Bimbo Sissy Stories

10,300 results
Orientation
Length
Source
Infinite Scroll

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

The Prostate Exam Pt. 06

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

"Just as it should be, now walk to quickly to the Langham hotel. Make sure you keep the bag out in full view, for all to see, it cannot go in your back pack. I want anyone who sees you to know what a slut you are.." "Go straight to the bar and order a triple G&T and 3 shots of good tequila. If the bar man asks you what you're doing you will tell him that yo...

Mommy Adriana Convinces Andrea

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

My thanks go to Cherysse St. Claire, who was so nice and edited my story! Without her my story wouldn't be as good as it is now! Dear Readers I hope you enjoy the ride! When they finally ended their embrace, I minced towards my wife and Mommy Adriana, head bowed, avoiding their eyes. I held out the tray and waited for Andrea to take her breakfast. "Greta,...

Sissification 101: Ch. 03

by silkstockingslover on Jun 8, 2020
Transgender & Crossdressers

Sissification 101 Ch 03 Summary: Eric(a) gets pegged for the first time. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by a very supporti...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

Sissy Whore Ch. 02

by DebbieDublin on Mar 7, 2018
Transsexuals & Crossdressers

I wrestled with my emotions for the rest of the afternoon, sitting on the sofa trying to distract myself from the mysterious web chat. I'd been at this a long time now and I was used to conversations that went nowhere. Most of the guys that contacted me followed up with a dick pic and were not really capable of continuing the fantasy beyond the scant descrip...

Girl's Night Pt. 06

by DifferentBreed on Sep 14, 2017
Fetish

This is a continuation of an earlier story. It contains themes of feminization, humiliation and other fetishes that don not appeal to all. If you are a fan of these, please read on and leave comments as to how to improve the story. Hope you enjoy it. ~ DB ********* Fisher climbed up the stairs to the brownstone, Sophie's jeans creeping down his ass for wha...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

A Dream Come True Ch. 01

by severomi on Sep 18, 2017
Transsexuals & Crossdressers

This is a two part story. Part I is reality and true while part II is my Dom's dream. PART I - The truth I'm an American abroad, been in Europe most of my life, now 58 years old and have been married twice with little success. I decided to change what I'm looking for, after having reflected on my previous relationships, where I had also two TG/TS relatio...

The Prostate Exam Pt. 05

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Since giving himself away in his first prostate exam to his Dominant Doctor Megan he had been prepared for use by an old Master, now Sissy was on her way to be used. Sissy was breathless as she read the text from Master V, she looked around the small airport to make sure she didn't know anyone, whilst she was looking at her texts. Thank goodness she didn't....