Sissy Bitch Stories

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Humiliated Sissy Slut

by Allice on Sep 16, 2017
Transsexuals & Crossdressers

I have been dressing as a woman at home in private for many years. No one has ever seen me dressed as a sissy slut before but I do it to feel sexy. I know I would never pass as a woman for I am 6 feet tall, 170 lbs and at the age of 45 not a real trim body. My girlfriend Rachel who lives with me is must younger at the age of 35 with a young trim body that h...

Sissy Manners Classes Ch. 01

by fridaysissy on Sep 12, 2018
Transsexuals & Crossdressers

It was late night, I am 10 km away from my room waiting for sharing cab or auto service to reach my room at last I joined a sharing auto service with two members including me. The other passengers stop came early, and I remain alone in auto waiting for my stop to come. Driver said he is stopping the service and returning to his home and asked me to get down....

A New Life Ch. 03

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

"Click on this link, sissy. I want to show you something," Mistress Sally said. And I happily followed instructions believing it to be some aspect of sissy porn like a caption, or little GIF video. I couldn't have been more right...or more wrong. My newly painted red lips parted in shock as my computer opened a new browser that showed what seemed to be an a...

The Night He Started Showing Me

by SissyCinnamon on Sep 16, 2017
Transsexuals & Crossdressers

Mistress walked into the kitchen where I was cleaning and informed me that I was to stop and get ready. "Get your swishy ass upstairs and clean up. You have a date tonight." Mistress said. "A date, Mistress?" "Yes, you ditz. There's a man in town who very much wants to meet you. And you WILL behave for him! Understand?" Mistress was quite stern. "Yes, Mi...

From Her Ex-Boss to her Bitch Pt. 04

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel his ex-employee, encouraged along the way, with a little titillation, a lot of flirting and confessions of her bisexuality. She'd used her submissive Claire to help...

Sissy's Shopping Trip Pt. 02

by SissyFaye on Jul 6, 2020
Transgender & Crossdressers

Hearing my beautiful mistress say that she needs to cum before continuing gets me excited. I have an idea of what she has in mind, but I'm not sure because this trip is different than any before. Mistress walks to the back passenger door and opens it, "Get in here on your back with your head on the edge of the seat," commands Mistress. As I comply, I not...

Meeting Miss Kate

by princess_nicole on Sep 16, 2017
Transsexuals & Crossdressers

been reading on this site a lot, my Mistress had me write a story of my own for Her, and i thought i'd post here. it's my first attempt, i know it's not terribly long, but hopefully some of Y/you will like it. ---------------------- i had been talking with my new Mistress online and via text message for about a month and a half now. my first Mistress reall...

First Time Meeting Master Gene

by sissysubTiffany on May 29, 2018
Transsexuals & Crossdressers

First off a little about myself as I am bi having been with both sexes, but lately only men. I have always it seems to have been attracted to a male cock, but not to men as weird as that may sound. For awhile now I have been going to an XXX Theater Book Store in a town about 45 minutes from me hoping no one would know me there sucking cocks and getting mine...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...