Prissy Sissy Stories

7,690 results
Orientation
Length
Source
Infinite Scroll

The Job Interview

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

I had been searching for an executive assistant for some time now and had interviewed a few really potential ladies and 'ladies' -- all very skilled and would be worthy of the position, but something was missing from them all until I interviewed Jessica. The first time I interviewed her was a general 'meet & greet' interview with about 15 other girls --...

Degrees of Intimacy Ch. 06

by bradley_stoke on Sep 16, 2017
Novels and Novellas

"She's a cow! A real fucking cow!" Prissy exclaimed, blowing smoke into the air of the pub where the wisping blue vapour was sucked into the smoke extractor. "I don't know why I stick with her!" "Me too!" agreed Cath. "My Jayne's so fucking uptight. All she fucking wants to do is sit in and watch telly." "So, you ditching her then, Cath?" Emily wondered. "...

TV Blowjob Slut for Blacks Ch. 03

by barbielovesbjs on Sep 11, 2017
Transsexuals & Crossdressers

The man sitting next to me driving is Darnell. He's a total black playah who owns a black bar near my house. He has his arm around my neck in a triumph of ownership. Basically I'm trapped in his black Lincoln Navigator, forced to listen to his gangsta rap and he's got a good buzz going. He's really happy because I'm wearing every piece of a little sexy outfi...

Weekend Warriors: Pay Day Whores

by DAMND ONE on Sep 16, 2017
Interracial Love

We believe that we know people, we laugh and wink at friends and strangers who we see doing the nasty, but aren't we suppose to know family, 'right'? I thought so too, but that was until that summer morning when I truly found out about my family, and myself. As I look back I'm astounded at my ignorance of the world. Money was tight, the economy a shit hole,...

David & 'Lyssa Ch. 05

by millennium_bard on Sep 15, 2017
Sci-Fi & Fantasy

Lady shadow tried to maintain a solemn mien, but she her smile kept sneaking up on her lips. Shana knocked politely on the parlor door. "Excuse me Mistress, General Darial reports that the grounds and mansion are clear of bog mimics." "Is there any report on our casualties?" 'Lyssa asked. Shana nodded briskly. "We have confirmed 30 of our staff and visito...

Lissy

by falteringtale on Oct 6, 2020
Exhibitionist & Voyeur

In spite of what her friends would tell you, Prissy Lissy wasn't a prude. In college, she had gone streaking down a quiet suburb boulevard. It was a drunken dare and a "mistake" that she would secretly regret. But when teased, she retained it as proof that she was a free spirit. Did it really matter that she'd only been with a few men in her life? She wasn'...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Keeping Up With the Joneses Ch. 05

by DarkBlush on Sep 25, 2017
Interracial Love

So, an in depth author feedback that I received in my email inspired me to do a three chapter arc on Prissy's past and upbringing. Not sure if this is one of the three or an intro to them. I hope you like it. ***** Emotionless threats aren't as scary as most would think. They're off-putting, sure, and effective but often don't get the point across to certa...

Keeping Up With the Joneses Ch. 04

by DarkBlush on Sep 25, 2017
Interracial Love

And I'm back. I hope you guys like this chapter. :) ***** I watched Dylan's mother peel an apple for me to eat. It had to be perfect and beautiful because according to Korean custom, pregnant women should eat beautiful and pure foods for a pure and healthy baby. She was getting to enjoy her heritage and I was learning a lot about her and my husband. "When...

David & 'Lyssa Ch. 04

by millennium_bard on Sep 15, 2017
Sci-Fi & Fantasy

"What's wrong?" Asked Black Eagle when he had revived 'Lyssa. "Don't you know how my species reproduces?" She cried in despair. "Tell me." Replied the Shaman. "The young are carried inside for several months. Then the mother seeks a safe place and goes catatonic. Her skin becomes hard and brittle, like an eggshell. She is still aware and alive as her of...