Sissy Jail Stories

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Sabbatical or Continuous Gang Bang? Ch. 02

by TonyaTV69 on Sep 12, 2017
Transsexuals & Crossdressers

I awoke several hours later still laying on top of Rick his arms holding me tight to him. His cock had gone flaccid as we slept and slipped out of me. I felt like I had run a marathon and my ass pussy felt like it had a marathon run through it. I slipped out of Ricks arms onto the bed and went into my bathroom to grab some aspirin and strip out of my damp cl...

Stevie's Journey

by gbr2004 on Oct 7, 2019
Fetish

I remember being so excited landing a position as a legal assistant at such a good law firm. My boss Mike Maddox seemed to be a great guy and I was looking forward to learning from him. I never imagined what it would be that I would learn from him. This job has changed so much and I can't even decide if I regret what has happened or if it was where my life w...

Afro Stress Relief Ch. 06

by llts1970 on Dec 12, 2018
Transgender & Crossdressers

I was running a bit late after I'd overslept my alarm clock, my shift at Missy Bee's and the hard riding I got from Leroy must have tired me out more than I thought. I managed to get into work just on time, once there I rang Sarah. "Oh hi Johnny, sorry I mean Tina, wow it's early," Sarah lazily answered. "Hi Sarah, is Marci OK? I can pick her up this eveni...

Luke's Field Trip

by LucyAnn51 on Sep 16, 2017
Transsexuals & Crossdressers

All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Hope you enjoy, love you dolls! Xoxo ------------------------------------------------- Luke was a sissy. The kids at school called him mean names and threw things at him. They played keepaway with his book...

Afro Stress Relief Ch. 11

by llts1970 on Oct 5, 2020
Transgender & Crossdressers

At work on Monday, things were once again running as usual, no one mentioned the Beer Bust, well almost no one, Mary cornered me when I was getting a coffee. "Would you like to know what I did this weekend?" Mary asked coyly. "Er...yes sure," I answered, trying to sound completely uninterested. "Well, I was recruited by a black pimp! I'm a real prostitute...

Trapped and Trained Ch. 02

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stocki...

Dry Valley Ch. 20

by RedHairedandFriendly on Sep 18, 2017
Chain Stories

Finishing Touches Three days had gone by since the break-in and attack on Jessica and Bailey. The women had been moved to the Walker Ranch, much to Missus O's soft muttering. But she knew the ranch was the place the girls needed to be to recuperate, she was however out there every day just to ease the burden on her friend Sissy, though Sissy didn't find it...

On Your Knees Ch. 09

by JinkiesFarie on Sep 16, 2017
BDSM

*Note to readers: Changed Victor's last name to Frost* Victor awoke groggily on a cold, hard floor. His memory was a blur to yesterday's events, when he first came to he thought he was on Nicole's floor being punished. The air was stained heavily of piss and booze. His body ached all over, his head throbbed in particular. He struggled to sit up, only man...

Sissy Lauren Pt. 01

by CdJade on Sep 12, 2017
Transsexuals & Crossdressers

Chapter One: Adjusting To Prison Life On a cold day in September, Freddie Jones sat on a bus on his way to prison. He had been caught four months ago and had recently been convicted to five years' imprisonment on a charge of armed robbery. He was not your typical criminal. He was just a scared young, 23-year-old man who had not wanted to risk upsetting his...

Malcolm On the Meddle

by CarrieQ on Aug 21, 2018
Transsexuals & Crossdressers

Malcolm was very lucky to get the job of caretaker at Lucania House. The owners were very selective but far from diligent; they took account of his military service, but failed to check out his dishonourable discharge... As for his time in jail, they didn't ask and he didn't tell! References from friendly former colleagues sufficed, together with his 'hones...