Sissy Jenny Cuckold Stories

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Infinite Scroll

The Sexy Cuckold Couple Pt. 11

by cuckcpl4play on Sep 19, 2017
Fetish

This is part 11 of the series and it is about the fantasy we have as a cuckold couple. We have engaged in many acts of cuckoldry, but the story itself is fiction. If you are offended by this type of lifestyle than please don't read. It amazes me that we continue to get such negative comments to this series from people claiming that we are uneducated or despi...

The Sexy Cuckold Couple Pt. 05

by cuckcpl4play on Sep 19, 2017
Fetish

Ceremony Preparation Continues as Does slave's New Life at Work (Day One) part 5 Background: we are a cuckold couple and one of our past Bulls ordered cucky to write a long story that included creative ideas that he could employ with us as a couple. As such, much of what is written here is based on fantasy and we would not live out many of the situations he...

Being Jenny's Summer Boyfriend Ch. 03

by Lucas96 on Jan 21, 2020
Fetish

Disclaimer: this story involves cuckolding, humiliation, cross-dressing, and gay incest. *** I have to admit, it was difficult to contain my excitement as Jenny invited my dad and brother over to show them what a little sissy slut I'd become. To prepare, Jenny let me try on the outfit she'd had on when we'd come over to Andrew's house: a pink, tight-fitt...

The Sexy Cuckold Couple Pt. 04

by cuckcpl4play on Sep 19, 2017
Fetish

Miss Jenny and I entered the home and there was a sense of relief to be in our own house and only then did we communicate. I asked simply...did you enjoy yourself and Miss Jenny smiled broadly...his cock is so huge and he felt so amazing inside me...the experiences we are all going to share will be amazing slave and she hung on that last word for a bit. It w...

Being Jenny's Summer Boyfriend Ch. 02

by Lucas96 on Mar 5, 2018
Fetish

Disclaimer: This story contains cuckolding, humiliation, homosexuality, and incest. All characters in this story are above the age of 18. ***** Here I was, on my knees between Jenny's legs as she sat back on the couch. Slowly, reluctantly, I stuck my tongue out and moved it toward her naked body, dripping with my dad and brother's cum. I was so grossed out...

The Sexy Cuckold Couple Pt. 09

by cuckcpl4play on Sep 19, 2017
Fetish

Part 8: The Ceremony We arrived home and almost like clockwork, a text came in to Miss Jenny's cell as we pulled up the drive. Master's text read...time is fleeting slut so you will have visitor's at your place shortly to help with your final task before dressing and officially submitting and devoting yourself to me as my owned slut Oh, and make sure slave...

Extreme Cuckold Fantasy Ch. 02

by Revan7 on Jul 29, 2019
Interracial Love

Prologue It's been two years since David and Jenny had started to fantasise about cuckolding. Two years after that jenny was pregnant with one of four black man's baby. They were on week away from a villa holiday in Spain with these four black men and were about to go out and get queen a of spades tattoos for Jenny. Jenny was pregnant with a black man's bab...

The Sexy Cuckold Couple Pt. 16

by cuckcpl4play on Sep 26, 2017
Fetish

PART 16: REST / EVENING EVENTS Showered with mixed feelings, I thought about the day's events thus far and looked at my beautiful wife. She gazed back at me and it was such a strange sensation as I could literally feel the love and energy between us despite all of the events that had transpired. My mind brought me back to the moment; we were absolutely exh...

The Sexy Cuckold Couple Pt. 12

by cuckcpl4play on Sep 19, 2017
Fetish

AGAIN, cuckold story with humiliation and if this offends you, please don't read! While fiction, we have experienced ample aspects of this story and this lifestyle. ***** Part 12 Vegas The men hustled out of the limo and rushed up the stairs to get a seat in close proximity to my wife. Master ordered me to keep sucking the used condom and rather than allo...

The Sexy Cuckold Couple Pt. 10

by cuckcpl4play on Sep 19, 2017
Fetish

After the crazy collaring weekend, our home life shifted slightly back to some form of normalcy. Master would send us occasional texts, orders, etc., but overall there was nothing significant that was transpiring and in fact Miss Jenny seemed sad that more activity was not taking place. At work it was a bit of a different story...Master was his typical domin...