Femdom Mature Sissy Stories

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Forced Femme

by Mrfriskay on Aug 11, 2018
BDSM

You've always been kind of a nancy boy. A little afraid of women, and awkward. The attraction has always been strong though, especially to dominant women. It was always obvious that you were a little different, but things changed when you met her. She wasn't typical in any sense of the word, and you find out the hard way.What's next? Annabel Lee, 6'1&q...

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Journey into Feminization Ch. 01

by KneelingNancy on Jul 14, 2020
BDSM

***Chapter 01 - The Beginning Like so many of our beginnings, mine started to what some would call a normal life. I grew up in on the west coast and would consider my family upper class. Both my parents had successful careers and my brother and I had a lot of great experiences growing up (private sports clubs, investment in the arts, etc.). During my chil...

Delving into Femdom Ch. 01

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 1. Growing up Oh my where to begin, I imagine it is best to start at the beginning (or as close to it as I can remember). I grew up in a relatively medium sized east coast city living what some may call a normal life with two sisters and both my parents. Growing up I was always into sports and when I entered middle school I had begun to focus on b...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

From Princess – Mistress

by subway1962 on Sep 17, 2017
BDSM

This all started about 6 months ago on a Saturday afternoon, my wife had said that she would be out all day, shopping with her friend, then she was going to the cinema to watch a film and said she would be back about 10pm. My little princess (Ana) was having a sleepover with her friends so she was out for the night, that's when I realized I would be by myse...

Sissy Academy

by Tricentennial on Apr 28, 2018
Transsexual

Your name is Allen George, you are walking home after work, when you get a message from your girlfriend, Samantha Conners, saying she has a surprise for you. With this is mind you hurry to your apartment. You get home and open the door to find it pitch black, you flick on the hallway light and take off your shoes. “Samantha?” You call out as you walk down th...

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Hubby Drop To Thy Knees! Ch. 01

by Ashesh9 on Sep 17, 2017
BDSM

CH1. : HUSBAND, DROP TO THY KNEES!!! IMMEDIATELY! "Husband drop to thy knees!!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!!! The vast assemblage...

Husband, Drop to Thy Knees! Immediately! Ch. 01

by Ashesh9 on Mar 7, 2018
BDSM

"Husband drop to thy knees!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!! The vast assemblage watched the spectacle appreciatively: male phalli th...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Sissy Manners Classes Ch. 01

by fridaysissy on Sep 12, 2018
Transsexuals & Crossdressers

It was late night, I am 10 km away from my room waiting for sharing cab or auto service to reach my room at last I joined a sharing auto service with two members including me. The other passengers stop came early, and I remain alone in auto waiting for my stop to come. Driver said he is stopping the service and returning to his home and asked me to get down....