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Preppy Assimilation

@dandyprep
Gay Stepfordization. Good Bois are Stepford Bois.
209 Posts
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dandyprep preppy-bro
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you know you wanna dress like this too, dude

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dandyprep preppymuscleboys
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Here is a prime example of a father satisfied with the results of his son’s mandatory reconditioning.

Previously an average humanities student with a poor level of fitness Zeke - now known as Zachary - is an avid rower. This newly minted athlete is also a rugby player, cricker and golfer.

Now studying psychology as per his father’s wishes, Zachary will help place all young men and boys on the correct path as he was.

So successful was the personality change, Zachary has also picked up a minor degree in sports science to assist in his volunteer work as an assistant rowing coach for his old high school

Reconditioning of young men results only in positives for the rest of society.

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dandyprep
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conner18803484-deactivated20260 conner18803484-deactivated20260

Sunday Best


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dandyprep preppymuscleboys
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Obedient mindless rugby sons after needed brainwashing

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dandyprep butchmes
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Oh yeah!!

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dandyprep preppyacademy
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The Bad Seed

From Grit to Groomed (A Preppy Academy Side Story)

I. Dispossession

The gravel of the driveway crunched under the worn soles of Matthew’s sneakers. The nineteen-year-old stopped in front of the imposing oak door of Blackwood Hill Manor, his heart pounding not from exertion, but from a dull rage. He wore his usual armor: baggy grey sweatpants, a faded t-shirt featuring a thrash metal band, and that aura of aggression that had always protected him on the track.

But here, the silence was heavy. Not a bird, not a breath of wind. Just order.

The door opened before he even knocked. His uncle Silas stood there. Tall, slender, dressed in a cream cashmere cardigan and impeccably cut flannel trousers. He surveyed his nephew not with disgust, but with the clinical coldness of an architect observing a ruin to be razed.

Uncle Silas : “Come in, Matthew.”

Matthew crossed the threshold, dragging his gym bag.

Matthew : “Thanks for… paying for the court, Uncle Silas. My parents…”

Uncle Silas : “Your parents are ruined,”

Silas cut in with a voice that was soft yet terrible.

Uncle Silas : “The fine for the damage you caused at the stadium, the legal fees, the public scandal… They lost everything to save you from prison. I am the only creditor you have left. You do not belong to me legally, Matthew, but morally, you are my property until I deem your debt cleared.”

Matthew clenched his fists, his sprinter’s muscles contracting under the cheap cotton.

Matthew : “I’ll work. I’ll pay you back.”

Uncle Silas : “Oh, you will work,”

Silas assured him.

Uncle Silas : “But first, get rid of that.”

He held out an open hand.

Uncle Silas : “Your phone. And those rags.”

Matthew : “What? These are my clothes, I…”

Uncle Silas : “They are the costumes of your failure. You ran like a wild beast, you screamed, you smashed everything. Here, we rebuild. Give them to me.”

Matthew hesitated. He felt the trap closing, but the alternative was the streets and shame for his parents. Trembling with contained anger, he placed his smartphone in Silas’s hand. Then, he removed his sneakers. The smell of travel sweat suddenly seemed vulgar in this hall that smelled of wax and lavender.

When he finished undressing, only his underwear remained: a simple white tank top and matching boxer briefs. Stripped of his urban armor, he suddenly felt smaller, more exposed. Silas picked up the clothes with his fingertips, like toxic waste.

Uncle Silas : “Let us burn all this. Follow me.”

Silas guided him towards the grand staircase. As he climbed the steps, Matthew discovered the interior of the manor: dark woodwork, thick Persian rugs that stifled footsteps, an atmosphere frozen in a time he had never known, an era of silence and absolute restraint.

Silas led him to a vast bathroom with grey checkerboard tiling. The air was cool.

Uncle Silas : “On your knees,”

The uncle ordered softly. Matthew froze. His pride revolted one last time, but Silas’s imperious gaze and the weight of the debt crushed him. He complied without conviction, knees against the cold tiles, looking up at his guardian.

Silas opened a lacquered drawer and took out a sleek metal chastity cage, its intricate design featuring a secure locking mechanism. He held the device up, his gaze fixed on Matthew’s lower abdomen.

Uncle Silas : “To signify that you are under my responsibility and absolute authority, I want you to be locked with this.”

He clicked the lock, a sharp sound in the quiet room.

