Crossdressing Sissies Stories
Crossdressing Sissies Stories
Somewhere to share all those stories you have about your crossdressing experience; the highs, the lows, your first experiences and your on-going successes
Crystal's StorySite is a free site containing many hundreds of stories dedicated to TG fiction.
Read stories related to crossdressing. Submit your crossdressing story to us and many other crossdressers will know about your story too.
With all the short items floating around this website, it's easy to lose track of what I consider to be my signature pieces: the stories that stand as complete works of fiction, with in-depth characters and a satisfying narrative arc. Captions and vignettes are fun, but they lack depth and detail. The reason I write…
Perfect for fans of crossdressing, sissy stories, and forced feminization fiction. 👉 Don't miss this unique story of submission and power dynamics.
Discover a wide range of crossdressing stories online, including tales of feminized bosses, sissified husbands, and more. Immerse yourself in the world of sissy fiction today.
I walked into the shop. It was full of a variety of long and short dresses and gowns made from satin and silks in a range of colours and styles. A strong perfume smell struck me as i entered, the door closed behind me and the immaculately dressed owner walked forward to greet me. 'How can i help sweetie' she said with a slight 'knowing' grin. I swallowed 'I would like to try on a ...
Read the true crossdressing stories of our customers and friends. All featured on Glamour Boutique's blog. Visit our site for affordable crossdresser clothing.
Discover uplifting tales that showcase the beauty of crossdressing. These heartwarming crossdresser stories inspire love, acceptance, and joy!
Crossdressing, the practice of wearing clothing typically associated with the opposite gender, has been a fascinating and often misunderstood part of human culture for centuries. What was once seen as a taboo or eccentricity is now more widely recognized as an expression of individuality, identity, and self-exploration. Crossdressing stories, from personal narratives to fictional accounts ...
Dec 13, 2025
Dec 30, 2024
As you read and explore the stories in this series, you will see female-led relationships, forced chastity, feminization surgery, physical and mental domination, tie ups, gags, hypnosis, sissy maid training, and so much more.
Nov 27, 2025
These stories are written to tease your mind, melt your will, and make you feel like the cute little sissy you've always dreamed of being.
3 days ago
Transgender and Cross-Dressing Fiction: Stories, Vignettes and Captions
A Crossdressing / Feminization / Sissification / TG Transformation Story with beautiful hand-drawn illustrations in colour. The story revolves around Chad, a young man whose dreams are falling apart as he helps his family cover up his sister's disappearance.
Jan 10, 2024
Jan 2, 2025
This subreddit is dedicated to stories involving crossdressing. The stories can be either real life stories or fantasy, but you should indicate as such in the title.
Thank you for taking the time to learn about my experience with crossdressing for the first time! I definitely think that it's important for us to communicate with each other, so go ahead and continue to follow my journey on social media and share with me your own stories of discovering a new part of yourself and finding ways to love who you are!
3 days ago
1 day ago
I just love dressing up with the makeup, hair, dresses and heels and I actually grew my light brown hair out past my shoulder and wear it in a pony tail so..
Sep 15, 2024
6 days ago
Dec 13, 2024
Retelling of my first experience as a crossdresser.
He's a crossdresser and he and his wife came in this morning to get some help in the shape department." The other customers looked at the dressing room with amused curiosity. "That probably won't fit, Addie," Celeste said without batting an eye. "He's probably too tall."
Caption: "Hold still Brian while i fix your lipstick" "Mom i'm kind of nervous, this is my first date as 8ecky, what if Josh just see's me as a boy in a dress?" "Honey he knows you're a boy becoming a girl and he still asked you out, you've been on hrt for two years now, you've become very pretty, trust me in that dress all he's going to see is what i see, a pretty girl named Becky, now let me ...
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One of my friends is a crossdresser, and he's been pushing me to crossdress for a long time. And I have had a deep down fantasy to crossdress since I was a kid.
