Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

Sharing Ch. 02

by thetoy on Sep 12, 2017
Fetish

Neither Miranda nor I referenced her plan until Monday morning as we were having coffee prior to her leaving for work. (I worked a sort of early second shift most of the week; she was a nine-to-five middle manager at a major corporation.) I was in jeans and a sweatshirt, barefoot, she in her work attire--sharp trousered women's suit, navy with a wide pinstri...

Black On Black Cuckolding : Hell

by Samuelx on Apr 3, 2019
Group Sex

Officially, we don't exist. That's what conventional wisdom tells us. If you were to type the words "Black Cuckolds" on Google, all you'd get are references to the standard-issue Cuckolding, which typically involves a big Black guy fucking a White woman while her husband or boyfriend, also White, watches. Nothing wrong with that if that's what moves you. My...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

Nancy and Her Boss Ch. 03

by MidniteSpanker on Sep 19, 2017
BDSM

Part 3 – The Weekend. The initial stories in this series Nancy Remembers Chap. 1 Nancy Remembers Chap. 2 Nancy Remembers Chap. 3 Other stories continuing in this series Nancy and her Boss Part 1 Nancy and her Boss Part 2 Nancy and her Boss Part 3 - The Weekend Nancy and her Boss Part 4 - More Weekend Then the following are separate but related stories...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Mistress Aimz

by hyperpress on Aug 17, 2017
Fetish

Mistress ordered me into my chastity device. I complied. "you may not cum this week," she told me. I didn't. I was good. I used depilatory cream and removed all my leg, clit and pussy hair for mistress. It was Friday. She told me to take off my chastity and jack off into a glass. She said I could cum as much as I want Friday and Saturday, but to cum in th...

The Sexy Cuckold Couple Pt. 07

by cuckcpl4play on Sep 19, 2017
Loving Wives

The Day of the Ceremony is Finally Here Part 7 As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoral...

The Sexy Cuckold Couple Pt. 08

by cuckcpl4play on Sep 19, 2017
Fetish

As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoralized submissive. My wife, who was the love of...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

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...