Free Shemale Stories

An unexpected kiss under the rain

Army Bear left that morning leaving me horny as hell. I couldn't go back to bed without playing with myself for a while. I opened my Pandora box and I took out my 9 inches, big dildo. I played with it for a few long minutes, burying it all deep in me thinking of him. Doing a few hits of poppers, I f... read more

HotVersatileTs October 5, 2011 100%

My First Encounter

I had just moved to a brand new city to take a high paying finance job. I had been some what of a workaholic my first six months here. I was working around the clock 7 days a week to make a good first impression. My hard work had finally paid off and I had received a promotion that came with a quite... read more

bman8816 July 8, 2014 97%

Purple Kiss, part 1

It happened during a week long trip for work. By the third night in a strange city I had grown tired of the hotel bar and broke away from my work colleagues for change of scenery. I told my coworkers that I was going to bed then quickly made my escape. The night was warm so I decided to take my o... read more

Transadmirer January 2, 2016 88%

Daddy looking for his sissy sub

You come over. Your cock is in a cage from last time. I go exercise so you can shower and dress up. You make sure your ass is clean. You put on lingerie, miniskirt, stockings, sexy top. Makeup. Wig. You now look like the woman you always wanted to be. You get ready for dinner and cook for ... read more

funexpat36 January 2, 2017 68%

Sally the Seducer

I had been chatting online with her for about a month and she finally asks me to stop by. My butterflies are churning in my stomach, as I have no real idea what to expect I have only seen tease pictures. You know the kind, no face barely a body part in the picture. I pulled up to the address s... read more

Quib January 23, 2017 71%

Glory hole surprise

I walked into the bookstore paid my way and went into the peeps; I usually avoid the theatres since there is not any privacy for playing. I guided my way in the dark letting my eyes adjust in the dark. I walked to the back where the stalls with the gloryholes are and found an open booth. I sa... read more

Quib January 23, 2017 76%

Tonia

One night I went to a different club to check things out. By now, I knew what I was looking for and where to find it. I was cruising the area with several bars for people with my kind of preferences you know women with more to offer a man. I parked out in the lot and began to walk in as I did ... read more

Quib January 23, 2017 66%

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%

CD is horny

There I was, all alone, unable to move. My wife Amanda and I had been playing about earlier and now I find myself stuck. She had helped me dress and I felt such a sissy. How did I end up in this position? Read on. Having already applied my make-up she made me squeeze and tuck myself into a really t... read more

Sexy Michelle April 11, 2014 73%

Purple Kiss, part 2

Continued... Naked and covered in cum, I followed Tiffany into the mansion. “How many people live here?” I asked in amazement. “There are sixteen of us right now,” Tiffany said. “Just think of me as Hugh Hefner, and this is my playboy mansion.” A gigantic set of double doors swung open as ... read more

Transadmirer January 7, 2016 85%

Spanish adult book store

A few years ago , when I was still experimenting with my Bi side , I went to Spain for a few days , walking round early one evening I chanced on a sex shop , .I went in and it was huge , I saw things that I hadn't anywhere else , I was in heaven. Going further in there was a sign for theater... read more

jakuk April 20, 2016 100%

Brianna

Rob asked me to house sit and I didn't hesitate since he lives in a beautiful big house on the end of a Cul de Sac. There is only one house next to his and no one can see his backyard except the house next to his. His neighbor Bryan is a local college professor at the community college a... read more

Quib January 23, 2017 76%

Third times the charm!

After my first 2 times with a ts it basically just became an urge that I had to have a need I had to satisfy! Just like regular sex the more I thought about it the more I wanted it. I finally asked Liz if she knew anymore from around where we were. Luckily for me she did and set me up with her frie... read more

Duke04 April 4, 2017 89%

Bikini Boy

I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... read more

shemale lover June 12, 2012 82%

The Creators: Book One by

Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... read more

sagga September 18, 2018 60%

Panty Town

Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... read more

shemale lover January 29, 2012 90%

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 Married Marilyn

"Class is dismissed. Don't forget the project due…" "Huh, what?" Marilyn woke up disoriented from her nap. When she finally came to, she vaguely remembered some project for Intro to Computer Science, gathered her legs from the chairs in front of her, dusted off her b... read more

shemale lover March 18, 2012 50%

Elaine & Me

- Chapter One – Our First Meeting - I had two weeks to go before the final degree exams and I was working hard. Perhaps too hard, because I desperately needed a break from the hours and hours of revision. It felt like I just couldn't take in any more detail about Quantum Mechanics or Solid ... read more

shemale lover March 31, 2012 83%

Bend That Gender

Shannon's Shocking Discovery Shannon leaned against Marilyn. She was definitely light-headed from her last drink. Marilyn's hand resting on her left hip pulled her closer, a move at once comforting and unsettling. She slid her arm around her new friend's waist, resting her head on the silk covere... read more

shemale lover April 27, 2012 100%