Sissy Maid Stories

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Infinite Scroll

Appointment by Card Only Ch. 06

by Sputnik57 on Sep 17, 2017
BDSM

His landlord was not best pleased when Bruce announced his immediate departure, but was happy to hand him a bill requesting three months rent in lieu of his vacation without notice. He packed his laptop and the few items of decent clothing and sparse possessions into a sports bag and slung it into his car, then drove back to the house, his mind racing; he co...

Girl's Night Pt. 04

by DifferentBreed on Sep 14, 2017
Fetish

"You want to cum too, don't you bitch?" Sophie said. "But pleasure is only reserved for Mistresses and Dommes. Not sissy whores like you." Sophie looked down at him, grinning evilly, turned on by the lips descending her body and the sight of him kneeling there in sexual servitude and agony. She let her hand fall lightly on the back of Jenny's head as she fel...

Recruiting of a Sissy Maid Ch. 10

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Ten: Changes Continue for Chantel as Her Relationship with Carl Grows. Awake and having a great breakfast superbly made by Carl, Chantel enjoys her morning with him. He has her in one of his robes as they talk about things and their future together. After breakfast Carl says, "Put on a pair of my jeans with your white satin blouse, you can wear yo...

From Husband to Man's Sissy Wife Ch. 03

by Pantypansy on Jul 15, 2019
Transgender & Crossdressers

'So how was it, sweetie,' Hamish asked me as I opened the door. I was still shivering with desire from licking up my wife's lover's cum off her huge, oiled tits in 'their' bedroom downstairs (actually my marital bed).. I felt a sudden wave of emotion, after being so overcome with desire to watch my wife's lover come all over her. I had helped him by pushing...

Sexy

by SweetOblivion on Sep 16, 2017
Transsexuals & Crossdressers

"Hi sexy," he grinned impishly out at her, blinking his eyes to adjust them to the bright sun, as he opened the front door to greet her. "Is Dora...?" She began and then did a double take: "What do you look like, Marcus?" "Don't you love the ice blue?" Lindsey looked the young man up and down and, smiled, despite the initial shock. He was wearing a pale...

Recruiting of a Sissy Maid Ch. 08

by Sissy_Chantel on Oct 15, 2017
Transsexuals & Crossdressers

Chapter Eight: Chantel Moves Up at The Jade Maid Club. Six months now into Chantel's new life as a t-girl maid and slut at The Jade Maid Club has her progressing well. Hormones have aided in her feminization and she has proven to be a very good and docile enslaved sissy girl. Not perfect but impressive to see that Mr. Luftgrin, Mr. Jenkins in reviewing all...

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...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...

Caught

by ImpureChastity on Sep 13, 2017
Transsexuals & Crossdressers

I had been planning my downfall for weeks. Putting together the right outfit, working out the best place to be in the house, practicing my lines to appear convincingly surprised, everything was lined up perfectly. For a few months the relationship between me and my fiancé, Janice, had been just a little kinky. She had cottoned on to my submissive tendencies...

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...