Free Shemale Stories

A Holiday Job Part 2

“Anne” was stunned by Nico’s offer. When Paul had discovered that his sister had left taking the wrong suitcase, the idea of becoming her for a week had been very appealing. The job in the bar, the innocent flirtation with Jorge the cute waiter over lunch had all been very enjoyabl... read more

shemale lover March 10, 2012 100%

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%

A Job in the Theatre Chapter 6

Paula fell back against the couch and closed her eyes. What a marvelous experience it had been! She absolutely loved to suck cock! She loved everything about it. She loved the taste of cum too. She couldn't wait to do it again. She could feel the dried sperm caught in her hair and knew there was ... read more

shemale lover March 12, 2012 100%

A Job in the Theatre Chapter 16

"Ted has invited me to his poker game" Paula let slip. "Oh really? Now that sounds interesting" Sarah said. "It will be if we come up with the right uniform. It's all boys so I am going to dress in some sort of domestic help type uniform. But of course it has to be the... read more

shemale lover March 15, 2012 100%

A Lady's First Time

When he'd first stepped into the bathroom, it had been Daniel who had stared back at him in the mirror. Now, the face that smiled back was almost complete, and Cassie was nearly ready to go. First had come all the undergarments -- the satin panties that felt oh so right, then the bra that had giv... read more

shemale lover March 16, 2012 75%

My Sissy Fantasy

I reach the campsite just as the sun is going down and the clear sky is bright orange as if in memory to the beautifully warm day it has been. The campsite is popular yet set on secluded farmland and as the season is just over it is practically deserted. The whole camp is surrounded by woodland and ... read more

shemale lover March 27, 2012 100%

Shemale secretary fucking

Ms Boss had said that I was to see her secretary concerning "letting of some steam". She and I had been at each others throats lately and Ms Boss didn´t like her two slaves to argue. So we were left alone in the break room after most people had gone home. And we were not to leave un... read more

shemale lover March 28, 2012 75%

Emily and Steve Part 1

As I pulled my cock out of Emily's ass and shot my load onto her flat stomach, where my cum mixed with the load the beautiful blonde cross-dresser had just shot from her throbbing cock a moment before, I thought to myself that work was suddenly going to be a lot more fun. My name is Steve and I w... read more

shemale lover April 6, 2012 100%

Emily and Steve Part 5

Emily, my beautiful blonde transvestite girlfriend and I were on our first out of town weekend trip as a couple. Emily had taken me up to a friend's farm, where we were going to go horseback riding. While I am pretty much a city slicker, Emily grew up in the country and had missed getting out and ri... read more

shemale lover April 6, 2012 100%

A Night to Forget

The day started out like every other day. Woke up, dragged myself to the bathroom; Stepping in the shower, (I sleep in the nude...) still not fully awake, I let the water cascade over my head. Mmmmmmmmmmmmmmmm, I closed my eyes and could feel the water flow over me. I pushed my hair back off my face... read more

shemale lover April 23, 2012 90%

My slave training continues

I stood there in only my 5 in red stilettos while Mistress walked round me, inspecting me. My budding breasts and erect nipples were quite obvious. I so wanted to be worthy for my Mistress and serve her well. She squeezed my balls "No sub, I own you now, you only get a hard clitty when I desire... read more

shemale lover April 24, 2012 66%

A Night to Remember

PREFACE I kept my female alter ego (Nicole) a closely guarded secret from my wife for over 15 years of our marriage. I've always enjoyed exploring my feminine side from a more realistic sense -- most cross dressers I met try to wear skimpy outfits and stockings that only a handful of genetic wome... read more

shemale lover April 28, 2012 0%

A Not-So-Small Piece of Heaven Chapter 3

I bit my lower lip, looking into her eyes. I didn't know what to do. I wanted to get on my knees and slide that gorgeous cock of hers in my mouth. But I'd never done it before, and I was scared. Sucking penis wasn't exactly on my bucket list. She lightly touched my arm, a puzzled look on her face. &... read more

shemale lover April 29, 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%

How i changed?!

I had been with my girlfriend for 4 years, after a drunken night i later ended up in a gay club. I came across a lad that went to my school who was always openly gay and he was shocked to see me in here. I just explained that I had only come in for a few drinks as most of the other places were start... read more

shemale lover May 15, 2012 100%

The Superbowl

I was very surprised when my brother-in-law Tom invited me to watch the super bowl with some of his friends. The only reason he would “invite” me over was to be his little sex sissy, since he had enough pictures of me dressed as a girl sucking and being fucked by him I had no choice but ... read more

shemale lover May 23, 2012 71%

A Reluctant Gang Bang

Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang rape at an adult arcade. I was dressed up in a white flowe... read more

shemale lover May 28, 2012 100%

Double penetration in Vegas

On a trip to Los Vegas for my Birthday we had a great time. Same old shit, we won and lost, saw all the sites and a few shows. The last night we were there however we were BORED…. That being said and knowing US, We took a stroll around the hotel. Maxx was checking out all the hot women in the... read more

shemale lover May 31, 2012 100%

Daniel, Dani, Dana Part 2

Looking in the mirror as I drove the highway, the new me felt and I thought looked great. A new hair color with the old one the trim, my face looked smaller and even more feminine. I never had this freedom at home and hated the idea of going back there. Final exams were all that was left to shed the... read more

shemale lover June 8, 2012 80%

Birthday Surprise

My girlfriend and I have the same fetishes and interests for the most part. We both find latex irresistible. We love the site of a tranny with a big cock. Robbie knew everything about me. For my birthday she went well out of her way to make me happy. The date rolled around. I figured it was jus... read more

shemale lover June 19, 2012 100%