Inmate And Guard Sex Stories Stories

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New Women's Prison Warden Pt. 01

by Gamahooch on May 29, 2018
BDSM

It was 1954 in a poor midwestern state. Small town lawyer Walt Conner had connections with a powerful politician and was able to be appointed the new warden of Abbotville state correctional institution for women. He was kidded by his friends that he would not have to look hard for pussy from now on. On his first day he drove up to the front gate of Abbotsvi...

Queen Jezebel Women's Prison Intl.

by DemocraticRepublicofBigBreastedWomen on Sep 17, 2017
BDSM

There exists a number of international corporate (private) prisons that were built and are owned by a bio-tech company for the incarceration of big breasted women; or small breasted women who were forced to have large bra cup sizes via surgery once they were committed to one of the penitentiaries within the organized corporate prison system. Queen Jezebel...

CFNM Prison Nurse

by ann_bbw on Sep 14, 2017
Exhibitionist & Voyeur

This is a fantasy story about Beth, who just turned 24, a slightly overweight but shapely young woman. She had dated however was not involved in a serious relationship while concentrating on her career. Beth, just out of nursing school was offered a most interesting and well paid job by her uncle, who worked at an all male correctional facility. She was an i...

New Women's Prison Warden Pt. 02

by Gamahooch on Jun 5, 2018
BDSM

Walt Conner, the new warden at Abbotsville state institution for women, had just arrived at his new job. Miss Jenkins, the chief guard, was showing him the Disciplinary Unit. A sobbing inmate, Anna Gaines, lay secured face down on a punishment table, her ass red with the paddling she had just received. There was a realistic looking dildo protruding from her...

Prison Woman

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I'm all about. A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison - and that is true. But I guess...

Lady In The House Ch. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended up in one the States high security prison? Well it had a lo...

The IFD Supermax Ch. 02

by prisonguy on Sep 17, 2017
BDSM

Jacqueline paced her small cell as she waited for word that the verdict was in. She hardly noticed the cold floor beneath her bare feet, having lost her boots because the guards feared that she might attempt suicide. She had become despondent earlier in the day when she had heard that both Dominique and Gabrielle had been convicted, and had agreed to five ye...

Sweet Gwendoline Ch. 10

by Schlank on Sep 18, 2017
BDSM

I was naked, my legs were spread indecently far apart and my bottom was pushed out towards Doctor Riemen. This would have been quite humiliating all by itself, however Doctor Riemen increased my mortification by spearing my asshole with her fingers and probing deep and mercilessly into my anus. "Now Gwendoline, I am going to ask you some questions," Doctor...

Persona 5: Choose your Confidant

by Nin10gamer on May 2, 2019
Fan Fiction

All characters in this story are at least 18 years old. It's been two years since you and the phantom thieves last defeated Yaldaboth. You now find yourself back in the velvet room. You are greeted by the twins who somehow have been separated from their true form. Petite, both velvet room assistants are dressed in their blue guard uniform with matching black...

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The Island Of Penal Correction

by MISTRESSTRESSA on Sep 16, 2017
BDSM

Part 1 After nearly thirty years as a career dominatrix, and with business faltering, I received an irresistible opportunity to relocate from the Philadelphia area and begin a new career. Located in the Caribbean Sea, due north from Venezuela, is the small island Republic of Lugash. As it was originally a British colony, English is the official language. T...