Free Shemale Stories

First Time Buying Lingerie

As a youngster, I couldn't help but notice the carousels of hosiery on display in various shops that my mother would visit. Displays of stockings and tights (pantyhose) for the discerning housewife. Brands like Pretty Polly, images of nylon clad legs on the glossy cardboard and a see through window... read more

Daddybear71 September 13, 2023 100%

Kylie and Chrissy

The following story is the first part of ‘Kylie and Chrissy’, a story documenting the blossoming sissy-hood of two teenage boys. It is partially autobiographical and partially fiction. PART 1 - THE INCIDENT ‘Stop… we really shouldn’t be doing this’ ‘It’s just a bit of fun. Now just hold sti... read more

chasingrisque January 9, 2017 80%

TEEN ET LE THÉRAPEUTE SCOLAIRE ⚧️ ⚧️

J'étais sur le point de quitter le travail tôt quand mon téléphone a sonné. C'était l'un des administrateurs de l'école. Ils ont également été mes secrétaires. « M. Caldwell ? Un étudiant est ici pour vous voir. Non, je n'avais jamais vu cet étudiant auparavant. L'étudiant n'avait pas voulu décrire ... read more

Femboy 2021 April 16, 2023 50%

Shool teen crossdresser first time sex

I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... read more

shemale lover November 21, 2014 84%

RANCUNE MATERNELLE ⚧️ ⚧️

"... Dois-je être ici?" Cole a demandé anxieusement. Sa mère s'était détournée de lui, occupée à sortir plusieurs plateaux de lasagnes du four. "Je peux rester chez un ami ou quelque chose comme ça..." Christina, comme sa mère s'appelait, soupira profondément. "C'e... read more

Femboy 2021 March 19, 2023 50%

Mis inicios y los vecinos mirones.

Hola chicas, mi nombre es Sandra, recuerdo que en secundaria era de los primeros que tenía computadora e internet por lo que me inicie viendo las primeras páginas porno, algo que me gustaba mucho era ver a las chicas vestidas con minifaldas, pantimedias y tacones. Tenia cierta atracción hacia las pr... read more

sexycd176 April 15, 2023 80%

LE CONTRAT DE MARGOT

Madame Margot Elizabeth Stott était l'objet de mes désirs, des désirs très secrets ; désire que je n'aie jamais eu l'intention de la laisser - ou qui que ce soit d'autre - le découvrir. Mme Margot Elizabeth Stott avait, au moment où je l'ai connue pour la première fois, environ 45 ans, peut-être ... read more

Femboy 2021 February 16, 2023 100%

LE CONTRAT DE MARGOT ⚧️ ⚧️

Madame Margot Elizabeth Stott était l'objet de mes désirs, des désirs très secrets ; désire que je n'aie jamais eu l'intention de la laisser - ou qui que ce soit d'autre - le découvrir. Mme Margot Elizabeth Stott avait, au moment où je l'ai connue pour la première fois, environ 45 ans, peut-être ... read more

Femboy 2021 March 25, 2023 50%

HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional

It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... read more

CDDIXIE4U January 8, 2019 91%

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%

BANGING AROUND BANGKOK

BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... read more

bkkldby June 17, 2019 85%

How I Became the Sissy Slut

It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... read more

Tvtrinity August 29, 2016 77%

ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn

Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... read more

SpankydeBautumn January 29, 2021 72%

Love is Grand

PREFACE Retired and independently wealthy, 60 year old Stan Berman discovered he had only 12-18 months to live due to a rare neurological syndrome that would sap his strength and motor skills, but the symptoms would not onset for at least a year. The widower's only family was his devoted son Pat... read more

shemale lover February 13, 2013 100%

Sissy schoolgirl and her black daddy

I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... read more

shemale lover June 22, 2013 92%

The Creators: Book One by

Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... read more

sagga September 18, 2018 60%

Bikini garçon

J'étais le garçon que mon père avait espéré après 3 filles avant moi. La vie dans notre maison à deux étages de la classe moyenne de banlieue était aussi normale que celle de n'importe qui d'autre. Mon père était un père aimant qui m'élevait et faisait les choses qu'un père aime faire avec son fils ... read more

Femboy 2021 January 24, 2023 50%

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%

SOUS LE CONTRÔLE DE MAMAN ⚧️ ⚧️

Jaime se tournait et se retournait dans un sommeil agité, ses yeux fermés et son visage grimaçant alors qu'il luttait avec ses rêves. Normalement, il s'endormirait paisiblement au son d'un podcast bourdonnant, mais pas dernièrement. Bien qu'il ne le sache pas, chaque nuit, sa psyché ... read more

Femboy 2021 March 18, 2023 50%

My aunt made me a transvestite

My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in... read more

shemale lover August 9, 2013 69%