Mature Woman Spanking 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,...

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...

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...

Nightshade becomes Nightslut

by thorprovoni on Aug 18, 2017
Fetish

A beautiful and athletic woman is alone at the top of a building. She is dressed in a superhero uniform. The superhero uniform is black leather and very tight. The woman is blonde and has a black mask. The woman's name is Nightshade and is a famous superhero. The woman is voluptuous and very tempting though it is thirty-eight years. She has big tits with big...

Caught By A Strict Lady

by pussylove69 on Sep 25, 2017
BDSM

Acting persons: Sandra Blackmore (53); Po Ling (18) Po Ling was on an exchange programme of her school in Hong Kong and had the chance to spend a whole year in Bristol. She was a shy, young girl of 18. She was only 1,65 m in height and her body was all quite tender and slim. Her breasts were firm and round like small plates. They were not very big, but per...

Going Out With Mistress Jessica

by pussylove69 on Sep 17, 2017
BDSM

This is the next day following our first evening with Mistress Jessica. So read “Two Slaves for Mistress Jessica” first. What happened before: I had agreed to meet an online-friend for the first time on her 25th birthday and to please her as a willing sub together with a mature lady. It was quite late when we awoke the next day. Elisabeth and I kissed an...

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...

Lucky Jack Learns to Obey Ch. 05

by Sputnik57 on Sep 17, 2017
BDSM

When Jack opened his eyes, Bella was sitting on the side of the bed smiling. His recently spent cock was being nursed to a full erection again by Marie; her scent and the thought of being dominated by her and Bella had him ready to perform again. He had never really given any woman over 30 a second glance before, but would now have the same attitude for wome...

Fun in the Pool Ch. 02

by buttcheeks777 on Sep 18, 2017
Mature

This is a story that involves some forced sex, group sex, dirty sex, and also anal sex with mature women. If you're not interested in that please don't read it and then leave negative feedback. If you are interested, please leave me a message, I'd love to hear your naughty thoughts. It's also not meant to be a great piece of literary prose. It's meant as a f...

Adult Education

by caring elf on Sep 13, 2017
Fetish

(Authors' note: The following story is pure fantasy written solely for the readers' pleasure...enjoy) * * * As the head of a night time adult education program I have to deal with a number of issues including troublesome students. One student in particular was memorable. Ms. Lynn was enrolled in a number of courses that she didn't want to take but which...