Free Shemale Stories

Painted Toes in Private Gym Showers

I'm soo thankful to have feminine feet and legs. My cock is around 6 and a half inches and I have a cute boi-pussy that is tight, but can take a sizeable dick. I would also like to point out that I have enemas on a regular basis so my butt is pretty clean. That part is true and the only part of this... read more

shemale lover October 2, 2011 75%

Bewitched, Bothered and Bewildered

Vivian flipped through his mum's mail order catalogue, turning to his favourite bit -- the lingerie section. She had asked him to choose something for his birthday, a new fishing rod perhaps, a couple of golfing irons to add to his set, or maybe even some new clothes. The catalogue provided some ... read more

shemale lover October 14, 2011 100%

and Daisies and Lollypops

One of the most intriguing television phenomenons of the past 10 years has been The Jerry Springer Show. From trash talking prostitutes to mother-daughter love affairs, the most shocking underbelly of American culture has been exposed to those who would never suspect. One of the recurring themes tha... read more

shemale lover October 24, 2011 50%

Heather in Leather

Dan walked into his video rental store and headed to the back section. As he moved past the curtain, he saw a good looking woman was also looking for some porn. It wasn't very often that he saw females in here, and he felt slightly uncomfortable. Starting on the opposite end of the XXX video shel... read more

shemale lover November 3, 2011 75%

Aunt Cindy's Bizarre World

My name was Jim Rogers Jr. at one time. I was born and raised in a small town in a rural county in Oklahoma. My father James had been the pastor of the local Pentecostal Assembly of Jesus. Dad was what was known an ultra conservative hell fire and brimstone preacher. My mother's name was Allison. Sh... read more

shemale lover December 2, 2011 60%

An Evening's Pleasure in Plastic Panties

Dear RubberPanties I have enjoyed wearing plastic panties for many years now. Although I don't have any at all the moment, I'll be ordering three pairs next week as a little Christmas present to myself. After the ones I'd had for a several years began to fall apart, the replacements I bought were... read more

shemale lover December 22, 2011 66%

And Life Goes On Part 2

So here I sit in my sexy black Miniskirt. The red silk blouse I am wearing shows off my ample sized breasts. Underneath I am wearing a red Satin corset which reduces my waist to a waspy 26 inches. I have on a pair of black satin panties with a matching black lacy bra. The red nylons I am wearing acc... read more

shemale lover January 10, 2012 100%

Nylon teasers

They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... read more

shemale lover January 30, 2012 76%

Cross dressed slavery

Oh just try it on, don’t act so…stereotypical.” I started to protest again, I mean I was not trying to be a jerk, but I did not feel like serving as Leena’s dress dummy all afternoon. I felt uncomfortable enough around her and her clothes. The way she dressed made me craz... read more

shemale lover February 1, 2012 100%

Dressing up

I have been ‘dressing’ from a young age, the usual situation occurring, finding an aunties pink satin brassiere, a long line one which just hung on me, but that didn’t matter and also the matching corset also too large, but it felt so natural to wear these items, it gradually devel... read more

shemale lover February 11, 2012 100%

A Flash of Lace

The insistent ringing of the phone broke my concentration and with great annoyance, I climbed off the bed and picked up the receiver. "Hey little brother!" My sister's sparkling voice filled my ear. "Di, Is that you?" I exclaimed happily "Got any more sisters I don'... read more

shemale lover March 3, 2012 100%

A Game within a Game Part 1

Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... read more

shemale lover March 5, 2012 100%

A Helping Hand

It was late on a Friday night when I heard my parents arguing. It always happened whenever they were getting ready to throw a big party. My mother played the role of party planner and handled all of the details, but between caterers, musicians, and the other help something always went haywire. My fa... read more

shemale lover March 9, 2012 95%

A cum slut is born

There's little doubt about what turns me on most -- just check out my favorite videos and photos. Cum, Cum, and more cum. I'm a late bloomer as far as discovering my kinky side. After a long, dull marriage consisting of vanilla sex, I got divorced a few years back and decided to explore some fantasi... read more

shemale lover March 16, 2012 100%

Becoming Herself

Mistress stood there watching her next make-over walk in his door. She had talked to him for months online, and always wanted to make his fantasy of becoming a male fem slut come true. So... here she was standing in his livingroom and he had yet to notice her. Clearing her throat loud enough to make... read more

shemale lover March 18, 2012 50%

Cross-dresser Drinks Cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she... read more

shemale lover March 29, 2012 100%

A Night to Remember

I have always had a strong fetish for stockings, garters, sheer panties, heels and other sexy lingerie. I've always required my women to dress this way for me. Even when I walk through the lingerie section in a department store or Fredrick's and I can't help but want to look at the panties and stock... read more

shemale lover April 26, 2012 100%

Lady in the House

How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended u... read more

shemale lover May 12, 2012 100%

It doesn't get any better than this!

15 years ago, I went into my older brother's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out m... read more

shemale lover May 17, 2012 57%

Betrayed Chapter 6

Monday was the most vile, loathsome day of my life – for no earthly reason other than having to be me. The first thing I had to come to grips with was who 'me' was that particular morning. 'Lance' had to put in an appearance at the office. Back to the old routine, go out there and make the big... read more

shemale lover May 30, 2012 80%