Free Shemale Stories

A Ski Bunny is Born Chapter 3

Kim and I are thrilled that so many people are enjoying reading about our adventures. We have received so many really nice e-mails from lots of lovely people, its good to know you girls and guys out there are enjoying them! We had promised each other a trip to Europe but hadn't really made any fi... read more

shemale lover June 22, 2012 60%

Discovering Mistress Sarah's World Part 2

Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "ki... read more

shemale lover October 3, 2012 66%

Hung Trans Lesbians Fuck Two Ladyboys

Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... read more

darrell January 3, 2022 100%

Latex succubus

The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... read more

Alicexiao January 6, 2023 0%

Crossdressed Lana - Hannover, Germany

Crossdressed Lana - Hannover, Germany Very Sexy & Compliant Sub-Slut Is Searching For Kinky BDSM Live-Dates At Hannover, Germany!!! I Am Bisexual And Want Men, Woman, Couples And Trans For Outdoor, Swingerclub, Porncinema And Public Sex. I Love To Wear Very Hot & Sexy Clothes Like Lingerie, Stoc... read more

Crossdressed Lana February 6, 2020 62%

A Stitch in Time Saves Nine

I'm lucky to have met Frankie. She's not one in a million, not with (at last count) one in ten males transitioning to shemales, but she's still a relatively rare find. We females who are transitioning to hemales, on the other hand, currently number thirty-three percent of the world's population! Fem... read more

shemale lover September 29, 2011 100%

My Awkward Phase

My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... read more

the greatest liar June 14, 2019 85%

Camming Down the Rabbit Hole Ch. 09

As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... read more

Dani_does_Dallas March 22, 2022 100%

Dottie's Back Chapter 4

Waking up on the single bed in the spare room was not the best way I could imagine to begin a day. Dragging myself from underneath the covers, I made my way to the bathroom and stepped into the shower. The previous night's events were still fresh in mind: Stacy having slept with another man and then... read more

shemale lover November 2, 2012 75%

A New Life Part 2

The next few days I spent packing and repacking. I would need to watch what I packed as I was taking a plain to meet Sara and Tom. Most if not all my toys would either need to be mailed or stay behind. I had packed five suit cases all of them filled with female clothing and shoes. My carry on was pa... read more

shemale lover April 13, 2012 100%

Camming Down the Rabbit Hole Ch. 11

I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... read more

Dani_does_Dallas April 25, 2022 100%

Camming Down the Rabbit Hole Ch. 07

Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... read more

Dani_does_Dallas October 22, 2021 100%

The day i bought my fleshlight and it was better then i expected

We have all been there, you want something bigger and better than just jerking off, not sex but something that you can enjoy solo. We have all seen that famous American Pie scene where Jim decides the apple pie will feel amazing to fuck and proceeds to shove his dick into it and if I really think ab... read more

BalkanLoco91Ri August 7, 2019 54%

Wie sich schlagartig mein Sex Leben änderte... Teil 1

ich war nun schon einige Zeit heimlicher Crossdresser. Nie wurde ich von meiner Freundin erwischt, auch wenn es manchmal wirklich knapp war! Ich hatte ein sicheres Versteck für meine schönen Sachen und meine Sextoys und konnte hin und wieder meine geheime Neigung ausleben wenn sie nicht da war.Trotz... read more

Holly Swallow March 20, 2019 72%

Kitten: A Pantyboy StoryKitten: A Pantyboy Story

It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first ... read more

shemale lover September 10, 2012 40%

LE PROGRAMME D'ÉCHANGE SISSY ⚧️ ⚧️

Kristy a travaillé pour Le Matriarcat. Cela semblait plus officiel que ça ne l'était vraiment. Comme si c'était un "Nouvel Ordre Mondial". C'était en fait un club dirigé par des femmes spécialisées dans certains services que les hommes paient grassement. Cela pourrait être appelé prostitution selon ... read more

Femboy 2021 March 25, 2023 50%

David to Dee

"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... read more

shemale lover July 29, 2012 100%

A LA DÉCOUVERTE DE L'AMBRE ⚧️

J'ai toujours aimé la lingerie féminine. De regarder des catalogues à voir des copines le porter, j'ai adoré le look et la sensation de la lingerie sexy et soyeuse, mais pour moi, cela a toujours été plus profond. À 18 ans, j'ai essayé ma première paire de culottes, oh mon Dieu, c'était merveilleux ... read more

Femboy 2021 February 17, 2023 50%

Brotherly Love, Sisterly Love Chapter 2

"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... read more

shemale lover September 28, 2012 60%

What Lies Beneath (Part 1)

A RENDEZVOUS WITH SUZY – What Lies Beneath (Part 1) It had been a busy last day of the week in the office and I had started something that needed a little more time to complete. The office was quiet with most people having already left. It was a great opportunity to finish with no interruptions or ... read more

The Adventures of Mia & Seth November 3, 2020 95%