Sorority Sissy Stories

10,264 results
Orientation
Length
Source
Infinite Scroll

Wife in Control Ch. 02

by wifetoy on Sep 25, 2017
Fetish

Almost two years ago, I posted the first part of a story detailing my punishment for failing to control my orgasm for my wife's pleasure. In an effort to appease her, I wrote her a poem offering acts of humiliation and service to account for my failure. She accepted my offering and executed the punishment with delicious cruelty. I lost the rest of the story...

Wife in Control Ch. 03

by wifetoy on Sep 25, 2017
Fetish

This is the third chapter in the story of my submission to my wife for punishment for failure to control my orgasm. My full offer of punishment for my transgression is fully set out in the first chapter for your reference. Each part of this story is true and is told as it actually occurred. As with the previous chapters, my wife told me to let the readers kn...

A Visit to a Mistress

by fun4all6969 on Sep 19, 2017
Fetish

I have always craved humiliation ever since I was with a girl who humiliated me for my premature ejaculation and my small penis. I saw an ad online for a girl who loves submissive guys and we chatted back and forth for about 2 weeks before my business trip took me to where she lived. She told me it would be $250 for the domination session and that I had to p...

Sissy at the Sorority

by secondsamuel on Oct 24, 2018
Transgender & Crossdressers

Author's note: I am recovering from repeated surgeries on both arms to correct a degenerative nerve condition. To write this, I am using a voice to text software which isn't always as accurate as I would like it to be. As my recovery time will take more than a year, I have decided to continue writing and give my best effort at doing the thing I love. Please,...

College Crossdressing Confessions Ch. 04

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. This is the fourth in a series in which I confess my past experiences as a panty thieving college cross dresser. I have changed some of the names, but the rest of the confessions are, sadly, true. Please read the first three installments for context....

Sorority Switch Pt. 01

by Sissy_simone on Sep 11, 2018
Transsexuals & Crossdressers

The summer leading into sophomore year at the university was like any other, until my I accidentally broke my twin sister's jaw. We were inseparable since birth and frequented many of the bars a few times a week, except for one fateful Saturday 2 weeks before work week started for her. Work week is the week before rush week when all of the sororities reunite...

Jenny Plays with the Big Girls Ch. 05

by Johnboy9 on Sep 12, 2017
Transsexuals & Crossdressers

Well, that was one fine mess we got our Jenny out of that last story, wasn't it? Whew! This story is a lot calmer and yet a promise of more to come. I again want to thank all supporters and interested ones who have urged me to continue this tale of our Jenny to see what will happen to her in the end of her journey through this unfortunate (?) web in which sh...

Sara Shows Her New Man Self Love

by Sexy_SaraCD on Sep 13, 2017
Transsexuals & Crossdressers

I felt vulnerable for the first time as Sara and while part of me was nervous, almost hesitant, the other part of me was exhilarated. I felt nothing more than curiosity as I faced an unknown scenario and what it would lead to. I met Daniel much like I've met most of the men I did as Sara. Except this wasn't a post of mine on Craigslist. This was his post a...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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Big U Pride Ch. 01: The Beginning

by latinarita4 on Jun 2, 2020
Transgender & Crossdressers

The college bus meandered down the winding side streets, making its way at a patient pace down the road. Along the side of the bus was emblazoned in big letters, "Big U Football" with the college mascot printed on it, a Rooster with arms in boxing gloves raised and ready for fisticuffs. Another banner tagged on the side of the bus by the mascot were the word...