Sissy Transformation Stories

14,811 results
Orientation
Length
Source
Infinite Scroll

A Beggar's Social Advancement Ch. 02

by dan57 on Sep 19, 2017
Loving Wives

Chapter 02 Kumar wants his wife Jodhaa back! Jodhaa had returned to India with Mark. Since then, Kumar had been pestering Leena and Peter to have his official wife back. As his demands remained unfulfilled, he became more and more restive although his next videos were just a series of hits, remaining in the top lists for weeks! "The awakening of the black...

The Stones of Years Ch. 03

by Adrian Leverkuhn on Sep 16, 2017
Romance

(note: part one of the story appeared under the title "Woman in Chains") The Stones of Years III She was everywhere – and nowhere... ... Everywhere he turned – at auditions and rehearsals, at lessons and work details – she was everywhere – and nowhere. He could not get her out of his mind, or her lips, especially the way her lips had found his. Oh God,...

'Ween Contest

by Nathan_Brazil on Sep 3, 2017
Erotic Horror

Greetings to everyone! Yes, this is my entry into the Halloween contest. It's sort of a Satire/Celebrity/Erotic Horror piece with some gay sex, group sex, oral, and even some implied fisting. Yes, something for almost everyone in the Literotica family! Oh yeah, there's some Fetish too. I hope everyone loves it and I get to sell the film rights! * "Oh look!...

Your Ex-Lover is Dead Ch. 04

by miserybusiness on Sep 14, 2017
Interracial Love

When I woke up, a male doctor was hovering over me, giving me the strangest look. When I followed his eyes, I saw he was looking at my boner, which was stabbing my blanket. I snatched the pillow from underneath my head and put it on my crotch. "I had a dream." "Sure you did," He didn't even look at me. He kept tinkering with his doctor supplies or whatever...

JOA: Damon's Chronicles Ch. 02

by rulehater on Sep 17, 2017
Celebrities & Fan Fiction

This story is a spin off of the successful and wildly popular “Journal of an Agent” by Carnage Jackson. At the end of Carnage’s story, the main character, Dean Simonds, faces a major dilemma, where he has to choose between staying in Hollywood with Alyssa Milano, or heading back east with Natalie Portman. Please note that this might not necessarily have been...

What's In A Dress

by newstylewife on Aug 31, 2017
Fetish

I noticed my wife had filled a few blue bags of old clothes to be taken to the recycle centre. I had a look through them to see if she was disposing of anything I may wish to dress up in. most things are far too small for me but there could be something I could stretch to breaking point and wear. As I started looking through I came across some items I had n...

His Son's Teacher Ch. 03

by GillianCD on Sep 13, 2017
Transsexuals & Crossdressers

~ 5 ~ Slowly Tiffany awoke from a very wonderful dream. The man she had been crushing on had asked her out and in a terror and magic filled evening, she had experienced her first sexual encounters with a man. Although not quite awake, she smiled and whispered his name: "Dave." What she did not expect was the bed to move in response! Slowly as she awoke to d...

The France Trip

by TJA on Sep 13, 2017
Exhibitionist & Voyeur

This is a story about a day I will never forget! I was in my last year at school doing my A-Levels. I had just turned 18 and it was the Easter holiday period. Because of our exams we were given extra time off (study leave) to revise. In the middle week my mother had arranged for me to go to France for a few days to brush up on my French (the subject I was no...

Long Hard Night

by MistyMorgan on Sep 17, 2017
Loving Wives

The loud chirping of the morning birds finally persuaded me to crawl from under the downy comforter that comforted me through the night. There were just the beginnings of a chill in the air as this was the transition between autumn and spring. My feathered friends must have been excited at the slight rise in temperature. I know that I was. Even though autu...

Video Booths

by Crystal_CD_Slut on Sep 13, 2017
Transsexuals & Crossdressers

You feel the urge, the inescapable urge to get dressed up in your hot lingerie. The feel of your smooth recently shaven legs, arms, chest and body on its own makes you dizzy with desire, but you know once your are all dolled up the urge will be so strong you will feel faint with swooning lust. You slip on your black and white bra and thong pantie set, the...