Free Shemale Stories

My story, more or less pt.3

Earlier on, when I was scouring through various drawers and closets for feminine clothes in my home I have stumbled upon two old skipping ropes. "A fun time" I thought to myself, not giving them another look and continuing with my search. Little did I know they would become the backbone of my "sessi... read more

Thigh_High_Boi January 6, 2023 100%

Pippa's Story

I was just entering my prearranged destination. It was 11 pm and just before I paid the admittance fee, I stopped to look at myself in the mirrored walls. Reflected before me was a sexy, if a little sluttish looking woman in her thirties. The only discrepancy being that I was actually a 37-year-o... read more

shemale lover April 4, 2012 100%

My Story...

Hy my name is Noemi and this is my story... I was nearly five years, my parents sleep and my sister stayed overnight at a girlfriend. I allways looked at her tights, skirts, dresses and shoes admiring (she is six years older)and i was jealous that she could wear such beautiful clothes. I liked to ... read more

Noemi27 July 22, 2013 66%

The story of how I became what I am now...

I was on a trip to Germany with some of my friends. I was 16 when this happened. We went to a club one night and I got really drunk. They challenged me to approach a cute girl and ask her for a drink with me. I was drunk so I didn't really care so I went there and bought her a drink. We talked and I... read more

FeetQueen January 8, 2019 71%

Meine sissy Story Teil 1

Meine sissy Story (wie ich zum sissyboy geworden bin )Teil 1 Es fing alles mit 12 Jahren an, meine Mutter war damals allein erziehend und war seit der Geburt von mir von meinem Vater getrennt. Sie hatte einen Freund von ich war ihr ältester Junge danach kahm mein Bruder mit 8 Jahren Eines T... read more

SissyAngelina August 15, 2020 94%

An amazing true story

okay never done this before but here goes =) So i had just broken up with a girlfriend a couple months ago, and had been feeling pretty down and unhappy. I had a friend of my f****y invite me over to hang out and play some video games and eat some dinner. When i got to their house Jan and Ted, they ... read more

shemale lover May 22, 2013 94%

My Seductive Secret (True Story)

During my childhood, me and my brother used to play with two other boys who were our neighbors every weekend. One day we decided to wrestle, and I took on the youngest one, (he was about 2 years younger than me, like my brother) and we wrestled in the shed while my bro and his bro (who was my age) w... read more

Chickzdigmeyup June 18, 2019 91%

Camming down the rabbit hole Ch6

In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... read more

Dani_does_Dallas October 11, 2021 100%

Camming Down the Rabbit Hole Ch. 12

We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... read more

Dani_does_Dallas May 9, 2022 100%

My story, more or less Pt.1

I always knew I was different. I enjoyed playing with dolls and being around girls, I felt safe and in my place. When I got my first smartphone I have discovered porn, and boy was it an adventure! I have watched every type you can think of, but eventually I settled on shemales, the perfect cross ... read more

Thigh_High_Boi December 22, 2022 100%

Samantha sissy TGTF

Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... read more

Samantha sissy world September 20, 2022 66%

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%

Camming Down the Rabbit Hole Ch. 08

A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... read more

Dani_does_Dallas November 15, 2021 90%

Porn site meeting and fucking ;)

We started talking on a site. I knew you were for real when you sent me a message introducing yourself. We only spoke for 2 days before we decided to meet up and I was excited to play with a real little slut. You told me the only things off limit were anal and scat otherwise i could do what I wanted... read more

BalkanLoco91Ri August 26, 2019 77%

A Night of Lust

I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... read more

JessicaEdwards August 7, 2018 96%

Virgin Slut Cravings.

There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... read more

Regina10 September 29, 2020 93%

Slut /W Bad Boy

I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... read more

Regina10 December 4, 2020 100%

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%

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%

LA CUPIDITÉ DE LA MÈRE

Nicholas a sorti son téléphone et a pris une dernière photo de sa maison. Nicolas emménageait dans une nouvelle maison aujourd'hui. Nicholas était un garçon de 18 ans, il était le plus petit et le plus maigre de l'école, il gardait ses longs cheveux blonds. Il n'était pas bon en sport et... read more

Femboy 2021 February 3, 2023 50%