Sissy Machine Stories

38,061 results
Orientation
Length
Source
Infinite Scroll

Mistress Kate Pt. 03

by corduroysissy on Mar 14, 2018
Transsexuals & Crossdressers

Jordan was in a daze. He was dressed in full drag with his face made up pretty and the feeling of sissy submission was wonderful, he hadn't felt it in a long time. Everything he'd experienced since ringing Kate's doorbell excited him tremendously, and even though her demand that he be a cock whore for all her slaves was disconcerting, he felt thrilled to be...

Cloned!

by Wholemanz on Sep 14, 2017
Sci-Fi & Fantasy

WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence, bad words, and strange ideas. It has only the strange things that dribble from my head. If you are not old enough, mature enough, open minded enough, and especially not smart enough to stop reading should you find yourself becoming offended viewing such a story, don't! I hereby gran...

Brianna Spends Time with Daddy

by Sissy_Sammi_ on Dec 31, 2017
Transsexuals & Crossdressers

It was Tuesday now, as Brian woke up in his bed at seven in the morning to the sound of his ringing alarm clock. It was time for him to go to school. As he rolled out of his bed and began to do his regular morning routine in preparation for school, he couldn't get his mind off of yesterday. As he passed the mirror in his bathroom he saw back to Brianna stand...

Older Man Watching Ch. 2

by Misieyes on Aug 30, 2017
Exhibitionist & Voyeur

Ken woke up the next morning at 5 A. M. and thought about what he saw the real estate sales man and Sissy doing. His cock started to swell. He wondered if she was up and maybe taking a shower. He grabbed his binoculars and looked through her open window. There she was asleep, naked and with nothing over her. How lovely she was laying there, her breasts so...

Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...

Letter from Carker's Rents

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- Since I taped this, I also have enslaved my brother-in-law Santiago and his basketball team. So I have real progress going on here in Carker's Rents! Love, Sugar Perez "Sugar, I am having a devil of a time getting these thorns out of my, um--" "Your diaper. Say it, Esteban." "Don't--don't you think it was punishment enough for me to...

I Adore Crossdressers Pt. 02

by Ab9095 on Nov 26, 2018
Transgender & Crossdressers

Day One - Part Two I put on a video and I moved a big mirror so she could see herself and watch the TV at the same time. I sat back in the chair and watched. She was a little slow but as she watched those big dicks she got hot. She was playing with that nice cock, stroking it, spitting on her hand and stroking some more. She pulls her panties down and reall...

Be My Baby

by Tomsparty on Sep 16, 2017
Fetish

Naked, you stand before her. 'Come to Mummy,' she coaxes. 'You called me and here I am. Take this step, why don't you?' She held out a pair of pretty white knickers towards you. 'These belong to you.' You stare back, unable to tear your gaze away from her warm, motherly face. Two eyebrows plucked to feminine arches; two bright blue eyes fix you in a hypnot...

Sister Mistress Ch. 15

by LilLindaMelons on Sep 19, 2017
Transsexuals & Crossdressers

Pulling back Kathy patted Jenny's still sore cheeks. "Catch ya later girlfriend." "MMMMM bye, you know I'm going to dream about you Mistress Katherine." "I hope so Baby." After watching Jenny disappear through the garage Kathy walked up the service steps and into her bedroom. She was eager to checkout the surveillance of her mothers' bedroom. Deborah ha...

Gloryhole First Timer

by SluttyChrissy on Oct 5, 2020
Transgender & Crossdressers

This is a true story of an experience I had a few years back. I hope you enjoy! It all started on a random Thursday on my lunch hour. I was feeling especially girly that day and I decided to make a detour to my favorite little adult bookstore/lingerie store. I walked in and slowly browsed around, looking at the lingerie and dresses, just enjoying the feel...