Prissy Sissy Stories

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Teacher's Descent into Ecstasy Ch. 02

by DDDDave on Sep 25, 2017
Erotic Couplings

"Big Tits, Big Dicks and Fantasy Fucking" ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) Ms. Carnale was sitting across the desk from Principal Fritz. She had finished describing, in limited terms, what had occurred the day before in her classroom. She had left out the part when she had handled Mr. Manhorse's enormous c...

Helen's Billy

by cheto1 on Sep 13, 2017
First Time

Cinnamon smells wafted by my nose and I thought I must be close to heaven. When I finally decided to open my eyes, just for a moment, I wondered where I was. Then I remembered the fantastic time I shared with the lovely Helen. A quick little shiver made me realize I wore no clothes and also, my dick felt a tad poorly. I lifted the covers - I nearly screame...

Keeping Up With the Joneses Ch. 02

by DarkBlush on Sep 25, 2017
Interracial Love

So, the comments from the last chapter made me want to explore Prissy's thought process in this. Again, under 2000 words which has actually made this a bit of a challenge. I have to be decisive on what I want to say. Anyway, I hope you like it. *************** I know there's something wrong with him. He shows you who he is, if you let him. I got to see it...

Dwight Has the Last Laugh Pt. 02

by ChaseAndSuck on Sep 18, 2017
Interracial Love

It had been a few months since Seth and Nicole moved into their new apartment. Seth was happy as ever. Work was going well, and he had his unbelievably sexy young trophy wife at home. They had the occasional quarrel, but nothing that couldn't be fixed. He was on top of the world and he relished it. One day, after eating the breakfast Nicole lovingly made f...

Better Observations from My Window

by uksnowy on Sep 16, 2017
Exhibitionist & Voyeur

Arising from my bed with a massive stiffy, I open the curtains, letting my knob end brush against the cold wall on this bright, late spring morning. Timing it just right, the first sighting of the day is Karen from up the road, swaying seductively from her front door to her BMW Z3. Its sleek silver lines are parked right in front of my place and from my firs...

Conceal Me What I Am Ch. 14

by Stultus on Sep 26, 2017
Sci-Fi & Fantasy

Never let anyone misinform you that 'violence never solves anything!' Violence solves a great many problems, especially when there are hundreds of people in your way all armed to the teeth with firearms and the willingness to use them upon you. Gleefully, and with all of the ammunition they can carry! I had to admit that the road block in front of us at Elk...

The Bottoms of My Heart

by SEVERUSMAX on Jul 3, 2018
Group Sex

"And then there's me, but I don't believe in such stupid taboos, anyway. And you have some dirt on me as well, don't you, at least by the same idiotic moral code that so many give at least lip service. I don't personally give a fuck. So, be that as it may, perhaps we should kiss ... and make up, eh?" Marsha told Howard and Kristin with a wink. "Or maybe I c...

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

N.U.D.E. Ch. 02

by bigrimmstales on Sep 13, 2017
Exhibitionist & Voyeur

Intro: In part one, Miss Helene Jean Ponsonby a sexually and emotionally repressed company director and owner of her family company saw a sign to a mysterious organisation situated next to her offices. She went in the day before to find out what they did, was mistaken for a client, and ended up exposing herself to the receptionist who reciprocated in a mutua...