Free Shemale Stories

Chrissie and the Professor

Possibly the after hours engagement with an English Literature professor at college may have been the thing that convinced me that older men might be more to my liking. It was during my Junior year at the university when we were discussing the poetry of Arthur Rimbaud, the French poet, that I beca... read more

shemale lover July 25, 2012 100%

Brad, Chrissie and the Laundry

It’s amazing how much fun you can get into when you use the laundry room In our apartment building. Let me tell you about one Saturday morning when I was busily doing a couple of weeks worth of laundry. I was all alone in the laundry room and waiting for the dryers to stop so I could retriev... read more

shemale lover July 28, 2012 100%

A Year in the Life of... Chapter 5

And now he found himself waiting at the door with Ibrahim, looking out into the dark, rain falling heavily outside. He'd managed to negotiate the stairs okay apart from one heart stopping moment when his heel caught and he thought he was going to go flying down the stairs. But he'd had a tight hold ... read more

shemale lover August 1, 2012 100%

Satin Jacket Slut and his Mistress

I arrived at my mistress' house at 7:30 promptly as she instructed. As she opened the door I had to gasp at how beautiful she looked. She was dressed wearing a black satin robe over her corset as well as a pair of long satin boots and a pair of satin panties with a huge black strap on. I am always a... read more

shemale lover August 4, 2012 50%

The Slave and the Sissy Part 4

Pepper and I knelt on the silky sheets of the bed and studied each-other in disbelief; our cocks rigid and ready for relief. I took her sweet sissy cock in hand as I sniffed and licked at her face and neck; her skin as white and silky as the sheets. She thrust her slippery little sissy cock back and... read more

shemale lover August 13, 2012 66%

My first time and loved it

My name is jay i have been attracted to shemales for a very long time i have always fantasizec of being with one but never happened.i dont know where to go to meet them and im real shy and quiet at first it sort of sucks trying to take to a beautiful woman never know what to say.so i decided to join... read more

Hbjay August 14, 2012 46%

Denial: Second Comes Humiliation

Janine had been slowly beginning to work Mark over by using 'creative discipline' and during the last day she had developed her hold even further. Mark woke up with DVDs and photo's laying around him showing himself in quite a few unsettling positions. He was sore all over and had a headache that... read more

shemale lover August 16, 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%

The Developing of Emma Part 4

Emma awoke in the softness of her silk sheets and wondered what the day would bring; her sissy cock bulged and dribbled sticky pre-cum through the outlet of her cage as she thought of sucking Kurt’s cock; her tight little anus clenched and released at the plug, which acted like a comforter. El... read more

shemale lover August 26, 2012 80%

Afternoon Delight Chapter 3

When we got to the cottage, the girls stripped me of my jewelry and took theirs off and poured me into the shower. They washed the cum off of me and got me hard again. Damn, Ally and Carmen were all over my cock, giving me a work out. Needless to say, I came a few more times, and we got into the hot... read more

shemale lover August 27, 2012 100%

The Developing of Emma Part 5

As Kurt caressed Emma’s sweetly pronounced bottom, she realised she had never felt so feminine before, despite her newly freed cock standing stiff in nervous anticipation. She looked at the powerful male and the leering male audience; the few females there would now witness her being used as a... read more

shemale lover August 27, 2012 100%

Tricked into threesome

I was online chatting to a beautiful lady on cam. She said how she loved to see men dressed in womens clothes and how excited it got her. She asked if i would meet up with her at her house and to come over all dressed up. So we arranged a time and day and ended chat. I could not wait for the day to... read more

shemale lover September 11, 2012 71%

Old tom

Me and old tom have the same friends which i was not aware of at the time, anyway i was visiting the mutual friend on an off chance that he was inn as i was passing his road, any way old tom and i were chatting and he mentioned that he had an old cement mixer that he was selling and did i know anyon... read more

shemale lover September 13, 2012 100%

Old tom Part 3

Since I had been at old toms place and enjoyed the part of me that enjoys lingerie and stockings, I had a mixture of excitment and nervousness as to when I was going to return to toms or knock it on the head due to guilt!. When my day off finaly hapened yes I had a few chores to do which gave me ... read more

shemale lover September 14, 2012 100%

Airport Arrival, With a Twist

Note: This story takes my Airport Arrival story and adds a twist. This story was written and published by me on another site under the name of "Kristy Kay". I hope you enjoy this version. I remember seeing your new skirt on the bed the day before I left and all I could think of was s... read more

shemale lover September 19, 2012 100%

Brianne Rides Again Chapter 1

After the last excursion at the rest stop I had to check it out again. I couldn't believe the fucking I got the last time. All the next day I couldn't even walk right because of the ass pounding I took. Days past and I kept wondering what kinda luck I would have if I went again. I was getting so exc... read more

shemale lover September 24, 2012 66%

The Arrangement

My wife and I have been married for 10 years and are very much in love but we do have our own little fantasies as we have learned over the years. She is 5'8" tall, blonde hair blue eyes, in my mind, quite a sexy body, with great legs, a nice ass, and ample breasts. She really looks pretty hot..... read more

shemale lover September 26, 2012 100%

Buying Heels

I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer ... read more

shemale lover September 30, 2012 100%

All Right I'll Do It Chapter 2

The door closed and I stood there in shock. John's cum was drying and pulling my skin as if he was pinching my cheek. I rushed to the bathroom. I had barely gotten the shower running when I had to kneel in front of the toilet and vomit. My mind swirled as both the humiliation and probably Robert's s... read more

shemale lover October 11, 2012 75%

Wife Meets a Trannie Chapter 2

Since discovering my wife, Lynn's fling with Jay and his TS wife, Tammy, I was constantly aching to know when they were going to invite me in. Lynn and I agreed that the right time would come for me to be let in on. I didn't mind too much because I'd occupied myself with the anticipation, the though... read more

shemale lover October 15, 2012 100%