Jealouscuck Stories

107 results
Orientation
Length
Source
Infinite Scroll

A Halloween to Remember Ch. 02

by jealouscuck on May 7, 2019
Fetish

The morning after the Halloween party, we woke up as usual. I felt a little different under the covers until I remembered what had happened after we made love the night before. We had showered and then I picked out two pair of sexy panties. One for Jeff and one for me. I looked over at him as he started waking up. Jeff had been at home from work for a while...

My Friend Ashley Ch. 07

by jealouscuck on Aug 20, 2019
Transgender & Crossdressers

I looked at Sheila's big cock and was amazed how such a beautiful creature could have such a marvelous package. On my HRT regimen, my once small little dicklet had become even smaller. It was barely a flap now and I had begun referring to it as my 'clitty'. I licked the bulbous head and tasted the precum starting to flow from her. She let her panties fall fr...

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. 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...

How Lisa & I Saved Our Marriage

by jealouscuck on Sep 19, 2017
Loving Wives

This is how my wife and I saved our troublesome marriage. My wife Lisa is a tiny vivacious blonde with a short pixie haircut. She was brought up in a strict religious household. This strict upbringing along with her southern roots may have been one of the reasons why she became so adventurous. Her family moved a lot all the way through her school years. She...

My Friend Ashley Ch. 04

by jealouscuck on Jul 2, 2019
Transgender & Crossdressers

In a few short months, I had gone from a broken-hearted little man with a small dick to dressing as a woman and having oral sex with women and one man. What really stressed me after our date with Kevin was that Gretchen had instructed me to suck Kevin's big cock and I had acquiesced without so much as a second thought. Afterwards, I had trouble deciding whet...

Obey Thy Neighbor Ch. 04

by jealouscuck on Oct 24, 2018
Transgender & Crossdressers

After I had witnessed Cecil and Li fucking I began worrying about what Chelsea might be missing out on. After all my cock was less than four inches long when erect. Seeing his massive cock penetrate Li's pussy and seeing her pussy afterward I was feeling so inferior that I almost wished Chelsea could have that type of experience. One of the reasons why I was...

My Secret Revealed Ch. 06

by jealouscuck on Jun 19, 2018
Transsexuals & Crossdressers

I had crossed a line by myself. Here I was at Sally's apartment, not knowing who was there for sure and transformed completely into a passable woman. I had ventured out and found a crossdresser shop on my own. The sales "person", Tammy had not only helped me with shoes and clothing, she had me come back in for a complete makeover before I was to go to Sally'...

Obey Thy Neighbor Ch. 07

by jealouscuck on Nov 19, 2018
Transgender & Crossdressers

We named our company C&M Consultants. I loved being Mel to some of my customers and Millie to most of the new ones. We did indeed grow beyond our wildest expectations. We recruited entry level accountants and other trained industry savvy people. There was a good blend of technical and practical expertise. After two years, we were able to hire a full time man...

Doreen is Pregnant Ch. 02

by jealouscuck on Sep 18, 2017
Interracial Love

My wife Doreen was pregnant by our landscaper, Raymond, a young handsome black man. In the previous chapter I explained how I went from a downtrodden cuckold to accepting Doreen and her pregnancy. I had done much soul searching and admitted that I loved her too much to divorce her. She did not want a divorce either. As she began to show her baby bump, we wer...