Sissy Girl Stories

198,414 results
Orientation
Length
Source
Infinite Scroll

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

Neighbourhood Terror to Sissy Pt. 14

by Fibaro on Dec 2, 2019
Transgender & Crossdressers

Chapter 16 The two women enjoyed looking at Mark as he had to swallow all the white goo he had just squirted. Just as if the way he had achieved his orgasm wasn't bad enough yet? This only added insult to injury. It was Linda who suddenly broke the silence. "It is good you have come here to learn how to handle a sissy and it is my pleasure guiding you int...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

High School Dilemma Ch. 03

by LaurenWestley on Sep 15, 2017
Transsexuals & Crossdressers

(Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. I suggest those who don't like this kind of story not to read on. I know I make both grammatical and punctuation mistakes. I promise all of you I will try harder every time to get it right. Hey what else can a sub...

Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

My Submission to a Real Man

by gbr2004 on Dec 28, 2017
BDSM

This is total fantasy and would never do many of the things I discuss. If not into really kinky play, humiliation, verbal abuse, and forced fem and strong discipline, please pass on this story. For all you other submissive boy and dominant men hope you like my fantasies. ***** MY SUBMISSION TO A REAL MAN It was our first actual meeting. We had emailed bac...

Panty Posers Ch. 06

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

We entered our building and bumped into our downstairs neighbor Jerry. He was taking his trashcan back to his apartment. He set it down at the landing and gave us each a good look. He wasn't at all phased by our appearances. "Little early for Halloween, isn't it...boys?" he asked. We both were fully aware Jerry knew we were sissies. It was fairly obvious...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...