Terror To Sissy Stories

359,934 results
Orientation
Length
Source
Infinite Scroll

Spellbound & Sissified

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

SISSY FOR A SPELL The Omega Psi Phi Fraternity loomed in front of him. The lights were on in almost every room. Frank's hopes, that maybe the brothers of Psi Phi were at the Halloween party across campus being thrown by their sister sorority Sigma Gamma Rho, were dashed. He took a step forward. His hand was shaking and the child's Jack O' Lantern bucket...

A Shell of A Man

by uppishcarrot on Sep 13, 2017
Transsexuals & Crossdressers

Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who li...

The Executive

by Bootfrau on Dec 24, 2019
BDSM

The Executive: or, How to Break a Slave in Seven Days * * * MONDAY. "Jesus Christ, lady," he choked. "Is that thing real?" I blatted the stun gun just under his nose. He recoiled, scattering papers across his desk. "Look, this is a business. You can't just come in here and--" "Kidnap you? Why yes, yes I can. In fact, you've been asking for it for month...

A Model for CC's

by Fibaro on Oct 5, 2020
Transgender & Crossdressers

(This story was requested by one of my readers. This is a stand alone story, but reading "Neighbourhood Terror to Sissy" first is advised as this story takes place in the same universe.) Intro Victor was just a regular guy down on his luck. A month ago he still had it all, a beautiful girlfriend, a nice apartment and a decent paying job working for an acco...

X-Change: The Frat House Blues

by MrYowman on Sep 16, 2017
Sci-Fi & Fantasy

The world had been changing rapidly. Maybe for the better, maybe for the worse, that was yet to be determined. But the progressive political movement of the early twenty-first century had definitely made grounds, if not economically, at least socially, especially where sexual and gender norms were concerned. Science too, had made this new world more bold and...

Keith's Caught in a Costume

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

It was the giggling that began to pull Keith out of his head. Sitting in English class, halfway through the fall of his senior year of high school at St. Michael's Catholic, Keith couldn't find the energy or heart to care about Hester Prynne or her scarlet letter. So, he'd let himself drift off into fantasy. This fantasy - like many of his since the beginnin...

It's a Wonderful New Life

by alexyzia on Sep 16, 2017
Transsexuals & Crossdressers

I met Sherry at a bar. Imagine that. I often picked up women at bars. I'm a good looking man, have a nice sporty car, cash flows freely from my pockets - at the bar anyway. So I do OK at snagging a tipsy babe for a nights folly. But all of the sudden karma has caught up with me. When I hit on her she told me to back off or I'd be sorry. When I persisted, pol...

The Hardest Kind To Be Ch. 04

by Joe Wordsworth on Sep 17, 2017
Exhibitionist & Voyeur

Hopefully, you've read the previous parts--as some of this won't make too much sense if you haven't. Either way, the cast is eighteen and I thrive on your love and affection. Vote me well, mon ami... vote me well. . . .. ... ..... The next morning was a hazy shade of warm beery tastes lingering in the back of Ginnie's mouth. She woke with a grumpy headache...

Topped from the Bottom Ch. 05

by cutebabysadie on Sep 14, 2017
Fetish

Summary of previous chapters: Chapter 1: Todd, college football quarterback and alpha jock make a bet with his short nerdy vocal music roommate, Mark. The bet was that Mark could fuck Samantha, Todd's girlfriend, better than Todd. To be more specific in just 10 minutes she would be orgasming and screaming Mark's name. It ends with Todd humiliated on his kne...

Eve Quest Pt. 03

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Sometime during the night I was released. That exquisite pain at the point my limbs were release must have dulled my recollection of the events. I'm reasonably sure I was given the Toilet command and I hope I did a good job. In any event, I was still on the bathroom floor when I heard my mistresses stirring around the next morning. I got up, crawled under th...