Sissy Bitch Stories

80,596 results
Orientation
Length
Source
Infinite Scroll

Mindy's Moving Day - CFNM Ch. 01

by BuckyDuckman on Sep 25, 2017
Fetish

Author's Note: Humiliation, CFNM and pegging lie ahead! I've had this idea for a while about an adventurous married couple on the edge of opening a new chapter in their married life. I hope you enjoy reading it as much I enjoyed writing it! On her first day in town, Debbie and I were Mindy's only friends. The professional moving company hired by Mindy's...

From Her Ex-Boss to her Bitch Pt. 05

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story includes extreme themes of sissification, interracial domination, watersports, cock sucking, if any of these themes are not your thing, please don't read it. ***** "I think you should have tattoo on your back above your pussy cheeks and another above your little Sissy clit." "But I couldn't do that Master, my wife would see." Amber was almost b...

The Awakening of a Sissy Pt. 11

by sissyjolie4u on Jul 13, 2020
Transgender & Crossdressers

We had been driving in silence for about 10 minutes, with me reflecting on the changes to my home and the 2 men I was going to be meeting. I was both excited and nervous about meeting with Roy and Ronald. Mistress Di broke my thoughts stating "I think Nikki has done an excellent job with her house transformation work, don't you agree Jolie?" I looked over a...

Sabbatical or Continuous Gang Bang?

by TonyaTV69 on Sep 12, 2017
Transsexuals & Crossdressers

My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My parents were fine with fine me taking a short break but adam...

Snowbunnies

by tori_tgirl on Oct 12, 2017
Transsexuals & Crossdressers

I was finding it hard to concentrate on my picture... the creaking sounds from the box spring grew louder with each passing moment, making it harder and harder to keep my crayons inside the lines. I didn't have long to finish my coloring, maybe another minute or two but it was already the prettiest unicorn I'd colored yet, and surely they'd be happy. I strug...

Recruiting of a Sissy Maid Ch. 05

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Five: Chantel Settling in with Her other Sissy Girls "Congratulations Chantel." as Maid Penny tells her today is her 3rd. month anniversary at The Jade Maid Club as they are sitting at the breakfast table with the other girls. Other girls also congratulate Chantel as well. Chantel replies, "Oh thank you all." As the girls eat their breakfast befo...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

The Surprise

by MissJAS on Sep 28, 2020
Transgender & Crossdressers

We started on kink, two friends seeing who could take a conversation farther. Two grown people with vastly different pasts but a mutual understanding that sex and what felt good didn't really have to make sense to anyone but you and who you were with. Not that we agreed on everything, but we agreed that if you and your partner were both consenting adult part...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...