Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

Thirty Days to Jenny Ch. 2

by monika ikon on Sep 12, 2017
Transsexuals & Crossdressers

day eleven Well, Alison, thought, Jeff had been listening to the 30 Days to Jenny tape for ten days already and the changes in his character were dramatic. He was sweeter, more helpful around the apartment, and even more satisfying in bed. He'd started a diet, been exercising, and had taken a renewed interest in his appearance. If the changes stopped there,...

Reality TV

by JJ Neal on Sep 25, 2017
Transsexuals & Crossdressers

I didn't recognize the number, but I certainly recognized the voice and understood the message, 5:30, Jackson, Bride. My Master isn't given to long conversations with me, or any explanations. My role is to make it happen. I met Master Fred in a sissy chat room and he swept me off my high-heels. By way of background my sissy name is Jamie Jo. I'm 44-years...

Exposing Cindy Ch. 02-03

by cindyexposed on Sep 26, 2017
Interracial Love

Coming soon: Chapter Two: Exposing Cindy - Facing my husband. The evening with Denzel was uniquely dangerous and exciting experience. It was degrading and humiliating; and yet, I came three times. But most of all, it was stupid. It was irresponsible. It was wrong. I violated one of the fundamental precepts of my marriage. My husband, whom I love dearly, ha...

I Think I'm Gonna Stay with You...

by trigudis on Jul 15, 2020
Romance

It's another return to those so-called thrilling days of yesteryear, this time to June of 1971. Nixon sat in the Oval Office, the Rolling Stones' Brown Sugar topped the Top 40 charts and Summer of '42 and Billy Jack played at the box office. Hot pants were all the rage and leisure suits were on the horizon. What we later took for granted, cell phones, person...

Stocking Sperm Challenge Ch. 02

by wordyone on May 7, 2019
Fetish

The second part of the story of the Stocking Sperm Challenge will make better sense if the reader is familiar with the original story. * Naturally, Ruby was enjoying telling April every saucy detail about what she had just put me through at my first and failed attempt at the Stocking Sperm Challenge and the history of my unsanctioned meddling with her inti...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

The Wedding Ch. 02

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake Part 3) Chapter 2 -- Party in Pink Purgatory... "Oh Wow Dale! You look fantastic! Very -- Very pretty... I can hardly tell that you're my boy anymore! Really sweetie I'm so impressed -- and Patti you look gorgeous too... I knew that dress would look stunning on you -- but Dale -- my pretty -- pretty -- son... That dress is perfect;...

Vicious Beach - Perfect Choice

by FictionbyFrozen on Sep 16, 2017
Fetish

"What are you doing back there?" The tall, dark haired woman called to him as he cowered, naked and embarrassed, behind one of the gnarled rocks that dotted the slowly darkening beach of Etanimod Cove. He hoped that she had not seen him, but it was obvious she had, and now she was calling to him again, her voice closer this time. "You do know this is privat...

Kidnapped (A One Week Chronicles)

by Louise69 on Oct 15, 2017
Transsexuals & Crossdressers

Prologue Crystal checked the address on her phone as she walked through the bustling crowds of Leicester Square. She had a few minutes before she'd be missed, so hurried quickly, her tall heels and tight fitting dress making the task difficult. The pub was just around the corner and she ignored the lustful looks she received from a drunken crowd outside th...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...