Sissy Academy Stories

10,735 results
Orientation
Length
Source
Infinite Scroll

Black Rose Ch. 02

by wardensteelwrites on Sep 14, 2020
Sci-Fi & Fantasy

Kira Moira and I are coming up to the entry to the Academy, an enormous brick gatehouse with a huge iron gate guarded by two uniformed soldiers. They stand with polished pikes and in plate armor and pretend they can protect the Academy. Other than drunks and curious citizens they don't deal with much anyway. I walk with the bundle of books and as we come c...

The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

[The Gillian McGuffin Academy Of Adventure]

by Nemo of Utopia on Oct 12, 2017
Fantasy

A chill mist surrounded the unreasonably large castle at the heart of the Valley of Quorn. This castle was both fortress and palace, yet, in truth, neither. Built over more than 500 years the castle was more like a small city than a castle, and rather than a palace, it was in truth a university. What did they teach there? Adventuring, the ancient and honor...

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Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...

Big Woman's Booty Cake

by Samuelx on Aug 31, 2017
Fetish

Booty Cake. The most delicious substance known to man. Finger-licking good. I love making them. My name is Ramon Tyson. I'm a tall, good-looking black man living in the town of Providence, Rhode Island. I'm a student of the Culinary Arts at Johnson & Wales University. The Denver Campus is my favorite hangout. I am an aspiring Chef and my culinary specialty i...

Sex Academy Ch. 01

by adia_23 on Sep 12, 2017
BDSM

I am shaken awake by the headmistress around noon. My eyes slowly adjust to the light as she says, "Hurry, get up. Your master wants you to be ready to go out tonight at 9:00." Yawning, I slip out of bed and walk fully naked down the hall to the showers, my nipples tautening in the brisk air of the hallway. Ginny, a petite blonde first-year student, is strid...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...