Jealouscuck Stories

107 results
Orientation
Length
Source
Infinite Scroll

A Halloween to Remember

by jealouscuck on Apr 10, 2019
Fetish

It started as a silly trick or treat fun game for our husbands on Halloween. I am Sandra. My husband, Jeffery and I had been married for three years at that time. I don't work anymore because Jeff makes very good money. He is an inventor and has contracts all over the world with small companies that manufacture some of his simpler products. Jeff is 30. He is...

Dressed To Please Kate

by jealouscuck on Sep 25, 2017
Transsexuals & Crossdressers

My name is William Michael. I go by Bill. I know, stupid way to start a story. My wife is Caitlyn and goes by Kate most of the time. You will see why I started with names. Kate is thirty and I am thirty-one. We had been married three years when all this started. Kate is a very perky brunette, five-four, about 130 lbs. She has very little body fat and is athl...

Dressed To Please Kate Pt. 02

by jealouscuck on Sep 25, 2017
Transsexuals & Crossdressers

Kate and I went from newlyweds to a loving dominant/submissive couple. I had been introduced to feminization and really loved to be dressed totally. We had close friends who had actually introduce Kate and ultimately me to the lifestyle. While most of our life was "normal", we became very active in the alternate lifestyle. We would go shopping with me dress...

Obey Thy Neighbor Ch. 06

by jealouscuck on Nov 6, 2018
Transgender & Crossdressers

When Chelsea returned from her out of town assignment she was excited above all expectations. She kissed me hungrily and thanked me profusely for letting her experience sex with a well hung man. She questioned whether I had any regrets. I did not. When she heard this, she expressed to me that the only second thoughts she had about it was if it somehow began...

Marriage Transformation Ch. 01

by jealouscuck on Nov 25, 2017
Loving Wives

Elizabeth and Chris got married very young. He was nineteen. She was eighteen. Chris was a very bright student, while Elizabeth was more average. Chris was already in college when they met. Elizabeth was still in high school. They both grew up in rural settings on opposite sides of the school district. They did attend the same high school, but Elizabeth was...

Husband is a Good Sport Ch. 01

by jealouscuck on Feb 26, 2019
Fetish

I married my husband Cameron when he was a junior in college. He was twenty-one and I was twenty-six. Usually the age discrepancy of couples is the opposite of our situation. He was going to university and living at home throughout his college days. He was working as a waiter in a local pub and eatery. I was there for lunch with my then boyfriend Alex. He is...

A Free Vacation Ch. 01

by jealouscuck on Nov 18, 2019
Interracial Love

It was merely a coincidence that Daniel Jeffers was looking for a company named FREEVAC. He googled it to see where their corporate offices were. During the search, he noticed an entry entitled FREE VACATION. He guessed the word free is supposed to appeal to one's subliminal mind. After finding the company, Dan returned to the search and clicked the website....

Pretty Chris-tine Ch. 03

by jealouscuck on Sep 26, 2017
Fetish

After I had learned to openly share all my fears and inhibitions with my wife, Sharon, we really began to enjoy our sex life even more. In the last chapter, I told about how she encouraged me to dress up "pretty" for her. This was not our entire role playing event, but rather a very titillating one we both enjoyed. And now, I totally enjoyed our evenings and...

Jenna - Sweet Size Queen Ch. 05

by jealouscuck on Sep 11, 2017
Interracial Love

After our Mexico trip where we swapped with Judy and Jeff, we returned home and settled back into our work routine. Things felt different for a while. Jenna and I talked about our experience with swinging and she said that she was so turned on by Judy fucking the young stud from the pool that she was in a zone of anticipation when we were at dinner. Jenna sa...

Obey Thy Neighbor

by jealouscuck on Sep 18, 2018
Transsexuals & Crossdressers

My name is Melvin Johnson. I am an accounting executive for a very large medical conglomerate. I have the luxury of working from my home office a good portion of the time. Not that it is all roses for I travel some and work some long hours out of town. My wife Chelsea is also an accountant. However she travels at least sixty percent of her working time. She...