Fat Bear & Twink Stories

PART 1: "First day in prison"

I’m Ethan, 20, 5'7", 135 pounds. Skinny twink, pale skin that never tans, soft brown hair that falls over my eyes when I'm nervous—which is always. I'm quiet, still deep in the closet, and my only real experience is a couple of rushed handjobs in the back of a car. But my fantasies are filthy, massive older men pinning me down with their raw weight, breeding me until I'm leaking, stuffed, helpless, craving more even as I hate it.

It was a house party at some guy from college’s place. Too much cheap beer, too many shots. I was drunk, stupid drunk. Laughing too loud, dancing like an idiot.

Then this cop shows up. Big guy, red hair, mustache, easily 72, 545 pounds. Uniform tight around his huge gut, sweat stains already under the arms even though it’s cool outside. Name tag says “Officer Vic.”

He’s there for noise complaint, but everyone scatters. I’m too drunk to run fast. I stumble into him—literally. My hands land on his belly, soft but heavy, pushing against the buttons.

I laugh like an idiot.

“Damn, officer… you’re… big.”

My drunk brain thinks it’s funny. I squeeze a little, slide a hand lower, brushing his crotch.

He freezes. Eyes wide. Then grabs my wrists hard.

“That’s assault on an officer, boy.”

I giggle. “Come on… you like it.”

Next thing I know, cuffs. Cold metal. Thrown in the back of his cruiser.

The ride is a blur. He’s breathing heavy in the front seat, glancing in the mirror.

“You’re in deep trouble, kid.”

I pass out.

I wake up with a pounding headache. Cold concrete under me. Naked.

“"What the fuck.”

I’m in a cell. Bars, thin mattress on a metal bunk. No clothes. Just me, curled up, shivering.

The cell door opens with a heavy clang.

A massive man steps in. 62, 530 pounds. Gray hair, thick beard, prison orange stretched tight over his gut and thighs. Eyes hungry, cock already half-hard in his pants, the outline visible.

“Doyle,” he says, voice low and rough, like gravel. “Your new cellmate.”

He closes the door behind him with a deliberate click.

I scramble back on the bunk, covering myself with my hands.

“Where are my clothes? What the hell is this?”

Doyle smiles slow, stepping closer, his belly swaying with each step.

“Clothes are a privilege here, boy. You earn them. One piece at a time.”

His shadow falls over me. The bunk creaks as he sits on the edge, the mattress dipping under his weight. His thigh presses against my bare leg—hot, heavy, sweaty.

I push against his chest with both hands.

“Get away from me!”

My palms sink into soft flesh over hard muscle. He doesn’t budge. Instead, he grabs my wrists easy—one huge hand around both—like they’re nothing.

Pins them above my head against the cold wall.

His full weight shifts forward.

The air leaves my lungs in a whoosh as his belly settles on my chest, crushing me into the thin mattress.

I gasp, struggle, legs kicking uselessly.

He leans in, beard tickling my neck, breath hot and stale.

“First lesson, boy. You’re mine now.”

His free hand slides down my side, rough palm over ribs, hip, thigh.

I twist, try to buck him off.

He laughs low, presses harder—his gut smothering my chest, making every breath a fight.

His cock, thick and hard, grinds against my thigh through his pants.

He shifts, frees it—hot, heavy, already leaking.

Lines up.

Slow push.

I cry out as he sinks in—stretch burning, his weight pinning me completely.

No escape.

He thrusts deep, rhythmic, belly slapping my skin with each move.

Sweat drips from his brow onto my face.

I protest the whole time—“stop, get off, I don’t want this”—but my body betrays me, tightening around him.

He grunts, speeds up.

First load—warm, flooding.

He stays buried long, grinding.

Pulls out slow.

Leak starts immediately, warm down my thigh.

He pats my cheek, still pinning my wrists.

“Good boy. You’re mine now.”

He stands, tucks himself away.

Pulls me up by the arm—firm, possessive.

“Come on. Time for walkies.”

