Free Shemale Stories

Seduced Willingly

Finally, I moved to a city that was exciting, Miami. I moved to Miami looking for something new and adventurous. I grew up in very conservative town where nothing exciting went on. In Miami I found different languages, gay people, different ethnic persons, art, and culture. However, my job keeps me ... read more

shemale lover April 16, 2012 92%

European Vacation

I was 18 when I first went to Europe. That month would change my life. My parents had died when I was five, and I was raised by family friends; they also controlled my trust fund. It's not a coincidence that I went to Europe just as I came into control of the money. I loved my foster-parents, but... read more

shemale lover April 21, 2012 100%

Beefy Buns

It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... read more

shemale lover April 22, 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%

Lady in the House

How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended u... read more

shemale lover May 12, 2012 100%

Bethany's First Bra

1 I think it was on our third date that I first learnt of Greg's 'preferences'. We were sitting in the cafe, having just seen the latest Woody Allen film, discussing whether it was funny or not. [I thought it wasn't. He loved it.] There was a few seconds' silence, save for the sound of the other pe... read more

shemale lover May 25, 2012 100%

Betrayed Chapter 3

There are, perhaps, a half-dozen places in the city to get a really good "big piece of meat" – at least, of the gastronomic variety. Morton's on North State Street is one of those, and a great place to see and be seen by everyone who is anyone. We valet-ed the Mercedes, then made our... read more

shemale lover May 29, 2012 100%

The Making of A Sissy Part 12

Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as... read more

shemale lover May 31, 2012 83%

Training Sissygirl Part 3

Sissygirl stood, shaking a little as the tall and well-built males crowded about her soft and vulnerable body, the scent of their glistening cocks making the poor t-girl delirious; she knew she had no choice but to strip. The men stroked their cocks as the pretty sissy meekly began to remove her clo... read more

shemale lover June 10, 2012 50%

Birthday Party

It was now about 11 pm and Sue and I have been at it for the past 3 hours. Sue had me get up and go into the bathroom. As I stood in the shower I thought of what we did. Sue knew how to pull the right strings on me or in me. And she knew what pleased me. I washed all over. I had no idea of what was ... read more

shemale lover June 14, 2012 75%

Caught by Dave!

Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed. No one I know even suspects that I'm a slut at heart or that I am the least bit bi. But more and more I keep fantasizing about one of my male friends. He's very good looking and keeps... read more

shemale lover June 15, 2012 100%

Dark Temptation

Ella's body glistened with perspiration as she twirled and spun her lithe body on the dance floor, loving the way the beat of the music thumped around her. The twenty-one year old loved Brighton's laid back, hippy, music generated atmosphere and long ago had fallen into dancing until the sun came up... read more

shemale lover June 22, 2012 88%

Birthyday Party Chapter 2

It was now about 11 pm and Sue and I have been at it for the past 3 hours. Sue had me get up and go into the bathroom. As I stood in the shower I thought of what we did. Sue knew how to pull the right strings on me or in me. And she knew what pleased me. I washed all over. I had no idea of what was ... read more

shemale lover June 24, 2012 100%

Bisexual Black Man's Paradise

The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... read more

shemale lover June 24, 2012 80%

Crossdressed bondage

She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or sometimes porn careers. Sometimes they had been bought outright to be used as sex slaves, but always they had gone in ... read more

shemale lover June 25, 2012 100%

Fantasy Reversal Chapter 6

It was late and the sun was shining through the window. The clock on the stand showed it was just before 11am. My hands wandered, to confirm I was still Katrina. As I did I recalled the night of dancing, well actually stripping and how turned on I felt. In particular, the sensation and thrill as Sam... read more

shemale lover June 30, 2012 100%

A Strange Affair

"I think you'd better come in," said the blonde-haired woman. She opened the door to the apartment fully, and stood aside as I walked through the door. She was attractive enough -- it was hard to see why her husband would want to cheat on her. She was very tall, and made taller by her b... read more

shemale lover July 1, 2012 100%

A Toy Party Story

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it... read more

shemale lover July 9, 2012 100%

Sissygirl's sweet Adventure Part 2

Sissygirl was a only a little nervous as the cab dropped them back off at her apartment; she had made sure everything was ‘just so’ at her place; a sweet perfumed incense hit their nostrils as she as eagerly gripped his hand and pulled him through the front door for the first time. Her h... read more

shemale lover July 10, 2012 100%

Becoming Alanna Part 1

My name is Alanna Monroe and i am currently a college bound 17 year old senior at St. Anne's school for girls in Middletown Conn. I was once Alex Monroe, but after one fateful day four years ago, I became Alanna. Being a proper “lady”, i have all of the assets of my classmates...well tha... read more

shemale lover July 12, 2012 42%