Sissy Truth Or Dare Stories

319,164 results
Orientation
Length
Source
Infinite Scroll

The Benefits of a Girlfriend Ch. 04

by sexless4ever on Sep 13, 2017
BDSM

Chapter Four: Haters, Assholes, and the Hands of Fate On the way home from school the next day, still feeling weird about the extra lubrication inside my girlfriend the night before, I decided to stop in the little drugstore to purchase some condoms for Adam so that he had no excuse not to wear one. When I got to the counter, the place was empty except f...

An Older Lonely Woman Seduced

by MissSade on Mar 31, 2020
Mature

I was the head of a boutique clothing company. I started the company in my early 20's and built it into one of the leading fashion wear brands over the last 20 years. The greater strides I made in business the more focused my time and mind came on my business. The men I dealt with in business were fake and I hated the idea that a compliment should make a wo...

The Rider

by FoxTied on Jan 16, 2019
Erotic Couplings

- Continues from Hard Rain, but can be read stand alone: You flinch, a reflex running from shoulder to toe, awoken, snapped awake. The rain pelting the windows, the wind blustering, rocking the carriage of your camper van, the trees "shhhhhushing" as they sway, and the thunder still rumbling hungry, hundreds, maybe thousands of feet above. Then you pick i...

Our Two Girls

by Britease on Sep 17, 2017
Loving Wives

Sorry, no explicit sex. No one burnt at the stake. Not a trace of a Navy Seal or an SAS soldier. Just a poor young lad trying to live his life out and running into problems as he did what he saw as the best thing for his family(s). It's a bit on the long side and I thought about splitting it up, but couldn't decide where without loosing the overall plot. So...

Transformation

by rlfj on Sep 13, 2017
BDSM

Richard Secourt watched his television screen raptly, half in awe and half in amusement. Bouncing across the screen was an amazingly awesome blonde beauty with the biggest set of tits he had ever seen. She was wearing a one piece red swimsuit and running down the beach, and those immense jugs bounced up, down, and sideways. How she avoided putting an eye out...

Complex Family Ch. 10

by PaulStevens on Sep 18, 2017
Erotic Couplings

Edited by luvtaread It was nearly a year and a half later after the incident in Boston that the trouble Jeff Yates had started finally hit home for Brandon. It was a rainy Tuesday in March when he found out that Jeff had finally won their little war. Despite his best efforts the project Brandon was developing was a bust, just as Jeff had planned it, and the...

The Adventure Ch. 01

by Harryandsally on Sep 19, 2017
Loving Wives

Laura downed another Jaegerbomb, it was her 5th. She was playing a game of truth or dare with her husband of 3 years, Paul, and their best friends Mel and Rob. Laura had refused to answer a rather personal question about her sexual preferences and had to pay the forfeit. Her head was spinning as the bomb hit her. Laura was 32 with shoulder length dyed blond...

A Flame in the Night Ch. 07

by dawei on Sep 13, 2017
Romance

THE FLAME (Act 1 of 3) Later one day, you (female) and I (male) decide to go out for some entertainment. But beyond the normal outing, I have secretly prepared something special to spice up the evening. Large utility bag? Check. Toothbrush and shaver? Check. Extra underwear? Whatever, check. I close the trunk of my car with everything appearing in place. Ye...

The Haunted Dungeon Ch. 02

by unpublaauthor on Sep 14, 2017
BDSM

This is the start of a new story that is the result of a dare from the Truth or Dare Room on the Literotica chat. All characters are older than 18 years of age. I would recommend reading the first chapter before reading this one. ******** Choices. Choices. I glared at the array of designer vintage gowns before me. Cinderella had no idea what dress to wear...

Izzy is Taught to Handle 4 Guys

by novella_champ on Oct 16, 2018
Group Sex

Story seven: Tif Teaches Izzy How to Handle More Than One Guy This is the seventh independent story of our teenage whore Tiffany "Tif". This story accompanies the Katherine "Kat" storyline. The timing of this event occurs between the end of Kat's first module and the beginning of the second module; specifically during the first couple of weeks of summer. Wh...