Tiffany's Gauntlet Stories

2,641 results
Orientation
Length
Source
Infinite Scroll

Valley Wives Ch. 05

by mistress_diana on Sep 16, 2017
Novels and Novellas

Darcy, Tiffany and Steph drive back from their work out. Darcy is driving and talking up a storm. Tiffany interjects with an 'uh-huh' and a 'right', but nothing more. Steph is quiet in the back seat. It has been two days since Steph and Tiffany's encounter and Steph is still reeling from the experience. Today is the first day she's seen Tiffany since that af...

Tiffany's Deal Ch. 04

by MicheleNylons on Jun 25, 2019
Transgender & Crossdressers

Chapter Four -- The River The app on Tiffany's phone buzzed and she checked it. Stephen Bateman wanted to book her services this evening. She declined his request by simply pressing a soft key. She didn't have time for him tonight, Tina Brinkman had requested that Tiffany come around for a drink. They'd talk about old times and bury the hatchet. Tiffany k...

Room w View Ch. 04

by orie on Sep 26, 2017
Exhibitionist & Voyeur

While I missed Ferry and kicked myself for screwing up the relationship, I also was pragmatic. Maybe I was becoming the asshole Ferry said I was, but I pushed her to the back of my mind and focused on the life facing me every day. My days blurred together. I met with the major client who liked my work and we seemed to hit it off. He got into a habit of call...

Gunther Gets Some Ch. 02

by Irish Moss on Jan 9, 2019
Celebrities & Fan Fiction

Note: if you haven't already, read Gunther Gets Some Ch. 01, which is a prequel to this story. *** Despite her desire for discretion so that she could have Gunther's thick cock and talented tongue all to herself, it was because of Tiffany that somebody eventually found out about their secret sexual relationship. There were more than a handful of people fro...

Single Again Ch. 16

by WhatIKnow on Aug 31, 2017
Group Sex

"So, nothing is happening with that little red-headed girl?" Andy asks. "Chrissy? What makes you think that?" "If I had a cute little girl like that living with me, I'd be in a lot of trouble." "How many times do I have to tell you that nothing is going on?" At least as far as I'm going to tell you, I think to myself. Andy and I are supposed to be instal...

Good Girl - Day 04

by secondsamuel on Jan 28, 2020
Fetish

Good Girl: Day Four Author's Note: This story involves pet play, watersports, cuckolding, cuckqueaning, and humiliation. For those who don't want to go back and read three other chapters, below is a brief recap. Caught cheating, Karen (Kay-Kay) has been convinced to live as a puppy for one week. During Day One, she is used as a pet by her husband Scott (Da...

Tiffany's Lessons Begin Ch. 06

by shin1to on Sep 16, 2017
Interracial Love

Tiffany made a stop at a sundries stand and bought a bag of Bic plastic shavers and can of men's shaving gel .... One week had passed since Tiffany had her sexual epiphany and, as is often the case with epiphanies and young people, she began to lose the immediacy of her experiences with Joseph. Years of pampering and adoring had made the beautiful young g...

The Move

by Odysseyker on Sep 13, 2017
Erotic Couplings

Before you read this work, please be aware that it is a very graphic depiction of a sexual encounter. This story is intended for adults only, and should by no means be read by anyone under the age of 18 years. I love to read your comments and would enjoy hearing from you if you like this story. I even want your comments if you didn't like it, provided you...

One Step Further Ch. 01

by writer4hire69 on Oct 12, 2020
Erotic Couplings

DISCLAIMER: Nothing in this story is real or should be considered as such. This story is very odd and is based on a strange fantasy I concocted that brings together some fetishes I'm into. This first chapter introduces the characters, sets up a little bit of where the story will be going, and yes, features hardcore sex between consenting adults. I do know wh...

His Son's Teacher Ch. 05

by GillianCD on Sep 15, 2017
Transsexuals & Crossdressers

~4~ Tiffany's world was black, almost pitch black although she knew it was still day. She tried to move, but could not. If she struggled too much the nylon ropes Dave had tied around her wrists and ankles would start to warmly chaffe. She could move her head from side to side and even lift it off the pillow. But she could not see anything through the thick...