Free Shemale Stories

bi to sissy caught and turned

It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... read more

redthongthong August 2, 2022 100%

Rubber Ball

Hi All, This is my first ever real attempt at writting a story to post. It is ALL fiction, and most of it is just made up and what I think it would be like but never experianced. I was inspired to write this after looking at some pics from a friend. I have an overactive imagination which is proba... read more

shemale lover August 18, 2012 100%

cindy and r.sissy

I meet cindy online we organized to meet at a motel l got there first l got ready l put on my black latex half cat suit my black with red trim latex blouse l put on my red platform thigh boots l was starting to get a hard cock but lhad makeup to put on did that and a great long shoulder length blond... read more

r.sissy October 5, 2017 54%

A Sissy (S)exercise Fantasy

I stopped going to the gym about six months ago, when money got tight and I had to find ways to reduce my expenses. I usually don't get to the gym much in the spring or summer months anyway, so it was an easy expense to cut. I hate going into the office all sweaty, so I avoid working out in the morn... read more

shemale lover June 14, 2012 90%

Sissy's Baby Ch 1-4

A CHILD FOR SISSY BY MISTRESS DIEDRE DAMON A submissive sissy whore who misses her “period” is forced to carry a baby for a full term as punishment for the transgression. CHAPTER ONE: SISSY’S BIG MISTAKE A friend of mine had a live in sissy awhile back who was required to... read more

deedamon October 10, 2012 65%

From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved t... read more

shemale lover September 12, 2012 75%

UN EXERCICE SISSY (S) FANTASY ⚧️ ⚧️

J'ai arrêté d'aller à la gym il y a environ six mois, quand l'argent s'est serré et que j'ai dû trouver des moyens de réduire mes dépenses. De toute façon, je ne vais généralement pas beaucoup au gymnase au printemps ou en été, donc c'était une dépense facile à réduire. Je déteste entrer au bureau e... read more

Femboy 2021 May 2, 2023 50%

My Journey and The Pleasure of Fucking a TG/CD/Sissy

I used to think I was crazy. Maybe a part of me thinks I still am. Whatever the case, I'm not going to stop, and I'm going to continue what I'm doing for a very long time. Why? Because it feels so damn good. As I sat there while my latest little Sissy slut was servicing my thick an... read more

JOAT April 12, 2018 78%

The Making of A Sissy Part 12

Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as... read more

shemale lover May 31, 2012 83%

The first day of a sissy bitch

She's preparing to become a sissy slut First long and extensive showering then a total shave and she started to turn into the femme of a sissy slut. Naked in front of the mirror, she applied the foundation and spread it evenly across all areas of her face and neck. Next she slipped into her b... read more

sqimyetxräa52 December 19, 2017 60%

Proud To Be A Sissy Chapter 8

I woke up to hear daddy lightly snoring and in my sleep I had draped a leg over him so that my body was almost covering him. I giggled to myself realizing that even in my sleep the sissy slut in me reached to grasp his flaccid penis. Then I curled closer up against daddy and contemplated about how m... read more

shemale lover December 24, 2012 95%

Sissy Maddie's New Apartment Gangbang

I’d just moved into the big city. Me on my own in a cheap apartment block. The flat was nothing special by any means, and the room next to mine seemed to be noisy with parties. But I was glad to be on my own. I had almost finished unpacking my belongings when I came across my stash of female clothi... read more

sissymaddiex September 25, 2020 93%

Becoming Sissy

I remember my first true and sober gay sexual encounter. The guy from the party that was my first BJ and first penetration was one of the closest friends of the group. He bought a house up north and 3 of the girls and me went to his house to help paint and work on some things. This was about a mo... read more

xspeeny April 28, 2023 100%

Kayla is back and horny AF!!! Needs boipussy filled!!

This goes out to all my friends and subscribers...Sry to u all I Haven't posted in a while. Life got busy. But I'm back and horny and craving cock pounding my pussy and in my mouth! I wanna taste ur delicious cum!! Feed me daddy! I want ur big hard cock inside my sexy little sissy pussy wh... read more

Sissy Kayla June 27, 2017 46%

A Picture Perfect Sissy

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... read more

shemale lover May 27, 2012 87%

Black Man's White Sissy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my ... read more

shemale lover July 3, 2012 72%

2nd date with Latina Sissy Destiny

So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... read more

AllenB April 5, 2022 100%

BBC Takes sissy slut and uses her properly.

I'm a dominate alpha man who loves to humiliate sissy girls and punish them when they aren't perfect submissive sluts. I want them to worship my big black cock and beg me to let them lick it then grab them by their hair and shove my cock deep inside their throat, making them gag. I like filling siss... read more

lemondropz November 27, 2023 66%

Diary of a Sissy

Dear Diary, This time I fucked it up for good... I am completely lost in the viscous cycle of sissy hypnosis. My beta girl nature was starving to be controlled by superior men. The desire to be owned was so intense that made me do something I have never done before in my whole life.. this time I ... read more

KittyHot December 21, 2023 100%

The Making of A Sissy Part 7

As Sandy pulled into the drive of Aunt Jane’ s house, Tara turned from the front passenger seat and eyed the forlorn looking sissy seated centrally between her two sisters with some satisfaction. “It’s a good thing your friend can stay with you tonight to console you; of course ... read more

shemale lover May 27, 2012 57%