Free Shemale Stories

Headmistress' Favorite Sport Part 6

At Mistress Rachel and Master Tony's house Denise was pushed into the role of maid along side her mother, Susanna. Susanna had been reshaped exactly as Mistress Rachel wanted it. She was now a devoted little nymphomaniac slave who loved her mistress and master and who would do anything for them. Lik... read more

shemale lover December 13, 2011 100%

Headmistress' Favorite Sport Part 7

At the academy Denise and the others immediately resumed their old routines. The training for the second year slaves had started a few weeks before the new batch of sissies arrived at the academy. Not many new elements were introduced in the training as the second year was mostly about perfecting th... read more

shemale lover December 13, 2011 0%

Bukkake and Gokkun

Bukkake and gokkun were introduced by the Japanese, who are nothing if not imaginative and creative in their depictions of pornography, especially of the sadomasochistic and bondage and discipline varieties. Rabid feminists are not apt to like bukkake or gokkun. They tend to see even heterosexual... read more

shemale lover December 15, 2011 57%

I am Baaack! Part 1

PROLOGUE: Ross Thorn, aka Nick Mitchell, paced back and forth in his office high up in the Hancock Building. He glanced out the corner windows. North you could see out over Chicago's North Side to almost as far as Wilmette, and east out over the lake almost to Michigan. It was a perfect spring da... read more

shemale lover December 15, 2011 50%

I am Baaack! Part 11

Now Rose upped her sincerity level. "I want that kind of friendship with you, Joan! I believe we are kindred spirits. If two manipulative bitches like us CAN be friends, I think we should be. I did this little scenario today as a show of skill, inclination, and sincerity. Could I do to other me... read more

shemale lover December 17, 2011 50%

Glory Hole Girlfriend

My boyfriend likes to take me to the local adult bookstore, into the back where the video arcade is. There's always a lot of men there, strangers that we don't know, and I feel funny when they look at me. They wonder why a pretty young woman would be back there. It smells too. A rich sweaty sc... read more

shemale lover December 18, 2011 71%

Being Twins

I knew something wasn't quite right but I couldn't be sure. My life for the past 10 years with my wife Jane was great. My name is Richard. Jane was 5'8", 120 pounds, lean trim body, 38D breasts, beautiful blonde hair and stunning features. I was 5'9", 148 pounds, and little chest or body h... read more

shemale lover December 19, 2011 100%

Debbie Part 7

As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... read more

shemale lover December 23, 2011 80%

Magician's Assistant - Friends & Lovers Part 2

Magician's Assistant - Friends & Lovers takes place in the Magatrix the Magnificent Universe, which was first introduced in my serialized seven-part story, Magician's Assistant. The premise upon which both that story and this story are based revolves around the fact that Magatrix the Magnificent... read more

shemale lover December 25, 2011 50%

Magician's Assistant - Friends & Lovers Part 10

Magician's Assistant - Friends & Lovers takes place in the Magatrix the Magnificent Universe, which was first introduced in my serialized seven-part story, Magician's Assistant. The premise upon which both that story and this story are based revolves around the fact that Magatrix the Magnificent... read more

shemale lover December 26, 2011 50%

The best sister ever Part 3

As always yes my sister is a shemale and yes this is all true every word of it. So since we have formed our new relationship we have been fucking not stop for about 4 years now so im 14 and my sister is 16 years old. I have now a thick 6" hard cock and my sister has a huge 7 1/2" cock a... read more

shemale lover December 27, 2011 66%

Dirty Tranny gang bang

Deep breath Charlotte, step into the night air and strut your stuff girl. This is what I was born to do; I snuggle into my short white fleecy coat as my 5” platform heels click on the pavement. Glancing down I can see my shapely stocking clad legs and, the all important, ankle bracelet glit... read more

shemale lover December 27, 2011 50%

One Torrid Night

I had no idea how a sexual impulse one night while we were fooling around would excite us so much later. We have been married for nearly 27 years and we have just found our love life again after some barren years. A year previous to this story I had come out of the closet and told my wife about my c... read more

shemale lover December 28, 2011 50%

They Were Right

They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... read more

shemale lover December 29, 2011 87%

How I Learned To Love Drag Part 7

The first two shows seemed to be unqualified successes. We had many solid skits that I thought were hilarious. But an Attack of the Clones parody had been scrapped. It would take a lot of work to either find a suitable location or to create a futuristic set. And the costuming costs might put a st... read more

shemale lover December 30, 2011 50%

How I Learned To Love Drag Part 8

When we stopped shooting to break for lunch, I hurried off to visit the men's room. Or rather, the washroom in my dressing room. Walking into the spacious dressing room area, I could see that Daniel and Sean were still hard at work. Daniel, with brush in hand, was styling an auburn wig. It was lo... read more

shemale lover December 31, 2011 50%

How I Learned To Love Drag Part 9

Standing in front of a full-length mirror in my private cubicle, I was almost ecstatic! Looking back at me was a buff, naked Sharon Stone. The blonde hair was pulled back neatly into a bun. She had that beautiful sultry smile, those perfect teeth, full lips, dark immaculate eyebrows, smoky smo... read more

shemale lover December 31, 2011 50%

How I Learned To Love Drag Part 11

At the bull session to begin the week, we kicked around a lot of different skit ideas. Dave brought up the topic of gay marriages. We ran with that concept for awhile. Then we took a stab at the film Spiderman. The possibilities were enormous, though potentially expensive. I suggested we do... read more

shemale lover December 31, 2011 50%

How I Learned To Love Drag Part 12

Sometimes when you hear a song on the radio, you like it immediately. You turn up the volume to full blast! The melody, the lyrics, and the beat just make you feel like dancing! Whenever, Wherever is such a song. I played the CD whenever I had the chance and wherever I could. Moreover Shaki... read more

shemale lover December 31, 2011 50%

Witch Chronicles

I have been asked to write down my perception of the events of the war. After what's just happened, I thought it best to wait and rest before writing things out, but the big wigs want me to get it all down while it's still fresh, so don't expect this to be an extremely military report. I... read more

shemale lover January 1, 2012 100%