very conscious of how strange he must look. 

He refuses to make eye contact with any of the dogwalkers and joggers he passes, but he swears a few give him strange glances. 

Despite the humiliation, he feels precum dripping into his tight whities. The fabric clings to his ass under the tight shorts. He feels at once both overdressed and exposed.

At the bus stop, an old man whistles at Preston. He ignores this.

When the bus arrives, Preston is unable to find a seat, so he stands. As he grips onto the ceiling pole with this arm, he suddenly feels very exposed as his vest rides up and his suspenders peak out.

He hopes no one can see the outline of his cage through his tight shorts. If they do, they say nothing. 

He spends the rest of the ride feeling very conscious of the eyes around him. The garment bags he’s carrying are suddenly very heavy. Once he gets off at his stop, he is thankful for the feeling of wind hitting his thighs.

As he reaches the front of his building, a wave of fear washes over Preston. Will his roommate Max be home? What will he say about Preston’s new clothes? Will he notice the cage?

Preston can’t worry about any of that right now. For the first time in a while, he makes a silent prayer, hoping he can slip into his room unnoticed. 

He turns the key, unlocking the door. He steps into the entryway gently, careful to shut the door as quietly as possible, before tiptoeing towards his bedroom.

Just a few steps from his destination, he hears footsteps bounding into the kitchen. 

“I guess someone had a fun night…”

Preston freezes. Max is here.

“Whoa, dude. What are you wearing?”

I've added a story index to my profile that will be updated with links to all parts and any future stories I write. I hope you all continue enjoying the story!

(All characters are consenting adults)

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Chapter 7 - Staying The Night

Preston gazed up at his new Master. Here he was, on his knees in his uniform with a chastity cage around his shaft. He had submitted completely, going as far as licking the dust from the soles of Brad’s dress shoes. 

And now, he was about to suck the man’s cock.

Brad slid down his pinstripe suit trousers, letting them pool at his ankles beneath his sock garters. His white briefs left little to the imagination.

He took off his jacket, laying it folded on the ottoman. Preston took in the man before him. Even with his waistcoat and tie still firmly in place, he looked almost naked. Preston realized he might rarely see Brad in a further state of undress.

Brad gazed down at Preston with a warm smile. “Go on boy.”

That was all the invitation Preston needed. He slinks forward, still on his knees, until he is face to face with his Master’s crotch. 

For a moment he just stares at Brad’s bulge, so well defined in his white underpants. Then, Preston begins feeling up his package through the fabric. 

Brad isn’t even fully hard yet, but his cock feels massive between Preston’s fingers. After more rubbing, Preston pulls Brad’s underwear down, revealing his prize.

Brad’s cock springs to life, hardening immediately. Preston would guess it’s at least 9 inches long, and much thicker than his own trapped dick. He imagines it’ll hurt inside his hole, but he’ll worry about that later.

Preston takes Brad’s shaft into his lips, swirling his tongue around the head. Brad lets a low groan, he must like it. 

Slowly, Preston takes more of Brad’s length into his mouth, inch by inch. He’s not used to sucking cocks this large, but he’s determined to please his new Master.

Feeling bold, Preston attempts to deepthroat the entire length. Halfway down, and he’s already gagging. 

Brad moans, “Yeah, just like that boy.”

With license to continue, Preston tries again, and again, and again, until his nose is touching Brad’s trimmed bush. 

With 9 inches in his throat, Preston is sputtering in seconds. It’s not long before he needs to come up for air. On his next pass, Brad begins pressing his head down.

Tears well in Preston’s eyes, but he isn’t a quitter. He holds the position for longer and longer as Brad’s moans increase in volume.

It isn’t long until Brad is fucking Preston’s throat, thrusting in and out. “Oh yeah, that’s my good boy.”

Even with his throat full, Preston’s cock strains through the bars of his cage.

After a few minutes of throat fucking, Brad tenses up. “I’m gonna cum in your mouth, boy. Swallow it”, he commands.

“Yeuuhhesss Suhhrr”, Preston attempts to reply with his mouth full. 

Brad smirks briefly before pleasure distorts his face. With a loud groan, Brad pulls out to orgasm, shooting rope after rope of cum into Preston’s open mouth. 

It feels like the load will never end as Preston struggles to swallow it all. Despite his best efforts, his face ends up covered in cum by the time Brad finishes ejaculating.

Brad flushes. “Sorry if that was too much boy, it’s been a while.” A rare moment of humility from the otherwise stoic man. 

Preston flashes a smile as cum drips from his face. “Tastes great, Sir.”

Brad grabs a towel, and proceeds to wipe the boy’s face clean. “Wow, you’re a natural, boy. I haven’t had service that good in… a while.”

“Thank you, Sir. I had fun too”, Preston replies. “Though I must admit, taking your cock in my throat was quite a challenge.”

“Then we’ll have to add throat training to your regimen, won’t we?” Brad replies.

Preston nods. Training could only help.

“Well… it’s getting late. Would you like to stay the night boy?” Brad inquires.

Preston can hardly contain his excitement. “Really? I’d love to, Sir.”

Brad smiles. “Glad to hear it, boy.”

Over the next few minutes, Brad begins getting ready for bed while Preston stay kneeling, awaiting his next order.

Brad puts away his dress shoes, folds his suit trousers, and hangs up his three piece suit while Preston watches. 

Brad finally loosens his tie and unbuttons his dress shirt, before revealing the key to Preston’s chastity cage on the chain around his neck. Preston feels his erection grow as the key to his freedom is suddenly in reach. 

The man’s chest is chiseled, speckled with a tasteful amount of salt and pepper hair. He must spend a lot of time in the gym. Left in just his white briefs, dress socks, and garters, Brad dons a silk robe and a pair of fuzzy slippers. 

“I have an extra toothbrush for you, boy. Come get ready for bed,” Brad says.

“Yes Sir”, Preston complies, following his Master into the bathroom. The two of them proceed to brush their teeth at the same time in the mirror, smiling at each other with foamy mouths.

After they are finished, they stroll back into Brad’s bedroom. Preston’s discarded clothes and the contents of his pockets were stacked neatly on a dresser.

“Since you’ve been such a good boy, you may remove your blazer, sweater, loafers, and suspenders to sleep. Make sure they are handled neatly.”

Preston is relieved. He wasn’t sure he’d be able to sleep in the full stiff uniform. “Thank you, Sir”.

