Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
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Infinite Scroll

Sat Night Cuckold

by gandj130 on Sep 16, 2017
Interracial Love

It was Saturday evening and all day Gary had been excited. He pulled me close and I felt the bulge in his trousers. "You're up to something." "Let's play tonight. On a scale of one to ten, how much of a slut are you?" "Ten," I whispered. "If you'll follow my instructions tonight, we'll have some fun," He said taking out an envelope from his pocket. I ca...

The Underground Cuckold

by Craig88 on Sep 17, 2017
Loving Wives

It was a warm Thursday night as my girlfriend and I strolled home from our friends house and we had been drinking, I felt quite tipsy. My girlfriend Madison looked so hot tonight. She was wearing a pair of heels and short plaid schoolgirl skirt that left little to the imagination. I was kind of glad we had left our friends house as one I had such a hard cock...

It was 2 Against the World Ch. 01

by eagle166 on Sep 25, 2017
Interracial Love

Hello my name is David I'm 40 years old 6 foot 1 inch tall 195 lbs. my wife is Katy 39 years old, very shapely 5 ft. 6 in. blonde, about 130 lbs. we have been married nearly 17 years now with one daughter Amy, 16 and she is a junior in high school. I am a co owner of a growing construction company. We build larger retail shops and malls. My partner has been...

The Creampie Journey

by sparkyinoh on Dec 16, 2019
Erotic Couplings

This is a story about myself, Mark and my second wife Jeanie. We are both 46 and on our second marriage. Being the second time around we both spent about 1 year dating before deciding on a 2nd marriage. Things that were lacking our 1st time around, we did not want to continue with the 2nd. We both had good careers, were each financially independent, kids wer...

Delivery Suprise

by AlwaysBiCurious on Nov 20, 2018
Transgender & Crossdressers

It was 3 hours and 45 minutes into the delivery window and I still didn't have my new washer and dryer. I picked today for delivery because my wife is out of town visiting her sister. I picked the afternoon time-slot so I could have an excuse to take off a Friday afternoon. I picked this Friday because my two daughters are off at college and weren't coming h...

Cuckold Love Story Pt. 01

by Anal Slave on Sep 12, 2018
Fetish

This story is about the love between a small cocked husband and his beautiful wife. If any of the following subjects offend you this story is not for you. Cocksucking, MMW, Man on Man, cum eating, worship cock, creampie, She male, sex without a condom, fucking, sucking, forceful sex.. For the rest of you kinky fuckers, read on. Kick back take out your cock m...

Cuckold CEO Ch. 05

by drdick69 on Oct 9, 2018
Fetish

Day three of our vacation started with a thud. I woke up rolled over and my wife informed me that she had started her period. Well at least I was getting unlocked from my cock cage for a week. Usually, when my wife has her period, she unlocks my cage and lets me jerk off to relieve myself for a week. Sometimes we play sexy games with each other, but mostly i...

Locked Away and Lovin' It

by dutchpantyraider on Oct 30, 2018
BDSM

We had a nice cosy dinner one Friday night after work, at Sophie's place. We is Sophie, Camilla and Dennis, who both work at the marketing dept. of our office, and Sam and her hubby. Sam works with Sophie and me. We all get along pretty well, sometimes having dinner together or a have a drink in a pub down town. This Friday we found ourselves at Sophie's pla...

Closure for Dylan

by Tiberius_Daniel on Jul 17, 2019
Loving Wives

After an affair people hurt. It's a fiction; any concordance with reality is only accidental. *** Patrick Stevens was about to enter his house when he felt a gun in his back. "Don't do sudden gestures," he heard a voice. It was not a firm voice, rather a hesitant one. "A beginner," Pat thought. "The most dangerous burglar, because he doesn't know wh...

Controlling Kali Pt. 01

by masterpwp on Jul 10, 2019
Loving Wives

I sipped on my glass of scotch as I looked across the table. Her name was Kali. She was a beautiful 27-year-old woman. This was the first night I met her, but I knew I had to have her. As she talked, I looked at her bright blue eyes, her long blonde hair, her short black dress that showed off her amazing curves, including her 34D breasts. How did I know he...