Jealouscuck Stories

107 results
Orientation
Length
Source
Infinite Scroll

Erotic Games Ch. 03

by jealouscuck on Jul 17, 2018
Fetish

MEREDITH'S STORY When Brad and I got married, I was intending to leave my wild side behind. I was a nurse and really enjoyed it. I had made it up to the position of a personal nurse to a very nice doctor. Brad called on my doctor and that is how we got to know each other. I had been in several relationships, but I was not ready to settle down just yet. I am...

Finding My Genie Ch. 02

by jealouscuck on Sep 14, 2017
Transsexuals & Crossdressers

My new girlfriend, Genie, had asked to borrow a pair of my underwear to wear home. She had already dropped some hints about approving of my men's styled bikini underwear. When I offered her a pair of cotton briefs, she refused stating that I was not going to pawn off old cotton briefs while I wore sexy bikini style underwear. When we got to her apartment l...

Pretty in Pink

by jealouscuck on Oct 8, 2019
Fetish

I always remember thinking how bland men's underwear was compared to women's. In the animal kingdom, the male usually has the prettiest colors. Not so in people. I suppose traditionally, men's underwear is supposed to be functional while women's are fashionable. I was a late maturing kid. I was probably about two years behind some of my classmates. When I d...

My Secret Revealed Ch. 02

by jealouscuck on Mar 14, 2018
Transsexuals & Crossdressers

My wife had accidentally found panties in my travel bag. Even though she was not trying to discover anything hidden in my bags, the deed was done. I explained the beginning of my panty fetish. (Chapter 1). What she objected to was my keeping part of my sexual preferences a secret. The trouble came from trust issues. After a trip out of town and us finally be...

Doreen is Pregnant Ch. 04: At the Party

by jealouscuck on Oct 15, 2017
Interracial Love

After our daughter, Patti, was about five months old, Doreen was invited to a special party at Sharee's house. (See Chapter 3- Doreen Delivers) I was left to baby sit. Since I had not met the other mothers or fathers, I was not yet invited to the guy's babysitting party. As I mentioned at the end of Chapter 3, Doreen dressed up for the party, but did not wea...

My Friend Ashley Ch. 05

by jealouscuck on Jul 29, 2019
Transgender & Crossdressers

Things were no longer in the experimental stage. Gretchen had set me on a path to feminization and Ashley was following her lead. Ashley had already broken one of her restrictions. She had allowed Gretchen to perform oral sex on her. The distinction that I was performing oral sex on the women while dressed as a female. When Gretchen ate Ashley's pussy, Ashle...

My Friend Ashley Ch. 02

by jealouscuck on Jun 19, 2019
First Time

After Ashley had sex with Rod, there was no mystery. She came out after Rod left and gently knocked on my door. I got up and let her in. "You're not mad at me, are you?" "No, Ashley. Matter of fact I could not help but hear the commotion in there. Was it good? It sounded just like you described. Did you fuck him into submission?" She laughed. "Well, it wa...

Erotic Games Ch. 05

by jealouscuck on Aug 22, 2018
Fetish

Meredith's Story We were fully engrossed in erotic game play when Brad went to great lengths to dress me like a prostitute and send me out on my own. It was really neat that he got himself new dork clothes and dressed up like a handsome Greek man. He even shaved his head and wore a fake mustache. His gay friend from the theatre arts classes really fixed him...

A Halloween to Remember Ch. 03

by jealouscuck on May 7, 2019
Fetish

I didn't want to get totally involved in Sonia and Keith's sexual fantasy, but I had shared that Jeff had cum in panties more than once. According to her, Keith was in a new world dressing regularly. He had a drawer full of bras and Sonia was going to purchase some breastforms for him. I wondered if we might end up having a little party in the future with Je...

Jenna - Sweet Size Queen Ch. 06

by jealouscuck on Sep 16, 2017
Group Sex

After Jenna and I had picked up a young black man for sex, we had added a new dimension yet again to our relationship. It was like we were closer than ever. Jenna getting it on with a big black cock would have been a sexy story by itself, but the way we planned and shared made it special to both of us. By now it was more evident that her pussy was made for l...