Sissy Tattoo Stories

17,774 results
Orientation
Length
Source
Infinite Scroll

Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Amy Moonlight's Stinky Knickers

by wordyone on Jul 14, 2020
Fetish

I had the panty time of my life. I was assigned the task of photographing the Edinburgh Festival for a fashion magazine, and my accommodation had been sorted out for me by a friend. I climbed three flights of stone tenement steps to a black door numbered twenty-three and rang the bell. The door was opened by a beautiful creature, little more than five feet s...

Memorial Day

by 9volt on Jun 9, 2020
Fetish

Memorial Day Weekend On Saturday of Memorial Day weekend I got up and went for a run. When I got back, Brandi was finishing up with breakfast for the kids and her parents were there to take the kids for the weekend to the family cabin on the lake. I grabbed a quick bite and headed to the shower after kissing the kids goodbye and wishing my in laws well. I w...

Sissy Girl Forever Pt. 03

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

Sissygirl forever continued. Sara stood there laughing at me as Mistress explained how things would be for the near future. She told Miss Andrea that if I wished she could fill them in with the red right now if I wanted. But Mistress said no. She was looking forward to my rushing off to work at times forgetting to polish them. Or eating out with friends and...

A Weekend Away Ch. 02

by SluttyChrissy on Sep 14, 2020
Transgender & Crossdressers

Author's Note: Thanks for all the kind feedback & comments on chapter 01. This chapter does a lot to set up the rest of the story, so there isn't a ton of sex. Please hang in there with me and there will be much more sex in the chapters 3-?? I hope this one is sexy enough to keep you interested! ---------------------------------------- I'm not sure how lon...

28 Days

by tinywhiteboi on Dec 2, 2019
Interracial Love

28 days. That's 4 weeks since my last orgasm. And I was so horny, to the point of constant distraction. It was all I could think about. My locked little penis was dripping into my panties, and my little balls were swollen. Six weeks ago my wife, Angie, caught me jerking off to interracial cuckold porn, a video with the cuck locked in chastity. She'd come ho...

A Sissy's Wish List

by slutty_lucy on Sep 16, 2017
Transsexuals & Crossdressers

Boys, boys, boys. First off, let me tell you that I have a butt plug shoved so deep in my little tranny pussy right now. That might help to explain how depraved I might sound. I really need some cock in my ass right now! I am sitting here stroking my tiny little tranny clit right now thinking of how to best share my desires. I want to be a perfect little slu...

The Sexy Cuckold Couple Pt. 04

by cuckcpl4play on Sep 19, 2017
Fetish

Miss Jenny and I entered the home and there was a sense of relief to be in our own house and only then did we communicate. I asked simply...did you enjoy yourself and Miss Jenny smiled broadly...his cock is so huge and he felt so amazing inside me...the experiences we are all going to share will be amazing slave and she hung on that last word for a bit. It w...