Mrs Silks Sissy Stories

35,037 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

The Care Girls Ch. 05

by Tomsparty on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 5 - Another Chance The following weekend you've almost forgotten about your transformation experience when the phone rang. 'I'll go,' you shout to your mother. You pick up the receiver. 'Hello,' you say in your formal telephone voice.' 'Hello,' the mystery caller says 'is that Lucy?' You swallow hard. Your heart misses a beat. Who is this? You...

Not Sick Maid In Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

Maid in Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

A Sissy Saga Ch. 20

by Snurge on Sep 15, 2017
Novels and Novellas

Mrs Boroclough lived alone, but her house was the biggest in Peasmarsh. It had tall windows with ornate guards, and a polished copper plate fixed on the wrought-iron gate engraved with her name - as if everyone for fifty miles around didn't know who she was. It was far too big for a widow-woman who's children had grown-up and departed, but she insisted that...

Which Are You?

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Which are you? A, B or C? A) You treat me well. You insist that I look stunningly pretty 24/7. You insist I always wear make-up, care for my hair and nails. You pay for me to go to a beautician once a week. You buy me sexy lingerie. You get angry if I wear slacks or jeans. You prefer dresses in preference to skirts. You make me feel special and lucky the mo...

I'm a Sissy!

by Queen_Diana on Apr 22, 2025

One day I woke up. Looked at my body, and thought to myself, I'd be way more sexy as a girl, I'd probably have more fun too. It's not like I'm overly girly, in fact, I'm quite masculine, girls can't have enough of me and I enjoy it. But there's this itch I can't scratch, I'm sure you know it too, a feeling of needing to be filled up and pumped full of, well...

Open in Reader

A Tale of Two Sissies Ch. 01

by SatinSlip on Mar 26, 2019
Transgender & Crossdressers

Author's Note- this story is a work of fiction. All the characters are eighteen or older unless noted otherwise. This story contains scenes of non-consensual sex, incest, interracial sex, gay sex, forced feminization, abuse, and rough sex. I hope you enjoy reading it as much as I enjoyed writing it. - ***** SMACK! My cheek stings from the big black te...

Our Sissy Slave Ch. 02

by purekink on Sep 25, 2017
Transsexuals & Crossdressers

Would you be our full-time cross-dressing lesbian boislut? Of course you would. I knew that from the moment we'd made you beg to be fucked whilst dressed in a red corset, knickers and stockings ensemble. Your clothes matched those of me and my new student girlfriend, and your makeup was messed only by our juices. It was easy to make you submit after that....

Panty Fantasy-Hurricane Kate Ch. 01

by eliasrotica3 on Sep 14, 2017
Fetish

'A day like any other,' thought Kyle to himself. The view outside his Research Triangle Park office was a little boring with the leaves all fallen and the snow not yet come. It felt good anyway to see the world and the weather. Kept him from getting office fatigue. He liked his job as a senior accountant but he did get a little bored by the routine at times...

Sunblade Ch. 01

by DonaldBelle on Nov 2, 2017
Novels and Novellas

** SUNBLADE OVERVIEW ** Sunblade is a free erotic fantasy novel that is written in instalments and posted to Literotica. It is an adventure that spans many timelines, dimensions and themes and is currently an ongoing work in progress. If you enjoyed this chapter, I implore you to check out the rest of the Sunblade story. ** CHAPTER OVERVIEW ** In this fir...