“Of course, boy. You earned it”, Brad replies.

Preston takes care to hang his blazer on a hanger in the bedroom closet, along with his suspenders. He leaves his loafers neatly on the floor.

As Preston sits down on the right side of the large bed, Brad gives him a kiss, before tightening the boy’s tie.

“Remember boy, keep your tie tight and socks pulled up at all times”, Brad reminds Preston.

“Yes Sir,” Preston replies. He’s never slept with a tie on before. His neck feels constricted in a way that’s both uncomfortable and a bit arousing.

Preston took a moment to take the contact lenses out of his eyes, stowing them in the case that was in his pocket earlier.

“You know, boy, you would look much more refined in a pair of glasses”, Brad said.

“I’ll think about it, Sir”, Preston replied.

As Preston climbs under the covers, Brad pulls the chain of his bedside lamp, plunging the room into darkness. Blackout curtains automatically descend, covering the windows. 

Brad scooches over in the bed until he is right next to Preston, turning his body to spoon the boy. Preston feels Brad’s cock pressing against his ass through the thin fabric of his shorts.

Brad reaches one hand over Preston, groping the boy’s cage through his shorts. Preston shudders at the stimulation.

“I’m glad you’re here, boy”, Brad says. “It takes a lot of courage to trust and commit so quickly.”

“I’m glad too, Sir”, Preston replies. “I feel safe with you.”

Preston turns his body, and they proceed to make out. Preston uses his tongue to explore every inch of Brad’s mouth. They kiss until his lips feel sore.

Finally, they pull apart. Preston lays his head on Brad’s chest.

“Good night, boy.”

“Good night, Sir.”

They slowly drift to sleep.

Chapter 1

Chapter 5

This one may not be for everyone, but there will be more coming for different tastes :)

(All characters are consenting adults)

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Chapter 6 - Starting Service

Caged and in his uniform for the first time, Preston felt a newfound air of confidence. He feels powerful, looking in the mirror at his true self for the first time. His dick swells in its prison, a bead of precum leaking from the slit.

Brad looks down at the boy, proud. In just a few hours, he turned an ordinary twink into a picture-perfect submissive. He can’t help but admire his handiwork, as any good Dominant should. 

“You know boy… with how naturally you’re settling into the new you, I’d love to see what you can do for me”, Brad crowed. His face settled into a flirtatious smile. 

Preston felt… submissive. “I’d love a chance to please you Sir, to prove my obedience”. He nearly got down on his knees to beg before Brad could reply. 

Brad smirked. “You might just get your chance, boy. Would you like to see my bedroom?”

The bedroom? Preston was expecting a hookup tonight but now he was ecstatic, practically drooling at the thought of worshipping the older man’s cock while he can’t even touch his own.

Preston nods. The wet spot in his underwear grows.

“Great. Follow me”, Brad says.

Brad leads Preston back into the hallway, the heels of the boy’s loafers clacking on the panels.

At the end of the hallway, Brad opens the door to the master bedroom. Like the rest of the house it’s a well-decorated room. Preston swears he recognizes some of the paintings on the walls. The bed is massive, at least a king size. The room is spacious and wide open, with carpeted floors. 

Brad strolls over to an armchair and coffee table on the right end of the room as Preston follows close behind. Sitting in the chair, Brad props his feet up on an ottoman, picking up a newspaper.

Preston stands at attention, awaiting instructions.

“Well, you said you like worshipping feet, so get to it”, Brad commands.

Practically salivating, Preston immediately gets down on his knees in front of the ottoman. His hands move to the man’s black leather oxfords, ready to remove them.

“Not so fast, boy”, Brad corrects. “I’ve been walking around in these shoes all day long, why don’t you clean them?”

Preston pauses, considering the man’s words. He looks around the room for a brush, but he doesn’t see one. “Do you have a shoe cleaning kit, Sir?”

Brad smirks. “You misunderstand me, boy. Clean them… with your tongue.”

Preston gulped. Who knows where those shoes had been? He feels his penis pushing against the limits of its cage. He might be even kinkier than he thought. 

“I…” Preston hesitates as Brad looks on expectantly. “Yes Sir.”

Brad smiles, pressing his shoes forward on the ottoman.

Preston knows what to do. Without another word, he leans forwards, opens his mouth, and presses his tongue into the sole of his Master’s right shoe.

As his tongue meets the leather, a surge of energy runs through Preston’s body. It tastes… good? Preston can’t help but let out an audible moan.

Brad chuckles. “Sounds like you’re right where you want to be.”

In response, Preston wraps his lips around the toe of the man’s dress shoe, audibly moaning with his mouth full. 

Preston really gets into it now, practically making out with the shoe. He drags his tongue along the sole of the shoe from top to bottom, making it shine. 

Brad tilts his foot forward, and Preston takes the hint, polishing the top of the shoe and working his way around to the heel.

Satisfied, Brad taps his left shoe against the ottoman. Preston immediately  switches shoes. 

“Very good, boy, you’re learning”, Brad says approvingly.

Preston spends the next few minutes worshipping the man’s left shoe, repeating his service with the same fervor until both shoes are spotless.

“Alright boy, why don’t you take them off for me”, Brad says.

“Yes Sir”, Preston responds. The boy proceeds to untie the man’s shoelaces with his teeth, one shoe at a time. He thinks he saw that in a porno once.

Brad smirks. “Very clever, boy. Continue impressing me like this, and I might just have to keep you around.”

Preston’s cock oozes at the praise. The puddle in his underwear is starting to feel like it might seep onto his shorts. “Thank you, Sir.”

With the laces undone, Preston gently slides the oxfords off of Brad, freeing his socked feet. The odor is immediately noticeable, sweat mixing with the fabric scent. 

Brad picks up one of the shoes, holding it out towards Preston. With his other hand, he reaches for the boy’s neck. Grabbing the back of his head, Brad nudges Preston forward, until the boy’s nose is planted inside the shoe. 

As the aroma hits Preston’s nostrils, he is intoxicated. He’s never smelt something like this before, simultaneously pleasant and off-putting. He can’t get enough, savoring the scent of stale leather.

Preston can’t help but feel shocked at how far he’s fallen in just a few hours. The things he’s doing and letting Brad do to him… he feels so degraded, humiliated, and ultimately inferior to the man he’s kneeling before. 

And the worst part is, he can’t wait to fall further.

Brad flexes the soles of his socked feet, spreading them out further on the ottoman. “Alright boy, why don’t you give me a nice massage?” 

