Sissy Academy Stories

10,735 results
Orientation
Length
Source
Infinite Scroll

Revenge

by PKenny5860 on May 18, 2020
Loving Wives

Revenge: Behold the Monster You Created Disclaimer: This is a story about betrayal, hatred, and extreme revenge. It is violent and it is about what happens when a trauma is so severe that a person just snaps. His sanity is lost and reason disappears and the thirst for blood and vengeance consumes him. It is BTB on steroids. This is a work of fiction and has...

Forbidden Lizzy

by Alex_Lockheed on May 19, 2020
Transgender & Crossdressers

NOTE: This is a transgender erotic romance with significant underlying themes of angst and emotional tension. It is a bit of a slow burner, but it gets there in the end. The main characters are a sexually dominant male (Mark) and a sexually submissive t-girl (Lizzy). There are some mild BDSM elements. If you are looking for a tale where a t-girl fucks and d...

Lucas's Older Brother

by Lucas96 on Dec 2, 2019
Fetish

Disclaimer: this story involves cuckolding, humiliation, etc. *** Lucas and Emily, both 21 years old, had been dating for about a month. While Lucas had had previous girlfriends, he'd never felt the way he felt about Emily. They'd met in class at their small liberal arts college, hit it off immediately, and gone on several dates. After a week or two, Emil...

Uncle Bob Ch. 12

by bad_hobbit on Oct 21, 2019
Anal

Chapter 12. The Hotwife © Bad Hobbit 2019 OK, folks. Life tends to get in the way of writing, so apologies for the wait. A huge thank you to all my readers who are hanging in there, despite my erratic publication schedule of chapters of Uncle Bob's story. I love writing this stuff but, as I say, life kinda gets in the way. According to the plan, the...

Memoirs of a Swinger Ep. 16

by M4bloke on Oct 21, 2019
Erotic Couplings

This is the sixteenth episode of my unreliable memoirs. Each episode can be read individually but it helps a bit with names to have read the previous ones. I hope you have enjoyed it so far. M4bloke ****************** Life returned to a certain level of normality at the end of the summer of 1982. Going back to do my final year of university was a bit of...

Patti Cake Ch. 07

by betamale08 on Jul 16, 2019
Transgender & Crossdressers

Pacing in my half of the house, on my living room floor, nervous and waiting for Patti's imminent arrival. It was hard to ignore the wonderful, tingling feeling as my silk camisole and fine stockings gave off as I moved, caressing me with every step, reminding me again and again what exactly I was wearing under my favourite dark, navy blue suit. I knew Patt...

The Psychiatrist Ch. 04: Proposition

by Willupboss on Jul 16, 2019
Loving Wives

THE PROPOSITION Over the next few weeks one thing made itself perfectly clear; our personal love life was out of this world! For instance, before that fateful night at Lou's Tavern, Holly would rarely give me a blow job. She just didn't like doing it and for sure she most certainly would never dream of swallowing. But now she gives them to me all the tim...

The Vengeful Tide Ch. 10

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

I would like to think that getting woken up by a blowjob be one of the best ways any man can ever experience the day. The feelings of drowsiness coupled with the warm, stimulating movements of a wet mouth give off a better feeling than almost anyone can ever realize. All the sensations of warming up and sexual arousal were blasting through my body like hot f...

First Contact: Into the Arena

by ShelbyDawn57 on Oct 19, 2020
Sci-Fi & Fantasy

Chapter 2, Rider, and the crew of the Phoenix begin their journey to Trellis, finding the warrior society of Diraki in their way. Unintentionally offending a local chieftain, Rider fights for her crew. Not as much sex as the first installment, but I think you'll like what is here. A few good fights, too. As always, please let me know what you think, your co...

Summer, My Sister's Best Friend

by SusanJillParker on Sep 12, 2017
Romance

This is a Summer Lovin' contest story. Please vote. * Stephen's love of his life is his sister's best friend, Summer, a woman eight years older than him. Summer, I'm in love with Summer, my sister Christine's best friend and I don't know what to do about it. Love at first sight, it all started the first time I saw Summer in the summer of 1968. She was in...