Sissy Anal Stories

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The twisted DM

by Nobody567 on Nov 21, 2019
Fantasy

Authors notes: please like and comment my stuff I desperately desire your feedback and approval. I am new at this and recently redid the intro hope you like it. A being beyond space and time whose goal is to torture, torment, pleasure and change his players in ways that you cannot begin to fathom for his entertainment and pleasure. He sits at multiple tables...

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A Sissy Saga Ch. 17

by Snurge on Sep 15, 2017
Novels and Novellas

Titled people were a weakness with Miriam Hancock. She frequently spoke of them with harsh condescension, but the snob in her heart secretly rated them higher than wealthy businessmen, and so it was with some delight she agreed to the visit of the ennobled Marchioness of Wiggleswick. The delight had doubled when she discovered that in both Debrett's Distingu...

The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Training Aide Ch. 02

by Angelscuck on Sep 16, 2017
BDSM

Mistress Elaine stoop up, causing me to roll off her lap onto the floor. I just lay there naked, sniffling like some little sissy, waiting for my next ordeal. My Mistress then said, "It's a good idea, at this time, to let your slave have a few minutes to recover. It also gives him time to let the realization set in, that he has been totally broken and is...

The Whore Wife, Sissy CD Husband

by MILF4black on Jul 27, 2020
Transgender & Crossdressers

This story is completely fictional. All characters in the story are over eighteen. Prologue: The Whore wife, Sissy CD Husband "That's it, you little sissy whore, suck that cock." Jennifer told her husband as his head bobbed up and down on the strap on dildo Jennifer was wearing. Her husband, Patrick, lifted his head and the seven inch fake penis slid out...

Those Shoes Threeway

by cd_donna on Sep 16, 2017
Transsexuals & Crossdressers

Ladies in the Ladies Room I was wearing the shiny black Merumote high platform shoes my man Rex had bought me. We went to the club hoping to find another man for a three-way since our usual buddy Mike was out of town. I stopped into the ladies room where I saw a fellow girlfriend, and we chatted, as ladies will do. "Honey, I thought your feet were too wide...

Robin and Jimmy Olsen - Sissies Ch. 03

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Part 3 Jamie’s story The few days before the date in Part 1... The car pulled up at the curb and Jamie got out of the passenger side door. She was a bit wobbly on her three inch heels. The car sped away fast, as if the driver was feeling guilty about what he and Jamie had just done. Jamie opened her purse and tucked away the fifty dollars she had stuck i...

Hubby Drop To Thy Knees! Ch. 02

by Ashesh9 on Sep 17, 2017
BDSM

CH. 2 :HUSBAND , BEND OVER & PART THY NETHER CHEEKS !!! Her ringing , humiliating command was heard all over the field “Husband, bend over the Punishment Table, bare thy delectable, horny bum & part thy nether cheeks for Thy Royal Monarch’s Pleasure !!! Immediately!!! Do it now, boy !!!!” The sweet girlish voice, the Commanding tone, the embarrassing Orde...

Sissy Chantel, New Reality Ch. 09

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Nine: It's Friday, I Have a Full Shift to Pull Today and Tonight. At 7:00am sharp we are all waken up. This is our daily wake up call and soon sissy Traci as our dorm room's head sissy maid has us all up and ready to go to our morning routine which will be a group enema, group shower, shave face and when need be the rest of our body hair then to do...