Cuckold Strapon Stories

8,753 results
Orientation
Length
Source
Infinite Scroll

Crystal: A Sissy Set Free Pt. 03

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

This is a direct continuation from Parts 1 and 2. You should probably read those first, if you haven't already. ***** Before he could think Ryan was gone, Crystal shut the toilet seat re-locked the door and sat down feeling a jolt from his plug, He suddenly felt very uncomfortable, his feet ached from dancing in ridiculous heels, his corset was way too ti...

CFNM Spanking by Roommate Pt. 03

by MithrilMath on Jun 1, 2020
Fetish

It was a chilly December night, but the apartment was a comfortable 27 degrees Celsius thanks to the wonders of modern climate control. The smell of warm, freshly baked bread wafted through the apartment. The television was on, tuned in to CNN. The anchor was talking about some debate, but his voice was drowned out the high-pitched moans slowly increasing in...

Seductress & Daemon: Sissy Pt. 02

by SeducedKnight on Sep 15, 2017
BDSM

********** A continuation of my initial story, the next morning... ~~~~~~~~~~ Zombe: a black rubber o-ring type bracelet worn locally, either on wrists or ankles (or both in my case, I have an oversized one that I wear as a necklace too). ********** I wake early the next morning, Seductress and the sissy are still asleep, the sissy and I are snuggled in...

Las Vegas Love Story

by Lesly Sloan on Sep 2, 2017
Erotic Couplings

© 2005 by the author, all rights reserved. The whore with a heart of gold is a myth; it's bullshit. I don't have a heart of gold. The only thing that turns me on is cash. I've worked at Sheri's Ranch in Pahrump, one hour from downtown Vegas, for the last two years and have done about anything a whore can be asked to do. The church-going hypocrites in Las V...

Cara has Fun with the Kardashians Ch. 04

by CallMeZero on Oct 5, 2020
Celebrities & Fan Fiction

*Disclaimer: This is all fiction, it isn't meant to be taken seriously. All characters are above 18.* *** The next day was an early one, Cara had woken up around 5. They had a special trainer coming for a yoga session. The Kardashian sisters all came down in their tight yoga pants that showed their curves. Cara was getting a free show here, she purposely s...

Dr. Chloe Burrell, Sex Researcher

by escriterra on Sep 26, 2017
Fetish

Chloe Burrell, Ph.D., was acutely aware of the irony of her situation. At 34, single (divorced after two years of marriage to the guy she'd lived with for three years before that), and attractive enough to be dating frequently, she was without a boyfriend, dateless for six weeks running, AND she was a "sex researcher" at a large Midwestern university. How u...

The Julie Journals: The Rain

by Shady_Lady on Sep 17, 2017
Loving Wives

She picked up her journal; the one she had kept ever since she had learned about adult life, and as she turned the pages she came across an entry marked 'Dirty Weekend'. She smiled as the memories came flooding back to her as she recalled the pleasure and knowledge it gave her. * * * * * Julie hummed softly to herself as she sat in front of the mirror ap...

Airport Anal Exam

by humbleslave on Dec 12, 2018
Celebrities & Fan Fiction

A few months had passed since the wild Christmas party, which had found me bound, beaten, ass-fucked, and humiliated in front of more people from my past. I was busy washing Mistress Chantz's convertible in a skimpy white string bikini and matching heels, with my hands bound behind my back, which was obviously quite a sight for the neighbors. By now I was us...

Home for Christmas

by Richard Norman on Sep 17, 2017
Mature

It was an amazing Christmas vacation this past year, thanks to Aunt Carla. She's my not really my aunt, but my mother's best friend. I've called her that since I was a kid. Carla is a literary agent who often visits New York, to see publishers there. I drove to my hometown of Boston, from New York. It had been a grueling semester at NYU. On top of that, I...

Welcome Nerd

by funbud on Sep 12, 2017
Fetish

Here is some background information for the story you are about to read. Brian is 18, 5'4 skinny and he has a 4 in. dick. All four girls are senior 18 year old cheerleaders and popular. Brandy is 5'6 and is a really bitchy but extremely kinky girl with 44dd tits. Melanie is 5'2 and is a slutty girl with 34b tits. Jodi is 5'4 and a really nice girl with 38d t...