Free Shemale Stories

My friend Pete

When I was 15 my friend Pete and I used to race around on our bikes nicking porn mags from corner shops. We used to take them to the local park and read through them with our cocks straining at our school shorts. As time went on we started to take turns going behind a bush or into the toilet an... read more

ryan31 October 25, 2014 71%

Ann

Ann was the woman who gave away free samples in the supermarket where I was manager, and as often as we could, the employees could find us sitting in my office, smoking, laughing and talking. Ann had a way of smoking a cigarette that drove me insane with sexual desire. Inhaling, her lips were pucker... read more

shemale lover October 27, 2014 94%

Tributes!

The weekend came fast and Miss Tranny Feet wanted to meet the man that had been sending her stories for weeks now. Each story had gotten more and more intense and now when she saw his name on the post, visions of long hours of touching her long slender legs worked her up into a rubbing frenzy. Sh... read more

shemale lover October 29, 2014 100%

Ann Part 2

The next work day, that evening as I walk up to my townhouse, Ann is sitting on the porch and tells me, “Since you didn’t call I thought I’d come by, I was in the area anyway.” Even though I’d been with her the night before, I have to laugh and Ann asks, “So wh... read more

shemale lover October 31, 2014 93%

Shemales in Barcelona

Due to my job, I had the opportunity to travel a lot. Once I had to travel to Barcelona and the complexity of the meetings required that I had to stay there for about 2 weeks for consultations with customers. After long working hours, normally we went for a nice dinner (nothing better than begin the... read more

shemale lover November 1, 2014 81%

Brief Encounter

On the way back from Sidcup one evening last Summer I was busting for a piss. Getting near Croydon, I was looking for either a toilet or a wooded area. They seem to be closing all the toilets down nowadays. Just as I was near the stage of wetting myself, I noticed a sort of drive-in between bushes s... read more

shemale lover November 3, 2014 88%

I want you used!

I'd been Will's little CD slut every time that I'd overnighted in his city for about a year. That was one night every other week. He was always very good to me, bringing wine to my room and spoiling me with his gentleness as he had his way with me. He loved to have me lie still while he teased me al... read more

shemale lover November 5, 2014 84%

Crossdressing fun

I always love to crossdress when Im horny I love the feeling of being a woman and seducing a man. Older men have always attracted me here is my fantasy. I dress up one day with a red thong red bra black nylons short skirt and blouse and get online. I find a man who likes me and is ready to play. I c... read more

shemale lover November 7, 2014 80%

Heather and Lori

This a true story about me and two very hot TS friends. I was down in Ft. Lauderdale and had hooked up with Lori and Heather. Two friends from my NYC days. They had relocated to Florida and told me to stop and see them when I came through. I met up with them at their apartment and we opened a bottle... read more

shemale lover November 9, 2014 95%

When I realized I was Bye and gay

I was a late bloomer I got married had kids bought a home had all the things to make a happy home but I was restless i needed something else. I was going out with other women about once a week and it was fun and sometimes very hot i even had a few three somes but I always felt I needed something ... read more

shemale lover December 9, 2014 100%

Job Description

My life changed recently and I’m still trying to figure out if it’s for the better. My name is Don and I’m 18 years old and fresh out of high school. My grades weren’t good enough to get me a scholarship and my parents make too much money to qualify for government money. So a... read more

shemale lover June 13, 2011 87%

How I Became a 'SHAMAN

Every one is programed by society to play a certian role in life,that they are taught is reality,how ever, the truth is reality is what ever you want to make it! this is what magic is all about,making your own reality. I played the manly role in life for fourty-four years until I realized this,and b... read more

shemale lover November 11, 2014 35%

Lady Blue

“Blue-eyed boys always get me in trouble,” she said in a sultry tone with an equally sultry smile. I smiled as I looked into those warm brown Latina eyes, so soft yet full of mischief. “I’ll be back in a sec guys,” said Tracy as she got up from the table and headed ... read more

shemale lover November 13, 2014 94%

Caught in the act

After my first encounter with John’s dick, I couldn’t get it out of my mind. Two weeks later we met at a friend’s party and we talked about it. He was worried his girl friend might find out. I told him he had noting to worry about as I had as much to lose as he had. But I also said... read more

shemale lover November 15, 2014 89%

Miss Tiffany Fulfilling Her Dream

Finally, I had everything I needed to dress up for a little fantasy today. Ever since I was a little boy, I had always thought my neighbor Steven was extremely handsome and sexy. At 6 feet 3 inches, Steven is exactly what is described as tall, dark, hard tone and muscular. Tonight, I would finally h... read more

shemale lover November 17, 2014 94%

One Night In Heaven

As I arrived at Ginny’s place she met me at the door dressed In a see thought black dress stocking clad legs and high heeled shoes We kissed and cuddled a t the door and then she turned round to lead me into the front room. As she turned I saw her sexy ass and my cock started to get hard. ... read more

shemale lover December 5, 2014 90%

My Girlfriend's Friend Shayla

I walk up to the door of my girlfriend’s apartment. As I start to slide the key into the lock, I can hear slight muffled noises from inside. As the door slowly opens, I am met by the sight of my girlfriend laying with her legs spread wide open on the couch and her super sexy friend Shayla, w... read more

shemale lover June 14, 2011 100%

Practically gang at a sex club!

About 6 months ago I went to my local sex club in Sydney. It was only about 8pm and not much usually is going on at that time. On the 2nd story there is called the "Orgy Room" a place where people go and sit on the bed with no locked door and it's just first cum first served. I stuc... read more

shemale lover June 14, 2011 84%

Painted Laddie for Mr. R

Gabe had had many strange photography assignments for the eccentric, but very rich Mr. R, an avid collector or erotica, but this was perhaps the most challenging. The money was better than good, however, and when he’d put a little thought into it, Gabe saw little problem in the execution of th... read more

shemale lover December 7, 2014 90%

The Convoy

Several years back I was driving down I-95 south through South Carolina. I was dressed in fishnet thigh highs; platform heels, g-string, bra, all black. Over it was a black zip up the front mini dress. I had a hand held CB radio so that I could hear truckers talk about me as I passed them, and I'd b... read more

shemale lover December 11, 2014 75%