Sissy Academy Stories

10,735 results
Orientation
Length
Source
Infinite Scroll

Nikki Goes to College Ch. 02

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

The next day, I awoke to the sounds of someone screaming, I didn't know what it was at first being disoriented. I looked around the room and quickly began to realize that I was still in Primington Academy. It hadn't been a bad dream. I saw my roommate, Missy, across the room sleeping still. She must have gotten used to the screams because she was still out l...

Repercussions Pt. 01

by astushkin on Jul 29, 2019
Romance

Derbyshire, England, Spring 1854 Chloe She never would have dreamt that she would miss her time at finishing school. One week returned home from Haversham Academy, Chloe stood upon a rocky outcropping gazing with a disquieted feeling down over her family's estate. Nigh a mile distant she saw Greystoke Hall favorably situated upon a gentle rise in the land...

2016 Literotica Reader's Choice Awards Winners

by Literotica on Sep 16, 2017
BDSM

The stories and authors below were chosen by our readers as the best of 2016, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of hot reading, and to all of the readers for your input, support, and a...

The Journey Pt. 05

by MissYellowPanties on Nov 25, 2017
Transsexuals & Crossdressers

Job Interview I received more special commissions, perhaps the strangest for me was Head Mistress Kendra, who had me in her office dressed as a school girl, she could have had everything she took and willingly, for free in my bedroom, but she needed it to be in her office. Afterwards she told me how she had wanted me the first time I bent my bare ass over...

The Settlement

by cathynylons on Sep 12, 2017
Transsexuals & Crossdressers

While my wife was away visiting her mother for a week I had a wild fling with Kate, the sexy new secretary at my office. A young tart about 22 yrs. old in tight skirts and spike heels. She drove me crazy and before I knew it we were doing it on my desk with our clothes mostly on. Then, at her place near the beach and then, on the beach at night. Wild times....

Initiation to Sexual Adventure

by Lyon on Sep 15, 2017
First Time

I must thank you for the good times we had when I returned to Wellington. I have always liked masquerade parties; wearing a mask brings out the wild side in people, including me. I also liked your Roman theme, because fixing up a toga is not much effort and there is great latitude if you want to use your imagination. I am not sure I expected to find an abso...

A Sissy Saga Ch. 16

by Snurge on Sep 15, 2017
Novels and Novellas

It was after supper, but the evening sun still shone through the lofty windows of the gymnasium to catch dust particles floated weightlessly in its slanting streams of light. A naked young man who promoted the delicate aura of a fragile girl stood fumbling over his words before the seated figure of Miss Twist, groping helplessly for an excuse to explain the...

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...

Marcia Goes Back to School

by Belongs2Beth on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: This story continues the adventures of eighteen year old Marcia (nee Marcus) Cicero. The tale opens a week after the events related in "Carol's Gifts". Marcia has shown visible signs of blossoming in the wake of Mistress Carol's injection of powerful hormones and is anticipating returning to her school for the first time as a girl. To answer an...

Hearts Academy Ch. 04

by RoseB on Mar 16, 2020
Transgender & Crossdressers

Disclaimer and Notes: Disclaimer and Notes: Hearts Academy is an dark horror/mystery story focusing on the reluctant feminization of a young artist. There are many themes such that cause it to be disturbing for those who cannot handle terror or dread well. This is a sequel to The Rose Diaries. While the characters are brand new, it does reference events an...