Sissy Tattoo Stories

17,774 results
Orientation
Length
Source
Infinite Scroll

New Gurl in Town Pt. 01

by GavinIsaNuisance on Jul 6, 2020
Transgender & Crossdressers

This work is entirely fictitious. Any similarities to actual persons living or dead is purely coincidental and entirely unintentional. All characters portrayed in a naked/sexual nature are 18 and up. *** The city of Los Angeles, California. A place once regarded as the focal point for entertainment and movie stardom now reduced to an over-taxed, grimy, dru...

The Society Ch. 04

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorr...

Shear & Piercing Love

by shear playzur on Sep 15, 2017
Fetish

They had been dating nearly two months, Jake, a handsome tattoo and body piercing artist, and Mattye the prim and proper advertising exec. They couldn't have been more different, yet, they possessed an explosive and riveting passion. If ever there were two total opposites who meshed so perfectly, it was Jake and Mattye. Jake had dreamed of getting his hands,...

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...

A Changed Man Ch. 1

by sub5000 on Sep 12, 2017
Fetish

Part One - Beginnings It had to happen one day I guess. I had such a collection of porn on my hard drive, that it was inevitable that one day my wife would stumble across it. It wouldn't have been so bad if it was average, everyday porn, but my collection consisted of more 'specialist' images. There were pictures of shemales with big hard cocks dressed in s...

My Sissification Ch. 02

by sissy171 on Aug 31, 2020
BDSM

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation. My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon...

Vacation Expectation

by IPleaseYouTease on Oct 6, 2020
Fetish

The wife's side of a conversation with her husband as she gets packed to go on a 10-day vacation with her lover and leave him behind. ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ "Okay Dearie. Up on the bed. It's almost time for me to leave. I have a plane to catch. Don't you worry. I know that once you're done binding your hands and fee...

Truth or Dare Takes a Turn Pt. 04

by Cutiepie183 on Sep 28, 2020
Transgender & Crossdressers

The next morning I wake up at around 6 and find a note on my chair and an outfit on the floor in front of me, I also notice my gag has been taken out. It hasn't fallen out though because it's nowhere around me. The note on the chair simply reads. 'Big day today, get dressed, cook breakfast then wake me up with some service with a smile.' Not entirely sure wh...

Jack and Jill Pt. 05: Thailand

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

The decision to move to Thailand was a big one, but Jill was glad that they had done it. Here they could live out all of their sexual fantasies in total freedom, without judgement or harassment. She had completed Jack's feminisation by insisting he had breast implants when they arrived, but that was months ago and they were all healed now. She loved to grab...

Mistress Cruel Love Ch. 02

by ChainedToAKeyboard on Sep 28, 2020
BDSM

Mistress Cruel Love Chapter 2 -- Total Commitment "Pookie, go fetch me a bag of apples." "Apples? What kind of apples?" "You know the kind. The good kind! Empire apples. None of those tasteless Cortland's or sour Granny Smiths. Good Empire apples from New York." "Baby, I don't even like apples." "Too bad, you're going to starting eating them. You're no...