Sissy Spanking Stories

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Owned by a Ghetto Bitch Pt. 03

by FantasizeAndRealize on Sep 12, 2017
Fetish

For the next few weeks things stayed pretty much the same with Sholanda. She would meet up with me about thrice a week at my house and demand at least four or five orgasms every time. She slowly grew more dominating and I was happy to let her have her way with me. Eating her creampie had become a regular activity that I had to do every time that I came in...

Tom and Friends Adventures

by Mobman1 on Oct 25, 2020
Exhibitionist & Voyeur

In the night of Falmon, we come to see over the house of the young characters of the Story.What's next? Lisa Emma Sori Paige Tom (sissy) Ethan (sissy) What's next? Lisa Emma Sori Paige Tom (sissy) Ethan (sissy)...

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Training of Mistress' New Sub Day 01

by naughtyboy082 on Sep 19, 2017
BDSM

As Mistress Sharon has requested, a written story... THE FIRST MEETING MISTRESS SHARON sends out a late night text that her new submissive has been waiting for anxiously all week long as he sought to prove his obedience and worthiness. "Congratulations, sub! You have successfully completed your probationary period...official training begins in the morning...

High School Dilemma Ch. 01

by LaurenWestley on Sep 15, 2017
Transsexuals & Crossdressers

I should have known better. It was such a stupid thing and it didn't even work out. Here I was graduating from High School. I had just turned eighteen and it was the last week of school. How could I have done it? Why did I take the chance? Kelly was probably the prettiest girl in school. Her hair was long and blond. Not much different then mine. Actually we...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...

Outed and Married Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

When I entered the room with their drinks on the tray I was carrying I thought I would be pleasing to my husband. I made sure that my skirt was properly adjusted the way he likes me to wear skirts in the house. He insists that my rear not be covered below my tight little hole, insists that he have instant access to it if he wants to use it for his pleasure....

Service Day 01: Sissy's Breakfast

by SissyHubbyD on Aug 7, 2019
Transgender & Crossdressers

His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today. Today is Service Day, and he couldn't be happier about it. He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

Spanking Night Ch. 06

by Angelscuck on Sep 14, 2017
BDSM

"On your knees slave!" Mistress Sheila commanded. I immediately fell to my knees in front of the beautiful dominatrix who was standing before me. "Who are you?" she asked. "Your sissy slave," I meekly replied. "That's right slave," she said as she hooked her thumbs into the waistband of her tight mini-skirt and slipped it down to her knees revealing her...