Sissy Contract Stories

32,406 results
Orientation
Length
Source
Infinite Scroll

Neighbourhood Terror to Sissy Pt. 16

by Fibaro on Jan 6, 2020
Transgender & Crossdressers

Chapter 18 Marcy had hoped the stop at CC's would have been the last one. She had suffered enough embarrassment for a day. Lisa's claim that they still had a few errands to run made her worry that it wasn't all over after all. Her worries were soon confirmed when they stopped in a rather seedy looking neighbourhood. Getting out of the car Marcy knew better...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

Cockland Island Pt. 01

by Sissyhalo1 on Oct 8, 2019
Transgender & Crossdressers

It’s actually called Huntington Island. And it’s been around a long time and most of us in the area didn’t know much about it except they brought in guests and stuff by sea plane and set out for a lot of food and deliveries. I mean it was a mystery and not around town. Most people worked there from town ended up staying there because it was this private re...

Appointment by Card Only Ch. 01

by Sputnik57 on Sep 17, 2017
BDSM

She had always been so vulnerable, growing up with the other boys it was so obvious she was not like them. Now in their late teens as adulthood announced itself to the others by adorning them with bodily hair and a developing musculature, they laughed at the soft hairless form of the one who was well known to them, but only from an external perspective. The...

The Two-Month Break Clause Pt. 02

by TheBiGuy on Mar 25, 2019
Fetish

After my first post, I received several comments. Some of the comments were positive and others negative. Any comments that were constructive, I will take the criticism and learn to incorporate those suggestions into the subsequent chapters and other stories I write. One of the comments was about numbering the story as Part 1 or some variation like that. Tha...

The Club Pt. 01

by Paulateevee on Jul 13, 2020
Transgender & Crossdressers

This is a continuation of 'The Trap'. It would be best to read that story (5 parts) first before reading this one although I will try to make this story as stand alone as I can. Background - Paul has been outed as a cock sucking sissy to his friends, family and work. He's lost his job, his wife and friends. Louise offers him a way out. Usual disclaimer. An...

Becoming a Sissy Maid & Slut Vol. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eighteen: Some New Friends for Chantel. A blissful night's sleep has led me to a wonderful Sunday day off. Master has told me I must accept that special Sunday plans are on the go after 3:00pm but today, this morning awaking at 9:00am I run my routine, enema, shower, put on fragrant body lotion. I then begin a day of dressing just for myself, but al...

The Landlady Pt. 01

by Manndee on Apr 3, 2018
Transsexuals & Crossdressers

I had been lodging at the address for 7 months now. When I first saw the advert, it made me smile because the lady advertising the room seemed to be so eager to have a lodger. You could see it in her photo. It was not my first choice when I looked through the properties that were available online, but it was the cheapest, and funnily enough, it looked the ni...

Please Take Baby Steps

by bawdybloke on Sep 15, 2017
Humor & Satire

She sighed at me, perusing my choice of items from the sex exhibition in the paper bag. "Why?" "Because they are all awesome," I cried excitedly. "I've read about this and ..." "Yes, I know you've read about it," my lover muttered calmly and ran her hands through her flowing red hair. "We discussed this and ..." "Come sit down," she cooed, calmly. I felt...

One of the Girls Pt. 02

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom, maledom and transsexual/cross-dressers niche, it is focused on humiliation. This is the second chapter of One of the Girls. Sorry for the long delay. ***** The studio lights blinded and disorientated me for a few minutes as Lana led me by...