Free Shemale Stories

by a Shemale Part 2

I was awaken early Monday morning when Felicia lightly kissed me on the cheeks and said it was time to start my hormone regimen. I looked at her and she had her left hand opened and she had a white pill and in her right hand a glass of water. I was no longer fighting or resisting especiall... read more

shemale lover August 29, 2011 100%

Shemale Fantasy - Suck Fest

This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... read more

shemale lover September 13, 2011 100%

Dance of Lust

I'd landed it. The hottest girl in school, Adelle, was dancing with me, the quiet, slightly-feminine-bodied guy nobody knows, at the school's Christmas Dance. But everyone would know now. The last slow song had just played, and all the while I knew both of us were thinking the same thing: my plac... read more

shemale lover September 14, 2011 100%

Gloryhole slut last night

Well I was a horny slut last night and went to this little arcade in the city last night. Fully slutted out and in a new pair of silky nude hose I was hoping not to be disappointed....I was not! I payed my fee and went into the back to the booths where there were a massive amounts of guys in the ... read more

shemale lover September 25, 2011 100%

Connie at an Adult Bookstore

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by i... read more

shemale lover September 30, 2011 100%

How i became a girl

Hi my name is Mandy and this is my story..in parts. I started dressing when i was in my early teens. At first it was just panties, maybe pantyhose and masturbating with my friend B, but it soon became wearing skirts and heels, little tube tops and sexy dresses, then it was makeup and wigs, and soon ... read more

shemale lover October 22, 2011 100%

Trying It On For Size Part 2

I looked up and saw the low slung scrotum swaying above my eyes, the long, thick, curved shaft pointing upward just in front of it. I heard a quiet tearing sound,"schshhhtt," looked further up and saw Tanya opening another one of her black foil Magnum condom wrappers. She placed the large,... read more

shemale lover October 26, 2011 100%

Birth of a New Sissy Part 3 Completion

I suppose at some level I knew it would happen. Or at least I should have. After nearly a month of servicing Jeff's cock and fucking myself silly on my dildo lover things took a turn. I came home from work a little early on a day Laura was off as well. When I got home she was out, but as soon ... read more

shemale lover November 17, 2011 100%

Seven Lessons Part 1

Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it ... read more

shemale lover November 30, 2011 100%

A night to remember

Josie wasn't a girl a man would turn his head for if he saw her on the streets. She was a small, petite girl, her breasts barely an B cup. She was wearing her light brown hair in an inconspicuous short cut and the thick glasses she needed for being able to see anything in her surrounding, didn'... read more

shemale lover December 11, 2011 100%

TV television

My girlfriend Gloria and I had just moved into an apartment together, having gone out for six months or so, before making the committment. We moved in furniture from each of our apartments, after deciding what would go best in the new place. With the exception of a television, we really had everythi... read more

shemale lover December 11, 2011 100%

The Hotel

The hotel room door clunked shut as we stood there embracing each other. The trip to the south coast had taken around three hours and I had plenty of opportunities to look across at Rachel's legs as I drove. Perhaps I should rephrase that - I had three very long hours of torment as I had just wanted... read more

shemale lover December 28, 2011 100%

Tilted Kilt Chapter 3

Girls Only Party I drove down to my sister Katie's house in Carlsbad on Saturday morning to spend the weekend with her and her girlfriend Brandi. I live in North Orange County so it was only an hour drive. She's 25 and I'm 24 so we grew up together and were always friends. We shared our lives and... read more

shemale lover January 25, 2012 100%

Hermaphrodite Obsessions

Through the years Chris had developed a magnificently hard body. He had played football in high school and college and as the quarterback had always been a much sought after date. Even though he had many offers from cheerleaders and coeds he had never lost his virginity. Chris had fooled around with... read more

shemale lover February 7, 2012 100%

A Brief History of Tina

1 - Monday It really has been one hell of a week and more to come maybe, though I really am not sure how this is all going to work out. An awful lot has happened since last Monday, I am just beginning to make sense of it. Or at least, some sense. On Monday I decided to 'shake myself out of it'... read more

shemale lover February 8, 2012 100%

My surprise

I have always been straight. I have a wife and kids and me and my wife have always told each other our secrets but there is one that she doesn’t know about. I was in my 4th year in high school and I liked this girl. She was a very pretty looking girl but she never seemed to have a boyfriend... read more

shemale lover February 19, 2012 100%

A Crossdresser Gets Fitted

Not long ago I was out shopping and stopped at one of the clothing outlet stores that I frequent when looking for sexy clothes and shoes to wear when I go out clubbing or to wear in my adult videos. I was looking through the display rack of my favorite brand of pantyhose, trying to find the colors I... read more

shemale lover February 25, 2012 100%

A Day Driving in the Country

Day off, out for a drive. What a predicament, standing on the side of the road next to my open car door with my hands straight up in the air; looking down the barrel of a Highway Patrolman's handgun. I'm about to pee my pants, that is what little bit of pants I have on. The Highway Patrolman is d... read more

shemale lover February 26, 2012 100%

A Natural Sissy Part 4

The Next Day I was up early, and called to set up a surgery for Stacy’s breast enhancement. The hormones were working but his tits seemed to have stopped growing at a B cup. I wanted him really top heavy. At least a D cup, maybe a DD. I let the exhausted sissy sleep. As I was finishing u... read more

shemale lover March 24, 2012 100%

Becoming Paula

I work in an office with 15 coworkers about 11 of them are women. I get along well with my coworkers and go out of my way to be helpful. I find it is more fun to work with friends than to work with strangers. My name is Paul and I work in an insurance claims office processing claims and making recom... read more

shemale lover April 5, 2012 100%