‘prison’ stories

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prison 

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Women's Bondage Prison Pt. 14

Lucy earns time in another punishment cell.

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Prison Ship - Dreadnought Ch. 06

Chapter 6 of poor Commander Josie and her crew's torment.

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Prison Ship - Dreadnought Ch. 05

Chapter 5 of poor Commander Josie and her crew's torment.

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Prison Ship - Dreadnought Ch. 04

Chapter 4 of poor Commander Josie and her crew's torment.

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Women's Bondage Prison Pt. 13

Lucy prepares and begins for prison exercise.

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The Prisoner Pt. 20

Tuesday comes to an end ... and Martin has something to eat.

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The Experiment Ch. 01

Mary participates in an experiment with corporal punishment.

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Seduction at Belinda's House Ch. 23

James handcuffs Sophie but then gets caught in the humbler.

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Prison Ship - Dreadnought Ch. 03

Chapter 3 of poor Commander Josie and her crew's torment.

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Ron's Redemption

A good man fucked over by fate, he comes back.

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Prison Makes Me a Sissy Pt. 01

Young feminine guy turns into a sissy in prison.

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Prison Ship - Dreadnought Ch. 02

Chapter 2 of poor Commander Josie and her crew's torment.

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Prison Ship - Dreadnought Ch. 01

Chapter 1 of poor Commander Josie and her crew's torment.

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Prison Sissy Cuckboy Ch. 01

Beta bitch joins a gang as a sissy cuckboy.

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A Prisoner’s Release

Anna will prove her love on the day of her father's release.

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The Good Soldier Pt. 05

Corporal Jones has her loyalty tested.

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Bottom Bunk Bitch Ch. 04

Brenda performs tricks for her master in the prison yard.

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Saving My Virginity for Father

Turning my Daddy after prison stretch.

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Women's Bondage Prison Pt. 12

Lucy goes on a prison inspection tour.

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The Prison of Pain Ch. 05

Christon Mann is now permanently branded as a prisoner!

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Bottom Bunk Bitch Ch. 03

Brenda sinks further into feminization as a prison whore.

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A Price Worth Paying

What a young man is willing to endure for his family.

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The Prison of Pain Ch. 04

Christon is inverted, fucked and punished with electricity!!

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The Prison of Pain Ch. 03

For his first day, Christon’s balls are kicked and punched!!

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The Prison of Pain Ch. 02

Christon meets Gino and the punishment begins with whipping!

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Prison Wife

Femboy in prison, gets turned into a Black Man's wife.

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Photoshopped - Julie's Story

Why Julie's anger drove her to extremes.

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Women's Bondage Prison Pt. 02.5

Lucy learns to be a better prisoner.

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Bottom Bunk Bitch Ch. 02

Brendan continues his feminization as Brenda in prison.

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The Prisoner Pt. 18

Tuesday continues ... and Martin is in for a shock!

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The Prison of Pain Ch. 01

Christon Mann is sent to the Prison of Pain to be punished!!

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The New Republic

The Republic has a very different type of justice system.

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The Prisoner Pt. 17

Tuesday continues ... as Martin's absence is noticed.

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Who Played Who? (A Prison Story)

A fiction about taking charge in prison, kinda…

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Blacked in Prison

This is my fantasy of going to prison becoming a prison bitch.

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Women's Bondage Prison Pt. 02

Lucy progresses in her prison training

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Birthday Wishes Ch. 01

T-girl gets the best present on her birthday: JAIL TIME

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The Prisoner Pt. 15

Monday comes to an end... and Martin goes into lockdown!

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Jasmine's in Trouble Ch. 19

The end of the road.. or so it seems.

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College Students Humiliated in Jail

Eric, Wes and Kyle are strip searched and deloused in jail.

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Bottom Bunk Bitch Ch. 01

Brendan enters prison and finds himself becoming Brenda.

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Correction Match Pt. 03

Joy prepares for her detention session.

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The Naked Prison Ch. 09

Steph's takes a cucumber up her ass.

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My First Year in Prison Ch. 23

Tyler spends the day at the beach.

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Dyker's Island Ch. 09-10

A look at life inside the worst women's prison in the US.

