Jealouscuck Stories

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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...

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...

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...

Pretty Chris-tine Ch. 02

by jealouscuck on Sep 26, 2017
Fetish

My wife, Sharon, and I were lifelong friends. We eventually began dating and then got married. The idea that eventually shaped part of our sex life was her grandmother remarking that I was too "pretty" to be a boy. She thought that my complexion and clean looking face was attractive. One time as a lark, Sharon asked me to let her put makeup on me. I initiall...

Creampie Lover Ch. 04

by jealouscuck on Sep 26, 2017
Fetish

Once Cynthia had actually fucked another man, we vowed to keep up our kinky side of marriage as time and opportunity permitted. A big limiting factor was our desire to keep this completely private and for special occasions. She was a hard working associate at a prestigious law firm and I was also known in the business community. We knew we could never be tru...

Creampie Lover Ch. 01

by jealouscuck on Sep 26, 2017
Fetish

The title of this story is the last thing I would have ever thought about when I was growing up masturbating to pictures in Playboy and Penthouse. I had heard all the stories about what masturbation causes, but like everyone else I kept on doing it because it felt so good. When I shot my first load of cum, I thought I had arrived. However, remember how caref...

Creampie Lover Ch. 05

by jealouscuck on Sep 26, 2017
Fetish

Cynthia and I came to an agreement early in our relationship. I knew that she had been with guys with bigger cocks than me. I experienced some rejection syndrome at first. Ultimately, she convinced me that vaginal sexual gratification is not the basis for marriage. We clicked on so many levels that it made sense to compartmentalize sexual events to a special...

Creampie Lover Ch. 02

by jealouscuck on Sep 26, 2017
Fetish

In the previous chapter, I shared how I met Cynthia and how our relationship had survived our first crisis. After we resumed our hot sex, we played hard and steady for about a month. However, one evening during some hot oral sex, she started talking dirty. She was saying things like, "Shove your big cock up my hot cunt." It excited me and I shot my load into...

Creampie Lover Ch. 03

by jealouscuck on Sep 26, 2017
Fetish

In the previous chapter I finally got a fresh creampie from my wife, Cynthia. I had encouraged her to seduce a nice looking man from South America. This was a watershed moment for it gave Cynthia a chance to experience a big cock and gave me a chance to eat another man's cum from her pussy. The following morning, I asked her if she had any regrets. She sai...