Cuckold And Stockings And Heels And Boots Stories

359,830 results
Orientation
Length
Source
Infinite Scroll

Under The Tree

by WordWizard on Sep 14, 2017
Erotic Couplings

It had been a long week. The usual stuff, too much to do and not enough time to do it. I was waiting for word on a new job, and although I thought I had it, I hadn't received the offer yet. I was glad it was Friday and I couldn't wait to get home and relax. Besides, Monday was Christmas and I still had some wrapping to do before the big day arrived. The rid...

Sissy Maid Son Pt. 02

by Robyn228 on Jul 18, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter wept on his mother's bed feeling violated and abused. The maid uniform still on...

Reclaimed

by hepburn666 on Sep 17, 2017
BDSM

This story is a fantasy I just had and like to share with you. I would love to hear your comments, advice and additions to the story. Please contact me via the CONTACT tab on my profile. If you've enjoyed this story, please write me too - then I might write more! [Synopsis] In the years after the German reunion a lot of West-German families claimed to g...

Pussy in Boots

by SlaveNano on May 15, 2018
Humor & Satire

"Pesky moggy," grumbled the caretaker taking a swing at the cat with his mop, "Go on, get out of 'ere." The cat, completely unflustered by the cleaner's attention, nonchalantly slinked out of the leather backed chair reserved for the chairman of Rutshire County Council and stretched her slender frame before shooting a glance of disdain at the caretaker and...

Ann's Trip

by sirdix on Sep 12, 2017
Loving Wives

This is my 1st tale about Ann, a mature wife who explores her growing sexuality with her husband's approval. Some parts are true, others well that is for you to figure out. In this world, there are no STD's and the heroine cannot get pregnant. Constructive criticisms are welcome. For the boo birds, please post your stories for our critique. * Ann was s...

High Society Pt. 03 - Extended Version

by shoguy on Apr 23, 2019
Loving Wives

In this chapter 18 year old stud, Taylor fucks his Principals 70 year old black wife for the weekend with his tireless twelve inch cock. Every woman the eighteen year old high school senior fucked, cheated on their rich husbands. All led High Society lifestyles. A big part of that lifestyle was cheating on their spouse. From tennis pros, to personal traine...

Staying with Mrs. Wentworth, Day 02

by softspokenstephen on Sep 11, 2017
Mature

This is the second part of staying with Mrs. Wentworth. A lot of people gave me great feedback and made suggestions I tried to use including more details on the clothes which I tried to look into more, doing some research and using some suggestions. Thanks to all of them for making this better than it would without the advice. I can see keeping going with th...

Testing Kate

by Mentor de Lyon on Sep 14, 2017
Group Sex

When Jen was satisfied with Kate's training with the strap-on cock, she proposed that we test Kate on its proper use. To make the "test" more challenging, we decided that we would have Kate fuck an attractive woman whom she had not previously met and that we would video the testing session. I suggested to Jen that Sophie, the wife of our friend Marc, would b...

David's Friend Vivian Ch. 03

by Thorilla on Sep 13, 2017
Fetish

(My name is David Thornberry. It happened when I was just 18 in 1958. I was alone in my parents' house with Vivian, the 20 year old daughter of some neighbours. I had always thought that she was unworldly and I would have to coax her even into letting me see her knickers. She surprised me in her interest in sitting on my face and wanking me off. This is par...

Mistress' Comfort

by perfectlygray on Sep 17, 2017
BDSM

Author's Note: This is my first attempt to post a story that I wrote from a female point of view. Not sure if I got it right, but thanks to those who helped with proof reading and coached me. As always, comments and suggestions are appreciated. I hope you enjoy. ================= It was a horrible day. After 3 years at the same office, you'd think that I...