Uncle Silas : “You will keep it on you constantly for the time being. Its cold weight against your skin will serve as a perpetual anchor, reminding you of your subordinate condition here. It is a physical boundary for a spirit that is too wild. It will channel your chaotic impulses and allow you to focus solely on your tasks, reminding you with every movement that you are no longer free to roam.”

Matthew hesitated, his eyes flashing with defiance.

Matthew : “No, I won’t wear it. I won’t be your puppet!”

Silas’s hand shot out, delivering a sharp, stinging slap across Matthew’s face.

Uncle Silas : “You will do as I say, or face the consequences. There is no room for rebellion here.”

Matthew gritted his teeth until his jaw ached. It was a leash, nothing less—a collar for a domesticated animal. He glanced desperately at the door, but the crushing reality of his debt barred the way better than any iron bars. There was no escape; he was trapped. Silas approached him, his movements deliberate and commanding. He took Matthew’s member firmly in his hand, securing the chastity cage around it with practiced ease. The metal clicked into place, a final and resounding lock that echoed in the room. Silas held up the small, ornate key, his fingers closing around it possessively.

Uncle Silas : “This key is mine, and so is your pleasure. You will wear this cage and remember your place with every step you take.”

The metal was biting, ice-cold against his skin, sending a shock through him that felt like a brand. It felt heavy, permanent. The sharp click of the lock resonated in the tiled room like a prison lock slamming shut, sealing his fate.

Silas stepped closer, his voice low and commanding.

Uncle Silas : “This cage will limit your wild, untamed desires. You no longer have need of your penis. Any excitement you feel belongs to me now. Your pleasure is mine to control, and it will be brided by this cage. Remember, every impulse, every thought of pleasure, is now under my command. You exist to serve, and your body is a tool for my pleasure, not yours.”

Satisfied, Silas issued a cold command.

Uncle Silas : “Now, crawl. Show me how a proper apprentice moves on all fours.”

Matthew, with a mix of humiliation and resignation, lowered himself to the floor. His hands and knees touched the grey checkerboard tiling, and he began to crawl, his movements slow and deliberate. Silas walked behind him, his footsteps echoing in the quiet room, guiding him to the room assigned to him.

Silas opened the doors of a huge walnut wardrobe. The interior was an explosion of pastels and geometric patterns. Rows of perfectly ironed Oxford shirts, strictly cut shorts, piles of argyle socks, tweed jackets, ties and bowties…

Uncle Silas : “Henceforth, this is your reality,”

Silas declared, stroking the shoulder of a blazer.

Uncle Silas : “You will wear only what is found here. Do not mistake this for a luxury of choice. As long as your subjugation is not complete, I will decide your outfits, every morning. This is the uniform of a good boy, the attire of those who serve their Master with dignity and obedience. Preppy style, crisp and refined, will be your constant reminder of your role. You will dress as I see fit, reflecting the image I have chosen for you.”

Matthew lowered his eyes to the waxed floor, his shoulders slumping slightly. He said nothing. Silence was his only form of signature at the bottom of this contract he hadn’t read. He was resigned. He no longer had a choice.

II. Taming by the Earth

The first week was a hushed hell. Silas didn’t have a gardener. He had Matthew.

The estate was a masterpiece of symmetry: boxwoods trimmed to the millimeter, white gravel paths without the slightest unevenness, rosebushes constrained on rigid trellises.

Uncle Silas : “Nature is vulgar when it runs wild,”

Silas explained from the terrace, sipping an iced tea while Matthew sweated in the sun.

Uncle Silas : “It is like you. It has too much energy, too much useless sap. It must be pruned, constrained, guided to become pleasing to the eye.”

Matthew was on his knees in the dirt. But he wasn’t wearing work clothes. That was Silas’s perversion. Every morning, a “transition” outfit was laid out at the foot of his bed.

One day, it was a short-sleeved pink gingham shirt and sky-blue shorts. Then another day, a short-sleeved yellow plaid shirt with a repp bowtie tucked into mint-green bermuda shorts. The next, a Fair Isle sweater vest over a shirt buttoned all the way to the top, despite the heat, and so on.

The clothes were always a little too fitted. The shorts, cut very short, exposed his powerful runner’s legs but enclosed them in an aesthetic he had always despised. And there were those socks. Knee-high socks, pulled up to the knees, which made him feel like a giant, ridiculous schoolboy.

Uncle Silas : “Stand up straight!”

Silas’s voice snapped.

Matthew had hunched over to pull out a stubborn root.

Matthew : “I’m working, Sir!”

Matthew grumbled.

Uncle Silas : “A gentleman keeps his posture in all circumstances. You walk like a thug, Matthew. You attack the ground. Here, we glide. Straighten up.”

