Sissy Anal Training Stories

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The Computerized Bed

by submissive~pet~ on Sep 14, 2017
Fetish

The year is 2020 all sorts of new inventions have been created. The time machine in which John Paul traveled was from the year 2002. He had no idea what was in store upon his arrival to the future. His machine carried him into a large bedroom. It was a very lovely room done in pinks and light blues. The bed was enormous in size, 4 times the size of any he...

Foxfire Stables

by centaur mare on Sep 16, 2017
BDSM

I was silently fuming as Marina worked the kinks from my lower back. Her oil slick palms and roughly digging fingertips worked the tension out slowly. The room was scented a deeply, rich with lavender and dragons breath from the incense burner cradled on a low bench in front of the massage table. I expelled a short “ugh” as Marina continued deeply stroking m...

Zoey's Basement Transformation Pt. 03

by SissyStoryTime on Sep 11, 2017
Transsexuals & Crossdressers

Zoey couldn't believe the cruelty of her Mistress. She shook her head desperately, feeling exhausted and sore everywhere from the waist down from already having so many awful things done to her. She didn't know if she could survive this fresh hell. Mia moved away from the tied girl, her helpless form bent over and restrained at waist height. "Aww, what's t...

Miss Annabelle Ch. 02

by Timewarp10 on Oct 16, 2018
BDSM

As Annabelle's first term at University drew to a close, I had become her slave: cleaning floors, laundry, ironing, cleaning her shoes, making her bed, sorting her clothes and other household chores. Each day was filled nonstop with toil, from early morning to late night, stopping only when she had gone to bed to sleep, and even then I would have to be alert...

Jack and Jill Pt. 03: Anna

by candyflosslover on Jul 13, 2020
Loving Wives

The next day Jill was at work in her office, a parcel had arrived for her and when she opened it to her delight she saw it was a double ended dildo. She had ordered it some weeks ago so she could use it with her sissy husband. It was longer and thicker than she imagined and she felt heat between her legs at the thought of what she would do with it. She was s...

Big U Pride Ch. 03: The Squad Forms

by latinarita4 on Jul 27, 2020
Transgender & Crossdressers

Remember to check on parts 1 and 2 before you read this! Also, please rate and review my stories! I love hearing feedback from readers! If you have suggestions, just send them right along! Maybe your suggestion will be featured in a future chapter... ________________ Most days at the campus health center were typically light affairs. Usually it's the rout...

Anal Training Ch. 04

by Catchandrea2397 on Mar 3, 2020
Transgender & Crossdressers

Hello Pet Welcome back. Are you ready to continue your training? Good girl. Yes thats what you are now. My little girl. My little slut. I hope you've been training as I instructed. Have you been teasing that desperate ass of yours? Good. Before we continue I want you naked and clean. Ready? Good. I need you to get a few things ready for me p...

Isabella's Reversion Pt. 03

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...