Shemale Mistress Stories

27,874 results
Orientation
Length
Source
Infinite Scroll

Joanna Jax

by Saffyre on May 13, 2020
Transgender & Crossdressers

This story is about a man, Aaron, visiting a transsexual pornstar who he has adored for many years. There are only two characters and when writing the story I imagined them as both being forty years old. ****************************** He stood hesitantly at the door of the apartment and, even at this late stage, wondered whether he could go through with i...

Trailer Trash Tranny Ch. 07

by Travel_by_day on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 07: Odyssey Jeannie boarded the bus in Omaha, excited to be finally moving to New York City and starting her dream. In her hand, she was clutching her tickets to New York and a catalogue from a school in New York that offered a fashion design degree. She could feel her heart beating quickly in her newly enhanced chest. Unlike the clothes which Jean...

Garnet: a Story of Submission Ch. 03

by frillypanty on Sep 16, 2017
Transsexuals & Crossdressers

3. A fashion parade and the appointment of a fourth Mistress The image of my three internet mistresses came up true to time, immediately after I'd logged on at 1.15am on the Sunday morning following my second shopping expedition to extend my feminine wardrobe – as directed by them. Like me all three were clad in lace trimmed and panelled underwear – bra',...

SheMale Sirens Ch. 04

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

I never thought I would wind up in what many would have thought was just some fantasy world. I would have considered myself one of those people who thought it was just someone's fantasy. I happened to stumble upon Anthemusa by total accident, which I would later learn was really how the majority of the men on the Island came across it. I had been heading t...

The Transformation of Ms. K

by parkerkwon on Feb 25, 2019
Transgender & Crossdressers

By day I'm an average Korean guy, a bit on the fat side, my whole life I haven't been very attractive to women. I'm very timid and shy as a boy, very much a beta. I never even had sex until after college and my dating life has always been pathetic. I've always had a bit of a tight rubber and latex fetish, as I became older I began buying some pieces of lat...

Making Dreams Come True

by Writer345 on Jan 7, 2018
Transsexuals & Crossdressers

Just a few points: firstly this story is written in British-English so the spelling and grammar may well differ from that of the particular dialect in which you were educated. Secondly it contains descriptions of shemale-shemale sex and anal sex... If these are not to your taste then read no further. Thirdly it is a story and nothing here is real, it's al...

Size Matters

by idahoboy on May 5, 2015
Science Fiction

Adam rushed into his room after school. His dick was already straining in his pants. It seemed like it was getting harder and harder to make it through a day of school without jerking off. The young man had taken to blowing a load in the toilet at lunch. Today, he couldn't find an empty stall before the bell rang. The boy dropped his pants wrapped his hand a...

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Sex Toys and Websites

by Equinella on Sep 14, 2017
Fetish

I didn't tell my girlfriend that I was moving out; just packed my stuff and disappeared while she was at work. There was no need to say anything. After weeks of sleeping on the couch she wasn't going to miss me. My new apartment was furnished so the move mostly involved traipsing boxes up the stairs and finding the right shelf, cupboard or drawer for their...

Code Name Tequila Ch. 03

by Travel_by_day on Sep 13, 2017
Transsexuals & Crossdressers

The same day that Ria Ortega boarded a plane to head to Argentina, Jarvis Cleethorpe was rushing down a hall in the Langley, Virginia headquarters of the Central Intelligence Agency. He had a meeting with the man known simply as "Black Oak," the man who was in charge of a number of projects at the CIA, including the one to identify and eliminate the South Am...

Sissy Girl Forever Pt. 02

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

No going back now. Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses, soft pullovers and ladies p...