Sissy Fantasy Stories

87,403 results
Orientation
Length
Source
Infinite Scroll

Natalie Finally Begins to Learn

by natalieukcd on Oct 6, 2020
Transgender & Crossdressers

Background I am a long-haired man in my forties. I have been married, divorced and married again. I have children from both relationships. I do plenty of manly things. Yet, behind all of this is the overwhelming desire to be a sissy. I cannot explain it to myself never mind to anyone else. I fight against it mostly as it does not fit in to my everyday life...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Loving Wives

by NemosFolly on Sep 14, 2017
Reviews & Essays

First of all, it must be noted that I am not a writer of erotica. I find it much more fun, and erotic, reading stories where I'm not sure exactly what's going to happen (even if it's pretty clear from the direction of the story so far) than writing ones where I have such absolute control. But I am an avid reader, and I have read many stories in each of the c...

Sissy Joanne Parr Fantasy Fucking Ch. 02

by Sissy Adele Howells on Aug 18, 2017
Fetish

Georgina Harris stood in front of me in her underwear. Her long, red hair was no longer tied back. It flowed against her shoulders, Her pretty, freckled face made me feel proud to be alive. I sat on my leather chair, holding my dress up. My erect cock, tight against my pink thong. Christine Wells tried to comfort a distressed Sue Lewis. Georgina removed her...

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

My New Neighbours Ch. 03

by csm1967 on Feb 25, 2019
Transgender & Crossdressers

I closed the bathroom door and looked at Katie. 'So, how was it?' I asked. She looked at me and smiled. 'It was great my love. I am a bit sore to be honest, but I can understand why you are so captivated by Angie and Tilly - they are amazing girls.' I nodded. 'They certainly are. I hope you weren't shocked by some of the things they said. Or I said for th...

Ugly Duckling to Sissy Princess Ch. 04

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Chapter 3) Several nights had passed after the party at the mansion and kissing Ted. Bernice called me Saturday and Sunday, but, both nights I told her I could not come by to see her. On Saturday, my girlfriend went to a party thrown by the basketball team. I knew she would end up fucking one of them, he would use her like a piece of meat,...

The Slave and the Sissy Ch. 05

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ayesha was not to be denied; slave was rampant after witnessing the erotic antics of the maids, and was anxious to please Ayesha quickly, so that he may watch over Pepper; she was so soft and vulnerable. Slave's cock rose quickly as he sniffed at the gloriously rich scent of the dusky beauty's thong. She smiled with a sense of admiration as he licked and lap...

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...