Dildo Sissy Stories

41,035 results
Orientation
Length
Source
Infinite Scroll

Elizabeth: Beginnings of a Sissy

by ElizabethJessica on Sep 16, 2017
Transsexuals & Crossdressers

I had a pretty good system going. My 18 year old sister would stay up to watch Sex And The City reruns with me (well she watched, and I smoked weed), and during the first ad breaks, would run downstairs and get changed for bed. During the next ads, I would go to the bathroom, and on my way, raid her hamper for her fresh dirty panties, usually buried under th...

Torturous Boots

by Fetish114 on Sep 17, 2017
Fetish

A story about perverted revenge Pete wasn't your average 19 year old boy. Unlike hanging out with guys and chasing girls Pete enjoyed dressing up in women's high heel boots and wearing sexy feminine leather. He was very much into the whole fetish S&M scene and enjoyed purvey nights at domination clubs and fetish balls. Pete lived with an old lady called S...

The Head Master and the Panties

by Misslexia on Aug 29, 2017
Fetish

Marion was beginning to wish her best friend Caitlin hadn't persuaded her to sneak back into school with her to retrieve her purse. The two 18 year-old sixth-formers were best friends. Marion was Head Girl and Caitlin was Sports Captain, yet as they stood by the sign reading 'Staff Only -- Entry to all pupils forbidden' that stood on the gate to the courtyar...

I Dream of Her

by MagnaCumLiterate on Sep 16, 2017
Letters & Transcripts

J, I've been thinking a lot about your question, the one about what I really want, and the answer has been writing itself in my head for weeks. It's time for me to put it into words for you. You asked: "What is it that you want — in your heart of hearts — that would make you really super happy? A rich woman to keep you and encourage you to pick up hot men?...

No Boundaries

by fitasfook on Sep 12, 2017
Fetish

Sally wasn’t sure if Pete would be able to make it - she knew how difficult it was for him to get away but she was ready and waiting anyway. She was wearing a cotton white blouse which just came to the top of her thighs and a pair of high heeled black boots, underneath she had on black stockings and suspenders, this was the only underwear she had on except f...

The English Ranch Pt. 01 Ch. 03

by slave_william on Sep 15, 2017
BDSM

(Warning –this and later chapters describe William's participation in Pony play and describes heavy BDSM and pain scenes which may not be enjoyed by all readers. Do Not Read if you cannot handle this type of fantasy and please remember, it is fantasy. If you do not enjoy this story or any of my writings, I'm certain that there are thousands of other stories...

A Sissy's Journey Ch. 02

by yukonnights on Sep 15, 2017
Transsexuals & Crossdressers

This work is authorized by the author exclusively to Literotica.com for publication. Introduction: A tale told in short vignettes which chronicle one young man's journey into self discovery. Please Note: This story series contains elements of homosexuality, cross-dressing, light femdom/submission and male feminization. All characters are fictional and port...

Lucy's First Submission Ch. 04

by StrictDom on Sep 12, 2017
BDSM

I would like to extend My thanks to everyone who has emailed Me with their comments. They have been filled with admiration, enthusiasm, encouragement, and different viewpoints which I have found immensely useful. Master. I had allowed My toy to come, after about six hours of light teasing and torture. For Me, it had been the most incredible evening of My l...

Marrying Sherry

by linedout5 on Dec 10, 2019
Loving Wives

SHERRY (Part 1 with Preamble) Words for our sexual nature have become established parts of our language. I am cuckold, submissive, sissy, and my wife is hot wife, dominatrix/submissive, slut wife. She loves controlling me but she also loves submitting to real men, bulls, studs. In the time period I'm writing about, we were in our early twenties, which wou...

Kim's Journey into Femdom

by humaleiated on Dec 24, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. *** Author's note: Please see Nana's Diary for the prequel to this story. Kim and her Mom have "the talk" Chapter 1. As Kim drove home, she mulled over the events of the day. She thought it would be like most other, but it turned into so much more after she had discovered Nana's Diary...