Sissy Whore Stories

50,992 results
Orientation
Length
Source
Infinite Scroll

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

My Mistress Ch. 03

by Kandy5647 on Sep 12, 2017
BDSM

Hello Peoples of Literotica! It's Drew Nelson again! And I'm back in full force! This time I'm here to not only tell you about my stunningly gorgeous Mistress Tameka. But! I'm here to tell you about my new Master Quentin Devonté Sterling as well. My God what a man he is! Wait! What am I saying?! He's a pure bred God! He's this 6'6, 210lbs, dark brown eyed,...

At Their Mercy

by Subserver on Nov 9, 2017
BDSM

Miss Erin and Miss Erika giggled and teased, pinched and fondled me as they made me into their feminized plaything. When they had finished I was wearing a short blonde wig, eye and face makeup, red lip gloss, red nail polish on my fingers and toes, small hoop earrings, perfume and black satin panties with lace insets, a matching bra that was filled with fal...

Girl's Night Pt. 09

by DifferentBreed on Sep 14, 2017
Fetish

*author's note* To the fans of this series I appreciate your patience as the chapters have been a long time coming. I am having difficulty fleshing out the club scenes that were to follow. I wrote this brief interlude which takes place immediately after the couple leaves the mall. Hope you will enjoy it. Thank you all for the positive encouragement and the...

Julie is Sold to Mistress Amanda

by Pretty_Sissy_Julie on Apr 1, 2020
BDSM

Julie followed behind her beloved Madame as they walked up the steps. Julie had worked at Madame's brothel since she turned 18. She remembered how she went to Madame after she was thrown out of her house. Julie's mum caught her in bed with her father and was furious and made Julie leave. After a brief stint as a street walker Julie was brought to Madame and...

Crystal: A Sissy Set Free Pt. 03

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

This is a direct continuation from Parts 1 and 2. You should probably read those first, if you haven't already. ***** Before he could think Ryan was gone, Crystal shut the toilet seat re-locked the door and sat down feeling a jolt from his plug, He suddenly felt very uncomfortable, his feet ached from dancing in ridiculous heels, his corset was way too ti...

Did that Really Just Happen?

by AnnaV on Dec 2, 2019
Transgender & Crossdressers

I'd been out with one of my best friends. We'd had a few drinks and ended up in this little bar with some cracking looking women. There was one woman in particular who we both fancied. She was very pretty, but not especially my type as she barely had any tits. Nice enough and eventually she went off with my mate, leaving me alone in the bar. It was too earl...

Back-alley Sissy Boy

by Travel_by_day on Sep 12, 2017
Fetish

I saw you while I was walking through the grocery store. You were bent over, picking up something off the bottom shelf. At first, I thought you were a girl, because of your nicely shaped ass and the fact that your low rider jeans were riding down, exposing a lacy white thong. I was so turned on, my cock started to get rigid right away. If I had been wearin...

Trip to LA Pt. 02

by gbr2004 on Mar 3, 2020
Fetish

This story is just a figment of my imagination and shouldn't be read if you aren't into forced fem, sexual service and discipline. Otherwise, I hope you enjoy the story and I love to hear comments about my writing. *** All I can think about is how out of control this all is. Here I am, in LA, god knows where, dressed up in pink and white and looking like...