“Yes Sir”, Preston replies, and he begins massaging the man’s socked feet with his hands, pounding and kneading as he goes.

Brad reads his newspaper as Preston goes to work on his aching feet. 

Minutes pass, but Preston does not stop. In a moment of weakness, he presses his nose into the ball of Brad’s foot, inhaling. Remembering Brad’s orders, he quickly resumes the massage, embarrassed. 

Noticing the boy’s reaction, Brad gives him some encouragement. “It’s ok boy, go ahead.”

Preston grins up towards his master, before quickly plunging his face into the sock, ravenous. He can’t get enough of his new Master’s feet.

Brad keeps flipping through his newspaper while Preston goes to work, taking care to savor each toe between his lips and tongue. He works his way up the man’s calves, pushing Brad’s trousers up, kissing the fabric all the way to the garters. He wants to appreciate every inch of Sir’s body, clothed or not.

Once Brad is finished reading, he puts down the newspaper and swings his feet off the ottoman. Preston dutifully backs up, kneeling at attention with his hands behind his back.

“You’ve done well boy”, Brad remarks.

“Thank you Sir. I guess I just really enjoy pleasing you”, Preston says as his locked cock strains. 

Brad pushes the ottoman aside, his feet settling on the floor beneath his armchair.

“Alright, boy. Since you’ve taken to my conditioning well and obeyed my commands with minimal complaint, I think you’ve earned the right to show me just how committed to my pleasure you can be”, Brad declared.

Preston grinned. Does his Master mean what he thinks? He could hardly contain his excitement.

Brad unzipped his trousers, grinning down at his new boy. 

“You know what to do.”