For every infraction—a rounded back, a slang word, an abrupt gesture—Silas extended the gardening session by an hour, and in addition, Matthew received twenty spankings across his bare ass skin each evening, the number of infractions multiplied by this harsh discipline. The routine was brutal and unforgiving, ensuring that every mistake was etched into his memory, both through the physical exhaustion of prolonged labor and the searing pain of the spankings.

Each evening, as the sun set, the garden became a place of penance, where Matthew’s body bore the weight of his transgressions, and his mind was molded into perfect obedience. The leather loafers, stiff and worn without invisible socks (or with those high socks), gave him blisters, preventing him from running even if he had wanted to. His body, accustomed to the explosiveness of sprinting, was forced into slowness, repetition, submission.

The physical breaking point came on the tenth day. Silas made Matthew sit on a stool in the bathroom.

Uncle Silas : “Your hair. It is a disaster. A barbarian’s mane.”

Armed with scissors and a fine comb, Silas took charge of Matthew’s hair. He didn’t cut everything off. He sculpted. He flooded the rebellious strands with a thick, heavy gel, plastering them against the skull until they hardened into an immobile, shiny helmet. Then, he traced a part down the exact middle—a severe, geometric line dividing Matthew’s skull into two well-behaved hemispheres. To Matthew, it was the dorky hairstyle of an outdated schoolboy, a humiliating look he would have once mocked mercilessly. But to Silas, this rigid middle part was the ultimate seal of discipline, a visual proof that the chaos of the mind had been tamed and plastered into submission. Silas also made sure to remove any hint of facial hair, ensuring that no beard or mustache remained. There was no place for such masculine traits on a boy like Matthew. His face was now as smooth and bare as a child’s, a blank canvas ready for his Master’s command.

Matthew saw himself in the bathroom mirror. 

With his gingham shirt, his sweater vest, and this strict hairstyle framing his now smooth face, he no longer recognized the enraged metalhead. He saw a doll. A docile doll.

III. The Metronome

Physical fatigue was Silas’s ally, but it was at night, in the dark study, that the true transformation took place.

Uncle Silas : “Sit down, Matthew. You worked well today. Your hedges were… acceptable.”

Matthew collapsed into the Chesterfield leather armchair. He was exhausted. His muscles burned, not from the healthy exertion of sport, but from the permanent tension of having to “hold” himself.

On the desk, a mahogany metronome beat time.

Tick. Tick. Tick. Tick.

Uncle Silas : “Close your eyes,”

Silas ordered softly.

Matthew obeyed. The sound was hypnotic.

Uncle Silas : “Do you remember the noise of the stadium, Matthew?”

Matthew : “Yes Sir…”

Uncle Silas whispered.

Uncle Silas : “It is chaos, it is noise. Scrap metal. Like your music. It gives you a headache, doesn’t it?”

The metronome slowed slightly.

Uncle Silas : “Rock, anger, running… It is dirty. You are covered in sweat. You are ashamed. You are alone.”

Matthew grimaced. In his semi-conscious state, memories of his disqualification mingled with saturated guitar riffs, creating an unbearable cacophony that made him nauseous.

Uncle Silas : “Now, breathe,”

Silas guided, his voice sinking deeper into Matthew’s psyche.

Uncle Silas : “Feel the fabric of your shirt against your skin.”

Matthew : “It’s… tight… it restricts me…”

Uncle Silas : “No. It is resculpting you,”

Silas corrected smoothly.

Uncle Silas : “The starch in the cotton is your new spine, stiff and upright. The buttoned collar that grips your throat is holding your head high, preventing you from looking down at the dirt. The high socks bind your calves, turning wild muscle into civilized elegance. These clothes are a mold, Matthew. You are being poured into a vessel of perfection. Without them, you are spilling over with chaos. Within them, you are solid. You are safe.”

Tick. Tick. Tick.

Uncle Silas : “And there, around your groin, the chastity cage. Feel its unyielding metal against your flesh. It is the anchor of your submission, the focus of your devotion. Every movement, every thought, is centered on this restraint. It is the key to your pleasure, the source of your discipline. If you feel yourself stir, if you dare to harden, the pain will be your reminder. It will be your reward. Embrace it, Matthew. The discomfort, the denial—it is all a testament to your devotion for your Master. Your body is mine to command, and this cage ensures your obedience. It is the ultimate symbol of your submission, the only thing that truly makes you whole.”

Tick. Tick. Tick. Tick.

