Cuckold Chastity Resort Stories

23,621 results
Orientation
Length
Source
Infinite Scroll

Melody Malone

by Just Plain Bob on Sep 16, 2017
Mature

I was in Los Angeles on business and one day I was in Century City for a business conference and when we broke for lunch I headed for a restaurant I'd heard about. I was walking down the street when something slammed into my shoulder and I heard a voice say: "Watch where you're going asshole." I turned and saw a guy standing there looking at me and smiling...

Angela’s Choice

by hunter_gatherer on Sep 13, 2017
Interracial Love

NOTE: This story contains sexual intercourse between a married white woman and a black man. If this offends you then please do not continue reading. This story is intended to be shed some light on Angela who features in another story titled Angela's Plan. Reading that story is not required to read this story, and vice versa. ***** It all began with a lunc...

The Cameraman

by spoilmwhole on Sep 12, 2017
BDSM

My new tenant is such a joy to have around. Take right now, for instance. This is my day off and as I write this story he is under my desk curled up keeping my feet warm like a good housecat. Later, he'll help me get ready for my date. Then, if and when I make it back, he'll be waiting to take care of all my illicit desires. It started a week after my new...

My Three Valentines

by SEVERUSMAX on Sep 12, 2017
Group Sex

I had gone to bed a little groggy the night before, assisted by some Jim Beam and sheer fatigue, as I had worked one hell of a day at Winthrop and Associates, a top-notch advertising firm, before I got home for a Valentine's Day date with Shelly, my wife of just one year. The date had gone well, partly due to Shelly's giving nature, where she had actually co...

Infatuation

by brain_damage on Sep 17, 2017
Loving Wives

My name is Roger and my wife is Beth. We are both 52 years old and have been married 31 years. We have two kids, both grown and married and are waiting for our first grandchild. I'm looking forward to it, but Beth said the thought of it made her feel old. She really has nothing to worry about. Beth has kept herself in great shape and can still turn heads. Bu...

Double Your Fun

by Hypoxia on Sep 17, 2017
Loving Wives

Author's note: This willing-wimp tale is probably fictional. Nobody under 30 has sex. Views expressed are not necessarily the author's. Enjoy ***** Double Your Pleasure, Double Your Fun ***** -- Late 1995 -- I'm Randy. That is both my name and my condition. Pretty funny, hey? My consulting business (details of which do not matter here) lets me control my...

Law of the Heart: Consequential...Ch. 04

by capecodmercury on Sep 17, 2017
Loving Wives

Law of the Heart: Consequential Damages Chapter 04 At first light, I woke from my restless slumber. I carefully disentangled myself from Jill and slipped out of bed. Over the course of the night, I had decided that this morning might be easier on Jill and I if it appeared to our classmates that I had gotten in late last night as Jill had told Juan. I wante...

The Big Webcast of 2004

by thebullet on Sep 14, 2017
Loving Wives

Nerd. It's a title I've worn proudly for most of my life. Actually it's a title I've cultivated. I've always had glasses with the elastic holder around my neck, even though my vision is 20-20. They are only reading glasses, but my public doesn't know that. I have my hair cut in a short, 1950's manner. My clothes are just slightly off kilter, geeky and diffe...

Unexpected Cuckold Adventure

by Oscar99 on Dec 2, 2019
Loving Wives

Diane watched as the remaining bath water swirled down the plughole. Once the bath was fully emptied, she took a deep breath and wrapped a towel around her body before heading through to the bedroom to continue getting ready for her date. Her new fiancé, Rick had made an agreement that she could decide on her outfit for the date as long as he got to choose t...

Carolyn & Randy

by chloejacobs83 on Sep 24, 2019
Loving Wives

"Hello." "Oh, hi...hi there...this is..." "Hang on...one sec please..." Phone noises, noises of a dog, a door closing. More dog noises. I was sweating. "OK. Sorry for that. Who is this please?" "Oh, Hi. I'm...well, is this Tom? I don't know if you remember me but this is Randy. From the other..." "Randy?" "Yeah, Randy. From the other night? At Cafe No...