Chapter 1

Chapter 4

(All characters are consenting adults)

~~~~~~~~~~~~~~~~~

Chapter 5 - The Uniform

Just a couple hours ago, Bradley Pemberton III was a stranger. Now he had the key to Preston’s chastity cage hanging around his neck. The man now had complete control over Preston’s orgasms.

Even worse, Preston just let the man paddle his ass, and he actually thanked him for it. Tension hung in the air as Preston wondered what would come next. Brad was in complete control.

Brad would be the one to break the silence.

“Alright boy, it’s time to get you into uniform”, he said.

”But Sir, I didn’t bring any other clothes with me”, Preston whines.

”I know”, Brad says. “But you’re in luck. I think you and my last boy are about the same size. Follow me”. 

Brad leads Preston out into the hallway, and the boy feels precum leaking out from his cage, dripping a trail behind him.

Brad smirks. “Don’t worry about that now, boy. I’ll make you lick it up later.” 

Preston flushes red. He imagines dragging his tongue along the floorboards and shivers.

Brad leads Preston into a doorway, revealing a massive walk-in closet. The walls are lined with two rows of clothing racks, with cubbies on top and dresser drawers below. There are several full length mirrors, cushioned ottomans, and laundry hampers.

The right rack is filled with more suits than Preston has ever seen in one room, in a wide variety of patterns and colors, with just as many dress shirts. A rainbow of ties dot the cubby holes. Brad is committed to his own style. 

On the left, there are a few suits in both dark and light colors, and many blazers in classic colors and preppy patterns with a school-style crest and gold buttons. There are more white and blue dress shirts than Preston can count, with plenty more in various colors and styles. There are only a few pairs of dress pants, but a multitude of shorts in khaki, gray, and green. 

Preston’s cock strains as he takes in his new wardrobe. After over an hour naked with his new cage exposed, he can’t wait to have some modesty.

“Like what you see boy? Better get used to it because this can be all yours”, Brad says. “When Josiah left, he didn’t want to take anything with him”, he concedes solemnly. 

“I do Sir, I love it”, Preston responds. “His loss is my gain.” They share a smile.

“Let’s get you dressed, boy”, Brad says, leading Preston to the left closet. He opens a drawer, revealing underwear of various styles, from lacy panties, to white briefs, to thongs and jock straps. 

Brad selects a pristine pair of see-through white briefs from the drawer. “These will look great over your cage. A lot of boys love how defined they make your cage print. Put them on.” 

Brad hands the briefs to Preston, and the boy puts the briefs on, sliding the fabric over his sore ass. As he pulls his underwear up, the cotton clings to his cage, leaving a bulge that feels even more defined as his balls are elevated.

Brad runs his hand over Preston’s bulge as the boy sits down on an ottoman. “Wow, you are so sexy”, Brad says. 

Preston blushes, “thank you, Sir”. 

“You’re welcome boy”, Brad replies, selecting a pair of gray ribbed dress socks from a drawer, complete with a pair of garters. 

Brad kneels down in front of Preston, taking the boy's bare foot in his hands before sliding each sock on one at a time, tugging the fabric up to the boy’s knees before carefully fastening the garters beneath the sock cuffs.

Preston is grateful for the sudden warmth on his legs, treasuring the intimacy of the moment as Brad fishes a white dress shirt off of a hanger. 

He drapes the shirt over the boy’s torso, taking the time to button each button, and smoothing the collar fold. A pair of shirt stays will further restrict the boy’s movement as they are fastened to his upper thighs.

 Next, Brad hands Preston a pair of khaki shorts. As the boy pulls his shorts up, he makes sure to tuck in his shirt.

The shorts are even shorter than Preston expected, leaving most of his upper legs bare. They’re tight too, hugging the contours of the boy’s ass and exposing a slight outline of his locked cock. 

“These are so short Sir, and my cage is so visible…” Preston whines.

“Nonsense boy, you only see it because you know it’s there. Besides, you’ll get used to it with time”, Brad reassures him.

Preston gives a resigned nod as Brad fastens suspenders to the buttons on the boy’s shorts. The support from the braces is surprisingly comfortable, calming the boy.

Next, Brad slips a pair of brown penny loafers onto Preston’s socked feet, carefully sliding his heels into place.

Brad selects a navy and maroon repp tie with gold outlines from a cubby, standing behind Preston to tie the knot. His hands caress the boy’s chest as he maneuvers the silk, affixing a perfect windsor knot with a dimple to the boy’s collar. 

Brad takes the time to make sure every detail is perfect before moving back toward the clothing racks. Preston feels a wet spot growing in his tighty whities already. He doesn’t know if he’s ever felt this horny.

Brad hands Preston a gray sweater vest, and the boy pulls it on over his head. As Preston stands in the mirror, Brad produces a comb and tin of wax, combing and slicking the boy’s hair into a classic comb over. 

Finally, Brad selects a classic navy blazer from a hanger, before slipping the boy’s arms into the sleeves and pushing the jacket over his shoulders. 

Preston fingers the crest on his breast pocket, an ornate coat of arms with embroidered lettering that reads “Pemberton”. His new master’s mark.

“That is my family’s crest, it goes back generations. When you’re wearing it, the world will know you belong to me. Any time you see it in the mirror, or your fingers graze the embroidery, you’ll be reminded that you represent me”, Brad declares. 

The men embrace, Brad squeezing the boy tightly for almost a minute before letting go.

Preston beams with pride. He can hardly recognize the boy staring back at him in the mirror. “It’s an honor, thank you Sir. This feels… right.”

Chapter 1

Chapter 3

I know it’s been a while since my last post, but I have much more planned and on the way :)

(ALL CHARACTERS ARE CONSENTING ADULTS)
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Chapter 4 - The Spanking 

When Preston left his apartment earlier that evening, he imagined a simple, forgettable hookup. The kind that’s only vaguely satisfying, leaving you cringing after you cum.

Instead, he let a man he just met lock his dick in a chastity cage and keep the key. And now, that same man was about to spank him.

Brad pulls a wooden chair from an alcove, positioning it in front of the boy. “Stand up”, he commands. 

Preston complies, looking confused. He wonders what the chair could be for.

“What now, Sir?”, the boy asks.

Brad gets behind the boy, positioning his arms to rest on the seat, before guiding the boy into an arching position with his body stretched over the seatback.

“This is how you will present for spankings from now on, unless I want to spank you over my knees”, Brad explains. 

“Hold this position until I tell you”, he finished. 

Preston flushes red, “Yes Sir.” 

Without a word, Brad walks out of the room. 

Preston wants to ask Brad where he’s going, but he doesn’t want to risk speaking out of turn. He’s still learning the rules, so it’s better safe than sorry. 

As Preston ponders, Brad’s footsteps fade down the hall.

A few minutes pass, but Preston is struggling to tell the time. He remembers seeing a clock on the wall behind him, but he can’t leave his position to investigate.

More time passes. Preston doesn’t bother counting. This might be a bit of an endurance exercise. Is Sir testing him? Seeing if he’ll obey? He’s not sure, but he heard the man’s command. 

As the clock keeps ticking, precum begins from the slit of Preston’s black plastic chastity cage. If he’s uncertain in his submission, his body isn’t.

After about an hour, Brad returns. Aside from some minor adjustments, Preston hasn’t moved. Underneath his caged cock, a small puddle has formed on the floor.

Brad explains himself casually: “My apologies boy, I had some errands to take care of. Now… where were we?”

Preston briefly contemplates his answer. Should he really be asking for a spanking?

“I believe you were just about to spank me, Sir.” He can hardly believe the words that just left his lips as his locked dick stiffens.

Brad perks up. “Ahh yes, thanks for the reminder. I appreciate the honesty, boy.”

“You’re welcome, Sir”, Preston replies, blushing.

Brad pulls a wooden paddle down from the wall. “We’ll start with six strokes until I can gauge your pain tolerance. From now on, your safe word is Calculator. Just say the word if the pain gets too intense, or if you need a break for any reason. If you’re unable to speak, shake your head back and forth. Understood, Boy?” 

Preston nods, “Yes Sir, thank you.” His cock is throbbing so hard against the walls of its cage that it’s starting to hurt. This is what he’s been waiting for.

Brad smiles. “Very good. Keep count after each stroke, or we’ll have to restart.” 

Preston gulps, bracing for the coming discipline. Brad takes his position behind the boy, winding up the paddle for his first stroke. 

Preston grits his teeth as the paddle connects with a loud WHACK! 

His cheeks stung with pain, and he nearly jumped from the shock. Remembering Sir’s instruction, Preston quickly muttered “One, Sir.”

”A little slow, but I’ll give you some grace for your first time”, Brad said. 

“Thank you, Sir”, Preston replied as the paddle connected with another WHACK, sending a shockwave of pain through his body. He felt his cock surge forward in his cage again, Preston was actually enjoying this! “Two, Sir.”

WHACK! Preston yelped. A moment passes in silence as the boy groans.

Brad frowns. “You forgot to keep count boy, I guess we’ll have to start over.”

Preston involuntarily moaned as precum dripped from his locked cock. “I’m sorry, Sir”. 

“If I didn’t know any better, I’d say you did that on purpose to earn some more strokes. Well, I suppose it’s your lucky day”, Brad smirks.

Preston wanted to protest, but he caught the words before they came out, accepting his punishment. 

“From the top, don’t let it happen again”, Brad lectured.

WHACK! “One, Sir”.

WHACK! “Two, Sir”.

By now, Preston was getting used to the pain. It almost felt pleasurable as he strained in his cage, and he fell into a rhythm as the strokes continued.

WHACK! “Three, Sir”.

WHACK! “Four, Sir”.

WHACK! “Five, Sir”.

WHACK! “Six, Sir”.

After the sixth stroke, Brad hung up the paddle as Preston remained in position. A tear streamed down Preston’s face.

“Very good, boy. You take discipline well”, Brad says. He massages Preston’s red cheeks with his fingers, soothing the boy’s sore ass. Preston had a feeling it would hurt tomorrow. 

Brad approaches the boy, hugging him from behind. “I know it hurts, but in time you’ll grow to appreciate spanking as its own special kind of release. They say it helps manage some of that pent up arousal.”

Brand stands, crossing in front of the boy. He wipes the tear from Preston’s cheek, bending down to plant a romantic kiss on the boy’s lips. 

Preston’s cock swells once again at the affection from his new master. Is this what all his boners will feel like from now on?

“Alright, you may stand”, Brad said. If it still hurts tomorrow, an ice pack should help”. The man really knows what he’s doing.

“Thank you, Sir”, Preston replied as he relaxed his posture and stood. “I think I needed this more than I knew.

Preston had just been spanked. He let another man spank him, and judging by the straining in his cage, he really enjoyed it. 

Preston’s mind felt clear for the first time in a while. There was a reason his past hookups with wannabe dominants never felt right. Those men had no interest in earning his trust, building discipline. 

Roughness didn’t always have to hurt.

Hi everyone! I've been blown away by the level of engagement with the previous chapters, and I appreciate all your comments.

From here on out, the story will dive a little deeper into specific kinks and scenarios, but there will still be plenty of focus on chastity. I have a lot of ideas for things to explore to keep the story fresh as I'm writing, but we'll have to see where it goes :)

Chapter 1

Chapter 2

(All characters are consenting adults)

~~~~~~~~~~~~~~~~~~~~~~~~

Chapter 3 - Learning the Rules

Preston looks down at his locked cock, barely an inch in its KINK3D Nub cage. He’s straining already, watching the head push against its confines. 

