Sissy Dare Stories

47,304 results
Orientation
Length
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Infinite Scroll

Trained by My Aunt Ch. 01

by Misslexia on Aug 18, 2017
Fetish

It was my Aunt's suggestion that, when I left home and got a job, I moved in with her. Although my job was a few miles from her house, I had my bike and the renting a flat in the city was not an option. Secretly I was delighted. Aunt Suzy was my mum's younger sister, jokingly described as an 'afterthought' or an 'accident'. Fifteen years younger than my mum...

Alex to Alexis Ch. 01

by TransPrincessMorgan on Sep 25, 2017
Transsexuals & Crossdressers

Thanks to Jack Murphy for being our volunteer editor! Enjoy! ***** Chapter 1: Feminization Alex was late home again. Once, maybe twice would have been acceptable, but this was the third time this month. His mother, Daniella didn't know what to do with him, especially considering her other children, the eldest, Hannah, who was 25, and the youngest, Amelia,...

Amy Moonlight's Stinky Knickers

by wordyone on Jul 14, 2020
Fetish

I had the panty time of my life. I was assigned the task of photographing the Edinburgh Festival for a fashion magazine, and my accommodation had been sorted out for me by a friend. I climbed three flights of stone tenement steps to a black door numbered twenty-three and rang the bell. The door was opened by a beautiful creature, little more than five feet s...

Unloading in Bristol

by DarkParamour on Sep 19, 2017
Transsexuals & Crossdressers

It had been a while since I last did the Bristol run. I texted Sonya from the services letting her knows I would be coming round. Now I have a few holes in several ports, but there aren't many like Sonya and Dave. The door wasn't on the latch like I had said, so I knocked impatiently. Dave answered, half hiding behind the door. "What the fuck?" I said imp...

Sissy Masochist

by _pdy_ on Sep 24, 2019
Transgender & Crossdressers

I'm writing this because, personally, I really enjoy writing about my sexual desires and turn ons. I find it very taboo to express these secret thoughts for strangers on the internet to see, and to be completely honest, I have a massive hard on as I write this. Well, not massive, quite the opposite actually, but you get the point. Reflecting on my previous...

Sissy Joanne Parr Fantasy Fucking Ch. 01

by Sissy Adele Howells on Aug 18, 2017
Fetish

Joanne Parr was 26 years of age. She had an obsession with the Barbie doll . She wanted to look like Barbie, as well as dress like her. One day in the office, I was so jealous of her. How dare she wear pretty dresses, when they would look much better on me. I want to be the new Joanne Parr, but I needed help to allow my kinky fantasy to take place. Georgina...

Movie Night

by lavskye on Sep 1, 2017
Group Sex

Samuel pulled his keys from his pocket and fumbled with them. He found the key just as he approached his vehicle. He opened the door, climbed inside, and started the engine, fiddling with the radio as he pulled away from his parking space. What a day it had been. His neck and shoulders ached from being so tense all day at the office and he was glad to be goi...

A Sissy's Forced Gangbang Pt. 01

by sissy77 on Dec 3, 2017
Transsexuals & Crossdressers

I have always seen myself more feminine than most guys I grew up with. Slim and hairless throughout my body, more curvy than muscular. Until my early teens (I am 25 now BTW), being a sissy for me meant not being masculine as other guys both physically and mentally. When i reached my early twenties it turned to me brainwashing myself through sissy hypo vide...

In My Dad's Panties

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I knew my parents hadn't been getting along at all well recently and I had even begun to fear that they may some day be getting a divorce, but still the discovery that my father could be having an affair came as both a shock and something really quite distressing. It was the first time I had to confront the truth that my parents' split was a very real possib...

Betty Finds My Story

by JackorJill on Sep 12, 2017
Fetish

The office was quiet at this time of the morning. I came in to get some paper work done. The phones never sounded better. I had put some coffee and stopped for a bagel. The applications on my desk had been piling up and that was a good thing. I never heard Betty until she was standing behind me. "Hey, you're early. Knock'em dead big guy." She was older then...