Free Shemale Stories

A Perfect Pandemic: A Transsexual Transition in a Troubled Time

A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... read more

the greatest liar November 16, 2021 100%

In My Place

I looked disbelievingly at the clothing on the bed before me. They were all mine; all of them. How did she know? How did she find them? I just could not believe what was happening to me. I could not do this. It was not what I had ever wanted, despite what she appeared to think. And him....... I h... read more

Loveto October 12, 2011 100%

Porshe's Escapade Chapter 1

Hi, it's Porsche back again and rather disappointed. I thought I would get a much better response to my first story "Interactive Crossdresser...Dare Me" but i didn't. I was kind of reluctant to put myself out there since i have never dressed in public or in front of anyone else but my Aust... read more

shemale lover September 3, 2012 100%

Randy Candy

I’m not usually into walking the streets but I found this day was too damn hot to work indoors. There is nothing worse than feeling stuffy whilst a guy is up his balls in my ass. The enjoyment quickly disappears for both of us when that happens. So when I had a call from a guy called Rod who wanted ... read more

iluvgurls November 12, 2018 80%

The Guy At The Pool

The Guy At The Pool Stepping out of my hotel room for a smoke I saw two young guys at the swimming pool which my room overlooked. One of them was standing outside the pool speaking to the other guy who was in the pool. The guy beside the pool immediately caught my attention, his shirtless bo... read more

pennypenny October 21, 2019 76%

Cheating Sissy Wife

My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... read more

Regina10 July 27, 2020 85%

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%

A Series of Perverse Dreams, Part 3

After my last couple dreams, I began to watch a ton of gangbang and bukkake porn. I had jerked to this kinda stuff before but now I was watching it constantly and this time around, it was to the thought of being the girl in the scene. Something about watching a beautiful woman taking numerous cocks ... read more

KaceyKlarissa March 8, 2024 66%

Vanessa and the workmen gangbang

The three workmen were slaving away in the back garden, in the hot sun. Vanessa watched them from the upstairs bedroom window, getting more excited by the second. Under her robe she was wearing a beautiful red basque with a red g-string, black stockings and five inch heels. This was topped off with ... read more

Vanessa Luv May 12, 2020 100%

Vanessa gets more than she bargained for!

Vanessa had it all planned out meticulously. She had taken the day off and planned on doing a bit of last minute shopping before checking into the hotel in the early afternoon. She eventually decided on buying a massive dildo to get her ready for the party. This would give her plenty of time to take... read more

Vanessa Luv May 15, 2020 100%

Late Night Snack (Touch me in the morning)

I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... read more

Regina10 March 28, 2024 100%

My First Cock Part 2

So he had finally got me on my knees licking the cum off the tip of his cock. I could feel my cock getting hard just from the taste of his cum, i could feel my cock trying to break out of my tight panties. I wanted more so i opened my mouth and put head of his cock in my mouth, whilst i had his c... read more

Nastasia69 June 7, 2018 84%

A happening in the bar

I was tired. I was tired with daily boring routine. I really needed to change something. My life had become boring and my sex life was expressionless. All women I knew proved to be untrustworthy, light-headed and superficial. I really wanted to take a break from the world. I just wanted to live my l... read more

shemale lover December 5, 2011 88%

A Job in the Theatre Chapter 9

What a difference a weekend could make Paula thought sitting up in bed that Monday morning. In just two short days her life had changed completely. She had discovered cock. Playing with hers was fun, but playing with others was even better. And there was a world full of cocks just waiting for her to... read more

shemale lover March 13, 2012 100%

Francis Meets a Black Stud Part 2

The first story was easy and this one went by pretty well. If you have any thoughts or suggestions for where Francis should go in installment #3 email me. I will respond to your email and sometimes I will send out previews of what I am working on if you treat me right. Thanks. As I was walking to... read more

shemale lover November 20, 2012 100%

MY Party Favor Fantasy

My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... read more

pennypenny January 8, 2019 92%

Castro - goddess of love (starter)

Nobody would have believed the scene was true, slender, smooth and tanned legs crossed is such a such deliberately provocative way as to reveal a glimpse of sharp white panties. A tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effect... read more

Law12 March 2, 2018 66%

Mistress Milks Me

It was a bright sunny spring day and I had gotten up early and made my self as sissy as possible for my mistress. I touched up my shaved body to make sure not a hair was anywhere on me. I gave myself two enemas to make sure my ass was clean in case my mistress might want to use me in some way. (I al... read more

shemale lover November 22, 2011 50%

Kidnapped (Adult Fiction)

Kidnapped I remember being normal. I was a young man in my 20's living in my parent's house struggling to get by. I was online more than I probably should have, but it was an escape from the harsh reality of my life. I didn't feel fulfilled or like a success, I felt like a failure on many differe... read more

Vennom June 17, 2019 73%

Samantha sissy TGTF

Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... read more

Samantha sissy world September 20, 2022 66%