He looks at Brad, smiling. “Thank you sir, this feels right. It’s like my cock is in a prison, but doesn’t want to escape. I thought it would hurt, but it almost feels… comfortable?”

Brad stands up, bending down to kiss his new boy on the forehead. Preston feels butterflies in his stomach, his new master seems to be just the right combination of firm and supportive.

“I’m glad, boy. It should feel comfortable, that means it fits well. The adjustment process will be difficult, but I’ll be here for you every step of the way”, Brad says. 

The two men share a romantic embrace, spending a moment in silence, feeling each other’s warmth. For the first time in a while, Preston truly feels cared for.

After a moment, Brad stands. “Over the coming days, you will become extremely horny, desperate even. As the semen builds up inside you, you might discover a whole new side of yourself… You might regret your decision, you might beg to cum, but it’s important that you remain steadfast in your submission. Eventually, your cage will come to feel like a piece of jewelry you never want to take off.”

Preston wasn’t sure if he believed all of this, but without the key to the bars around his penis, he was committed now.

”Yes Sir. I’ll try my best to be open with you about how I’m feeling”, the boy replied.

Brad smiled affirmatively. “That’s all I can ask for.”

Preston beamed. He might be pretty natural at this whole submission thing.

“Alright boy, get on your knees for me. It’s time to discuss the rest of my rules”, Brad commanded.

Preston complies, stepping down from the desk and kneeling on the carpet with his arms behind his head. He feels exposed with his caged cock on display, but he kind of likes that feeling. 

“Very good”, Brad eyes the boy. “You said you wanted to give up control of your appearance. Well it’s time for you to get your wish.”

Preston felt his cheeks growing hot, but he held position.

“You don’t have much body hair, so it won’t be hard to take care of, but I like my boys clean shaven from the neck down. Your hair will stay cropped, and it should always be neat and combed into a slick side part”, Brad continued.

“Yes sir”, Preston answers quickly. That seemed like a lot of daily maintenance to keep up with, but isn’t that what he wants?

“You have a very nice body, boy, but casual clothing just won’t do for a refined young gentleman, I take a very keen interest in how my boys present themselves", Brad explains.

“As you are in service to me, you will wear a uniform. I will pick your clothing for you daily until I believe you are disciplined enough to do it yourself. Every morning, before 7am, you will dress and present yourself to me for inspection.” 

A uniform… The thought of wearing the same thing every day scared Preston, but it might be nice to not have to worry about what he wears anymore.

“You will wear a dress shirt and tie, uniform shorts with suspenders, knee high socks, and polished loafers. You will also wear a blazer and a sweater vest, weather permitting. Underneath, shirt stays and sock garters will leave you feeling tugged at all day”. 

Preston felt himself leaking through the slit of his chastity cage, turned on by the idea of submitting to constant formality. The man’s words almost float over his head.

Wait a minute… Did he say shorts? Does he want Preston to become a schoolboy? He feels far too old for such a thing, but aroused nonetheless. Somehow, Brad is tapping into his deepest fantasies. 

As if noticing the boy’s arousal, Brad elaborated: “You will wear this uniform constantly, staying proper even as you sleep, unless I grant you permission to remove it or wear other clothing”.

Even to sleep? Preston was used to wearing pajamas or nothing at all to sleep. This would certainly be a big adjustment. It wouldn’t be comfortable, but he wants to prove himself to his new master

“If you behave well, I may allow you to remove your blazer, loafers, and elastics to sleep, I find positive reinforcement can go a long way”, Brad finished. 

“Then I’ll have to be a good boy, Sir”, Preston retorted. 

He’s enjoying himself now, but he can tell the man is serious from his matter-of-fact demeanor. Preston isn’t the first boy to submit to these rules.

Brad isn’t moved by Preston’s humor. He scowls, “Do you understand boy?” 

Preston snaps to attention, firmly replying “Yes sir”. His new Dom isn’t one for joking around.

Satisfied with the adjustment, Brad smiles, noticing the boy’s straining cock. “Very good, boy”. 

“You will follow my every order without complaint. Failure to comply may result in a spanking, or other punishments as needed. While you’re learning discipline, you will receive maintenance spankings at my discretion”, Brad continues. 

“What’s a maintenance spanking, Sir?” Preston asks. 

“Maintenance spankings are a way for me to reinforce your submission beyond punishment. They will strengthen our connection and remind you of your place as my submissive. Over time you might learn to enjoy them”, Brad explains. 

Preston is doubtful, but he doesn’t voice this thought.

“In fact… I think I’ll give you your first spanking right now”, Brad continued. “It’s clear you’ve been lacking the discipline you need in your life, but today we will fix that”. 

Preston’s cheeks flush red. Part of him wants to protest, but he can feel his locked package swelling. 

“Y- yes Sir, I want to be a good boy for you”, Preston stutters. 

Brad grins approvingly, “It seems you’re a quick learner boy”. 

Preston smiles, shuddering with arousal.

Chapter 1

(All characters are consenting adults)

~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Chapter 2 - Locked Away

“Ca-caged??” Preston stammers, his cheeks growing even redder. He expected this, but the real thing was much scarier than a fantasy.

Brad continues: “Yes boy, if you are going to serve me you will wear a chastity cage, no exceptions. My last boy did it, and you will too.” 

Preston had fantasized about wearing a cage before, but he thought they were most commonly worn by cross-dressers and trans women. “But Sir, I don’t want to be a girl”, Preston whines. 

“Nonsense, boy, refined young gentleman wear cages too”. Brad looks down at Preston’s rock-hard cock, “Besides, it seems like you enjoy that idea.” 

Preston did kind of like that idea, but he cursed his cock for betraying him. He instinctively moves his hands to cover his erection, but changes his mind, letting his shame show. 

“You’re right Sir, I’ve always fantasized about being an owned faggot deep down. Having to earn every orgasm, focusing solely on my master’s pleasure and following his every order”, Preston admitted.

