Sissy Truth Or Dare Stories

319,164 results
Orientation
Length
Source
Infinite Scroll

Steve to Stevie to ?? Ch. 08

by gbr2004 on Sep 19, 2017
Fetish

Ms Storm has exposed me to my boss, showing her that I'm nothing but a sissy faggot. It was so embarrassing. Then she watched as my Mistress took my virgin asshole. Ms Storm talked to my boss, Ms Hunter, telling her that she wanted her to keep me in line at work and make sure that I remembered my place while at work. She gave Ms Hunter permission to use me i...

Demanding Satisfaction Ch. 1

by kyriele on Sep 15, 2017
Fetish

Austin came home on Friday... like every other Friday. My kids were ready to go to their father's house and I told him to take them. The house would be empty and I could no longer wait to extract... revenge? No... too strong a word. Satisfaction. Now there was a word to describe the myriad of thoughts running through my brain. I had gone on the computer an...

Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...

Rene and Gene

by Bakeboss on Sep 16, 2017
Novels and Novellas

Part l My first Friday as Jean: Although I work at home, I still took the day off to make sure all the housework was done. Rene called on her lunch hour and said she bought a surprise for me, that she felt naughty and wanted us to spend the weekend doing naughty things. I was hard at the word naughty; my beautiful wife is such a tease and enjoys role-playi...

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...

Step by Step Sissification Ch. 02

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff. -- "Oh, well,...

Meeting your Goddess

by theroomman on Mar 7, 2018
BDSM

I showed up to the bar late, I knew keeping you waiting would have you wondering if I'd show up at all. You get so excited when you see me. There's no question I'm the girl you were waiting for, my dominance is overt: dark lipstick, high heels, and a tight revealing black corset style dress. Before you can even say hello, I shush you with a finger on your li...

Sissy Shopping with Princess T

by Subboi23 on Apr 1, 2020
Fetish

I excitedly pull my tight red lacy panties up over my small, limp penis. They feel so nice. Tight, but soft, containing the perfect amount of room to hold my little package. My penis does not attempt to get hard despite the pleasure, if anything it seems to shrink a bit in order to fit more comfortably. This was my first time seeing Princess T without her in...

Counselling Changed Our Marriage Ch. 03

by Quietoldie on Dec 25, 2017
Transsexuals & Crossdressers

The fourth joint Interview Emily sits comfortably in the waiting room, texting and smiling. There is no question in my mind with whom my lovely wife is texting, nor much less any doubts about the lewd and obscene content of their texts. Emily looks totally ravishingly beautiful, dressed smartly in her business attire, her generous breasts bobbing up and do...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...