Free Shemale Stories

Shemale Gangbang

I am not your average female. But I guess I am not your average male either. You see, I am a tranny. I make a really hot woman. I am 5'10", am slim and have dark, wavy hair that comes down to tight between my shoulder blades. The only thing I was missing was beautiful tits. So I got those as we... read more

shemale lover August 27, 2011 70%

His Perfect Shemale Partner Part 2

Quite a few things have changed since the last chapter. OK maybe not that many, I am still lusting after Sally's body needing to have my dick in her and feel her in me, but we are a lot closer now as we are living together. Sally has gone to her 1st choice University and I decided I would rather get... read more

shemale lover August 28, 2011 100%

Career Shift

Receptions are not my favourite things in the world to attend. I don't mingle and 'rub elbows' like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one ... read more

shemale lover March 6, 2012 80%

A Harmless Fantasy?

I lie in bed at night, trying to get to sleep, but my mind wanders. I think of all sorts of things, and eventually my mind heads off into a land of fantasy. In fact, it is one fantasy in particular, and it's one that I have been having ever more frequently over the last couple of years. Each time it... read more

shemale lover March 9, 2012 50%

Working with Trista

Day 1: I had just started my new job; only a month in and so far it was ok. I was laid off months earlier and forced to start working in a temp firm. The hours were all right, the pay was reasonable, and I couldn't complain about the commute. I was told this position could potentially turn into a... read more

shemale lover September 23, 2012 87%

Halloween with Movie Stars Chapter 4

Pete and Tim...first time without the girls There was a knock on the door. Pete knew it was Tim. They saw each other earlier at class and decided to get together after school. "Hey Suck Buddy," he said with a crooked grin. "Come on in." Tim returned the smile as he walked ... read more

shemale lover January 29, 2013 100%

Getting caught with sub Roxi in the forest

I met TV sub Roxi in the car park & we drove in her car to a pull off area in the forest where I had been before.. It was drizzling slightly as we got out & walked across the grass to a shelter with a seat. I went to the ladies toilet on the way & then joined Roxi. We had a good ... read more

MISSJENNIFER April 10, 2019 57%

The Girl Next Door Ch. 02 by derezzed ©

Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... read more

StevelovesTgirls June 11, 2019 92%

Showing my femininity

When I was still little guy, my stepfather always told me I wasn't a real boy, but I was his little girl. One day, he was drinking beer with his friends, so he grabbed me by the arm, pulled my shorts down and showed off my teeny cock to them. I remember that all of them laughed at me. They made fun ... read more

Shemale Dill April 27, 2020 92%

Fucking with Gina!

Hi! Here I am with my own story! I’m a young white guy, a good looking son of a bitch! When I was a college student, one of those numerous young people who always rush for something, then I was a focus of interest for lots of chicks around! But then something changed. Changed a lot. As I remem... read more

shemale lover May 13, 2014 85%

First cock in skirt

Another little hot story from our forum. A guy who goes by nick Stephen54 writes about his very first experience with a hot CD, getting and giving his first blowjob and having anal sex for the first time. Hello. Was wondering what peoples first time experience was? Mine was back in the 70's, d... read more

shemale lover April 17, 2015 61%

She Seemed To Love Shemale Video Chat

The wife and I have a really nice sex life. It’s all fine, although I’ve told her a couple of times that I’d love it if she could try and improve her ‘oral’ skills, if you get me. She didn’t seem to mind my comment and I can tell you that she really tried to work ... read more

shemale lover April 22, 2016 68%

The Terrace View Apartments Part 7

My new life had settled into a wonderful routine. I would wake very early in the morning, usually still wrapped securely in Mistress Kendra’s arms. I would spend an hour or so working on my figure maintenance exercises, enjoy a cleansing enema, a refreshing bath and body shave, then I would la... read more

shemale lover November 19, 2011 100%

TV-TV

My girlfriend Gloria and I had just moved into an apartment together, having gone out for six months or so, before making the committment. We moved in furniture from each of our apartments, after deciding what would go best in the new place. With the exception of a television, we really had eve... read more

shemale lover December 16, 2011 75%

Teacher Student Confidentiality

It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... read more

shemale lover February 11, 2012 83%

A Drive in the Country

It had been a rare hot dry day and the evening promised to be hot as well. Toni the lovely CD I have met down here in Wales arrived as arranged just before dusk in his car to collect me and take me somewhere secluded he had found for some outdoor fun. We drove about a mile before Toni pulled over... read more

shemale lover February 29, 2012 80%

Fulfilling A Girl's Male Fantasy Part 2

Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a ... read more

shemale lover April 4, 2012 100%

Dear Karen Chapter 5

06.02.09 Dear Karen, Following my successful luncheon, I was simply giddy with success. One result of this was I became man hungry. I wanted the warm, full feeling that only a hard cock could provide but I didn't want to demean myself by submitting to being fucked by my sissy husband. In fact,... read more

shemale lover August 6, 2012 100%

Pandora's Box Chapter 1

I discovered transsexual women completely by accident when I was 18. I was watching one of those Real Sex shows on HBO, and without warning, two women who were showering together for a video shoot turned around and I was shocked when I saw cocks where I expected to see pussies. What probably shocked... read more

shemale lover August 31, 2012 82%

Both Sides Of The Coin

Jessica and I were back at the scene of the crime, so to speak. Her work friend, Mike, hosted a costume party every year on the Saturday night 8 days before the Super Bowl, "Because there's never anything else going on that weekend." Last year, that tagline on the invite offered suffic... read more

shemale lover January 28, 2013 87%