Brad sits back down, smiling. “Good boy, I knew I saw something in you.”

Brad crosses one leg over the other, his pinstripe trousers riding up. He pauses for a moment, looking deep in thought. “So… tell me boy. What else do you fantasize about?”

Preston blushed. Was he really about to share his deepest fantasies with this man he just met? If he was going to take this seriously, he’d have to open up.

The boy started: “Hmm… I guess I like the idea of worshipping socks, shoes, and feet…”

Brad nodded, as if to say “go on”. 

Preston continued: “Maybe my Dom takes control of my appearance… What I wear, how I do my hair…”

Brad smiled. “You’re in luck boy, I have plenty of rules for how my boys present themselves.”

Preston smiled, gaining confidence. “I guess I can imagine myself eventually becoming a houseboy. Moving in, doing chores around the house, being available to tend to your every need. I like the idea of submitting completely.”

At this point, Brad was enamored. His posture eased up, and he uncrossed his legs, revealing a sizable bulge under his suit trousers. “Well, we’ll have to take it one step at a time, but I could see that happening if everything works out.”

Aroused, Preston tries to sneak a glance towards the man’s crotch, catching the outline of his tenting bulge. He likes knowing that Brad is enjoying himself. 

Brad takes notice of the boy’s gaze. “You’ll have plenty of time to enjoy that later, boy. For now, we have business to take care of… Now, tell me about your prior experience with submission.”

“Honestly Sir, I don’t have much experience. Most guys who say they’re dominant just want to fuck rough without respecting you. Once I ask for anything deeper or explain my fantasies, they ghost. It’s always been easier to just jerk off and forget it”, Preston explained.

Brad frowned. “I see… It takes a lot of care to be a good Dominant. Most boys who say they’re submissive can’t handle it once things get tough either. I’ll tell you what… This is an opportunity to explore your fantasies, and I promise I’ll be here to care for you along the way as long as you stay honest with me”.

Preston smiled, “I’d like that Sir”.

”Very well then, boy. I think you’re ready”, Brad replied.

Preston beams with pride as Brad reaches into a desk drawer, revealing a small black bag. Preston knows what’s inside. 

Brad reaches into the bag, unearthing a black plastic chastity cage. It’s small, but Preston can tell it will fit.

“As long as you are in service to me you will wear this chastity cage as a symbol of my ownership. I will keep the key, and decide when, if ever, you are released or permitted to orgasm. You will follow all of my rules and do as I say, otherwise you will be punished”, Brad declared.

If ever? Suddenly, the man’s words began to sink in. If Preston puts the cage on, he might never cum again. Judging by the reaction of his dick, Preston actually liked that idea. No more fantasies, this was about to become his reality. 

Seeing the reaction on the boy’s face, Brad questioned him: “How do you feel about that, boy?”

Preston hesitated briefly before answering. “Honestly Sir, I’m both excited and afraid… I like the idea of giving up control, but I won’t lie, the idea of never cumming again is pretty scary.”

Brad’s face shifted, his tone becoming gentle. “We will take things at your pace, nothing will happen without your consent. Understood?”

Preston smiled meekly, nodding. “Yes Sir”.

Satisfied with the boy’s answer, Brad continues: “Over time I will learn what gives you pleasure and what makes you feel submissive, we will try various punishments and protocols to learn what works best for you and adjust accordingly.”

Preston felt his cock swell as his mind swirled with fantasies he didn’t even know he had as his new master continued outlining his expectations.

”You are to tell me immediately if you experience major pain or discomfort. I will remove the device periodically for cleaning or milking, but you will not be allowed to touch your cock without permission, understand?” 

”Yes sir, I understand”, Preston replied dutifully.

“Are you ready to submit your manhood entirely to my authority, boy?” Brad looks at Preston intently. 

The boy does not even process Brad’s statement before replying, “Yes Sir”.

Brad smiles, “Very good, boy. Come here”.

Preston complies, moving towards Brad’s chair. Brad lifts Preston’s frame onto the desk top, beaming with pride. He pulls the key from his desk drawer, unlocking the cage’s lock and pulling the contraption apart.

Brad grasps the boy’s balls, pulling them through the snug base ring. Brad gets up from his seat, looking for something, “Stay right here, boy”. 

Preston responds nervously, “Alright Sir”. He can’t help but wonder what’s coming next.

After a moment, Brad returns with an ice pack. 

“What’s that for sir?”, Preston asks. 

Brad gestures to the boy’s erect penis, “Can’t lock you up in this state, now can we?” 

Preston gulps, “No sir”. 

Brad presses the ice pack onto Preston’s cock until it softens, sending a shiver through the boy’s body. Eventually, Brad is able to slide the boy’s shaft into the cage head. Once Preston’s package is firmly in place, he swiftly locks the cage. 

Without a word, Brad loosens his tie and unbuttons his collar, revealing a chain necklace. Brad unclasps the necklace, sliding the key onto the chain. 

“For safekeeping”, he says, smiling up at his new property. 

All Preston can do is watch as his new master tucks the chain beneath his shirt collar, fastening his tie neatly in place. 

Preston hasn’t processed it yet, but he is now owned.

I haven't posted a long fictional story before, but I wanted to try my hand at writing something that explores some of my fantasies. The chapters might be short, as I want to keep it to manageable chunks until I get the hang of this. If people like it, I'll keep posting.

