Free Shemale Stories

Joanna the Tranny Prostitute

Joanna stood on the street corner and casually shifted her posture from one leg to the other. So far it had been a quiet evening for her with few punters around. Not many girls were plying the streets either. She’d had one customer earlier. He had been an Asian guy in a Toyota who’d stop... read more

Joannacd1 November 7, 2011 100%

My tranny slave

My biggest wish is to own a tranny slut a cheap worthless little cumwhore. Is make wear stocking suspenders a short skirt and black lace panties. I would rule her with an iron fist. First I'd make her crawl on all fours like my lil pet I may even keep her on a leash. She would be forced to obbey my ... read more

shemale lover December 9, 2011 88%

My Virgin Tale

It was a brutally cold winter night, even by Minnesota standards. It didn’t matter. I was just beginning my journey towards womanhood and needed to get out on the town for some much needed male attention. Technically, still in the closet, care was needed to make sure it went undiscovered anytime I s... read more

Tawny Preston February 22, 2016 100%

Can I Be This Lucky?

I had just broken up with my wife of 4 years. So I was definitely not feeling good about myself. My time in the Navy was just about up, & not a second too soon. Now that I was done with my wife, I had no reason to stick around here anyway. I decided to go check out a movie to get my mind off thi... read more

shemale lover March 3, 2012 100%

Why did I settle for that?

Just made it back from Miami, was a great visit, but it could have ended after the first night, and that would have been alright. Hated the dirnking and the smoke, but did meet another lovely tranny who did give me the tour and the break from this horrid northern weather. Although the sex with he... read more

shemale lover March 6, 2012 66%

My Frist time with a tranny

My Frist time it was back when AOL frist came out. I was in a miami chatroom and I met a tranylicous. We Started to chat. I remember going to the profile on the side of the message window and I found out throu pics what a tranny was. I must of been 13 at the time or so. She gave me her address. it w... read more

shemale lover March 14, 2012 83%

My 2nd tranny date

My second transexual Encounter was years later my First, I was sixteen At the time. And I was driving home from my girlfriends. I was living at my parents, my curfew was 2 am. That nite I had taken my moms fleetwood with me. I left her at her house and I had a hard on. On the way back I passed by 8s... read more

shemale lover March 18, 2012 80%

A Love Story

The bisexual lifestyle can be a lot of fun. Let no one tell you otherwise. My name is Lawrence Henderson and I'm a six-foot-tall, good-looking black man living in the town of Boston, Massachusetts. I work as an executive at Anderson & Winston on Boston's Financial District, one of the top invest... read more

shemale lover March 18, 2012 100%

My first tranny Part 2

It felt so good to cum in her mouth. that wasn't planned. her mouth just felt so good. nice & wet. told her what really got me off so fast was having her cock in my mouth. "in that case, come here & suck it some more." she laid down with her legs open & her dick in the ai... read more

shemale lover March 21, 2012 77%

Stephon fucks Sora and her sexy tranny ass

Ya know what fuck it since my last story wasn't good apparently imma just cut the bull and tell the whole story now shit. So my dick is in her ass and im in heaven, like on some cloud nine shit.the head board is knocking she screamming, im not sure how loud though cause im pretty focused.And like... read more

shemale lover May 25, 2012 71%

Tranny Threesome

I met Chrissy about a year ago at a bar. We really hit it off. She was about 5'5" 120 with a nice, athletic body. She was Filipino. Her face, well, unless you knew, you would never know. She was different than the rest of the girls at the bar. While she was there to make a living, she w... read more

trentdolby May 27, 2012 76%

Drinking Decisions

I was at a dance club one night a few years back. It was one of these goth/electro sorta things, it kinda looked like something out of a Marylin Manson video. I had been drinking most of the night with my friends and had a pretty good buzz on. This girl comes to the bar next to me, black vinyl corse... read more

shemale lover August 5, 2012 100%

My Tranny Experience

Hey all I am about to tell for the first time my tranny experience! This happened last year on a trip with two of my divorced guy friends. We went to Costa Rica on a surf trip and while we were all single guys we took advantage of Costa Rica's night clubs and strip clubs and were having a very fun ... read more

shemale lover August 20, 2012 100%

Fantasy fuck

Sitting in the toilet cubicle I have been horny all day my cock is semi hard and I run my finger over the eye as pre cum oozes from the slit, I taste it's salty flavour as I strain the pro out mmm wish there was something going in rather than out! There is activity in the next stall and I see some f... read more

shemale lover September 11, 2012 80%

My favorite time with a man as a Tgirl

I was in the dance clubs with my friends and we were very sexy dressed in heels and low tops and I was in high heels and a mini dress that was flowers all around it. My ass looked so big and round in that dress. It was low on my big boobs and very tight so my boobs looked like they have coming out. ... read more

shemale lover September 29, 2012 100%

Don't "DRAG" It Out Of Me...

I was a Service Brat; living near FT. Hood Tx. at the time, and had just turned 14. My friend Peter was a little more than a year older than I, and we had started getting each other off with hand jobs but nothing else during the previous summer. One day after we'd finished swimming, he asked if ... read more

DJFreak201 November 22, 2012 100%

Something new...

Andrea was out all morning, running around doing things and getting ready for our trip. She was taking me to some erotic retreat somwhere, sounded like a lot of fun. I showered and got dressed and was standing in the kitchen at the table, when Andrea come home........ She loked at me gave me a li... read more

shemale lover June 1, 2013 94%

Karlie

After seven long years of sitting around, questioning my sexuality and fantasizing over the one thing I thought I could never have, I finally decided it was time to make a move. I was going to experiment with my sexuality, I was going to look for a real live hot tranny to meet up with and have sex w... read more

shemale lover July 16, 2013 100%

Horny tranny

Let me tell you a little bit about myself I'm five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the parking lo... read more

shemale lover November 29, 2013 85%

Best booty i ever had

there is a certain part of the big city where the community partys everyday of the week called boys town i worked in the area and never knew but what i did know is i had a fetish for an extremly large ass i love big bootys and desired a tranny after watching shemale videos this didnt happen until i ... read more

jrryder December 8, 2013 88%