“Walkies?”

He leads me out of the cell—naked, leaking, hand in his huge paw like I’m his pet.

The block is long, cells on both sides. All occupied by older men—60s, 70s, heavy, hairy, staring.

Whistles, catcalls.

“Fresh meat!”

“Look at Doyle’s new boy—already leaking down his leg.”

“Pretty little thing. Can’t wait for my turn.”

I burn red, try to cover myself with my free hand.

Doyle squeezes my hand hard.

“No hiding, boy. Everyone gets a look.”

We walk the whole block slow.

Every prisoner eyes me up, some stroke themselves through pants.

Doyle proud, like showing off a prize.

Back in the cell, he sits on the bunk, pulls me onto his lap again.

“Rule here is simple,” he says, hand on my thigh, smearing the leak.

“To get out, you serve every man in this wing. Prisoners. Guards. All of us.”

I shake my head.

“No way. I’ll fight. I’ll tell someone.”

He chuckles.

“No one to tell, boy. This is the Elders’ Wing. Special rules. You serve… or you stay forever.”

Morning comes.

Vic, the red-haired cop, opens the cell.

Sweating already, shirt dark under arms.

“Time for your morning duty, kid.”

He grabs my other arm.

Doyle hands me over with a wink.

Vic leads me naked down the hall to the officers’ bathroom.

Private, tiled, one toilet, sink.

He stands over the toilet.

“Kneel.”

I hesitate.

He pushes me down hard.

“Remember last night? You wanted to touch. Now you serve.”

He unzips.

Morning routine.

He pisses—warm stream hitting the bowl loud in the silence.

I have to watch.

Then strokes himself slow, red face flushed more.

“Your breakfast, drunk boy. Open.”

I protest, turn my head.

He holds my jaw, forces it open.

First load of the day—thick ropes down my throat.

I swallow, gagging, tears in eyes.

He laughs, wipes the last drop on my lip.

“Every morning. Every guard. Every prisoner. That’s how you earn your freedom.”

“Or stay my little pet forever.”

Back in the cell, Doyle waiting.

Pulls me onto the bunk.

“My turn again.”

The day has just begun.

And I already know…

I’m Ethan, 20, 5'7", 135 pounds. Skinny twink, pale skin, soft brown hair that falls over my eyes when I’m nervous—which is always. I’m quiet, still deep in the closet, and my only experience is a couple of awkward kisses in high school. But my fantasies… late at night, I lose myself in porn of massive older men taking total control, filling boys like me until they’re leaking and helpless.

I need money bad. Tuition is killing me. I answer an online ad: “Personal Assistant to private businessman. Live-in option. High pay. Discretion essential.” The interview is set for Friday evening at a secluded estate outside town.

I arrive at 7 p.m. The mansion is huge—Victorian stone, long driveway, iron gates that close behind me with a heavy clang. Snow flurries swirl. No cell signal.

The door opens before I knock.

Victor stands there, 72, easily 545 pounds. Oldest man I’ve ever seen up close. Thick white hair, flushed face, shirt soaked with sweat—dark patches under the arms, collar clinging to his neck. His belly strains the buttons, and his eyes linger on me a second too long before he smiles too wide.

“Come in, Ethan. Right on time.”

His voice is shaky, excited. He smells strongly of sweat and cologne trying to cover it.

He leads me through dim hallways to a small office—big wooden desk, leather chairs, one-way mirror on the wall (I notice too late).

“Sit,” he says, wiping his forehead with a handkerchief already damp.

The questions start normal—school, experience, availability.

Then they get weird.

“How do you handle… close supervision from an older man?”

“Do you mind physical tasks? Lifting, carrying… being under someone’s direct control?”

His breathing is heavier. He shifts in his chair, belly brushing the desk edge.

I stammer answers, face burning.

He stands, comes around the desk.

“Stand up for a moment. Let me see how you carry yourself.”

I stand. He steps close—too close. His sweaty shirt brushes my arm.