Feel free to comment if you have any suggestions or ideas for things you might want to see later in the story :)

~~~~~~~~~~~~~~~~~~~~~~~~~~

(All characters are consenting adults)

Chapter 1 - Making Contact

Preston sat on the couch, scrolling through his phone. Another lonely Friday night with nothing to do. His roommate was out for the night, so he'd have to entertain himself. With a sigh, he opened Grindr.

He isn’t ugly, but he wouldn’t call himself pretty either. At 5’ 6’’ and 130 pounds with wavy brown hair, he might as well be just another twink. His cock is about 4.5 inches with an average girth, not very exciting, but he doesn’t use it very often anyway.

Looking at the grid, he saw a sea of familiar faces and even more blank profiles, nothing interesting. He massaged his package through his jeans, working up a semi as he perused the profiles. He sighed, resigning himself to jerking off instead, but right before he could close the app, he got a tap notification. He usually ignores those, but this one caught his eye.

The display name “Dom4Sub, 45” was hardly anything new, but this man was very handsome. With a chiseled jawline and coiffed graying hair in an elegant business suit, Preston found his type.

Preston loved to fantasize about submission, but he hardly ever followed through. It was much easier to jerk off and push the thoughts into the back of his mind.

He scrolled down to read the profile, 6’0’’ and 180 pounds, a total top. The bio read “Looking for boys to tame. If you think that might be you, send a message.” Preston rolled his eyes, but he could always ghost, so he decided to send a message. He wasn’t sure what to say, so he went with a simple “Hello Sir”, and put his phone down. 

He noticed a long list of tags on the man's profile: "kink", "dom", "sub", "chastity", "spanking", and so much more.

Preston's mind was reeling, caught up in the fantasy. He'd always wanted to give up control to a suited daddy. Would he be spanked? Caged? Forced to wear a collar and leash? There were so many possibilities, the boy practically drooled.

After a moment, his phone chimed with a reply, “Hello boy. No games here, if you don’t want to waste my time, come over and let me tame you.” There was a location pin attached. Usually, Preston would get scared and ignore this invite, but he felt the need to see this one through. After a quick shower, Preston threw on a jockstrap under jeans, a tank top, and a hoodie. He texted the address to his roommate, Max, with the caption "just in case". Better safe than sorry. Then, he was on his way.

The bus dropped Preston off a few blocks from the address, he'd have to walk the rest of the way. After a while, he arrived at the pin, a fancy suburban house. He cautiously knocked on the door, and was greeted by a man who was even hotter than the pictures.

The man towered over Preston, in an expensive three-piece navy pinstripe suit with shiny black dress shoes. The man reached out his hand, “Hello boy, I’m Brad, it’s nice to meet you”. Preston nervously shook his hand before replying “Preston” and following the man into the house. 

The house was an old money dream, ornately decorated with artwork and antique furniture. Preston gasped, taking in his surroundings. “You have a lovely home, Sir.” Brad beamed with pride, “Thank you boy. I work hard to keep it that way.” 

“Does anyone else live here with you Sir?” Preston asked. “No, this place is all mine. I used to share it with my last boy, but he had to move away for work…”, Brad replied, a hint of sadness in his voice. “I’m sorry to hear that”. Preston hardly knew the man, but he felt the need to comfort him already.

“That’s kind of you to say, boy, but such is life”, Brad replied. “Good boys come and go, but I’m hoping to find one I can spend the rest of my life with.” 

Preston gave a soft smile. “I must admit I’m not very experienced with this kind of dynamic, Sir. I’m not sure if I’m what you’re looking for.” He frowned. Two minutes and he already ruined a chance to live out his deepest fantasies. Preston began to turn towards the door. 

“Stay, boy.” Brad commanded. “We may not know each other well yet, but I can see a good submissive in you. You wouldn’t have come if you didn’t want this deep down.” 

Preston smiled, turning back towards the man. “You’re right Sir, I should give this a shot.”

Brad met his smile before speaking. “Consider this a trial session… We’ll take it one step at a time. I’ll explain all of my protocols to you, and you’re free to go at any point if you’re uncomfortable. Sound good boy?” 

“Yes Sir, that sounds perfect”, Preston replied. Brad grinned, satisfied. “Very well, follow me, boy”. 

Brad led Preston down the elaborate hallway and towards a polished wooden doorway. He opened the door to reveal a study with a large and beautiful wooden desk, matching bookshelves, and a chair that felt more like a throne.

Preston eyed the bookshelves, noticing several books about topics like “Disclipline”, “Elegance”, “Domination & Submission”, and Preppy culture. In the corner, there were two wooden chairs. On the walls, Preston noticed various wooden paddles and canes hanging next to the man’s various accolades and a map of the world. A nameplate on the desk read “Mr. Bradley Pemberton III”. Whoever this man was, he was clearly very intelligent, wealthy, and serious about his passions and proclivities.

Brad unbuttons his suit jacket before sitting down casually, as Preston stood in front of the desk, taking the room in. Brad props his shoe-clad feet up onto the desk, leaning back into his chair comfortably. Preston’s cock swells in his jeans as he catches a glimpse of the man’s ribbed navy dress socks and purple sock garters peaking out from his pant legs.

Brad picks a wooden tobacco pipe up from atop the desk, producing a small tobacco tin from a desk drawer, before packing the pipe meticulously. When he is satisfied, he pulls a small monogrammed lighter from his jacket pocket, lighting the pipe between his lips. He takes the smoke into his mouth, savoring the warmth before exhaling a cloud. 

Brad is silent for a couple minutes, casually smoking his pipe while Preston stands in front of him, futilely trying to cover his erection with his interlocked hands. Preston knew he had a thing for suited daddies, but he never knew he could find smoking so hot. The boy faded into a trance, eyes fixated on the man who hoped would become his new master.

“Strip.” 

Preston hardly heard the soft-spoken command, still caught up in his daze. “I said STRIP.” This time, Brad’s tone was louder and more firm.

Preston snapped to attention, blushing. “I’m sorry. I guess I was just daydreaming” He begins to take off his hoodie, pulling it over his head. “You will address me as Sir when you speak to me from now on, understand boy?” Brad eyes Preston with authority, and Preston stammers an apology: “Yes Sir, I’m sorry Sir.” Brad smirks, “Much better, boy.”

Preston takes off his tank top before undoing his belt and sliding off his sneakers. As he drops his jeans and pulls off his socks, he is standing before Brad in nothing but his jockstrap. 

Brad stands up from his desk, circling around Preston before gripping his exposed butt cheek and delivering a smack on the boy’s bare ass. Preston lets out a yelp of surprise as Brad chuckles. Brad’s smirk subsides as he notices Preston’s bulge, “Oh this won’t do.” Brad moves the flap of Preston’s jockstrap before yanking on the boy’s hard cock: “No no, all my boys are caged.” Preston gulps.

I haven't posted a long fictional story before, but I wanted to try my hand at writing something that explores some of my fantasies. The chapters might be short, as I want to keep it to manageable chunks until I get the hang of this. If people like it, I'll keep posting.

