Exploring Sissy Fantasy Stories

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Sissy Amy Loves Mummy Belinda Ch. 01

by Sissy Adele Howells on Sep 17, 2017
Fetish

My world had turned upside down, when realising that my favourite fantasy was about to come true. The story that I am about to narrate, is about my obsession of being a kinky, sissy, little girl. Everything seems so real and I could not stop myself from falling deeper into this kinky world of fantasy. For the benefit of the reader I am forty eight years of a...

My Sissy Boss

by newbie88 on Sep 24, 2019
Transgender & Crossdressers

I knew this is why you'd hired me. I knew it from the start but had wanted to be sure before I actioned any of the dirty thoughts that filled my head on a daily basis. I had watched you watch me, had seen the desire in your eyes. I knew you wanted me, knew what you wanted and I could not wait to give it to you. I chose my outfit carefully that day. A loose...

The Cuckold is Black This Time

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

After months of hesitation and much soul-searching, a momentous decision finally got made. The big Black dude burst into Mistress Chocolate's den in downtown Ottawa, Ontario, and told her of his rather unusual request. The six-foot-tall, gorgeous Black Canadian female dominant listened to him, and then agreed to make his most forbidden fantasy come true. It...

BWC for Black Male Sissy

by Samuelx on Sep 12, 2018
Transsexuals & Crossdressers

Meet Bass, which is short for Bashir Malong, a six-foot-seven, dark-skinned and ruggedly handsome man originally from the nation of South Sudan. Bashir is definitely more than he seems, and that's just the tip of the iceberg. A lot of people, upon meeting the tall, handsome brother with the deep voice, wonder if he's some sort of professional athlete, and Ba...

Falling for my Sissy Father in Law

by eroticWonder on Apr 22, 2025

All of this began with a single lottery ticket. I had never been particularly lucky when it came to gambling and lotteries, but all of that changed when I scratched off the grand prize on a $20 ticket I had bought on a whim; in an instant, I had become a millionaire, and for a time I could hardly believe my luck. When I finally stopped shouting and celebrati...

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Kiah The Black Goddess

by Samuelx on Sep 17, 2017
BDSM

What's up dear readers? My name is Kiah Halls and I'm a young Black woman living in the City of Atlanta, Georgia. After completing my bachelor's degree at Spelman College, I enrolled at Georgia State University for my MBA. When I'm not in class, or at work, I'm having wicked fun in the realm of BDSM. I've become a dominatrix, kind of, and I'm really enjoying...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Sissy Crossdresser Needs to Please

by Interested4L8R on Dec 11, 2018
Transgender & Crossdressers

My wife is out shopping. I have just a couple of hours to indulge my fantasy before she returns. Yes, that fantasy. The same fantasy you have. The one in which I open my wife's closet and decide what clothing of hers I'm going to wear. I want to dress up. I want to dress up for you. And my little smooth, shaved cock is quivering in anticipation. What will I...

Teacher Made Me into Sissy

by johntamilandrea on Sep 13, 2017
Fetish

HI! I am Sissy Andrea. This is one my fantasies about my teachers. This story is about feminization, fantasy. If you don't like these topics Please don't read. ALL THE CHARACTERS IN THIS STORY ARE ABOVE 18 YEARS OF AGE. My special thanks to "mywifesslave" for helping me in editing this story. ***** The story happened when I was 19 years old I loved sho...

The Dance

by yr_sissy_toy on Sep 14, 2017
Transsexuals & Crossdressers

It was almost too good to be true. Lounging in my bed wearing one of my few pairs of really cute panties I'd had the guts to buy at Victoria's Secret, I'd been scanning Craigslist ads. Just for fun -- I'd never actually do anything; I just wanted to look. To dream. To fantasize about being bold enough to answer that ad about sucking that gorgeous cock. To se...