Free Shemale Stories

R Is for Rita

After my debts began to mount, college fees and all that, one of my mates from Brum suggested I try to earn a little extra cash. I was surprised when he told me how. He said he'd done it and ended up with a couple of hundred extra most weeks, sometimes just for an evening's work. "It's easy,... read more

shemale lover September 5, 2012 100%

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%

Janine awaits

My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... read more

bunny cat February 4, 2019 83%

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%

fuck by my best friend's family

= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... read more

Onikky June 25, 2019 80%

She also conquered my soul...

Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... read more

hippocampus_171 November 22, 2022 50%

Maddie and the public bathroom antics

I had put on my lingerie and my dress underneath my manly clothes and was preparing myself to go to a public bathroom. The idea was to enter a cubicle, take off my boring man clothes and sit there looking like a sexy sissy where I could video myself on my smartphone. I needed some hot new pics, so I... read more

sissymaddiex January 6, 2023 100%

La fille d'à côté

J'ai toujours aimé porter des vêtements pour femmes. Regarder des Playboys et des Penthouses avec des modèles presque nus portant des soutiens-gorge sexy, des culottes, des bas avec des jarretières, des talons hauts, etc. Éditeur de Hustler Magazine Bob Guccione a rapidement emboîté le pas. Les modè... read more

Femboy 2021 January 24, 2023 50%

SISSY, HYPNOTISÉ

Il avait fallu six mois pour en arriver là. En sortant de la salle de bain, je me vis dans le miroir en pied et frissonnai. J'étais rasé sous les sourcils, sans poils et lisse, à l'exception d'une jolie piste d'atterrissage au-dessus de ma cage de chasteté verrouillée. À part la cage... read more

Femboy 2021 February 4, 2023 50%

TRANSFORMÉ ⚧️ ⚧️

J'ai été conduit dans le bureau de M. Sharad. Ce travail allait complètement transformer ma vie ! Je pourrais rembourser mes dettes et commencer l'hypothèque. Ma voiture ne serait pas saisie, et je ne serais pas mis sur liste noire. Tout tournait autour de ce travail. Je n'avais même pas postulé pou... read more

Femboy 2021 March 29, 2023 50%

Crossdressing fun

I always love to crossdress when Im horny I love the feeling of being a woman and seducing a man. Older men have always attracted me here is my fantasy. I dress up one day with a red thong red bra black nylons short skirt and blouse and get online. I find a man who likes me and is ready to play. I c... read more

shemale lover November 7, 2014 80%

My Cock Dream

My name is Iris Cal. A few weeks ago, I had a dream. This is an account of that dream, with some holes and details filled in by my own fantasies. From what I remembered as I tried to write down as much of the dream as I could, I had woken up in the house in which I lived when I went to high schoo... read more

shemale lover April 14, 2016 85%

How I Became a Girl

My name is now Stephanie, once it was Stephen. I would like to relate how I was turned into a girl (really a transvestite slave) by the beautiful young lady who has become my mistress. I have always felt that I should have been born a female. I definitely have female traits. I have a very feminine... read more

shemale lover December 30, 2018 89%

My First and Last Girlfriend

Zeta was my first girlfriend. Together we discovered how to make love and how to enjoy good sex! She was quite shy, and it took me 6 months before I managed to push my dick up her little virgin slit, and make her a woman. She was 16 at that time and I was 19. After her defloration, she became ... read more

shemale lover September 28, 2011 90%

The Terrace View Apartments Part 4

I woke up on the third day of my new life, sore all over from having slept the night in my car. Sore, but quite satisfied. After all, I’d been treated to a nighttime tour of Houston’s most erotic sights and capped off the evening with a backseat blowjob from a somewhat masculine, but adm... read more

shemale lover November 18, 2011 85%

Showing off

So for those of you that know me and what I like to get up to, know that I like to dress in sexy lingerie, heels and skimpy outfits. I was doing just that earlier today, just driving around some of the quiet spots that I frequent with my camera. I deceided to go somewhere new, a small industrial ... read more

shemale lover January 6, 2012 100%

College cumming out party!

Aaaaaahhhhhh...where to begin? I guess it all really started in my teens, when I discovered the joy of dressing with one of my close friends. Like many others we started off slow, wearing panties and giving one another hand jobs and feeling at least a little bit like we were doing something we shoul... read more

shemale lover April 9, 2012 100%

Bi Pantyhose Passion

I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dress... read more

shemale lover June 4, 2012 100%

Alex Two: The Next Time

Part Two of ??? (there is another series I'll start too, Hopefully its not too repetitive and my fetishes aren't showing too strongly. heh. That is sort of a prequel to this, I guess. I had forgotten about it till just now when I found it in a misnamed folder.) Alex Two: The Next Time.... read more

AlexShouse July 12, 2012 100%

One Special Night

Marilyn called me at the office with just three words. "It's on tonight." After a few moments of listening to the silence on the other end of the disconnected call, I realized what she was referring to. Immediately my cock began to swell, sliding slowly inside my satin panties unti... read more

shemale lover September 2, 2012 100%