Uncle Silas : “You crave this constriction. You need the tightness to feel real. You love being a handsome, obedient object for me.”

Matthew’s head lolled, his resistance dissolving into the rhythm.

Matthew : “I… I need the tightness…”

He murmured, a vacant smile touching his lips as the idea took root.

Matthew : “I am chaos without it. I want to be held… I want to be an object. I want to serve you, Sir, with every fiber of my being. The cage… it focuses me. It reminds me of my place. It is my pleasure and my pain, and I accept both with gratitude.”

The former athlete’s voice was nothing more than a trickle. The mental resistance, eroded by days of meticulous gardening and sensory deprivation, was collapsing. The image of himself running suddenly seemed grotesque, animalistic. The image of himself, static, perfectly dressed, brought him a wave of artificial dopamine.

Uncle Silas : “A good boy,”

Silas concluded, stopping the metronome.

Uncle Silas : “Go to sleep now. Tomorrow, the old you will be gone forever.”

IV. The Final Molt

Three weeks after his arrival, Matthew woke before dawn. There was no more anger. Just a feverish haste. On the valet stand, another outfit awaited him. It was no longer a suggestion; it was a consecration.

He began with his grooming. He shaved his already smooth cheeks, then combed his hair, tracing the middle part with geometric precision, fixing it with a heavy, shiny pomade.

Then, the dressing. He slid his feet into the white socks with brown argyle patterns . He pulled them up slowly, carefully, until they perfectly hugged the curve of his calves, stopping just below the knee. He put on the shorts. A brown model, high-waisted, vintage cut. The fabric was stiff. He pulled it high on his waist, well above the hips, and the very short cut revealed a length of thigh he would once have found ridiculous. Today, he found it aerodynamic. Elegant.

Came the white shirt. Cotton of absolute purity. The collar was a club collar, its rounded points offering a deceptive softness to the uniform’s rigidity. He fastened the top button, enclosing his neck. Then, he tied the bowtie—a yellow and brown repp tie. As he pulled the knot tight against his Adam’s apple, he gasped. The silk dug into his throat with constant, authoritative pressure. It felt like Master’s grip, a beautiful, suffocating reminder that he was no longer allowed to speak freely. The tightness made him swallow hard, forcing his chin up in a permanent gesture of attentive submission. Finally, he attached the burgundy suspenders.

Snap. Snap.

They snapped onto the waistband, pulling the high-waisted shorts taut against his torso. The tension was immediate; he could not slouch without the straps digging into his shoulders, forcing him into a rigid, upright posture. It was a mechanism of control woven into the fabric itself, locking him into the perpetual, unthreatening silhouette of a “good boy.” Lastly, he slipped his feet into the brown leather Oxford shoes. He knew they were stiff, slippery, and utterly unsuited for gardening—they would offer no grip in the dirt. But practicality was irrelevant. It was Silas’s decision. To wear them was to walk in his Master’s will, regardless of pain or logic. He laced them tight, binding his feet into beautiful, impractical cages of obedience.

He turned to the full-length mirror. The rebel athlete had vanished. In his place stood a neat young man, frozen in an outdated aesthetic, a mix of an elite student from the 50s and a collector’s doll. Matthew stroked his flat stomach, highlighted by the high waist of the shorts.

Matthew : “Perfect.”

He whispered. He felt protected. He felt in his place.

V. The Exemplar

The midday sun flooded the garden of Blackwood Hill. The air was still, warm, scented by the docile rosebushes.

Uncle Silas was seated in his rattan chair, in the shade of the great oak. He was reading the Financial Times, a steaming porcelain cup within reach. He wasn’t really looking at the newspaper. He was looking at his work.

A few meters away, at the edge of the immaculate path, Matthew was on all fours in the grass.

He was being careful. Oh, he was being terribly careful. He knelt directly on the grass, his white argyle socks unprotected against the soil. He required no cushion; he was an object, and objects do not need protection—they simply exist where they are placed, on all fours on the ground, serving their purpose. His movements were of surgical delicacy. With a small silver trowel, he extracted a one last remaining weed that had dared to grow in the middle of the English lawn.

The position made his high-waisted shorts ride up, exposing his muscular thighs, but they were now totally harmless, domesticated by fabric and convention. His burgundy suspenders stretched over his immaculate white shirt as he leaned forward.

He grabbed the weed, uprooted it, and placed it in a wicker basket.

Silas rustled his newspaper slightly. The noise made Matthew react instantly. The young man straightened up on his knees, dusted his clean hands against each other, and turned towards his guardian.

