Sissy Task Stories

44,281 results
Orientation
Length
Source
Infinite Scroll

Lessons: First Time

by InYo on Sep 13, 2017
Fetish

I found her name in the back of a local swingers newspaper, in small print, at the bottom of a column. "Mistress Jade, Private training sessions, Become the man I want you to be." I clipped the ad and carried it around in my wallet for almost a month before I got the courage to call. A formal sounding older woman, who told me that the Mistress was busy with...

Cuckold Striptease Game

by Iftheshoefits on Sep 12, 2017
Fetish

I'd forgotten my damn key again. And my wife was taking forever to answer the door. What was she doing in there? I was mildly irritated by the time she finally opened up, but before my lips could even form the words to some smart-assed remark about how long I'd been standing there, my senses were overloaded with the sight before me. I gave her a once ove...

Neighbourhood Terror to Sissy Pt. 05

by Fibaro on Apr 3, 2019
Transgender & Crossdressers

At least he didn't have to wait long for his bus to pull up. Not that it helped with any of his suffering. He vowed right there that he would never visit that store again. There were few people on the bus and yet he felt like all eyes were on him. Passing two girls his age at front he heard some whispers. "What the fuck, I never thought that store would ever...

Life With Miss Ida Ch. 06

by Sheermistress on Dec 5, 2017
Transsexuals & Crossdressers

Life with Miss Ida – Part 6 - A New Development On most weekends Mistress and I would enjoy a nice wine or two with our evening meals however, on this particular Saturday, Mistress was enjoying more wine than she usually drinks – we had decided to do the twin, 'Schoolie-Slut' thing this evening, with both Mistress and I in matching, tartan mini-skirts, whi...

LeAnn Turns Dan into Desiree

by desireethtttv on Sep 12, 2017
Transsexuals & Crossdressers

I'd never shown my friends my true personality. Always in the forefront was a normal guy who loved girls and all things boy, when in fact, with each passing year, the things that excited me were all things feminine, including actual men and their boy parts. This remained status quo, until I met LeAnn. Introduced to the long haired blonde chick by a mutual f...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

An Evening in Red

by poule_mouillee on Aug 21, 2018
Transsexuals & Crossdressers

Jack was nervous. As a young man in his early twenties he had his fair share of fantasies, however this was going to be his first true time exploring them. And with what a woman to explore with! They had only just started dating, a few weeks all up, which wasn't enough when going around busy work schedules; but enough to know he was smitten. Victoria was som...

Night Out at the Pinky Finger Ch. 03

by Cap_N_PieSissy on Sep 13, 2017
Transsexuals & Crossdressers

He felt a little dizzy going over the night in his head. She is a he, but she...he...it...is really cute. And it felt so good holding...her, he anchored that word firmly in his mind, in his lap. He was starting to get a headache trying to process everything that had happened in the last...how long had it been. Before he could lose himself even further down...

Tales of Sub Asian Sissy Ch. 02

by subASIANsissyJADE on Apr 9, 2019
Transgender & Crossdressers

Once the door closed and I heard the deadbolt latch, I panicked. How on earth could I walk to my car in my current state! I stood there, my heart racing, in my black fishnet thigh highs, no panties, a glass butt plug with a big pink fluffy tail firmly lodged in my tight asspussy, my black lace bra, and my face and chin and neck covered in drying cum. I des...

Mass Sissy

by Jman236 on Sep 16, 2017
Transsexuals & Crossdressers

Well my mistress wanted me to post this short story of my latest sissy humiliation for even more humiliation so here goes... So it was a typical Saturday and I was on my way over to my mistresses' house, she wanted me there bright and early. I arrived at her house promptly at 4:00am and when I arrived I was informed that I would be spending the entire weeke...