Sissy Stories

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Crossdressing at the Girls' Academy

by TiefBlau on Sep 19, 2017
Transsexuals & Crossdressers

How do I start the story of my transformation, from a young punk to a cock-hungry whore? I guess it begins with the summer of senior year of high school, a night I still look back to with shame. Those were dark times, when I was mostly a bundle of hormones and vanity. Still, I guess I need to start from the beginning. Looking back on the night, I never shou...

Dirty Dan Pt. 01

by R410a on Dec 17, 2018
Erotic Couplings

How does one come to possess the moniker Dirty Dan? Glad you asked. I grew up poor, not simply without, but dirt poor. My two sisters and I had little to nothing outside the very basics, all of our clothes were hand me downs, we had no indoor plumbing, we did have electricity and heated our small three room shack with wood. We would take a bath every Satur...

The Welcome Home Spanking

by RoseWilder on Dec 17, 2018
BDSM

Author's note: The protagonists of this story, Rebecca Eriksson-Garner and Sarah Garner-Eriksson, already featured in my stories "The 14th anniversary", "My beautiful sub(missive)" "Sarah acts out" and "Choosing Corner time", This is just another vignette about their life together and their love. A warning: The setting of my world may seem real enough and th...

Brittany's Travels Ch. 05

by YDB95 on Aug 26, 2019
Novels and Novellas

Brittany had long since accepted that her new life meant a lot more people would be seeing her naked than before she'd lost everything. She'd grown used to it in prison, and the perks of her new life were well worth it, but there were still times when it could be a shock to the system. Watching Angie stroll into the hot tub room in her bathrobe while Britt...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...

Granddad - Party Time and Beyond

by WirdSmiff on Jun 4, 2019
Mature

It's Party Time! Girl's Nite To those of you that have not read the previous parts this will make much more sense if you start back at the beginning. Comments always welcum. ***** We were late, predictably. Despite being assured that she was probably less than half the age of any of the other attendees, Anja seemed to be obsessed with 'will I do?' and 'w...

Better as Riley Ch. 04

by cactusaur on Jul 16, 2019
Transgender & Crossdressers

Riley finally gets her sister Themes: Feminization, trap, anal, incest, promiscuity, free use, exhibitionism, creampie, lesbian, cheating ***** Riley woke hours later, curled under a thin blanket on bare mattress next to Kate and Becky, all three naked with cum oozing out of them. They were in a dimly lit room and she could hear the thump of the party...

Jaimie's Birthday Party

by jon.hayworth on Jul 13, 2020
Transgender & Crossdressers

JAIMIE'S BIRTHDAY PARTY (or Farewell James - Welcome Jaimie A She-Male cum slut is born) Jon Hayworth ©June 2020 With many thanks to my very patient editor NaughtyGeminiGirl96 the improvements to the original story are due to her, and any errors are where I have ignored her advice. * Birthdays when I was little were a problem, I was born on Christmas Ev...

A Most Unusual Girl Pt. 02

by R410a on Dec 24, 2019
Romance

The holiday cookies are baked and frosted, the candies are made and the Christmas decorations are up. It's time to submit part two. I wish you all a pleasant and joyous holiday season. All parties portrayed as having sex are 18 or older. ***** It was time to pick up Joann for our first date. I went to the garage where I kept my pride and joy housed, a 19...

The Business Trip

by OOAA on May 11, 2020
Fetish

My wife and I had been married for about 3 years when I first developed an interest in enforced male chastity. I had always had a very kinky and active fantasy life to fuel my almost daily masturbation habit. I was a 22-year-old virgin when I met Irene and I was looking to resolve that problem. Irene seemed like an exciting 20-year-old girl and I thought tha...