Sissy Shemale Stories

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Slow Descent into Sissy-Hood... Ch. 02

by Slipperylock on May 11, 2020
Transgender & Crossdressers

I started pretty slow. I'd wear it for at first hours, then a day, and then finally overnight. That one had been the hardest, no pun intended. I would wake up multiple times a night, locked in sweet torture between the inevitably erotic thoughts in my head and the bittersweet tightness between my legs. The first time I'd tried it, I'd made it till 2 a.m. bef...

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

Dr. Landry and Nurse Lisa

by newfield1981 on Apr 17, 2018
Transsexuals & Crossdressers

This story is a spin-off from the "Neighbors sissy son" series. Though it stands alone, it will eventually cross over with NSS. SPOILER This series falls in the transsexual crossdresser category for the first story. There will be very little in the way of men participating in gay sex. This series will sometimes revisit this subject. After that it will be ba...

Compromised Pt. 03

by HorribleHenry on Oct 5, 2020
Transgender & Crossdressers

COMPROMISED PART THREE CHAPTER EIGHT Park Green Private Hospital specialised, and probably still does, in mending wealthy people, particularly those with kinks. There was nothing that people did to themselves, or each other, that fazed the dedicated staff of the hospital. A patient with a torn arsehole caused by anal sex was very low down on their list of...

Making Francesca Ch. 07

by Spango on Sep 16, 2017
Transsexuals & Crossdressers

After the glorious sex with Mistress Celia, Frank spent the rest of that day doing housework with Justin. His mind was all awhirl. To all outside appearances, Mistress Celia seemed to be the beautiful woman he had lusted after when she was a waitress at his favorite bar, but now he knew that underneath her clothes she hid a wonderful piece of man-meat. His n...

The Virgin Tranny & the Bride Ch. 09

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Dear Friends, A MESSAGE FIRST. I am submitting a further chapter in the series The Virgin Tranny and the Bride. However I am concerned that I may be doing something wrong at this stage which is preventing these articles from registering in the Top 500 chart despite a number of votes and a high rating. Perhaps it is me, or perhaps there is a technical probl...

A Shemale Vacation Ch. 01

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for me, wild sex was something I wasn't exactly familiar with. I was s...

Jock Princess Ch. 01

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

I'm Alex. And I got to admit that life's been kinda good. Cake actually. I'm a jock, left winger hockey player and all through high school it's done me pretty well. My family owns a good business in town actually a few of them. Grand dad on mom's side had a dairy farm and actually did okay, Mom's a registered nurse, my dad owns a big hardware store and ad...

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...