Sissy Spanking Stories

28,144 results
Orientation
Length
Source
Infinite Scroll

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

Stevie's Journey

by gbr2004 on Oct 7, 2019
Fetish

I remember being so excited landing a position as a legal assistant at such a good law firm. My boss Mike Maddox seemed to be a great guy and I was looking forward to learning from him. I never imagined what it would be that I would learn from him. This job has changed so much and I can't even decide if I regret what has happened or if it was where my life w...

The Awakening of a Sissy Pt. 02

by sissyjolie4u on Jan 6, 2020
Transgender & Crossdressers

As I drove away from her home, my mind was racing with thoughts of what had just happened earlier. The sweet odor of her pussy juices filled my nostrils. I could still taste her in my mouth. I was so overcome by the experience, I barely kept my mind on the road. Once I arrived home, I quickly stripped down to my panties. I had to see what they looked like on...

Classroom suprise

by william125 on Mar 10, 2015
Transsexual

A recently qualified teacher, today is your first day at Tower sixth form college. You stand at 6' 2" and keep your self in good shape. On your way in this morning you saw a group of girls giggling and looking at you. Obviously talking about the new teacher. The bell rings and a little nervous you welcome in your 18 and 19 year old students. Note to r...

Open in Reader

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Spanking Night Ch. 08

by Angelscuck on Sep 14, 2017
BDSM

As I held Master Dan's cock steady for my wife to sit down on I noticed her eyes were staring directly into mine. She had an amused smile as she licked her lips. Her labia were moist and dripping as they parted to accept the head of his cock. Her breathing quickened and a soft moan escaped her lips. Her eyes seemed glazed over and half shut as his huge m...

Sissy Sisters

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

This was the letter I wrote to an older Sissy in an attempt to convince Her to accept me as Her littler sister and use me. * Stop, You make me blush. I too luv wearing feminine luxurious things. I believe now I need to wear sensuous feminine things under the direction of some one else. Could that possibly be You. Please. You would treat me like a little...

Cruise Ship Cuckold Ch. 07

by Angelscuck on Sep 14, 2017
Novels and Novellas

Eve continued to tease and chide me as I watched my sweet bride being groped and felt up by the captain as they danced at the Boathouse Lounge. I could hear other people laugh and make crude remarks, as Angel and Adam publically humiliated me with their show of intimacy. Eve said, "Look how beautifully they move together, I'll bet you wish you could dance...

Man Disciplines Sissy Ch. 05

by LanaBehave on Oct 21, 2019
Transgender & Crossdressers

This is a fantasy. Scenes in reality should be built on consent, safety, and communication. No character in this story is less than 21 years of age. * I was jittery all the next day. I hadn't slept well, at first, either. As I lay in bed thinking about Daddy, the things he said, what we had done, alone in the locker room, I squirmed, tossing and turning....