Free Shemale Stories

Little cock convention

They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... read more

shemale lover July 7, 2014 100%

HELPLESS TO MY CRAVING FOR BLACK COCK

This is a totally true account of my addiction to meth and its hand in turning me into the he[pless sissy I've become to my weakness for BBC. My name as a regular male is Richie Budd. But by reading this you'll soon realize that nothing is normal. Not only was I Richard Budd. I spent an equal, if ... read more

Tvtrinity April 7, 2021 100%

Interracial Sissy Story

(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... read more

shemale lover May 1, 2015 93%

Sissy Ghetto bitch part 1

-The Guys 4 ghetto guys was inside a porn site looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked it that specific one with a tranny dressed so girly with mouth open. The guys had such a stone hard erection by watching al... read more

shemale lover June 1, 2013 76%

Sissy Slut: Gang Favored

I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... read more

Regina10 March 2, 2021 94%

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%

What are Friends For?

I was over at a friends house for guys weekend. I was up early Saturday and went downstairs to watch TV, so I wouldn't wake anyone up. Nothing was on cable, so I checked what else was on, Net Flix, etc.... There was Firestick, so I checked what movies were on there. I found one that was marked ... read more

MARKUS6969 April 9, 2018 63%

"SISSIFIED": 12 JOURS DE SISSY-MAS

JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... read more

Femboy 2021 January 20, 2023 50%

A Sissy's New Daddy Chapter 2

I hope you enjoy this second installment of 'A Sissy's New Daddy'. I worked hard on it and hope that it brings all of you the same pleasure reading it that it has brought me writing it. There are some extreme moments in this chapter but also some very tender ones. There was a line in the first piece... read more

shemale lover June 16, 2012 85%

Slut indiscretion

At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... read more

Regina10 September 16, 2020 77%

My new life

It started 3 yrs ago when I was 19. I had just graduated HS and was off to college to study arts. At first college was great but I wasn’t making many new friends and felt kind of lonely away from home. Then I met Charles, he worked at the local coffee shop and we began gaming and hanging out. He ... read more

Sissy Vikki November 8, 2022 83%

Creating Alyson

"Is it an acid?" Diana answered hesitantly. My snigger from the back of the room told her it wasn't. I knew people thought me arrogant, and a know-it-all, but as usual I couldn't resist. All year during the chemistry classes for the science course she was following, Diana had strug... read more

shemale lover January 11, 2013 71%

CD and BBC Gangbang 1

My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, mid thrities, white, 5' 9' 165, reasonably handsome, both in and out of women's clothes. One of the ways I express my sexuality is to dress as a woman and get fucked by other men. Preferably in a humiliati... read more

FionaFucked October 27, 2014 94%

Slutty Sissy's 2 Loves

Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... read more

Regina10 November 23, 2020 100%

Cross-Dresser Fucked by Hot Sissy

Today I was feeling particularly horny and decided it was time to get some action again...! I jumped online and setup an online account with adult friend finder! With my online account setup under my assumed identity I tentatively chose some revealing photos to upload... It didn't take more tha... read more

shemale lover January 22, 2013 100%

Ginger's First Gangbang

I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... read more

Ginger__57 March 26, 2018 95%

Proud To Be A Sissy Chapter 4

As usual, Mr. Clark was sitting in his recliner when I went into his house. "Good morning daddy," I beamed kneeling before him. "Morning," he grumbled but smiled and said, "more like afternoon." But you do look sweet." "Thank you daddy," I rep... read more

shemale lover December 24, 2012 100%

My first big cock

So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective. I tried an online dating site ... read more

Cbosh40s March 31, 2015 91%

Alessia Travestita Hung Mature Blonde British Porn Star

Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... read more

darrell January 3, 2022 100%

A Natural Sissy Part 2

The Party Just before we reached the entrance, which was manned by a doorman, I said, "Now remember, Stacy, you just do what I tell you, and everything will be fine." "Ok... okay." His nervousness was showing, but that was to be expected. He had no idea what was going to me... read more

shemale lover March 24, 2012 100%