Sissy Contract Stories

32,406 results
Orientation
Length
Source
Infinite Scroll

Jack and Jill Pt. 06: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

They had been trying for a baby for some time and had come to the sad realisation that it wasn't going to happen without some intervention. The doctors wanted them to use donated sperm and have insemination, but it seemed so clinical. Jean had told them about a breeding club that she had worked in and they both liked the sound of it, but as she was walking t...

A Year To Remember

by Dirt Man on Sep 16, 2017
Interracial Love

The stars are lovely this time of year, the sky as clear as looking through crystal makes you think that you can just reach up and grab hold of your favorites, and hold them twinkling in the palm of your hand. I always feel at one with these nights as the sky and I are both black as pitch. It's always late at night when I at last go out looking for some acti...

The Wedding Ch. 03

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 3 -- Dildos, Deeds and Dates... Riding back to the Gate-House in the golf cart, we had an extra passenger, my Uncle John... They were staying with us that night and with my slowly getting used to his comments and barbs, saying he was going to make me Patti's cuckold -- but knowing that he would be sleeping with Mom...

Helen Ch. 06-07

by Philippasubmaid on Jan 2, 2018
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive transgendered male and a n other. If you are offended by tales of BDSM and sex between consenting adults then read no further ......... other wise enjoy It is best if read with previous chapters. Feel free to leave honest comments or suggestions, it really does encourage those of us who write t...

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

My New Friend Amy Ch. 03

by DRobbie06 on Dec 23, 2019
Fetish

As I drove home that evening I had the replay of the days events running on a loop in my mind. I can't believe I paraded around in panties at lingerie store in front of strange women at the instruction of my new mistress. Hell, I signed a contract to obey her no matter what she says! Then I begged to jack off in front of her. I'm even a panty wearing sissy n...

The New Routine:

by subservient_husband on Sep 17, 2017
BDSM

Saturday morning, I woke with Jennifer's warm body next to mine. It was wonderful and I did not move until she woke. We locked eyes and she gave me a morning kiss on the cheek. "Go ahead and make me some eggs and toast". I left her in bed to go get her breakfast ready. While I was, I heard the shower running and as I was putting it on the table, she came in...

Tara has a Threesome

by SissyTara on Oct 13, 2017
Transsexuals & Crossdressers

I was lying in bed one morning. Dave stopped by on his way to work at the construction site down the street. I answered the door in purple bikini panties and a matching baby doll nightgown. We had fucked a few times since our first encounter when I had walked by the construction site. He stepped inside without asking and kissed me hard on the lips. I respond...

Becoming a Sissy Maid & Slut Vol. 09

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Prefix: I will be fast forwarding a few days in my sissy maid, sissy slut lifestyle story here. From the last chapter ending on a Tuesday night going into my second week as Master George's full time sissy maid and slut to that of me getting ready for the following Saturday night of slut service. I feel the story's journey no longer has to follow a linear da...

Be Careful what You Ask For

by Wanttobefemme on Jun 8, 2020
Transgender & Crossdressers

This is a continuation of a story that began when a new neighbor moved in. Chapter two - Be careful what you ask for He had always imagined what this would be like. He thought it was just a fantasy, but it was actually happening! A beautiful woman (whom he barely knew) had enticed him into signing a contract which ultimately stated that he was her slave. O...