Sissy Surgery Stories

14,633 results
Orientation
Length
Source
Infinite Scroll

Eve Quest

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,000.00 and an eighteen percent interest in an insurance company...

Amazon Sissy Jock

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

All parties involved are over 18 years of age. *** It started me going to a party. Now that's not unusual because I'm popular, I've always been popular like ever since junior high. I shot up like a weed getting tall and my dad worked me out while I was going through my growth spurts and had me in lots of stuff like to round me out before I got into footba...

Halloween Pool Party Pt. 05

by sissymissyct on Sep 14, 2017
Fetish

We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about m...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

I Become Wendy's "Wife"

by Quietoldie on Sep 16, 2017
Transsexuals & Crossdressers

After the amazing weekend I thought things would settle back down to our usual routine. She was out working all day so I had to wait until the next weekend to go shopping with Wendy for my new wardrobe. In the meantime she allowed me to wear any of her clothes that I liked but most were a bit too big for me and Wendy had only a few dresses and skirts to choo...

Coming Home, Coming Out Pt. 10

by EiryCGar on Jul 6, 2020
BDSM

Author's note: This chapter marks the end of this series, which seems to have run its course. I am grateful to my readers who have commented on my story. As ever, I should remind them that this is a work of total fiction. All characters are at least 18 years of age, and everyone who participates in any of the sexual practices described does so consensually....

Twelve Years

by Imoverit41 on Mar 17, 2020
Loving Wives

Twelve years had passed and I still can't get past her or our combined families betrayal. Trust! No bloody way! There is no forgiveness from me. No accept it, get over it and move on like they wanted. I knew it would take time, but I'd have my day! I've worked hard for the last twelve years after our divorce. I have lived like an impoverished monk to save e...

Becoming Marc's Sissy

by grizzley123 on Jun 19, 2018
Transsexuals & Crossdressers

This is a story with themes some may not like. If that is you, read it, don't read it, your call. But if you are going to comment, keep in mind that no one required you to read it, and no one requires you to like the themes. Writing nasty comments only makes you look foolish. For others, I would love to hear your comments. And I hope you enjoy the story....

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

The Doll's House

by Velvety on Sep 14, 2017
BDSM

He stopped the car on a deserted country road, calmly turned the ignition off, then turned to look at her. His eyes trawled over her. She was wringing wet, and her dress clung to her skin, clearly outlining the shape of her slim, shivering thighs. Push-starting a car in the dead of night was not her idea of fun. 'I'm cold,' Sissy said, wrapping her arms aro...