Training Sissy Stories

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Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

Pantsed Again

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

Lori ensured I was always appropriately dressed by picking out my sissy girlie things for me everyday; school girl, cotton, bikini panties with support to make my bum round, my padded training bra with built-in forms and knee socks; all white. Lori selected high heeled Mary Janes for me to wear around the house. When I was allowed out or had to go to work,...

A Girl And Her Sissy

by TollWard on Sep 18, 2017
Transsexuals & Crossdressers

Life is good. Life is really, really good. As I write this I'm sipping on a very expensive wine and wearing a very expensive dress while sitting in my very expensive apartment. I no longer work, having not needed to earn my own income for little more than a year now. That probably leads you to wonder how I pay for all my nice things. Well while I enjoy my lu...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...

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...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

Darling Nikki Pt. 02

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1 - The Morning After The next day, Nick awoke thinking it was just a really messed up dream. When he got out of bed and found that Samantha had unlocked and removed the dress, panties and shoes, but everything else was still on, he was pulled right back to reality. He looked in the mirror on his wall and saw that he was standing there in a very tig...

Balls On The Line In City Trading Ch. 02

by gomorrah on Sep 16, 2017
Transsexuals & Crossdressers

So with much apprehension, I turned the handle on the blue door. Stepping through, I struggled to adjust my eyes to the brilliantly white light streaming out of the other side. I raised my hand to try and filter the glare, and heard the door click shut behind me, and then double-click again. Instinctively, I tried for the handle on my side, but there was no...

Trapped as a sissy in a fanasy world.

by Duke Montefort on Nov 14, 2019
Fetish

Eugene has an obsession with video games almost shutting out his friends and family. Feeling they have no choice the family begs a videogame company to help them bond with him. The company agrees they test the family can beta test the game, and bond. They even promised that he could not come out until he had properly bonded with each family member seprately....

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