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Interrupted.... and Resumed

Two SSBBWs make the best of a bad situation.

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Corrective Measures

Punishment is incurred for a breach of prison rules.

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Women's Bondage Prison Pt. 01

Lucy learns who in this bondage prison will violate her.

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My First Year in Prison Ch. 21

Tyler (re)discovers some old porn from his college days!

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Pegging Her Alpha Inmate

A female prison officer dominates a defiant hunky inmate.

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A Sissy Goes to Jail

When the late night photoshoot goes 'wrong'.

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My Life Behind Bars Pt. 01

Young man turned out on his first night in prison by BBC.

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Keyholder Demoness Ch. 12

...ever again. No one will touch...

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My First Year in Prison Ch. 20

Tyler discovers mourning sex.

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My First Year in Prison Ch. 19

Shock. Denial. Anger. Bargaining. Guilt... SEX!

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Hot Neon - Segment 01.6

Caged birds still sing. Warm eyes and goodbyes. A new road.

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Hot Neon - Segment 01.5

Among the beasts. A light in the dark. A new pathway.

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Locked Up Autumn Ch. 03

Young woman reports to prison and strip searched thoroughly.

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My First Year in Prison Ch. 18

As a fight breaks down, not a single inmate is safe.

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Colony Pt. 02

Pennie recalls first interrogation & meets Officer Claude.

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Women's Territorial Bondage Prison

A new prison for female jailbirds keeps inmates from escape.

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Trust Issues

A paranoid spouse is emotionally draining.

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My First Year in Prison Ch. 17

A bachelor's party in prison: things are bound to get wild!

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Colony Pt. 01

Pennie plays prisoner in a Penal Colony for kinksters.

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My First Year in Prison Ch. 16

Tyler's cellmates find a great way to release the tension.

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David and Becky - Resolution Ch. 02

What really happened the day Elena brought me the laptop.

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Becca XXX - Hard Time Ch. 06

Becca has a shock when she meets with her solicitor.

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My First Year in Prison Ch. 15

Tyler plays with fire one time too many.

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Locked Up Autumn Ch. 02

Morning sex for young woman before reporting to prison.

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My First Year in Prison Ch. 14

Tyler reconnects with a former lover.

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Locked Up Autumn

Young woman online the day before she reports to prison.

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Dyker's Island Ch. 01-08

A look at life inside the worst women's prison in the US.

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My First Year in Prison Ch. 13

Tyler welcomes a new inmate in prison.

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Women's Bondage Prison Pt. 11

Lucy learn more about her prison and serving hard time.

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My First Year in Prison Ch. 12

Tyler is unsure if he should listen to his brain or his dick.

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My First Year in Prison Ch. 11

Tyler gets much closer to one of the inmates.

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Women's Bondage Reformatory School Pt. 04

Claire serves time in detention.

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My First Year in Prison Ch. 10

Tyler learns more about the prison (dirty) secrets.

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My First Year in Prison Ch. 09

A heatwave inside the prison makes some inmates go wild.

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Bailee’s Punishment Ch. 03

Bailee gets her first judicial whipping in prison.

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Bailee’s Punishment Ch. 02

Bailee meets the other inmates on the block.

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Bailee’s Punishment Ch. 01

Bailee goes to prison for having hairy arms.

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My First Year in Prison Ch. 08

Tyler reminds himself of the time he fucked with his patient.

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My Sister-in-law Paola in Prison

A story of fiction about my sister in law and me.

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My First Year in Prison Ch. 07

Tyler pays his debt to the guard and things get messy.

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Tracking Evil, a Podcast Pt. 05

Erica and Arlene pursue separate lines of enquiry.

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My First Year in Prison Ch. 06

Tyler learns to stand up for himself.

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David and Becky - Foolish Choices Ch. 22

I go before Judge Olarescu to hear my fate.

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David and Becky - Foolish Choices Ch. 21

Humiliated in front of my representative.

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My First Year in Prison Ch. 05

Tyler is confronted to the other inmates' twisted games.

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My First Year in Prison Ch. 04

Tyler is experiencing communal showers in prison.

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4.52
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