Free Shemale Stories

Tranny suck me off

I have a new found love for trannys I love convincing polling tv,ts and cds. The other night i met a tv from Halifax a town close to my home town. Wed arranged a meet online I d agreed to pick her up on a street corner like a cheap street walker. I pulled up at the side of the curb and a woman stepp... read more

shemale lover December 14, 2011 62%

Taken and in Public Part 3

I tried to go to sleep but was just so horny; I wanted to dress up again; I wanted to go out; I wanted to be fucked! All these emotions were running thru my head and I just lay there. My mom told me she would be starting the 7pm to 7am shift at the hospital for some time and thought I should get... read more

shemale lover January 14, 2012 100%

Trannie in Training

Caught Again Things have been great since I started my new job and secret life as a crossdresser. I have had a lot of experience dressing and actually passing on the street as a woman. Actually a very sexy woman at that. The visits from my supervisor were always memorable and he has taught me ... read more

shemale lover February 2, 2012 100%

Becky's Video

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later -- all men had some, somewhere. A few days later, I'd completely forgotten... read more

shemale lover February 25, 2012 100%

Daddies New Girlfriend

Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... read more

shemale lover March 9, 2012 100%

A Murder Misstery

When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the younge... read more

shemale lover March 20, 2012 50%

A Natural Sissy Part 3

The Reward Once we were at home, I still couldn't keep Stacy quiet. "When do I get my reward, Mistress Gail?" repeated every other breath. Constantly. Finally, after I had changed into my bedtime attire (a pair of 4-inch heeled mules, and a see-through short nylon robe, in pink, like my... read more

shemale lover March 24, 2012 100%

Freshy

It was to be my first day of highschool. I had spent a week out of town on the East coast and had already missed the first three days of school. I had my class list, books and the usual items and went to school. School was kind of a bore during the day. Finaly 8th. period came along. As I was aproac... read more

shemale lover April 26, 2012 33%

Head Cheerleader Mikki Part 3 Michael is Back

To understand this story you must read the previous chapters. It's Sunday morning and I'm just waking up. I'm in bed alone. As I get up I see myself in the mirror. Still dressed in powder blue lingerie and a blonde wig. I wonder where the girls are. I leave the guest room and go into mine. I stri... read more

shemale lover June 14, 2012 100%

A Sissy Surprise

I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs. I walked into th... read more

shemale lover June 15, 2012 90%

Extreme cuckold

There i was typing away on the keyboard chatting to others in the hope of a meet up for dressed up playing together. The private screen popped open to reveal a message from a genuine girl requesting a chat, well as I was there and hopeing for a meet what was there to lose, she started by the intr... read more

shemale lover June 19, 2012 40%

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%

Blame Abba Chapter 4

Part 10 Jeff again It was about half an hour before closing time that Saturday. Eric had just sent me off since we were very busy and I hadn't had a break since we opened. I sat in the back room, behind the bar, sipping on my lager. Then Jeff appeared, looking very sheepish, at the door. "... read more

shemale lover July 18, 2012 100%

Fender Bender

It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one... read more

shemale lover July 26, 2012 100%

Dear Karen

01.06.09 Dear Karen, I just want to tell you what a pleasure it was to meet you at the contract negotiations last month in San Francisco. Because of you, it was a delightful trip and one that I hope to make again soon. You are such as beautiful and loving person. You showed me the absolute ecs... read more

shemale lover August 5, 2012 100%

My biggest ever-scary, but rue!

Since I'm pretty much sub, I don’t really ever say no, but maybe sometimes I should? I got an IM from a guy on a hookup site I sometimes visit and after a little bit of chit chat about the weather and what sorts of music etc we liked, he invited me to his place for an afternoon of fun. I'm usu... read more

shemale lover August 14, 2012 100%

Yellow Polka Dot Bikini(s)

"She was afraid to come out of the locker. She was as nervous as she could be. She was afraid to come out of the locker. She was afraid that somebody would see. Two, three, four, tell the people what she wore. It was an itsy, bitsy, teenie, weenie, yellow polka-dot bikini that she wore for the ... read more

shemale lover August 22, 2012 100%

In Hose and Heels for Daddy

It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and... read more

shemale lover September 30, 2012 90%

Double Take Chapter 3

Sandy and Ashley switched off the television and stared at one another in disbelief. Normally, they didn't stay up to watch the network telecast of Wet Girls, which came on at 10:00 on the west coast. After all, they had to get up at 5:00 the next morning. But they knew the entire country would be t... read more

shemale lover November 3, 2012 100%

Mi primo y yo (2da parte (historia con mi vecino))

Bueno ahora toca el turno a la historia que les prometí con mi vecino. Recuerdo bien que todo comenzo un dia que mi primo y yo estábamos solos en mi casa como de costumbre por uno de los tantos viajes de mi familia, ese día me arregle super linda para mi hombre pues había comprado un conjunto de ... read more

Janin December 27, 2019 100%