Free Shemale Stories

Khwaish Pune fucked me hard

I am a shemale trans lover. Me 6 ft tall, muscular, handsome , fair man 52 resides at pune. I use tobe top but last two years I am living being bottom too. I love sucking shecocks and hv sucked quite few in pune. Story begins when I was looking for some trans partner on Planet Romeo I came acro... read more

Stud4Shemale April 14, 2024 100%

HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH

It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... read more

CDDIXIE4U January 8, 2019 100%

How I became a cute femboy CD

Chapter 1 Hello, my name is Natalie…well that’s what I named myself when I dress. Before I get started with my story about myself and when and why I started dressing and my first sexual encounters, I would like to give what I hope will be a brief rundown of myself. As I mentioned my name is Na... read more

Cute_Femboy April 5, 2016 77%

Good hardcore fuck with a shemale from Vancouver

Our reader Tommy writes about one of his adventures with a shemale. Sure, it turned out to be not as romantic, but, as he says, nevertheless it was a good hardcore fuck! Thanks to him for this great story. One night on biz in Vancouver I saw some adverts in the paper for shemales and got hot and ... read more

shemale lover March 25, 2015 85%

SISSY RULES!!!

There are a few things a sissy must understand in order to attract, and then keep, her man. Let’s look at them, these Sissy Rules. (✿◠‿◠) 1. Men are superior to you. This is rule number one for good reason: it is a simple statement of fact. It is so important that many questions that a potent... read more

KittyHot June 18, 2021 94%

Sissy For My Flatmate

My heart was racing as I gazed up at my flatmate, there was an something of an evil gleam in his eyes as he looked down at me and my mind kept jumping back to the events that lead to this moment. I'm a closet crossdresser, yet now my flatmate (whom I managed to hide my “hobby” from fo... read more

shemale lover July 25, 2012 71%

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%

Sweet Sixteen

Sissy rachel walks in the house and curtsey's before her Mistress and asks permission to clean up before her Sweet Sixteen Party. Mistress Staci Lynn waves her torwards her room, and off the little sissy rachel prances to her pretty sissy pink bedroom. Sissy rachel has more than earned her Swe... read more

shemale lover January 21, 2012 100%

A Natural Sissy Part 8

Just as Stacy came back upstairs and told me the recreation room was ready for his tattoo application, the doorbell rang. "That's fine, Stacy. And just in the nick of time. That must be Heather at the door. Go let her in, please." Stacy looked at me like he could stab me in the chest wi... read more

shemale lover March 25, 2012 100%

The Slave and the Sissy Part 3

I was more frustrated than ever now; Ella laughed wickedly as I was led away on my leash, my cock pulsing and dribbling like mad in its cage, was there no end to this torture? We turned a corner and we were approached by a smiling harem girl who, giggling passed a sack to mistress. We stood by a doo... read more

shemale lover August 12, 2012 55%

I've come to turms about my prefs

I consider myself as bisexual, I luv pussy and cock equally, so I thought except lately I've been feeling more femme and wanting to feel and act like a slutty gurl. I like to dress lke a gurl and do things women normall y would rather not do like swallow a mans load,get fucked in the ass and ju... read more

cdwendy4u May 27, 2015 83%

My sissy experience

I guess you could call me a sissy, maybe even a whore but one things for sure... I love cock. So my story begins as a young teenage boy, curious like most. I would raid my sisters panty drawer for the excitement of trying on her sexy lingerie. It became an addiction, I couldn't help but want mo... read more

Emilysweetxo June 26, 2017 69%

Sissy slut gang bang Part 1

I hear a knock at my door and go to answer it even though I'm only wearing a little black see through lace top, black lace assless panties, thigh high fishnets and stiletto heels. I open the door to see all the men from this group I started on kik. "Guess this is my lucky night. Come on in... read more

Sissy Kayla July 5, 2017 76%

Am I now a genuine Sissy Slut?

I started Crossdressing when I was about 16 years old, the usual story , mother and sisters panties from out of their drawers when I was home alone. As I got older and married I stopped Crossdressing and consentrated on being the family man. As the years rolled by and the kids grew up and left hom... read more

Sissy Kirsty October 27, 2023 95%

Elizabeth: Beginnings of a Sissy

I had a pretty good system going. My 18 year old sister would stay up to watch Sex And The City reruns with me (well she watched, and I smoked weed), and during the first ad breaks, would run downstairs and get changed for bed. During the next ads, I would go to the bathroom, and on my way, raid her... read more

shemale lover April 2, 2012 66%

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%

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 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%

Owned sissy girl

I met the mature dominant couple that I now call Mummy & Daddy on the internet. Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for... read more

Andrina62 September 23, 2015 80%

How I Became the Sissy Slut

It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... read more

Tvtrinity August 29, 2016 77%