Sissy Maid Spank Stories

37,458 results
Orientation
Length
Source
Infinite Scroll

Being a Sissy for Viv Ch. 02

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

After Viv's stimulation it took me a few moments to recover. By the time I looked around Viv was sat on the couch sipping at her almost empty wine glass. A slight smile on her lips and a satisfied look on her face. Our eyes met for a moment before hers wandered down to her pink lace fronted panties I was wearing. A wave of awareness swept over me as I sudde...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

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...

Turning into His Toy Ch.02

by vaultdweller111 on Sep 13, 2017
Transsexuals & Crossdressers

I couldn't believe what was happening. I am on a plane flying from my home state of Ohio to Los Angeles to meet my new owner. It started when I met him on a gay chat room and told him I wanted to become a feminized sissy slut. We talked and before I knew it he sent me tickets to fly to California. I left my home in the middle of the night and left my parents...

Making a Cuckold

by jessijazz66 on Sep 19, 2017
BDSM

Brandi spoke nervously to her friend Jessica before she hung up the phone, "you're sure this will work?" Jessica understood her friend's fears, ever since they had begun discussing this plan of action. Jessica knew that Brandi was just starting to explore the depths of female dominance, and she knew that Brandi was worried about how her boyfriend, Brian, wo...

Ginger the Living Sex Doll

by njcaptionlover on Sep 16, 2017
Transsexuals & Crossdressers

Growing up I've always felt like I was born the wrong sex. That I should have been a girl rather than a boy. However, living in a traditional family where I was made to suppress these feelings. The majority of my teens were spent trying to be boy and not the girl I wanted to be. After turning 18 years old, I moved out of my parents' house and decided to li...

Lessons: First Time

by InYo on Sep 13, 2017
Fetish

I found her name in the back of a local swingers newspaper, in small print, at the bottom of a column. "Mistress Jade, Private training sessions, Become the man I want you to be." I clipped the ad and carried it around in my wallet for almost a month before I got the courage to call. A formal sounding older woman, who told me that the Mistress was busy with...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

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...

Aunty's Toys Ch. 01

by novelcriss on Aug 21, 2018
Fetish

Simon rang the door bell, prompt at 2 pm, somewhere between nervous and excited and wondered quite how he had reached this point. He had met Sally in, of all places, a crowded cafe at King's Cross when all the trains were late. She'd pulled up a stool next to him , asked if it was okay to sit and started chatting. She was so easy to talk to, middle aged, n...