Free Shemale Stories

My ideal first time

We talk online for long enough to build trust. He is aggressively letting me know how much he wants to fuck me. His size is bigger than 6. He is physically larger than me and slightly older. After cumming to and on my pics several times over the course of weeks or months, we finally decide to meet. ... read more

sexysugar December 14, 2011 100%

Magician's Assistant - Friends & Lovers Part 1

Magician's Assistant - Friends & Lovers takes place in the Magatrix the Magnificent Universe, which was first introduced in my serialized seven-part story, Magician's Assistant. The premise upon which both that story and this story are based revolves around the fact that Magatrix the Magnificent... read more

shemale lover December 25, 2011 0%

The Mole

Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practi... read more

shemale lover January 26, 2012 100%

Thai Holiday

On Friday afternoon I had the car go around to collect Krissy at her office, then my wife, Mei, from home, and then me at my office. The girls were both wearing light, summer dresses and looked beautiful! Unfortunately as I was coming from the office I was wearing a Suit (But as usual with Black Lac... read more

shemale lover February 5, 2012 0%

A Bit of a Kiss and Cuddle

This is a story about my first time with another man, so if that makes you uncomfortable, well, frankly, I don't care. Don't get me wrong, I wasn't under age or anything at the time, I was 20, but some people, for some reason, don't like that kind of thing. Personally, I find it hot as hell (N.B thi... read more

shemale lover February 8, 2012 50%

A Brand New Year

He stood in the center of the party drinking from a bottle of Coors Light. He wore a black t-shirt and pair of faded gray jeans and converse sneakers along with a Flyers cap hat and had a go-T. 25 year old Mike had been invited to this new years party by his best friend Danny who he had known since ... read more

shemale lover February 8, 2012 100%

The Triple X cocktail - Wife Shares Shemale With H

"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an ... read more

shemale lover February 21, 2012 100%

Carla

I lay on the bed naked. My cock was hard and my hand was down at my ass and my fingers were teasing with my asshole. "I want you in here" I purred And I slid my first finger into my lubricated ass. I gasped and savored the sensation as it slid all the way into me smoothly. My cock tw... read more

shemale lover March 7, 2012 100%

A Mate's Trans Date

I had been seeing Nikki for about 6months and taking her out as you would any girlfriend, sharing our groups of friends socially of course. One evening we went to a friends place and when Nikki has snoozed off to sleep on the sofa me and my mate called Al got talking, we had been drinking most of th... read more

shemale lover March 19, 2012 100%

I've always wanted to meet a gurl!

First of all I would like to apologize for my English. Hello there! I live in a small country's biggest city and here people are strange. If they are crossdressers, shemales, trannies, tgirls, gurls (actually we have only 2 words for a shemale, so I don't know which one is NOT offending please excu... read more

shemale lover March 30, 2012 100%

A New Dawn Chapter 4

After their little escapade in the office toilets, Tom and Dawn had decided to be a bit more careful at work. As enjoyable and exciting as it had been for both of them, it wasn't worth risking their jobs over. Besides, it just meant that it was all the more pleasurable when they finally got home tog... read more

shemale lover March 31, 2012 100%

Becoming Paula

I work in an office with 15 coworkers about 11 of them are women. I get along well with my coworkers and go out of my way to be helpful. I find it is more fun to work with friends than to work with strangers. My name is Paul and I work in an insurance claims office processing claims and making recom... read more

shemale lover April 5, 2012 100%

Emily and Steve Part 7

On our drive back to the city, Emily and I stopped for dinner at a Chinese restaurant about half an hour outside of the city. Emily was a little concerned about entering the restaurant, still unsure that she was "passable" as a woman, despite all my reassurances that she always is. The hos... read more

shemale lover April 7, 2012 100%

Where Am I??

I was at the bar on a Saturday night drinking as usual. I was scoping out the girls and hoping I could find something to spend the night with. I found absolutely nothing. I continued to drink and drink and drink until I blacked out for the most part and cant really tell u anything after that. When I... read more

shemale lover April 13, 2012 100%

A Night Out Chapter 2

As excited as I was to see Neerja again it took me a few days to get up the nerve to call her. When I finally got the courage and dialed her number I was put to ease by her sweet voice. She was so easy to talk to and any nervousness I had went away. We talked about how our week was going and other s... read more

shemale lover April 19, 2012 100%

The Boutique

Sharon had been working in the little boutique, called The Fabric of Temptation (a name that Sharon secretly thought was just a little corny), for almost four weeks now. She'd applied for a number of jobs for the summer vacation, wanting to make some more money than the allowance her parents gave he... read more

shemale lover May 13, 2012 100%

My Philippine Girl

My name is Angel Smith I am a 23 year old guy with a nice toned fit body, and about a 8 inch dick and for 2 or 3 years I have been fantasying about having sex with a Shemale/Transexual. well T-Girl for short I say. I work as a construction worker and had just recently start going after my fantasy. I... read more

shemale lover May 14, 2012 100%

A Revenge Fuck

It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... read more

shemale lover June 3, 2012 50%

Fantasy Reversal Chapter 6

It was late and the sun was shining through the window. The clock on the stand showed it was just before 11am. My hands wandered, to confirm I was still Katrina. As I did I recalled the night of dancing, well actually stripping and how turned on I felt. In particular, the sensation and thrill as Sam... read more

shemale lover June 30, 2012 100%

Fender Bender

It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one... read more

shemale lover July 26, 2012 100%