Sissy Training Literotic Stories

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Sissy Training Vol. 01

by depositdutchess on Nov 27, 2017
Fetish

Being feminine is taught. Correcting your nasty masculine behavior with feminine manners and class is what you need. Being a sissy is your new reality. I am going to make you the pretty little girl you have always dreamt of being. You need to be taught ho live your every day life properly. You can only dream of being as sexy, girly and attractive as a real w...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

Sissy Training Week 01: Induction

by Peggylea on Mar 17, 2020
First Time

Some years ago I was under the supervision of a Domme Mistress called Neve who organised for me to undertake a course in sissy training so I fully understood my role as a smalldick submissive. She found me a place on a 6 week sissy training course with a teacher called Mr Deal who was very experienced and had devised such a program. I was to meet Mr Deal a...

Sissy Training Week 02: Obedience

by Peggylea on Mar 17, 2020
First Time

Week 2 Obedience I arrived at Mr Deal's my Master for the second week of the sissy course. Nervously I knocked on the backdoor to be greeted again by Mistress Rhea. She took my coat and led me straight to the changing room where I stripped naked as last week. Mistress R led me into the kitchen area and told to wait for my Master. Then assistant Toby came...

Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

A Sissy Saga Ch. 15

by Snurge on Sep 15, 2017
Novels and Novellas

A fine day, thick and hot making Miriam Hancock's face dewy with sweat. She gazed at the house. Was this the place? She checked the card in her hand. No mistake. It was an unimposing Edwardian terrace house in a street of equally unimposing houses, narrow fronted, three stories high, the windows heavily draped. She went up a set of steps to a porticoed door...

A Sissy Saga Ch. 08

by Snurge on Sep 15, 2017
Novels and Novellas

In the gymnasium a practise was in progress. "One, and two, and three and four," Hardwick's voice brayed above the tinny jink, jink, jink of an elderly piano. Ten students arranged in a double row of five were dancing to the beat as he called it. It was part of Hardwick's routine. Groups of them came to him daily, either for dance, deportment or gymnastics...

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

A Very Public Sissy Adventure

by DivinaTellsAll on Jun 4, 2019
BDSM

At Madame Vega's instruction I had spent the last hour edging myself. This is not always an easy task for a sissy who is not allowed to stroke her clitty. The edging was primarily accomplished by the use of a vibrating wand inserted in my fuck hole, and an Hitachi wand that I could rub my clitty on, as I teased my fuck hole deep inside. I had been banned fro...

Mistress Joan Ch. 01: Punishment

by slutty_sissy_nikki on Mar 10, 2020
BDSM

BASED ON A TRUE STORY! All characters are over the age of 18. This is my first short story and I welcome constructive feedback. PRELUDE The cane cut through the air to deliver another mark onto my plump bum. I tried, unsuccessfully, not to flinch when I heard the wish sound of the cane travel through the air. Knowing it was coming was the worst part, or ra...