Sissy Transformation Stories

14,811 results
Orientation
Length
Source
Infinite Scroll

The Cruel Step-Mother Ch. 03

by Croony on May 13, 2020
Mature

'Good morning Timmy, how are you today? Did you sleep well?' asked Joanna, his step-mother as he walked into the kitchen. Timmy felt like telling her he would have slept a lot better if her mother had let him sleep. Joanna's mother Jean had been to his room after they had all gone to bed complaining she was horny and needed Timmy to do something about it....

Straight Crossdresser

by silkstockingslover on Oct 22, 2019
Transgender & Crossdressers

Summary: Guy dresses as a girl on Halloween and ends up performing as one. Note: This is a Halloween 2019 Contest story, so please vote. Thanks to: Tex Beethoven, and Robert for editing. * As I draped the sheer pantyhose onto my legs to finish off my Halloween costume, preparing for a night of cock sucking and bottoming at the annual Halloween men's onl...

The Tales of Crissy the Sissy

by EPCene on Oct 5, 2020
Transgender & Crossdressers

Chapter 01 Halloween night 'Those guys are real fucking assholes,' Chris Masters thought as he walked alone down the crowded street. He had known most of them for the better part of a year and never thought they could do this to him. They had met at work. Chris was the new guy and was instantly brought in to meet the rest of the middle management team. Th...

Halloween Dress-up

by sirhugs on Sep 12, 2017
Transsexuals & Crossdressers

"Tim, can you please come on over? I have to go to a party later, and I'm already dressed in costume." "Why are you dressed up so early?" "I had to take my little brother Teddy trick or treating. But now my parents have taken him to a party at the club." Even though I was a guy, and she obviously wasn't, Sally Brown was my best friend, and had been since...

Reformation on Couples Therapy

by Marriedkinkylife on Oct 10, 2018
Novels and Novellas

Authors note: This is a multi-part series following the sexual journey of two married couples, as they explore various fetishes and kink, including their own sexuality. Please read the story tags. You've been warned. * I was suddenly awoken from a deep sleep. The alarm hadn't gone off, yet. Fuzzy-headed, I started to sit up and as I was gathering my sense...

The Halloween Dangler

by weftandwarp on Sep 16, 2017
Romance

The Difficult Seduction of the Halloween Dangler, Snake Cracker, Bull Dropper and Pacifist Contender. * Christie was ready. Dressed in black with a tall conical hat and carrying a straw broom. She'd even had time to paint her face black. And her legs. And her arms. She'd been ready for a while, was extremely excited, and I was the slow poke. I didn't reall...

Pain of the Goblin

by justincbenedict on Sep 17, 2017
BDSM

10/24/05 As I write this, my left leg is cuffed to the chair. I haven't been to the bathroom in thirteen hours, and Miss Stephanie has insisted that I am not working hard enough on journaling her attentions! The misery is palpable, I must confess. She spent most of last night teasing my poor cock to near distraction..."Now that you keep web journals, dea...

Lucian Ch. 05

by angiquesophie on Sep 11, 2017
Transsexuals & Crossdressers

Spring arrived at Norton's Academy of Excellence. It painted the drab lawns with blazing green, causing desolate bushes to burst into a zillion flowers. Chaotic birdsong filled the sky, and Lucian Gaines ran, seeing it all happen - the yellow of daffodils, the purple of crocuses and the pure white of snowbells. Not that he had the faintest idea what th...

Silver Moon: Bk. 02 Ch. 06

by maxd01 on Dec 24, 2019
NonHuman

Authors note: Thanks for the patients for this chapter. I thought I had posted it and then ended up in the infirmary with a severe skin infection of one leg and rather was out of it for a few days. In any case I am already partway done with the next chapter and will hopefully have it done by this weekend. As usual all relationships are 18+. ***** Pam slow...

I Love You Because

by _Lynn_ on Sep 11, 2017
Non-Erotic

Note from Jake Rivers This is my sixth semi-annual "invitational". The initial one was based on the Statler Brother's song, "Bed of Rose's". The second used the Marty Robbins El Paso trilogy: "El Paso", "El Paso City", and "Faleena". The third had stories based on the various versions of "Maggie May" or "Maggie Mae". The fourth invitational was based on any...