Sissy Bimbo Stories

10,300 results
Orientation
Length
Source
Infinite Scroll

Caught by the Past Ch. 03

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3 - Friends United Previously - When you dressed as a sexy tart for James he showed two sides to his character. Bent over his knee, stuffed with a butt plug and forced to suck his cock. What more could he possibly do?... Read on After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your...

Stevie's Journey Ch. 03

by gbr2004 on Dec 2, 2019
Fetish

I get up and put on some of my regular clothes, workout shorts and a t-shirt and flip flops. Try to digest what happened yesterday and how everything just spiraled out of control and now I find myself in this impossible position. It's like all choices have been taken from me and this group of people took over my life. It was exciting but I can't be doing the...

The Suitcase Ch. 01

by SissyGeorgina on Sep 19, 2017
Transsexuals & Crossdressers

Enjoy the story, more to come, as soon as I'm able. It all started when I was 25. After graduating with a 2:2 degree in English from Plymouth University, I'd moved to London and gotten a job as a journalist for the Evening Standard. The pay wasn't great, and I was making next to nothing after paying off my rent, travel and living costs. I certainly didn't...

Elaine's Neighbors

by Hotenuf4u on Sep 14, 2017
Fetish

Elaine's Neighbors: Their Story Tammy's mother had divorced her father just over a year ago. It seems that his lack of trust got the best of him which ultimately led to his downfall. Tammy was home on a vacation from her college studies when she noticed a change around the house. It seems that now her father has turned into a workaholic which left Mom prett...

AliExpress and Sissy Downfall Pt. 06

by His_fag_wife on Mar 6, 2018
Transsexuals & Crossdressers

"Ok, now you've been fed, back in the chair and Candice will get your make up done, so that you are as pretty as you can be when you return to your Mistress and Master." "Get all that mess cleaned off her face please Candice and start making her up to look pretty." "Yes Miss Bell." Charlie got back in the chair and Candice prepared to make her look as pre...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Lexi's Interview

by Jemina004 on Mar 17, 2020
Transgender & Crossdressers

October 5th, 2063 Lexi reached for his purse and took out his compact mirror. Mostly out of nervousness, he had to check his appearance again. Alexandra St. Claire was sitting in the waiting room for Carter Logistics on the 56th floor of the MacArthur Building in Chicago, trying to get one of the most coveted jobs available for white bois these days. Being...

Remote Control

by Wholemanz on Sep 15, 2017
Transsexuals & Crossdressers

WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence, bad words, and strange ideas. It has only the strange things that dribble from my head. If you are not old enough, mature enough, open minded enough, and especially not smart enough to stop reading should you find yourself becoming offended viewing such a story, don't! I hereby gran...

Girl's Night Pt. 12

by DifferentBreed on Sep 14, 2017
Fetish

This a continuation from an earlier story. It contains fetish themes of forced feminization, public humiliation and other erotic themes that may not be to everyone's taste. If you enjoy these, please read on. - DB **************************** Fisher slumped in his seat as the last of their party climbed into the stretch Excursion limousine that was usherin...