Free Shemale Stories

Becoming a Chrissy - Chapter 1

I always knew I was a little sissy slut. When I was ten, I took a pair of my mommy’s panties to try on. It was a hot pink G-string that my petite mother must have worn when she was ready to get fucked by my daddy. It was just the right size to cover my prepubescent clitty and also stretch through my... read more

mindlessrobot45 May 13, 2024 100%

1st time giving head

1st time giving head I had just broke up with my gf. I had been dressing off and on since I was a kid. Always been turned on by it. I use to sneak into my older sisters room and try on her on her panties. Love the way they felt. I would get hard and rub my little clitty but did not know how to mast... read more

Rachelcdfun May 8, 2024 83%

My first time with a guy

MY FIRST TIME WITH A GUY Another true story it’s kind of long but I think you will enjoy it I lived west of Lake Worth Florida. At that time we were surrounded by 1500 Acres of woods. There were 10 of us and we all had dirt bikes and would go out riding all the time.. On Saturdays we had a game ... read more

Stephanie101 April 26, 2024 80%

My sex education from my hot aunt pt. 2

My aunt was just enjoying the newfound freedom from the oppressive control over every aspect of being a woman. Everyone thought she was a slut because she was too sexy looking in anything she wore. I got to see my first set of titties in full glory from walking into the bathroom when she was in the... read more

Pabloduro April 25, 2024 100%

Working the Glory Hole

After so many nights of torrid fantasies plaguing my sleep, I took a long look at myself in the mirror. I had been slowly embracing my femininity over the past few months. My hair had grown past my shoulders, I was shaving my entire body on the regular, and I would wear panties under my guy clothes ... read more

KaceyKlarissa April 15, 2024 100%

I and the old man's story 后面中文

I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... read more

Oldslut Sissy April 15, 2024 50%

A Win-Win

A Win-Win By Sabrina G. Langton *** Author's Note: Hi, just a quick, crazy story about a wife actively participating in her CrossDresser husbands sex life. Just a bit of fluff, hope YOU like it.) *** We were laying in bed, sex was done, my wife could now relax for the rest of the month ... read more

Brina Giselle March 31, 2024 100%

Beginnings

I always knew I was a bit different though due to social stigma I didn't fully accept it till later in life. I wish I knew then what I know now and had embraced it sooner. Puberty hit and gynecomastia (formation of women's breasts) hit harder (36C). I was teased, groped constantly and was even force... read more

CD_Danielle_Doggy March 26, 2024 100%

The reason why I became a crossdresser

At first, I was just a straight and ordinary boy who was into sexy lingerie, stockings and heels. But one day, I suddenly thought that I wanted to try on my mom's panties, stockings, and high heels. So I did it. It was so excited and I started to get addicted to cross-dressing. Before dres... read more

cdmisato February 28, 2024 100%

My cross dressing journey

I am a man who likes to cross dress, currently single and living alone in Beijing. I like to dress up as a woman and go out, passing through every street, entering nearby shopping malls and supermarkets, as well as the women's restroom inside, and live streaming on a live streaming platform. I also ... read more

boysgirls February 15, 2024 100%

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%

Dress-Up-Girly Time!

"Let's go, 'Little-Missy,' it's our 'dress-up-girly time.'" Sandy knew better than to argue. Besides he really didn't mind being dressed up as a girl. It was kind of weird at first, when he first started playing 'dress-up-girly time.' His mom had brought home several boxes of clothes that no lo... read more

ALEXEAMES January 27, 2024 100%

Ladies who Lunch - At the Gloryhole

Ladies who Lunch - At the Gloryhole By Sabrina G. Langton *** Author's Note: Hi, just a quick little story to make us all wet and squishy. Three mature crosssdressers have a little more excitement than they are used to after lunch. I hope YOU like it... *** The Boynton Tavern So w... read more

Brina Giselle January 6, 2024 100%

The Interview

The Interview By Sabrina G. Langton *** 'A crossdresser goes on an interview in lots of pink, of course she gets the job' 'Author's note, just a quick little story with some really graphic sex, and a little tiny moral. I hope YOU like it.' *** "Okay, sit, sit, let's get started. S... read more

Brina Giselle December 4, 2023 100%

A true first time.

I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... read more

Gtaaddict3 November 21, 2023 100%

It had been a while...

The first time I dabbled with cross-dressing was as a horny teenager. I discovered my grandmother’s vintage collection of lingerie, and I had to know how it felt to be encased in girdles, basques and corsets, to feel the taboo delight of having my legs encased in sensuous nylon, to figure out how to... read more

Daddybear71 October 12, 2023 75%

How to Convince Your Wife to Try Black Cock

I didn't write this - but it's great info for all my sissy cuckold sisters out there desperate for their wives or girlfriends to go Black. I hope all your cuckold dreams come true! There are so many stories out there from white guys who admit that they want to see their wives and girlfriends,... read more

Sissy Annabelle October 7, 2023 50%

Miss Patricia

Miss Patricia: (A True Story from around 1998) What an adventure I had Monday afternoon. Did I say adventure? It was more than that! It was a lesson about myself, and was most certainly a point of change in my life. I had better explain... A few weeks ago I received a letter(snail mail) from a ... read more

Colette_Scott September 21, 2023 100%

Pee-Boarding

Pee-Boarding (Another True Story)  It all started with a weeks holiday in 1997 at a Holiday Camp in Somerset, a place called St Audrie's Bay which was by the coast overlooking the Bristol Channel. St Audrie's was, and still is I think, a place Transvestites, Transexuals, and Sissies, could stay ... read more

Colette_Scott September 21, 2023 33%

Miss Patricia

Miss Patricia: (A True Story from around 1998) What an adventure I had Monday afternoon. Did I say adventure? It was more than that! It was a lesson about myself, and was most certainly a point of change in my life. I had better explain... A few weeks ago I received a letter(snail mail) from a ... read more

Colette_Scott September 21, 2023 100%