Free Shemale Stories

My first shemale

This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when... read more

shemale lover February 12, 2012 94%

MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... read more

shemale lover December 1, 2013 88%

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 August 14, 2013 90%

His first anal!

Andrew was a very simple guy. He was not aggressive, very quiet and nice. Actually he was not quarrelsome, just a man of peace. But we all know that still waters run deep. Over the past few years, Andrew had longed for being penetrated. Vehemently. He needed to be bent over something and fucked thor... read more

shemale lover May 9, 2014 70%

First Time - Surprise Shemale

I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so ... read more

shemale lover September 19, 2014 87%

Hung Shemale has Motorcycle Trouble near Vegas

I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... read more

darrell February 2, 2024 100%

Las Vegas Swingers

It had been over 6 months since I seriously dated someone, and I was getting depressed and in a rut. I had directed my attention to my work and it kept me from feeling sad about my loss of someone I almost married. I had met a transsexual girl that absolutely adored, but she was tragically killed. (... read more

Jon Paul June 11, 2018 83%

A Shemale Vacation Part 2

We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... read more

shemale lover September 5, 2011 100%

A Perfect Pandemic: A Transsexual Transition in a Troubled Time

A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... read more

the greatest liar November 16, 2021 100%

C'EST LA PATRONNE

Le rêve est mort. L'écriture était ma passion, mais cela n'a jamais servi à rien. La réalité a une mauvaise façon de vous rattraper, déchiquetant vos désirs dans son sillage. Ce cycle d'épargne et de vie de ces économies s'est progressivement révélé intenable et maintenant, à ving... read more

Femboy 2021 February 6, 2023 100%

My Girlfriend's Mother Has a Secret

A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-). Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pr... read more

shemale lover February 27, 2015 98%

Aunt trip

In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... read more

Rebba April 25, 2024 75%

Oh My, You Have a Cock...

It was a regular Friday night no different from others I'd experienced before. I was lonely having broken up with my girlfriend earlier that week. What a bitch! I needed to find me a sweet woman capable of matching my libido. My last lady was all about the lights off, missionary position sex, come t... read more

shemale lover August 9, 2013 88%

The Experience of a Lifetime

My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... read more

therefill05 November 30, 2020 100%

Tasting the good FLESH

I am no longer Virgin, en bon et du forme Thing never dared since I taste the enjoyment by all the senses and in all its senses... I discovered her when she smiled at me as a thank-you for giving her the way to the small-town supermarket where I was on business. Sandals at her feet of Cinderell... read more

hippocampus_171 November 10, 2022 100%

Dame et jardinier

Piotr se tenait sur les escaliers de la villa de Klonowa Street, située dans le quartier à la mode et riche de sa ville. Il était environ midi par un chaud samedi de juin. C'était son dernier arrêt ce jour-là. Il avait déjà collecté l'argent des autres clients avec lesquels il traitait des jardins, ... read more

Femboy 2021 January 24, 2023 50%

Bisexual Black Man's Paradise

The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... read more

shemale lover June 24, 2012 80%

HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH

It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... read more

CDDIXIE4U January 8, 2019 100%

Jo, Shemale Goddess! Part 1

Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... read more

shemale lover September 4, 2011 100%

The Greatest Liar, Deal With The Devil

The Greatest Liar, Trans Erotica With a Purpose By Alexandra Rios, © 2019 The Lost Chapter, Deal With The Devil This is a work of fiction. All characters (including the narrator), products, places, events and incidents are either the products of the author’s imagination or used in a fictit... read more

the greatest liar August 7, 2019 20%