Jealouscuck Stories

107 results
Orientation
Length
Source
Infinite Scroll

My Secret Revealed Ch. 03

by jealouscuck on Mar 28, 2018
Transsexuals & Crossdressers

I was wondering what Karen had in store for me. When I got up the next morning, showered and shaved, I had little time to wait. She was holding her tiny g-string that she had worn the day before. A certain twinkle in her eye told me that something else was about to happen. "Honey," she said, "Like I told you last night, even with your smaller than average c...

Is It Happening?

by jealouscuck on May 12, 2020
Interracial Love

The role playing was getting more specific. Lucas was being named in their lovemaking. Both Stan and Charli were alluding to him finding her just fucked by Lucas and Stan eating Lucas' cum load from her pussy. They were painting some scenarios that while not extremely complicated, were targeting Charli having just been fucked. The most recent progression was...

Marriage Transformation Ch. 05

by jealouscuck on Dec 31, 2017
Fetish

Elizabeth enrolled in college. She negotiated with Bill and Maureen a three day week and loaded her classes on the two off days. Her receptionist job took little effort and she could do some of her homework during the traditionally slow times. This seemed to suit everyone at the store. She also got to catch up on everything with Cindy during her working days...

My Friend Ashley Ch. 03

by jealouscuck on Jun 25, 2019
Transgender & Crossdressers

Having broken up with my girlfriend, Karen, (or rather being ditched because of my little dick) I had moved in with my childhood friend, Ashley. Ash was a college track athlete, tall and gorgeous. Way out of my league. However, one night I drunkenly tried to move on her and she saw my little dicklet. She had sex with me anyway. This was the start of my educa...

Pretty in Pink Ch. 04

by jealouscuck on Sep 25, 2017
Fetish

Having a lifelong fetish for sexy lingerie was exciting, but my concern was having someone catch me wearing. After my wife, Jessica found out about my stash of women's clothing, I thought my marriage might be over. Her eventual understanding, learning and acceptance of my little kink was a life changer for our marriage and my peace of mind. When in fact she...

Pretty in Pink Ch. 02

by jealouscuck on Sep 18, 2017
Transsexuals & Crossdressers

I could not believe my good fortune. Not only had Jessica accepted my crossdressing, she had changed her whole attitude toward my fetish. We talked about it afterwards and she told me she was continuing to research the topic. In the meantime she made me promise that we would have no more secrets between us. Over time, she got me to tell her the full extent o...

My Secret Revealed Ch. 08

by jealouscuck on Jun 25, 2018
Transsexuals & Crossdressers

We had one more evening left in the Bahamas. Karen and I were still worked up sexually. I suppose that it was the adventure and the short mini vacation. We woke up late and had brunch. She kept smiling that "I know what you did smile". "Why do you keep smiling at me?" I asked. "Oh, silly, I was just thinking about last night. Girl, have you come a long wa...

Pretty Chris-tine

by jealouscuck on Sep 26, 2017
Fetish

Sharon and I got married when we were twenty. It was the magical fulfillment of our life-long friendship. Our families are very close, going back to our grandparents. On family outings, we were always together, for neither of us had siblings. We learned to play together and were comfortable from the beginning. To digress, Sharon was classic in some ways al...

Before It Happened

by jealouscuck on May 11, 2020
Interracial Love

Stan learned plenty about promotional sales from his father. He often marveled how his dad had managed to be so successful in the no-computer era when he began. There were no websites. Only mailouts and signs. Yet his father was the old-fashioned salesman. He did it with hard work, long hours and shoe leather. Stan had inherited is father's work ethic and in...

Not the Way I Planned It

by jealouscuck on Sep 18, 2017
Loving Wives

I met Traci in high school. We were in Chemistry together during our junior year. We lived close to each other and joined study groups with other friends in our neighborhood. All in our groups were very compatible and the association was somewhat like a club. The groups were fluid and dynamic with people coming and going off and on. Exam times brought everyo...