Sissy Anal Tasks Stories

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My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Wife in Control Ch. 01

by wifetoy on Sep 25, 2017
BDSM

I originally posted this story almost two years ago, but lost the other parts of the story when my computer crashed. I am reposting this part and will be posting the other parts of the story over the next few weeks as I finish retyping them. While I may post some fictional stories in the future, all of the events in this one and the other parts to follow are...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...

Girl's Night Pt. 02

by DifferentBreed on Sep 14, 2017
Fetish

Fisher was upstairs, making the bed when he heard the front door opening, signaling Sophie's arrival home. He looked down at the list on her dresser, frowning. He had not completed four tasks. He reapplied his pink lipstick and kissed the paper above the words "make bed with gold satin sheets" as he was instructed. He then scurried downstairs, incomplete lis...

Becoming a Sissy Maid & Slut Vol. 09

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Prefix: I will be fast forwarding a few days in my sissy maid, sissy slut lifestyle story here. From the last chapter ending on a Tuesday night going into my second week as Master George's full time sissy maid and slut to that of me getting ready for the following Saturday night of slut service. I feel the story's journey no longer has to follow a linear da...

His Fantasy Brought To Life

by ksha on Sep 16, 2017
Anal

To my surprise, my first story was received quite well! So thank you to everyone who read and liked it, hopefully I can continue to make enjoyable stories. As per a request in the comments on the last story, I am writing this. It's a stand alone from the other story, but follows similar lines. It's also going to have a long build up, but I'm hoping the end...

Property of the Master Ch. 02

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy head." The sound of curtains being drawn open was accompanied by a blinding light as my bleary eyes blinked open. "Wha... What? Huh? Hello?" I struggled to come up with coherent words as my brain wasn't fully awake yet. "Good morning Rosie, I hope you slept well," said the same voice as before. "Umm... Yes. Who are you?" I asked. "My...

Uncovering the Sissy Beneath Pt. 07

by jefferyscott745 on Aug 6, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part seven of my previous work. Be sure to read parts 1-6 if you wish to understand the background of this section. Three days had gone by, since Sherry and I had our intimate session together. We had practiced multiple times after t...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

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...