The club collar held his chin high, locked in place by the suffocating tightness of the bowtie. His middle part hadn’t moved a millimeter. Matthew offered his uncle a smile. It wasn’t a forced smile. It was an empty, blissful smile, of absolute serenity. The smile of a spirit that has stopped running to learn how to sit still.

Matthew : “The garden is perfect, Sir.”

Matthew said in a poised voice, devoid of any roughness.

Uncle Silas : “You too, Matthew. You too”

Uncle Silas replied turning the page.

VI. Eternal

Time passed, indifferent to the metamorphosis, but the order established by Silas never wavered.

One icy autumn afternoon, Silas set up his armchair directly in the garden, protected by a large black umbrella, while the rain drowned the garden. Matthew was busy planting vegetables. He was not cold, for his Master’s presence was enough to warm him. Raising his eyes toward the shelter that was not offered to him, he addressed his uncle with an obedient smile, dripping with rain but pure of any rebellion. Happy to get wet so that the view remained beautiful, he was, forever, fully obedient—a good preppy boy for Uncle Silas, his Master.

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dandyprep preppyacademy
dandyprep reblogged preppyacademy
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dandyprep preppymuscleboys
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The fag is so proud now of its new look, its new personality, and its new attitude. Thanks for this positive change!

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dandyprep prepford
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catolysttfs catolysttfs

Applying the Retro Filter [Retro TF]

Fred had to show his boyfriend, Jonas, the new photo app he had just downloaded. The app had all kind of filters, but the one Fred wanted to try out with him was the “retro partners” filter.

Sucked back in time to 1930’s America, the former couple turned business partners, will now be working together to maximize profits. And they’ll only be engaging in 100% heterosexual activities, of course!

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Ayy looks like Business Partners Franklin Mason and Joseph Smith gonna only be advocating for their OWN rights from now on.

Really great sequence, I like how both boyfriends turned into their own form Retro businessmen at the end, especially the new ‘Fred’ with his incredibly devious grin.

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dandyprep hypnopreppy
dandyprep reblogged hypnopreppy

These boys were rowdy and rambunctious until they joined the biggest frat on campus. Through a rigorous training and initiation program, they have become the epitome of propriety as all boys should be.


If you want to become a good preppy boy like them, DM me.

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dandyprep mrstepford
dandyprep reblogged mrstepford

Now Timothy, make sure your head is properly in the device just like Randall’s is. We wouldn’t want those rebellious thoughts to come back, would we?

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dandyprep stuff1
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No need to think for yourself when you’re a Preppy Flattop Boi.

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dandyprep vintagebarbershop
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He’s really happy with the new haircut 💈

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dandyprep prepford
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dandyprep hypnoprep
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Every boy is a happy preppy boy! Forever! And ever!

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dandyprep asatraditionalman
dandyprep reblogged asatraditionalman

YOU are supposed to be old fashioned.

YOU are supposed to dress more formally than your peers.

YOU are supposed to be chaste, cleancut, wholesome, and exceedingly polite.

YOU are supposed to live as if it were the 1950s.

This is who YOU are. This is what YOU need. Give YOURSELF permission to give in and accept the fact that YOU are a vintage man.

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dandyprep hypnoprep
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The Stepford Enforcer! Making sure that all preppy boys are happy boys!

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scullandoars scullandoars

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dandyprep suitnskinboy
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Tie, tie, tie, don’t forget your tie.

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Stepfordized. 😵‍💫

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Daddy’s just home from the concert.

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Happy Stepford Sunday. 👔😵‍💫

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Master triggered him with just one word “DEEP SLEEP BOY”. He stoped, his eyes went blank, his face turned mindless and his mind empty of toughts. He turned back facing his master. Now he was completly under his control.

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dandyprep flattopboy
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dandyprep flattopboy
dandyprep reblogged flattopboy

Like father. Like son.

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dandyprep sartorialreform
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Just let go, stop thinking, it’s that easy!

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Mister Puffy Preppy Pants.

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dandyprep spinkes
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There are three whole ways to be a preppy boy! The diversity at the academy is endless!

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The “Clean-Cut Grooming” ordinance was passed a week ago by city council. Any man caught in public looking scruffy and unkempt are apprehended and taken to a correctional pod. An hour in the chamber and that scruffy man is no more. We now have a newly contented Flattop Gentleman reintroduced into society. Are you too scruffy buddy?

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dandyprep
dandyprep

Daddy knows best. And Daddy has decided your old look has to go.