Sissy Mistress Spanks Stories

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Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

Miss Danver's Crime Prevention Ch. 03

by VeryCuriousIan on Jul 14, 2020
Fetish

William lay wide awake in his bed knowing this was to be his final day with Miss Danvers. The sheer thought of her majestic presence sent his cock hard and he closed his eyes and dreamt of her. Her perfume seemed to be permanently in his nostrils and it sent his senses swirling. She had changed his world upside down and made him into a subservient cocksucke...

Sissy Lesbian Rita Meets Lisa

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response! Enjoy and please ta...

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...

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...

The Humiliation of Mistress Penny

by accidentalmistress on Sep 14, 2017
Fetish

My daughter and my husband were out shopping, and I was eagerly anticipating a long evening to myself. Ali had just come home from college, having completed her first year, and she and Robert wanted to spend some father-daughter time together shopping. It was obvious that she was helping him pick out just the right gift for our 25th anniversary, which was on...

Black Sissy For White Mistress

by Samuelx on Sep 16, 2017
Interracial Love

Right now, I'm lying in my king-sized bed. And I'm getting fucked in the ass. Picture this, if you will. A big and tall young Black man of Haitian descent getting fucked by a tiny, blonde-haired white chick wearing a strap-on dildo. My name is Stephen and this is actually my idea of heaven. I live in the Vanier sector of the City of Ottawa, Province of Ontar...

Mistress Encounter

by WellBehavedMan on Sep 15, 2017
Fetish

Eva gets back to her hotel room from her business meeting, glad to be back, the meeting went ok, could've been better, they could all be better she reminds herself, as people don't give everything for nothing. As she flicks on the main lights she jumps as she see's you on her soft double bed, right where she left you before she went out, however she did not...

Sexy Slut Fantasy Ch. 04

by pdavis616 on Sep 15, 2017
Transsexuals & Crossdressers

The story continues with Sasha and Nicole heading to the sex shop As I sat in the car waiting for Sasha to start driving I pulled the mirror down to take a look at my face. As I glanced in the mirror I saw the strange beautiful woman staring out at me. I licked my lips and gave her a sly smile and I was really surprised to see how good it looked. God I can'...

Slut for All Pt. 06

by Knightofround on Sep 19, 2017
BDSM

"That's it baby! You are such an amazing cock sucker!" Anthony stands towering over me from my knees. Like a proper slut, I make sure to keep eye contact with my new master. I moan around the cock in my mouth as I bob up and down quickly. Anthony puts his hands on the back of head to grab my hair and stops me from moving up and down the amazing nine inch c...