Sissy Piss Stories

29,113 results
Orientation
Length
Source
Infinite Scroll

Aficionado Gets in Trouble Ch. 04

by His_fag_wife on Mar 17, 2020
Transgender & Crossdressers

Taryn told me to sit down, which I did with difficulty as I was only just getting used to breathing with the corset on. She knelt down in front of me, but this time it had no hint of submission. She was plainly completely in charge of me at this moment. She took the first shoe off, and prepared the first stocking, rolling it over her thumbs. I put my foot o...

Jennifer Monroe & the Ladies Ch. 03

by corduroysissy on Jan 31, 2018
Transsexuals & Crossdressers

Debbie gave Miss Jennifer's boot one last kiss, took a few seconds to straighten out his dress, then walked over and knelt submissively next to Patty in front of Miss Marsha. She let Patricia continue to suck her dick and lit a cigarette, she didn't even look at him, in fact she totally ignored him for several minutes. She did however blow smoke in his face...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

Card Shark

by Turned on Sep 14, 2017
Loving Wives

I returned to my hotel room from a poker tournament and realized I'd forgotten my key, so I knocked. After a few moments the door swung open and my pretty, young asian wife was waiting for me behind it. "Hi honey," she said, giving me a very strange look, "How did you do in your poker tournament?" "I did ok. Third place. I made a little money," I said, s...

The Making of a White Sissy Slut

by AfroerotiK on Sep 18, 2017
Transsexuals & Crossdressers

When he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by sayi...

Mark to Mary Ch. 02

by trannyslut on Sep 16, 2017
Transsexuals & Crossdressers

I decided to just go down the list in its order. The first thing was to wash the dishes so I went into the kitchen and saw them sitting in the sink. It was not very many dishes and I was done very quickly. Sweep and mop the kitchen and bathroom was next, that will not be hard. I went to the broom closet where Mistress Amanda said supplies would be and I got...

Made Over Ch. 03

by gbr2004 on Sep 15, 2017
Fetish

This story involves forced cross dressing, gay sex and bdsm scenes. Don't read if not into these scenes. * I had met a man in my apartment building and he had invited me to join him at a club he goes to in LA. I was a naive boy from Kansas attending USC and I had no idea what I was getting into. The club ended up being a gay leather bar and before the nigh...

Slave History

by timeagain93 on Sep 17, 2017
BDSM

These are my recollections of my slave history. Four Goddesses have dominated me. I'm writing this to let my current Mistress understand my story. Mistress D read "Variations" magazine and spanked me with a wooden spoon. She tied me naked to a chair and blindfolded me. She made me sit there in silence. I was wearing her panties while talking on the phone w...

Tales of Sub Asian Sissy Ch. 03

by subASIANsissyJADE on Apr 23, 2019
Transgender & Crossdressers

(Thanks so much for taking the time to read my story! This is just my third post and I'd love to hear any feedback, questions or comments. Also, please feel free to contact me if you just want to chat with a very submissive asian sissy. XXX, jade) *** While it's only about fifteen minutes away, the drive back to my apartment seemed to take forever. I had t...

First Time Meeting Master Gene

by sissysubTiffany on May 29, 2018
Transsexuals & Crossdressers

First off a little about myself as I am bi having been with both sexes, but lately only men. I have always it seems to have been attracted to a male cock, but not to men as weird as that may sound. For awhile now I have been going to an XXX Theater Book Store in a town about 45 minutes from me hoping no one would know me there sucking cocks and getting mine...