3 days ago
Feb 16, 2025
© Spandhana Ram I'm Umesh, 24 years old and the only son of my parents. I am jobless even though I have completed my Master's Degree. I never really found a job ...
Dec 16, 2025
Four stories, three bonnie lasses, connected through time and spirit -- by blood, and something more.
A young man makes a mistake and finds his destiny.
Crossdressing Stories: Explore Shannon's journey as an experienced crossdresser. Discover the challenges, triumphs, and lessons learned.
Read thousands of free transgender erotic stories online. Browse the world's largest collection of transgender fiction, erotica, romance, and adult literature. New stories added daily since 1992. No subscription required.
Dec 16, 2025
Dec 27, 2025
PART 2 | ALL STORY LIST "Sit down, young man. We are going to have a little talk. You've been coming home with bad grades, staying out late on school nights and even later on the weekends, and giving me a lot of lip for over six months. You're going to be a freshman next fall. How are these report cards going to look on your record?
5 days ago
Welcome to CD stories Welcome to CD Stories, a vibrant platform where writers and readers unite to explore the captivating world of crossdressing stories. Immerse yourself in tales of transformation, identity, and self-expression, beautifully narrated in prominent Indian languages. Whether you're here to share your story or discover inspiring ones, CD Stories celebrates the art of storytelling ...
Co-written by Victor G. A special thanks to Victor G who co-wrote 'A Mother's Love' at Sapphire's site. Vic has a litterary way of making a boy look as if he walked out of the pages of a fashion magazine. He's a fantastic solo writer and I'm thrilled to have the opportunity to write this story with him. Now for a little info about the story. Darren Peterman is a 16 year old high school ...
Read the most popular cross-dressing stories on Wattpad, the world's largest social storytelling platform.
I will always hold dear to me that summer, those days we spent together and that gift she gave me of accepting myself for whom I am.
2 days ago
Mar 3, 2025
4 days ago
Printer-friendly version Author: Samantha Jenkins Audience Rating: General Audience (pg) Publication: Fiction 17,500 < Novella < 40,000 words Genre: Crossdressing Character Age: Teenage or High School TG Elements: Girls' School / School Girl Jewelry / Earrings TG Themes: Caught with Consequences School or College Life Sisters Permission: Posted ...
2 days ago
First Time Out Dressed and Wow, What a Night! Home / Articles / Crossdressing Success Stories / First Time Out Dressed and Wow, What a Night!
🎥Story Name: Sisters Plan & My Beginning: Part-1 #crossdressing #mtf #crossdresser 🌈 Join me, on a captivating adventure as I delve into the enchanting world of crossdressing, transgender ...
"Cross-dressing keeps me sane. My female part is always with me, even when I dress like a man."
That is a great story, and I'm sorry for the loss of your father. My story is similar, and concerns mine too. I had put on one of my Mom's satin slips and was relaxing on my bed before supper, and I somehow I dosed off.
This is the story of Mikaela, and Charlotte, twin princesses (born to the protagonists of Demon Queened), forced to become adventurers as a rite of passage. In theory, it'll be easy! They're literally demi-gods after all.
Jun 20, 2025
We have played this game in the past and billie quietly and skilfully crawled under the desk and set to freeing my dildo from my trousers and knickers. For the next half an hour my sissy maid husband entertained me though what was a rather dull presentation!
First time crossdressing stories from Alexia, Casey, Jamie, and Taylor reveal the challenges, triumphs, and self-discovery of embracing feminine identity. Their journeys highlight the significance of gender-fluid expression.
A Journey of Obedience and Humiliation Craving for New Tasks As a sissy at heart, every day presents a mental and physical challenge for me. Deep within, I have always yearned for new humiliation …
Browse through and read crossdressing fiction stories and books
A Girl for Halloween: A Slow and Sweet Gender Realization Story By: Mysterious Stranger AKA Jennifer Sweet "Alright Dad, I'll go to the interview!" I said, finally giving in after a long debate. "You're making the right decision, Jason." My father had recently lost his job working a desk job for a local brewery.
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