‘prison’ stories

The news cinnamon was expecting, yet dreading.

Electric Chair Play.

Brendan enters prison and finds himself becoming Brenda.

How does Cinnamon feel about Jay now?

What would you do if you had to please your hot girlfriend?

In the future, prisoner gladiator games are reality TV.

Kidnapped and conditioned for sexual servitude.

A legal secretary meets her wildest fantasy in a prison.

Mother Dani atones and comforts her son on death row.

Institute of Corrections for Beautiful Girls.

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

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

Characters from Brit soap act out escaped convict orgy.

Erica's story of submission comes to its conclusion.

Holly is sent to debtor's jail.

Neville starts his new life.

Preparation for a thorough exam.

Hot jailouse sex.

The day to day activities of a sissy in an adult arcade.

When does a wife know all about her husband?

Christina’s family men work to spring (and use) her.

A powerful prisoner sets his eyes (and balls) on Drew's wife.

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

Sparks fly in a prison visitor's room.

Katie's boss becomes a prison slut rag.

James continues to bend Sam to his will.

A perverted and degrading punishment.

Guard shows another the benefits of working nights.

The tragic saga concludes, but does it ever end?

A Caucasian couple go black!

Prisoner forced into school pushes back against teacher.

Cassia is captured by modern-day pirates.

A stroll in the night with a bound and gagged reporter.

Erica's next teacher Toni has a shocking secret.

four penitentiary inmates transfer to a prison school.

Institute of Corrections for Beautiful Girls.

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

Michael Brand is arrested for a felony and goes to jail.

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

A prison story about visiting college girls.

Paris' time in prison has a surprising twist.

Street girl slides into survival prostitution.

Jessica's service as Miss Bimbo begins.

Two friends discuss the time one of them was in prison.

A short conversation between husband and wife.

Maintaining balance in the universe.

Anne Richards faces her toughest assignment yet.

Jennifer let her friend choose Halloween costumes. Big oops.

Politicians' wives become an embarrassment.

Cinnamon and Jay grow closer.

Mother grows close to her son while doing time.

Unfair prison sentence isn't the end.

Lauren's in prison, so its prison rules.

Interrogations, intrigue and a mad tea party.

Transvestite prison prostitute gets a visit from the Warden.

Belinda and James and a house with a cell.

American dominatrix accepts position at a foreign prison.

Kaitlyn becomes a free-use prison fuckdoll.

Ex-Con Uncle and nephew get acquainted.

Jock pays off cost of prison.

A beautiful & insatiable Russian Noblewoman enslaves a serf.

An alternate version of Prison Pet where Blair wins.

To get an A she goes to jail to experience what it is like.

Julie carries a night stick and loves women.

Holly meets her new cellmate.

Unlikely lust in an unlikely place.

German lady engineer arrested.

Jayn and her cell mate need each other to survive.

Selected, inspected, and used.

Jedi Jaina Solo goes undercover in a women's jail.

I found my Daddy.

Ellie gets inducted.

On men's island prison, she is the only woman.

Jay left a surprise for Cinnamon.

The former warden is fucked and humiliated.

A married man is seduced by his childhood friend.

A prisoner is punished with a whipping.

A dangerous prisoner is held in Whiterun's dungeons...

After 6 years in prison, he fucks the shit out of me.

A warning changes Brian's life.

Percy goes into heat at the worst time.

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

My further sexual encounters as a Prison Officer.

It was worth the fight.

Sent by mistake to the women's facility.

Cami finds out what to expect in prison...

Lucy is arrested, transported, and booked into the prison.

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

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

Mistress runs the prison with an iron hand.

The cost of posting a sign you don't understand.

Father's fury.

Beth finds hidden desires while keeping her brother safe.

Tyler is about to experience his first day in prison.

A Spoilt Princess learns some hard humiliating lessons.

Arrival at the Lodge and in processing of the slaves begins.

Sometimes you get what you seek.

I'm finally released from jail, but a new experience awaits.

Jayn and her cell mate need each other to survive.

A beautiful psychologist is caught in a prison riot.