Free Shemale Stories

Baroque Buggery

All through college, Jim Benson had earned a reputation for being a little... eccentric. More than a little eccentric, actually. He had an unusual sense of humor, strange taste in fashion, and probably the worst luck of any human being on the face of the earth. Nonetheless, with his good look and ch... read more

shemale lover February 25, 2012 0%

A Good Shower

Where do you start describing an evening like this? First is a description of us. My wife of five years is still the girl of my dreams. Putting aside her sparkling personality, she still meets all my standards for a perfect ten. I like them small, she is 4' 10', blond and built just right. I towe... read more

shemale lover March 8, 2012 0%

Panties For ME

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me.... read more

shemale lover March 11, 2012 83%

My dream encounter with a tranny

There is nothing more hot than to have a slim, pretty body on my hands to fondle. To feel their erections starting to grow and to taste their cocks in my mouth. I lose control when I'm around a shemale. I have fantasized a lot about getting fucked for long periods of time and in a lot of differen... read more

shemale lover March 13, 2012 100%

A Job in the Theatre Chapter 20

"Be careful Rex," Ted pleaded. He was tied to the four corners of his bed with a pillow shoved under his ass. He felt completely helpless. It was a feeling that he was not used to. He was always in control, had everything worked out. Not this time. He barely knew Rex. The one thing he did ... read more

shemale lover March 15, 2012 100%

Becoming His

I need to tell you how it started and then maybe you'll understand. We had always had a great sex life, and one night she was a little tired, so she gave me a hand job instead. While she was stroking my cock she began to tell me a story that got her hot. It was about a threesome, and form that point... read more

shemale lover March 20, 2012 90%

Shy girl with a big secret Part 2

After Maria unloaded her seed in my mouth, I was amazed at the flavor, for it was sweet like sugar but had a bit if a salty tang. I kept most of her seed in my mouth, turned around, and kissed her full on the lips, letting the delicious cum flow from my mouth to hers. As this was going on, I started... read more

shemale lover March 25, 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%

First Time Out

I am a 21 year old straight male and have had fantacies about wearing womens clothing. I have never acted on them and surpressed my desires to dress as a woman. One day I was one the internet and came across a website with crossdressres on it and my desires came back. Well as I kept looking throu... read more

shemale lover April 19, 2012 100%

Becoming the Neighbor's Wife

I like my neighbors and I am grateful for the way we look out for each other. Take Tony, the 60 year old, barrel-chested guy who lives alone in the house next to me. My garage faces Tony's house, and a couple of times last fall he came over to warn me that my garage door was left open. I thanked ... read more

shemale lover April 20, 2012 100%

Working Like A Slave

This story takes place in an unnamed third world country. A slave auction is going on for some very wealthy customers. "We have this stud, here. Raise your arms. He is..." "What about him?" the blonde woman points, interrupting the auctioneer. She is a wealthy older woman and own... read more

shemale lover April 20, 2012 66%

European Vacation

I was 18 when I first went to Europe. That month would change my life. My parents had died when I was five, and I was raised by family friends; they also controlled my trust fund. It's not a coincidence that I went to Europe just as I came into control of the money. I loved my foster-parents, but... read more

shemale lover April 21, 2012 100%

Be Careful in the Park

One was jet black; he looked the oldest, wearing white rugby style shorts and a black T. The youngest looking was also coloured, more a coffee colour, in his case wearing denim shorts and a polo shirt. The others were white but standing more in the shadow so I couldn't make them out so clearly at th... read more

shemale lover May 3, 2012 60%

My Overseas Experience With A Bunch Of Shemales

I spent my first year in the states and then got transferred to thailand where my story really begins.We landed in bangkok and after we got settled in we headed downtown because we knew this place was full of whores. We spent the whole night drinking and fucking. I saw some of the most beautiful wom... read more

shemale lover May 4, 2012 90%

The Night Before

Dannielle felt Mark's hand rubbing gently up and down her side, caressing her soft skin and tracing the thin, silky material of the tiny, black thong she was wearing. Danielle loved the tight feel of female thongs - the sexy way they rode up and tightly dug into her ass crack. Mark began ... read more

shemale lover May 6, 2012 100%

Best of Both Worlds

Keith, 37, and Linda, 35, are very liberal people. Both enjoy sex although Keith had bi-sexual fantasies, he would never act on them, but also thought his wife was maybe a little shy and too submissive. Keith was a fairly attractive man, but his wife was still gorgeous at her age. With her long b... read more

shemale lover May 9, 2012 100%

My Gangbang

It was junior year of highschool. There was this one girl who I liked but was too afraid to do anything about it. Her name was Jessica. I thought she was too "cool" for me. She always hung out in a group of 3 other girls. She was short, about 5'2, her body was alittle plump, not too fat, b... read more

shemale lover May 9, 2012 100%

Hose and Heels in School - I'm a bad girl

A knock on the door? Who could that be? After all it was mid-evening on a Friday night and I certainly wasn't expecting anyone. I was looking forward to a night of relaxing on the sofa and nothing more. I opened the door and there stood Liza, staring at me with a smile on her face. "U... read more

shemale lover May 11, 2012 100%

Crossdresser gets Gangbanged

So one night i decided to be daring and go for a walk in my city dressed in my sexiest girls cloths (i'm just a 26y.o. italian 5'5" 125lbs body man). I had a skimpy pink top on the revealed my sexy pink bra and cut just above my belly button, for my piercing to show. I also had on a micro-skirt... read more

shemale lover May 20, 2012 55%

The Trip Part 2

I awoke suddenly feeling dazed and with my head pounding. "Kara, baby...you okay?" asked Chris Chris roused from his slumber and reached for me. I was sitting up, breathing hard. "It was nothing. Just a dream, I guess."

 "Okay. If you say so." He rolled ove... read more

shemale lover May 20, 2012 100%