Feel free to comment if you have any suggestions or ideas for things you might want to see later in the story :)

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(All characters are consenting adults)

Chapter 1 - Making Contact

Preston sat on the couch, scrolling through his phone. Another lonely Friday night with nothing to do. His roommate was out for the night, so he'd have to entertain himself. With a sigh, he opened Grindr.

He isn’t ugly, but he wouldn’t call himself pretty either. At 5’ 6’’ and 130 pounds with wavy brown hair, he might as well be just another twink. His cock is about 4.5 inches with an average girth, not very exciting, but he doesn’t use it very often anyway.

Looking at the grid, he saw a sea of familiar faces and even more blank profiles, nothing interesting. He massaged his package through his jeans, working up a semi as he perused the profiles. He sighed, resigning himself to jerking off instead, but right before he could close the app, he got a tap notification. He usually ignores those, but this one caught his eye.

The display name “Dom4Sub, 45” was hardly anything new, but this man was very handsome. With a chiseled jawline and coiffed graying hair in an elegant business suit, Preston found his type.

Preston loved to fantasize about submission, but he hardly ever followed through. It was much easier to jerk off and push the thoughts into the back of his mind.

He scrolled down to read the profile, 6’0’’ and 180 pounds, a total top. The bio read “Looking for boys to tame. If you think that might be you, send a message.” Preston rolled his eyes, but he could always ghost, so he decided to send a message. He wasn’t sure what to say, so he went with a simple “Hello Sir”, and put his phone down. 

He noticed a long list of tags on the man's profile: "kink", "dom", "sub", "chastity", "spanking", and so much more.

Preston's mind was reeling, caught up in the fantasy. He'd always wanted to give up control to a suited daddy. Would he be spanked? Caged? Forced to wear a collar and leash? There were so many possibilities, the boy practically drooled.

After a moment, his phone chimed with a reply, “Hello boy. No games here, if you don’t want to waste my time, come over and let me tame you.” There was a location pin attached. Usually, Preston would get scared and ignore this invite, but he felt the need to see this one through. After a quick shower, Preston threw on a jockstrap under jeans, a tank top, and a hoodie. He texted the address to his roommate, Max, with the caption "just in case". Better safe than sorry. Then, he was on his way.

The bus dropped Preston off a few blocks from the address, he'd have to walk the rest of the way. After a while, he arrived at the pin, a fancy suburban house. He cautiously knocked on the door, and was greeted by a man who was even hotter than the pictures.

The man towered over Preston, in an expensive three-piece navy pinstripe suit with shiny black dress shoes. The man reached out his hand, “Hello boy, I’m Brad, it’s nice to meet you”. Preston nervously shook his hand before replying “Preston” and following the man into the house. 

The house was an old money dream, ornately decorated with artwork and antique furniture. Preston gasped, taking in his surroundings. “You have a lovely home, Sir.” Brad beamed with pride, “Thank you boy. I work hard to keep it that way.” 

“Does anyone else live here with you Sir?” Preston asked. “No, this place is all mine. I used to share it with my last boy, but he had to move away for work…”, Brad replied, a hint of sadness in his voice. “I’m sorry to hear that”. Preston hardly knew the man, but he felt the need to comfort him already.

“That’s kind of you to say, boy, but such is life”, Brad replied. “Good boys come and go, but I’m hoping to find one I can spend the rest of my life with.” 

Preston gave a soft smile. “I must admit I’m not very experienced with this kind of dynamic, Sir. I’m not sure if I’m what you’re looking for.” He frowned. Two minutes and he already ruined a chance to live out his deepest fantasies. Preston began to turn towards the door. 

“Stay, boy.” Brad commanded. “We may not know each other well yet, but I can see a good submissive in you. You wouldn’t have come if you didn’t want this deep down.” 

Preston smiled, turning back towards the man. “You’re right Sir, I should give this a shot.”

Brad met his smile before speaking. “Consider this a trial session… We’ll take it one step at a time. I’ll explain all of my protocols to you, and you’re free to go at any point if you’re uncomfortable. Sound good boy?” 

“Yes Sir, that sounds perfect”, Preston replied. Brad grinned, satisfied. “Very well, follow me, boy”. 

Brad led Preston down the elaborate hallway and towards a polished wooden doorway. He opened the door to reveal a study with a large and beautiful wooden desk, matching bookshelves, and a chair that felt more like a throne.

Preston eyed the bookshelves, noticing several books about topics like “Disclipline”, “Elegance”, “Domination & Submission”, and Preppy culture. In the corner, there were two wooden chairs. On the walls, Preston noticed various wooden paddles and canes hanging next to the man’s various accolades and a map of the world. A nameplate on the desk read “Mr. Bradley Pemberton III”. Whoever this man was, he was clearly very intelligent, wealthy, and serious about his passions and proclivities.

Brad unbuttons his suit jacket before sitting down casually, as Preston stood in front of the desk, taking the room in. Brad props his shoe-clad feet up onto the desk, leaning back into his chair comfortably. Preston’s cock swells in his jeans as he catches a glimpse of the man’s ribbed navy dress socks and purple sock garters peaking out from his pant legs.

Brad picks a wooden tobacco pipe up from atop the desk, producing a small tobacco tin from a desk drawer, before packing the pipe meticulously. When he is satisfied, he pulls a small monogrammed lighter from his jacket pocket, lighting the pipe between his lips. He takes the smoke into his mouth, savoring the warmth before exhaling a cloud. 

Brad is silent for a couple minutes, casually smoking his pipe while Preston stands in front of him, futilely trying to cover his erection with his interlocked hands. Preston knew he had a thing for suited daddies, but he never knew he could find smoking so hot. The boy faded into a trance, eyes fixated on the man who hoped would become his new master.

“Strip.” 

Preston hardly heard the soft-spoken command, still caught up in his daze. “I said STRIP.” This time, Brad’s tone was louder and more firm.

Preston snapped to attention, blushing. “I’m sorry. I guess I was just daydreaming” He begins to take off his hoodie, pulling it over his head. “You will address me as Sir when you speak to me from now on, understand boy?” Brad eyes Preston with authority, and Preston stammers an apology: “Yes Sir, I’m sorry Sir.” Brad smirks, “Much better, boy.”

Preston takes off his tank top before undoing his belt and sliding off his sneakers. As he drops his jeans and pulls off his socks, he is standing before Brad in nothing but his jockstrap. 

Brad stands up from his desk, circling around Preston before gripping his exposed butt cheek and delivering a smack on the boy’s bare ass. Preston lets out a yelp of surprise as Brad chuckles. Brad’s smirk subsides as he notices Preston’s bulge, “Oh this won’t do.” Brad moves the flap of Preston’s jockstrap before yanking on the boy’s hard cock: “No no, all my boys are caged.” Preston gulps.