“You’re perfect for the role,” he mutters, almost to himself.

Then louder

“You’ve passed the first stage. The boss wants to meet you now.”

He leads me down a long corridor, hand on my lower back longer than necessary.

We enter a massive study—dark wood, roaring fireplace, huge leather armchair behind an antique desk.

Mr. Harlan sits there, 68, 560 pounds. Calm, commanding. Neat beard, expensive sweater, eyes that see everything.

Victor stands beside me, sweating harder.

Harlan nods once.

Victor’s restraint snaps.

He grabs me from behind, arms like vices around my chest.

“I tried to be professional,” he pants in my ear, voice trembling.

“But you’re too perfect. I didn’t want this… but I have to.”

I struggle. “Let go! What are you doing?”

Harlan watches silent, unmoving.

Victor pushes me over the desk, binds my wrists with his belt behind my back.

Strips me rough—shirt, pants, underwear gone.

His sweaty body presses on mine, belly heavy on my back.

“I didn’t want to do this on the first day,” he whispers, voice cracking with lust. “But the boss said it’s okay. Stop fighting… it’ll be easier.”

He breeds me fast—ordinary load, warm, leaking quick.

I cry out, protest the whole time.

Harlan finally stands.

Victor steps back, breathing hard, cum dripping from him.

Harlan undoes his pants.

Then I saw these massive balls. He slowly approached from behind, stroking my back.

He lays his monstrous balls on my lower back.

Feel the heat, the impossible weight.

“This is what a real man carries,” he says calm.

Out of the corner of my eye I saw Victor jerking off all the time. At the same moment I felt a large penis rubbing against my hole. Before I could say anything, his thick penis was already inside me, stretching my hole slowly.

He uses Victor’s leaking cum as lube—thrusts slow, pushing it deeper.

Slowly, he pushed his cock deeper and deeper until I finally felt his thick cum leak out. Hot, so thick that when he pulled his cock out, nothing came out, just a white drop on my hole.

"Can you feel it, boy? My thick cum, still inside. Haha!"

I thought this horror was over when suddenly Mr. Hark turned to Viktor and said in a serious voice,

"His hole was too tight, fix it."

Victor laughs shaky, takes me rough again on the desk while Harlan watches.

He fucked me, slowly at first, then suddenly picking up the speed until the whole desk was shaking. He was sweating constantly, and I could feel his sweat dripping down my back, all the while saying dirty things to me. "See? Master was dissatisfied with your hole! But don't worry, I'll fix it!" He farted constantly while fucking me. It was disgusting. I thought I'd faint. Prrrrrffffff "Oops. Get used to it, boy, this will be your morning routine with me in bed!"

It felt like the fuck had been going on for over an hour. My back was covered in sweat from Victor, the stench of his farts hung in the air, my thighs covered in cum that poured from my hole. I came several times myself from the pressure.

Suddenly, Mr. Harlan said Victor should finish the rest in his room.

"Y-Yes sir!" said Victor.

Victor untied me, turned me around, and began kissing me, one long, sloppy kiss, his tongue covered in saliva, pushing it deep into my mouth. He wrapped his arms around me and held me close, feeling his sweaty body against my skin.

Meanwhile, Harlan pulls a leather belt from a drawer and ties it tightly around my neck.

He puts on a silver chain.

Victor looks on, exhausted, with hungry eyes.

Harlan tugs on the chain and hands it to Victor.

"You got the job, Ethan. Live-in personal assistant. Starting tonight."

Victor grins.

"You'll be with me most days." Victor said, licking his lips.

I begged Mr. Harlan to let me out when suddenly Victor pulled the chain and drove the plug into my hole, covering my mouth with his sweaty hands.

"Look at that naughty boy! He's talking back to the boss! You need to learn some discipline!"

After that, he lifted me up like I weighed nothing, put me on his shoulder, and spanked me.

"See you tomorrow, boss! I have to teach this boy some manners!"

After that, we found ourselves in the room, Victor, excited again, put me to bed until dawn…