‘prison’ stories

A man gets on with his life after cheating.

Is there a penalty for infidelity?

Chloe's prison humiliation.

Beta bitch joins a gang as a sissy cuckboy.

Protecting Hayden turned into more than KT wanted.

A man goes to jail and is soon bullied into a new life.

He goes to jail to get gang banged.

After the arrest, prison proves to be a surprise.

Jennifer let her friend choose Halloween costumes. Big oops.

First day at prison.

Unholy alliance of rough sex in a dangerous place.

Females dominate, breeders fuck, cuntboys get fucked.

A Sheriff Ryan Caldwell story. Conclusion.

Mother grows close to her son while doing time.

Ann is used for research while in debtors prison.

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

Two blonds have a vacation nightmare.

An FBI agent visits the town of Riverside.

Charlotte arrives at a nude, all women prison.

Timmy takes the HGH mutated prison daddy monster cock.

Young woman becomes a chemical concubine to pay her debts.

Daddy takes Billie on a shipping trip.

James realises that the Guards aren't going to help him.

A young straight lad succumbs to his cell mate’s charms.

She's owned and used.

Man pays price for treatment of a wife.

Miles to go...

I found my Daddy.

Teen twink Noah is forced to suck his first dick in prison.

A sequel to He Reminds me of my Husband.

Sissy Lauren begins her prison journey.

A young man is sent to a prison for men with small penises.

A cuckold husband gets more than he bargained for...

Percy goes into heat at the worst time.

Investigative journalist Terri London wants an "inside look".

James continues to bend Sam to his will.

Twink takes advantage of sex-deprived parolee.

A wife gets a shocking letter from her incarcerated husband.

Brendan continues his feminization as Brenda in prison.

We go forward with her plan to have me arrested as a hooker.

Erica begins her first day of training.

My first time licking her cunt and fucking her doggy style.

An alternate version of stev2244's original.

My sexual encounters as a trainee Prison Officer.

An innocent virgin finds out what prison is all about.

A bondage theme prison tests Lucy and her fellow prisoners.

four penitentiary inmates transfer to a prison school.

TV journalist goes to jail to earn ratings points.

White boy Brad goes to prison.

Guard catches her and discovers her love for cocksucking.

Young woman sent to prison.

FBI agent violates the dress code and pays for it.

Timmy is reunited with an old buddy from the streets.

Jailed dad cuckolded by MILF stepmom & buddy's younger bro.

Prison is not the place to pick a fight in the name of love.

... in the land of offenders, the warden is king.

A married man is seduced by his childhood friend.

Jason's home from prison and has fallen in love with Rain.

After being arrested, I'm taken to jail in my hooker-wear.

Kidnapped and conditioned for sexual servitude.

A Halloween ghost story of revenge & redemption.

A young woman is imprisoned for her part in a violent crime.

Katie's Atonement.

Avette teaches Erica the wonders of anal sex.

Flirting, Seduction, Imprisonment on a visit to the Old Gaol.

She learns to LOVE cock in prison.

Black female convict surprises white guard amazon.

Young feminine guy turns into a sissy in prison.

Neville starts his new life.

Duchess and her highwayman are reunited in jail.

Yvonne Strahovski goes deep to do research for her role.

He bribed the judge to send him to the women's penitentiary.

Hot jailouse sex.

But, her lovers would.

All I had to do was to find a daddy.

A socialite heiress discovers the other side of life inside.

Female convict is caught masturbating and pays the price.

Belinda and James and a house with a cell.

A female prison officer dominates a defiant hunky inmate.

Trouble hits the Morrison family hard.

Brenda sinks further into feminization as a prison whore.

First time in prison for spoiled jock.

A New Owner.

Julia is discovered and made more fully into a slut.

Steven goes from frat boy to Prison Bitch.

It was worth the fight.

Erica's story of submission comes to its conclusion.

Drew gets into prison while his gorgeous wife seeks pleasure.

The hardships a man goes through in life.

Tyler is about to experience his first day in prison.

Drugged CIA agent struggles not to give in to aphrodisiac.

The sexual fantasy of Michael's wife and daughter continues.

Sexual torment continues for drugged CIA agent.

Cassia is captured by modern-day pirates.

Convicts line up to fuck him, but he has a favorite.

Unfair prison sentence isn't the end.

In the future, gladiator games are reality TV.

As the night ends, I have to choose; cumming or leaving?

Mike becomes Michelle.

Erica faces her most difficult test yet: A night with Blair.