Free Shemale Stories

Extend Sissy

Extend pls! https://sissy.fun/sissy-bimbo-whre-mayatsarina-chained-up-big-butt-tranny-wth-toy-in-asshole/ , https://xxxposed.fun/prostitute-fucktoy-slave-bimbo-mayatsarina-for-rent-cheap/ , and also this https://xxxposed.fun/dumb-bimbo-whore-may... read more

MayaTsarina Bimbo March 14, 2024 20%

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%

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%

A Sissy's Reward

Every time he does this to me he drives me crazy, keeps me addicted to his hand. I feel my sissy-like penis strain to escape from between my legs. I'm very small, only about 3" when hard. I keep it tucked for him, hold it tight between my legs at all times...except for when he does what he's ab... read more

shemale lover June 19, 2012 62%

Humiliation & full outing

I'd been meeting 2 older men regularly for a few months when we started to talk of more 'humiliating use of me'. They soon arranged to meet me in a hotel in the next city across from where I was living at the time & I made my way across one night to meet up with them. Wh... read more

sissychloe September 2, 2016 100%

Sissy story and 1st meet humiliation

I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before tal... read more

shemale lover November 19, 2014 90%

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%

First Time Sissy Maid

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... read more

shemale lover October 27, 2012 70%

The Making of A Sissy Part 5

Bella washed away her tears and the various aromas of the night in her en-suite shower cubicle, shampooing her soft brown hair free of the semen deposited by the males and the womanly essence of Tara. After drying her soft downy body she retreated to her silky bed, shuddered and cried a little more ... read more

shemale lover May 24, 2012 100%

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%

A Natural Sissy

Stacy is a natural sissy. I knew it the first time I laid eyes on him when he came to visit at my request on an Internet forum. After 3 months of Internet chat, I was ready to implement my plan. I knew he had money. He inherited most of it from his parents when they died in horrible automobile accid... read more

shemale lover March 23, 2012 71%

A Natural Sissy Part 7

Stacy has a bad? morning The next morning I slept in a bit. Stacy woke me by climbing onto the bed and spreading my legs as was the method prescribed for such times. Stacy was a world-class pussy eater, and I guess I have his sisters to thank for that. When my orgasm came I opened my eyes to see ... read more

shemale lover March 24, 2012 100%

Submissive sissy Jennifers first cock

There is a shy knock on your door. You open it, wondering who it can be. A stranger hands you the end of a dog chain, you can see that it leads to a red strap round his neck. "I'm Jennifer, Sir" he whispers, softly & huskily. It becomes clear now - you remember the conversation on the... read more

shemale lover May 1, 2013 100%

A Sissy's Wish List

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... read more

shemale lover June 19, 2012 66%

From Husband to Castrated Sissy

"Oh my god!" My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. "Hi honey. What are you doing home early?" "Kelli what the fuck's going on here?!" At that, the black guy... read more

shemale lover December 2, 2012 75%

My Awkward Phase

My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... read more

the greatest liar June 14, 2019 85%

PRÉDATEUR ET PROIE ⚧️ ⚧️

C'était il y a entre deux et trois ans, bien sûr, quand j'ai rencontré Kitten pour la première fois. Ou plutôt Taylor. Ou plutôt sa mère. C'était un vendredi soir et je faisais le tour des bars, faisant passer de l'herbe, des pilules et des trucs plus durs. Je travaillais habituellement d'un bout... read more

Femboy 2021 April 26, 2023 50%

My 1st Time was Not the Only Time.

One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... read more

LesFuax February 16, 2019 100%

Young Sissy Chapter 1

I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... read more

shemale lover January 4, 2013 100%

FAGGOT COMES OUT TO HIS WIFE!

I was married for 3 years before I finally got caught. It happened when my Filipina wife went through my notebooks and found all the gay fantasies I had been writing about. The story she found was one I had just written. It was about a young guy who applies for a modeling job at a gay magazine calle... read more

Kevyn-JeanneHarris December 25, 2015 97%