Sissy Nephew Stories

10,440 results
Orientation
Length
Source
Infinite Scroll

High School Dilemma Ch. 04

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. However, I do know many parts of my stories will not appeal to all of you. I only wish there is enough to make each of you happy. To those who have given me constructive criticisms as well as those with praise tha...

Facing the Daddy

by Buildaworld on Sep 16, 2017
Transsexuals & Crossdressers

Awaking the next morning, I felt like I was in heaven. Gabrielle was snuggled up to my chest, her feminine arms wrapped tightly around mine. I stroked her cheek with my free hand and smile as she mumbled in her sleep, something about me and shampoo. I chuckle softly as I hear this before sliding my hand down her back and over her smooth ass. She moans sof...

Recruiting of a Sissy Maid Ch. 03

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Three: Training Done, Chantel is On Her Way. Waking up back in her cell, Chantel finds that her days being trained, orientated and broken off will here with the Burrows brothers are wrapping up. Mitch enters her cell and has her come back out and back into the house with him and Nate. Mitch says, "Well Chantel, time has come for us to part our ways...

The Whore Wife, Sissy CD Husband

by MILF4black on Jul 27, 2020
Transgender & Crossdressers

This story is completely fictional. All characters in the story are over eighteen. Prologue: The Whore wife, Sissy CD Husband "That's it, you little sissy whore, suck that cock." Jennifer told her husband as his head bobbed up and down on the strap on dildo Jennifer was wearing. Her husband, Patrick, lifted his head and the seven inch fake penis slid out...

Simply Friends

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

"Hey, Eli," the common law wife and mother of two spoke into her cell phone. She paused a moment then said, "We're around the corner for your place." Valencia Williams ended the call. She looked at her husband, Durrell, who was driving the cash rental car. It was a metallic white gold 2010 Volkswagen Passat station wagon. Durrell, at 34 years of age, was a...

Generation Z Pt. 02

by contactsteph77 on Sep 24, 2019
Transgender & Crossdressers

Hi Guys This is the second part of my Generation Z story. This story follows a young transvestite, this particular chapter is more world building, developing the character. There is a little dressing, and some male on male smut. Hopefully it is worth it in the end. * Chapter 3 - Market Day James A new world had opened up for James. It wasn’t long befor...

Auntie's Panties Ch. 03

by EasilyConfused on Sep 14, 2017
Transsexuals & Crossdressers

The air in the lounge was filled with both aromatic and visual sexual pleasures as Phoebe continued to enjoy the skill with which Anna ploughed her Mistress's slit with her tongue. Phoebe's hands were on Anna's head ensuring that the penetrations from the latest addition to her brood were deep and long. Anna made muffled sounds as she battled for air whilst...

Proud To Be A Sissy Ch. 05

by Kary_M on Sep 26, 2017
Transsexuals & Crossdressers

I awoke in almost total darkness, only a soft glow came into the hall from the kitchen. At first wondering where I was, my bed at home wasn't as soft as where someone, probably my new daddy had carried me after falling asleep on the floor. I shivered in delight remembering how my daddy had shared me with his two friends. It was wonderful having three very di...

Runt of the Litter

by grimbous on Oct 9, 2017
Transsexual

(This story involves a lot of humiliation of the main character, futa on male action, incest, and other fringe fetishes. If these aren't your thing turn back now. I also wanted to give credit and thanks to the artist Mafen for the above picture which helped inspire this story.) The hall is quiet. You were pretty sure nobody was at home. You creep carefully d...

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Miles's Conundrums Ch. 05

by justincbenedict on Sep 16, 2017
BDSM

It seemed like forever, standing in the corner. My dick still stung and my butt felt like ground beef. Gretchen seemed to have forgotten my existence. Staring into a corner is terribly boring, and I couldn't seem to entertain myself because I was in so much pain from the whipping. I assumed that Gretchen would eventually forgive me and invite me over for...