Sissy Truth Or Dare Stories

319,164 results
Orientation
Length
Source
Infinite Scroll

Cruise Ship Cuckold Ch. 08

by Angelscuck on Sep 14, 2017
Novels and Novellas

Story from Angel's point of view: My husband asked me to write this next installment due to the fact that he is a bit tied up at the moment. I am more than happy to tell you our story. As you may or may not remember, my husband and I were in the captain's wife's cabin with him and his nephew Daniel. We were there to pay up on the bet my husband lost to Ev...

Barry's Submission: The Initiation

by woozydye on Sep 17, 2017
BDSM

The Initiation It was a lovely evening, mildly cold and slightly romantically misty, and a perfect one to start my married life. After three years of convincing and cajoling, Amanda had finally given in – and I hoped more out of love for me than pity on my sorry state – and we tied the nuptial knot on a fine Sunday morning of January last year. The proceed...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

Truth or Dare Leads to Cuckolding

by Dark0007 on Jun 9, 2020
Loving Wives

Hello people, I am Jeff. I and my wife had an arrange marriage, in the beginning she acted all interested and in love, but little did I know she was a gold digger. She just married me coz our family was one of the wealthiest families. I'm a 5'7 guy very skinny and not much of facial hair. My wife Karen is a boom shell with figure 36-25-38. She is 5'4 with...

Young Master Ch. 05

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My purs...

The Domme Club: The Fucking

by NancyPan on Sep 14, 2017
Fetish

This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated. ***** Mistress Monica left Tom the standard list of chores to do while s...

A Cuckold Earns His Horns Pt. 02

by lapraline70 on Sep 16, 2017
BDSM

This is part 2 in a series of letters about my cuckolding. For context, read part 1. We open with O/our Bull knocking at the door on the fateful evening. ==== Already on my feet, i walked to the door and, fumbling with the handle a bit, opened it to see Him. Our eyes met. i saw His immediately slide down my nightgown as His grin widened. "Ah, good evening...

An Evening in Red

by poule_mouillee on Aug 21, 2018
Transsexuals & Crossdressers

Jack was nervous. As a young man in his early twenties he had his fair share of fantasies, however this was going to be his first true time exploring them. And with what a woman to explore with! They had only just started dating, a few weeks all up, which wasn't enough when going around busy work schedules; but enough to know he was smitten. Victoria was som...

The Proof is in The Pudding

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

When my girlfriend of two years mentioned she liked to watch female impersonators perform, I seized the opportunity to confess my lifelong addiction to cross-dressing. The expected reaction of disbelief was no surprise but her reply of, "Well, let me see you dressed," was although welcomed, a bit of a setback. I'd not planned the truth to be revealed at suc...

Domme Club Humiliation

by NancyPan on Sep 19, 2017
BDSM

I would never say that life was routine with Mistress Monica. She kept me on my toes—or, more literally, on my heels—at least around the house. On days when I got home from my law office before she got home from her corporate job, I would immediately take off my suit and tie and put on one of the frilly aprons Mistress preferred me to wear at home, and a pai...