Caning My Sissy Husband Stories

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Owned by my Mother-in-Law Ch. 05

by Sputnik57 on Sep 13, 2017
BDSM

Further confident and severe looking women arrived, smiling and sneering at the gimp, and pointing at me contemptuously. My erection raged as I watched the superbly dominant Arabella stride positively toward the cellar door; her willing gimp, the once proud and dignified headmaster, on all fours with a tail swinging from his plug. The women laughed at him an...

Owned by my Mother-in-Law Ch. 06

by Sputnik57 on Sep 13, 2017
BDSM

I was overwhelmed as I emerged from the cellar door, leashed and on all fours; I was ready to beg and whine for relief as I viewed Blanche's magnificent buxom curves and folds flex in the latex; a 62 year old woman who had shown she owned me completely within a matter of hours. I willingly followed on all fours, hoping she would allow me full use of the Viag...

Appointment by Card Only Ch. 02

by Sputnik57 on Sep 17, 2017
BDSM

Madam Ruth was more than pleased with her days work as she descended to the bed and stroked the soft white body of the helpless sissy, Poppy mustering a whimper as the dominant Madam. Cupped the soft pink scrotum and gently worked the dainty cock to an erection; she was scared but the surreal situation along with the gentle warmth of the two females, combine...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Ultimate Sissy Weekend Ch. 04

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Susie is lying in the store supply closet next to Tinkerbell. It's six in the morning, and they've only just finished cleaning the entire supermarket. After changing each other into fresh diapers, and using the few left over to make pillows for them both, the two exhausted sissies lie side by side in the cramped supply closet. Tinkerbell's right hand, handcu...

Clara Bow's Academy for Ladies Ch. 03

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Pepper returned to the room and sat on her new bed as she unpacked her things; Marie helped her stow things in a wardrobe and chest of draws allocated to her. The blonde smirked at the new girl as she blew on the brunettes nails she'd just completed; she would enjoy painting Pepper's nails. Pepper bounced softly on the large double bed; the plug felt so nice...

Clara Bow's Academy for Ladies

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she'd also chose...

Mum & Sister Dress Him Up

by Quietoldie on Sep 14, 2017
Transsexuals & Crossdressers

"This is my rented flat you know Michelle. It's not fair you being like this with me. I've always been good to you haven't I?" Peter says. He often seems to get into situations like this. He was never very good about sticking up for himself. Now his girlfriend is chucking him out just because she found him dressing up in her things. "I just don't want to l...

Appointment by Card Only Ch. 07

by Sputnik57 on Jul 1, 2019
BDSM

Bruce was now under no illusion as to the ruthless level of cruelty the woman who had claimed him as her own, and her feminine associates, would go to in order to sate their sexual lust for the domination of masculinity, and their pleased indifference at the fate of Miriam's husband at the cocktail party he now observed on his knees in a corner, further emph...

Owned by my Mother-in-Law Ch. 16

by Sputnik57 on Sep 13, 2017
BDSM

As the morning of fourteenth day arrived, I cowered at Blanche's feet and kissed them again and again. In just two weeks the women had seized the element of my submissive nature and trained and broken my will completely. I was on the point of begging Blanche to allow me to see the noose again; I would rather have been despatched than go back to Cherie, her m...