Sissy Schoolgirl Stories

13,642 results
Orientation
Length
Source
Infinite Scroll

Marine Girl Ch. 02

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 2 - Bikini Girl The walk from the changing room to the outside pool meant a lonely exposed trek across the cold wet tiled floors. In front of the whole wide eyed class who all laugh like crazed hyenas. Sir was joined by Miss the girls tutor who looks at me sympathetically. 'Have you met our new girl?' Sir says briefly explaining the situation to...

Escapism: Nightingale

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

I slobber on the thick, veiny cock in front of me. I slurp away like it's an ice-pop on the hottest day of summer. I'm dressed in a red plaid skirt, a white shirt with a matching plaid badge that reads 'head girl', the neckline just low enough to reveal my leopard print bra. The skirt is riding high enough to reveal the matching thong and floral patterned...

Three Old Tarts and a Sissy

by Sissy Adele Howells on Oct 13, 2017
Fetish

At 50 years old, I have started to have kinky thoughts about older women. This fantasy that I am about to narrate to you concerns three neighbours of mine. Between them their ages total 200 years. They have found out that I'm a kinky sissy, but this seems to make them crave for more sexual activity. The eldest of the three Joan Harries, encourages the other...

Three Old Tarts and a Sissy Ch. 02

by Sissy Adele Howells on Oct 13, 2017
Fetish

We all sat in the living room of Diane Bennett's house. I was proud to be sissy Charlotte Church. My wife to be, Joan Harries sat naked on the sofa next to Sonia White. Joan's body could have done with being ironed over, but for 70 years of age, she had a fantastic figure. Having kinky sex with Joan, two hours earlier was the icing on the cake. For her to ex...

A Sissy Saga Ch. 07

by Snurge on Sep 15, 2017
Novels and Novellas

The following morning Sammy was in Mrs Pardoe's class sewing a plain white collar onto a skimpy black dress. It was a compulsory project. During their first term all sissies had to produce their own parlour maid outfit, and it had to be done by hand because Mrs Pardoe claimed exclusive use of the only sewing-machine in the house. Sewing was one thing he hate...

Kinky Dentist Sian And Sissy Rachel

by Sissy Adele Howells on Dec 12, 2018
Fetish

Most people hate going to the dentist, but I get a sexual pleasure every time my appointment comes around. That is because my dentist is the sexiest women, that I have ever set eyes on. Sian Harris is in her late thirties. She is of medium height with short, brown, mousy hair. Sian is very pretty, with a smile to melt any perverts heart. Sian's husband worke...

Trapslut

by Alexia Wright on Aug 20, 2015
Fetish

Today is the day. Your erotic crossdressing blog videos have earned you your first practical job as an escort. Being the famous online sissy slut Annie, you used to pay the bills selling your horny pictures and masturbation videos to guys on the Internet. You got out of bed, still in your pink babydoll nightie complete with a baby blue thong and head for the...

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Daddy's Sissy Staircase Ch. 01

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

I've cleared my calendar for the afternoon and going to be spending this time with my fwb Daddy. On the drive over to his place, it got me thinking, he and I have been FWBs for a long time, and this story is an attempt to chronicle how I went from being a newbie sissy wannabe to his addicted, shameless cock slut. This is my first submission ever here; I hope...

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...