Free Shemale Stories

Anal Queen

Amanda fell to her knees in the darkened theater and slowly unzipped my pants. My cock throbbed. As she pulled down my underwear, I felt my manhood spring forth. Amanda took the whole sausage into her warm, soft mouth. I could barely see her face in the darkness, but I could feel her between my l... read more

shemale lover November 24, 2012 66%

A Job in the Theatre Chapter 20

"Be careful Rex," Ted pleaded. He was tied to the four corners of his bed with a pillow shoved under his ass. He felt completely helpless. It was a feeling that he was not used to. He was always in control, had everything worked out. Not this time. He barely knew Rex. The one thing he did ... read more

shemale lover March 15, 2012 100%

Earning a Dollar

Being an escort was proving to have many advantages lately, being insatiable I'm thankful business was good. The limousine ride to the city seemed so long ago, though it was just 24 hours ago. Here I was getting dropped back off at my humble apartment wishing that somehow I could start the previous ... read more

shemale lover March 30, 2012 100%

Why I’m a Cock Whore!

Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... read more

Samantha Cummins April 18, 2023 100%

Andy as Mandy Lose His 'Virginity'

Andy continues the tale where Polly left off... just heading home after a trip to the sex shop. I couldn't really believe what was happening to me, nor what had happened so far. I had just walked out in town as a slim and sexy woman, with my new friends in tow and my cock tightly constrained in t... read more

shemale lover November 28, 2012 100%

First time Crossdressing

I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... read more

shemale lover July 17, 2013 37%

My first encounter

I started dressing in my s****r's clothes when I was about 11, she would have been around 13 then. It was wonderful, just Mother, s****r and me at home so when I got a little older, I promoted myself to Mother's clothes. She was a real fashionista back in the 1950s to 1970s, always very elegant and ... read more

shemale lover January 6, 2012 80%

First Time

I'll start with a description. I'm 46 years old 6' tall and fairly thin. Oh and I'm a cross-dresser that when dressed goes by Lisa. I have been for years. Don't know why other than it pleases me. I love the feel of stockings and garters and for a few years now have gotten to where I enjoy having a n... read more

shemale lover October 2, 2012 100%

Bi male and anal sex

Thru out my adult sex life I have always enjoyed having my ass teased and played with. Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. Then one night things changed. After a hot night of wild sex,... read more

shemale lover October 10, 2012 100%

My sissy secret

I am a male, but I have a secret. In private I dress as a beautiful sissy and no one knows. I have a large selection of lingerie and outfits, that make me hard when I wear them. Recently things have got even more exciting, since I've discovered how horny performing things on web cam. I don't car... read more

shemale lover June 18, 2013 90%

Erotic Dreams come true.

You start having intense erotic dreams — and the faces you see is one you don’t recognize but that feels familiar. Mandy was that girl that Chad had been dreaming of, the kind where to see her made a rush go through you like a hot flash. Chad had just broken off a relationship, and his sister war... read more

Jon Paul May 26, 2023 100%

Dressed in holiday style Part 2

I was up by 1 p.m., showered, changed into some fresh panties and donned some hated boy clothes to hit the streets. I stopped by a local coffee shop (not the national chain-brand type) and over a mocha latte the barrista was kind enough to give me a few pointers about where she thought the best holi... read more

shemale lover November 20, 2011 100%

First Time

I'm not really sure how I ended up where I am. However, the events below are true and only the names have been changed. It happed to me over 15 years ago and my life has never been the same. It was my freshman year of college, being 35 in the middle of a mean divorce I decided to sell my condo an... read more

shemale lover September 28, 2012 100%

Anal Therapy

My new psychiatrist wasn't at all what I expected. When I saw her name in the phone book, I pictured a dowdy old lady wearing a long, gray skirt and flat-soled shoes. What else could Dr. Edith Doss look like? I got my answer when a tall, leggy redhead stepped into the waiting room. A tight, black... read more

shemale lover November 24, 2012 78%

My first shemale sex

I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... read more

shemale lover July 17, 2013 94%

mein erstes mal

Nur ein paar Häuser weiter wohnte Bernhard, 56 Jahre alt, hatte einen kleinen Bauch, sonst aber sehr gepflegt. Seit 3 Jahren war er geschieden und lebte nun alleine. Schon seit einiger Zeit besuchte ich ihn regelmäßig, um in seinem Pool zu schwimmen, um ihm manchmal im Garten auszuhelfen oder einfac... read more

trans_sabine October 3, 2022 100%

My Last Duchess

"I'm happy to do it, of course," Thaddeus said, "but, remember, that every correction--" "It's not a correction," I interrupted. "--or revision," Thaddeus continued, "is an extra hundred dollars, minimum." "Fine," I said. I wanted ... read more

shemale lover September 22, 2011 100%

Party Surprise - First sex as a Crossdresser

This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... read more

shemale lover May 21, 2012 100%

First Time Fantasy

I'd never had a real experience before. Years of wearing panties and fantasizing, but nothing legitimate. I imagine it's the same story as many other panty lovers: started when I was about 13 by stealing some of my mom's things. Bras at first, then panties. Soon I began looking forward to being home... read more

shemale lover October 14, 2012 100%

First Time With My Best Friend

My friend John is really sexy. He is tall and blond with a lean strong body. I have often imagined what it would be like to have his sweet cock between my lips, or between my virgin buns. He’s too good a friend though, and I’ve never had him give me any hint that he might like to be with... read more

shemale lover October 30, 2012 100%