Sissy Academy Stories

10,735 results
Orientation
Length
Source
Infinite Scroll

Exposing Cindy Ch. 02-03

by cindyexposed on Sep 26, 2017
Interracial Love

Coming soon: Chapter Two: Exposing Cindy - Facing my husband. The evening with Denzel was uniquely dangerous and exciting experience. It was degrading and humiliating; and yet, I came three times. But most of all, it was stupid. It was irresponsible. It was wrong. I violated one of the fundamental precepts of my marriage. My husband, whom I love dearly, ha...

Silver Moon: Bk. 02 Ch. 02

by maxd01 on Sep 11, 2017
NonHuman

All sexual relationships are 18+. Enjoy. ***** While she was resting she felt Arthur wandering around and feeling rather confused. She didn't know why but felt he needed to talk to someone. Amariah gently nudged him in their direction since he was from Dan's country. When he was close enough she would wake Dan so he knew the man was nearby. Beyond that she...

The Applicant

by bunny3374 on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 1 I worked in an office as a secretary, and my friend Margaret worked there too. It was our job to interview new candidates for positions opening every few weeks. This week, we were to interview for another secretary position in our building. Margaret and I met in my office one afternoon to look over the potential applicants for the job, selecting t...

Exotic Pussy Cum Extortion

by Alluring_Crimson_Shifter on Sep 14, 2017
Anal

Leon struggled in his science class and was almost giving up at the idea of graduating from high school. As an 18 year old he did not see good prospects as an adult. His teacher coached him and encouraged him. She was his science teacher and sometimes spent time after class helping him with his studies. He admired her intelligence and her looks, and grew fon...

Carnal Cravings

by mutterguffin2 on Sep 13, 2017
Anal

After my dad passed away at 86 I decided it was time to move in with my mom to take care of her. She was 84 at the time and I just didn't feel good about putting her into a home for the elderly. With the help of caretakers who looked after her during the day while I worked, I spent the next five years watching over my mom until at 89 she finally joined my da...

Lucian Ch. 02

by angiquesophie on Sep 11, 2017
Transsexuals & Crossdressers

Why do we think in absolutes so often, like good and bad, fire and water? Why, for instance, do we insist that there only should be men and women, and call that the natural order? Isn't that just a lack of imagination? Lucian sat on a bench in the shadow of a big tree with a crown of flaming leaves -- a sycamore, maybe? He loved the word, but he knew not...

That Was No Lady: Ending Pt. 03

by vastiesmith on Sep 16, 2017
Loving Wives

Couple of weeks passed and nothing seemed to change for Deborah and Lewis. Lewis was now meeting with Leah on their set date as well as Fiona and Margaret. When he came home he stayed home the next day which was Wednesday. Sometimes his wife Deborah would be there waiting for him and they would have sex and talk about what he and she were doing when they wer...

That 70's Show-Happy Halloween

by shaggy77 on Oct 8, 2019
Celebrities & Fan Fiction

A fictional story about fictional characters. ***** "No, not that. Anything but that," Red Foreman implored his wife Kitty, " you know I hate...people." "I've thought about this long and hard, Red," Kitty explained. "Last month I put up with your visiting mother for over a week, and you promised that you would owe me big time...anything I wanted, you said...

Mistress Cane's Femdom Gym

by LewisCrane on Jun 5, 2019
BDSM

It's too early when you swipe in to the gym. The air inside is cold and stale, the lights blinding. It's Saturday morning, so normally you would be nursing a hangover that would make the fluorescent glare unbearable, but it's been weeks since you had a drink. But even after all these weeks, 5:30 am is still too early. You're bleary-eyed and nervous. You feel...

Marion's Story Ch. 03

by Cagivagurl on Jul 6, 2020
Transgender & Crossdressers

Credit here to my friend and fellow author EM Kay (Marina Kelly) who helped with the story and kept me on the straight and narrow and of course did all the editing so thanks Marina.... A few days later I picked up my new guitar and it was perfect. Walking home you couldn't wipe the smile off my face. I locked myself in my room and spend the rest of the nigh...