Free Shemale Stories

Passionate Sex with a Beautiful Shemale

a man and his shemale lover get down to business Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sa... read more

shemale lover March 23, 2014 86%

First work day!

Having just graduated from college in Miami I took up fashion as a career! Impressed? In fact, I managed to land a job as a clerk in ready-made clothes shop. Sounds not as impressive as I’d like to have but that is just a beginning. You think there are no other interesting places in the whole ... read more

shemale lover May 31, 2014 100%

Two girls out for a night on the town

Some of my best friends are transvestites. I met them at a nightclub in L.A. It was pretty famous back in the day. They had a drag and dinner show. Some very talented people worked there. Some actually lived their lives as women, but a lot didn't. I used to hang around with Daniel. He was a very att... read more

shemale lover July 9, 2014 86%

What I do best

I lick my lips and taste the gorgeous deep red lipstick applied so carefully; I glance at my image reflected in the minicab windows and gaze at the evening revellers as they make their way to the clubs and bars in London’s West End. I am amazed that here I am dressed as a complete slut in an o... read more

shemale lover October 13, 2014 100%

Lady Blue

“Blue-eyed boys always get me in trouble,” she said in a sultry tone with an equally sultry smile. I smiled as I looked into those warm brown Latina eyes, so soft yet full of mischief. “I’ll be back in a sec guys,” said Tracy as she got up from the table and headed ... read more

shemale lover November 13, 2014 94%

My Filipina transsexual penpal

I too feel very attracted to Ladyboys, especially Asians. Since I started looking at the Ladyboy sites a part of me feels deperate to one day date, and maybe even be with a transsexual the rest of my life. I feel that I will never be sexually complete until I have finally had sex with an Asian Ladyb... read more

shemale lover July 3, 2015 50%

Shemale Love Story - part 2

He slid his tongue all around the head, the peeled her foreskin back, and started to suck just the sensitive head. She was in heaven! No one had spent this much time worshiping her cock before! She moved her hand down to jerk off, but he pushed it away. She realized that he had not removed his cloth... read more

shemale lover October 7, 2015 95%

Victoria

I started towards the local theater in my Chevy Corsica to see the midnight showing of some sort of vampire movie. I guess it was a love story where this one girl falls in love with a vampire and vice versa. Oh well... supposedly the books were popular, so might as well see what all of the hype is a... read more

shemale lover May 8, 2016 95%

Shemale Dating

We arrived late in our hotel room. The date was going well... but I didn't know what to expect, being new in shemale dating - I was excited and a little scared at the same time. She was a beautiful Latina: busty, dark exotic skin, fantastic lips; we couldn't stop kissing each other in the elevator. ... read more

shemale lover February 12, 2017 69%

We’ve First Met Her At Shemale Chat Room

I know it’s lame. Being a regular visitor at a shemale chat room is not something that I was proud of. However, I live in a small town and I can’t just go out and find a shemale. And I craved one so badly! It’s kind of embarrassing for me to talk about it now, but at the time I ... read more

shemale lover August 11, 2011 100%

2 Girls Out for a Night on the Town

Some of my best friends are transvestites. I met them at a nightclub in L.A. It was pretty famous back in the day. They had a drag and dinner show. Some very talented people worked there. Some actually lived their lives as women, but a lot didn't. I used to hang around with Daniel. He was a very ... read more

shemale lover August 14, 2011 100%

Out of Town Meeting

Dinner was seamless, the food, the music, the wine, the company. Tony’s out of town business meetings were usually painful, in that he hated living out of a suitcase and eating alone in overpriced restaurants. This trip, he was enjoying every second of it. He’d met up with Chantal, a wom... read more

shemale lover August 14, 2011 50%

Transgender Storylines

Stories about transsexuals and transvestites typically involve one or more standard themes concerned with such characters' treatment of themselves, their treatment by others, their treatment toward others, the events and circumstances of their transitional period, their outing themselves or being ou... read more

shemale lover August 28, 2011 60%

An Appreciation Part 1

Andrea Dworkin has long opposed pornography. She has also rejected erotica. This essay is a refutation of Dworkin's position. Allow me to begin with a quote from a SilkyOne Literotica story, "Silky 09.' Someone tells Silky (the eponymous heroine of the Silky Series) that she is Gorgeous. ... read more

shemale lover September 7, 2011 50%

Modified Covers

As a hobby, some artists enjoy modifying vintage magazine covers so that their original topics are transformed into transgender themes and shemale models replace the female faces and figures that originally graced the periodicals' covers. In the process, the titles of the magazines are sometimes cha... read more

shemale lover September 9, 2011 100%

Down and Out

Our divorce had been final for three months. I was devastated, my wife had been sleeping with her boss for a year before she finally got the courage to admit it and ask me for a divorce. I felt horrible. I stopped exercising and started eating poorly, gaining more than twenty pounds. I felt like a l... read more

shemale lover September 14, 2011 83%

Shemale Art and Artists

Several erotic artists specialize in comic books, cartoons, or illustrations that feature buxom hermaphroditic, pre-operative transsexual (shemale), or t-girl characters. Such shemale art ranges in style from three-dimensional, computer-generated images and anime, hentai, or manga comic book-style s... read more

shemale lover September 22, 2011 50%

Bitch Maker Part 3

"Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay there silent, his cock trapped in it's new c... read more

shemale lover September 23, 2011 100%

The Installment Plan

“I never heard of anyone buying a Versace gown on layaway,” Karen, the fresh-faced young blonde said, admiring the designer dress on which her customer had just made another payment. Shaped to flatter, the gown was a gorgeous peau de soie satin. Its boned bustier created an incredible... read more

shemale lover September 28, 2011 75%

Downloaded Lust

That was the sexy signature I posted with all my stories, the erotic invitation I issued to my readers. Usually, they'd just reply with a sexy thank-you, and maybe share a fantasy. Occasionally, though, I would get an email from someone who wanted to meet. They were usually men who'd fantasized ... read more

shemale lover October 23, 2011 50%