Jack And Jill Stories

359,762 results
Orientation
Length
Source
Infinite Scroll

Jack & Karen Ch. 01

by Ahabscribe on Sep 19, 2017
Mature

Chapter 01: The Motel Clerk and the Wedding Present My wife, Karen and I had left immediately after work Friday evening to attend a friend's wedding in another state. The wedding was Saturday evening and the plan was to arrive late Friday night and then relax at our motel all day Saturday. Karen works as an agent for a real estate firm and I sell advertisin...

SheMale Sirens Ch. 03

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

Chapters 1 and 2 seem to have done great, so here is number 3. This will probably be the last one. In the future though, I plan on doing a longer series based off of this, but it will focus on one main character and him adjusting to life in Anthemusa. I don't intend to start that right away, as I have a few other ideas in mind before the end of the year, but...

I Am Jack's Life Ch. 11

by Finis on Sep 13, 2017
Novels and Novellas

Author's note and acknowledgements This story has sat on my hard drive for four years now. I wrote it, all twenty chapters and 95,000 words of it in eight days of a frenzied, near trance-like state, sitting on my couch with my wife's laptop. She would occasionally have to remind me to eat. When the dust settled, and I looked up, I realized a couple of...

Just a Love Story

by Rob5373 on Sep 24, 2019
Loving Wives

Chapter 1 The Present It's been four years since I blew up my wonderful marriage and lost the love of my life of 18 years. I'd like to say it was a drunken binge and I didn't know what I was doing but that would be a lie. Was I getting a revenge fuck for an unfaithful wife? Hell, no! My wife is the most loving, loyal, faithful not to mention sexiest woman I...

The Bookkeeper

by Miltone on Sep 16, 2017
Anal

"Well, I'll be taking off now Jack," called out Hal, the sales manager, as he headed toward the back door. "Make sure that you don't lock in our auditor when you leave!" "Oh, is she still here?" I asked, jumping up and stepping over to the door. "I thought she would be finished and gone by now." "So did the rest of us, but I guess she had to stay on to fin...

Harmless Flirting - Ending 02

by fritz51 on Sep 23, 2019
Loving Wives

Forward If you have not read my "Harmless Flirting" story already, I strongly recommended that you do so BEFORE reading the any of the three endings. I was very torn over how to end this one so I decided to offer a variety. I will be interested in the acceptance of each ending and am uploading them one at a time to allow the reader to digest an ending befo...

The Ad Ch. 03: Todd

by tedsgirl on Sep 16, 2017
Group Sex

"Hey, are you sure they won't mind me coming over like this?" Todd asked Jennifer as they made out in the living room. "No, they won't mind, they said I could have company over any time I wanted too." Jennifer said as she rubbed her hand over Todd's bulging jeans. She did love to tease him and get him hard, then lick and suck his cock. She had been living w...

Cass's Capture Ch. 05

by xsweetvixenx on Sep 15, 2017
Romance

Greetings readers, I know that this took a little bit longer than intended, but you will see that it is well worth the wait! As always I appreciate all the feedback that you send, it encourages me to continue. Dont forget to vote!! A special thanks to a fellow writer that helped me with my vision in this chapter! Enjoy! When Cass finally woke up, it w...

I Am Jack's Life Ch. 02

by Finis on Sep 13, 2017
Novels and Novellas

Author's note and acknowledgements This story has sat on my hard drive for four years now. I wrote it, all twenty chapters and 95,000 words of it in eight days of a frenzied, near trance-like state, sitting on my couch with my wife's laptop. She would occasionally have to remind me to eat. When the dust settled, and I looked up, I realized a couple of...

Sorting Out The Smiths Ch. 05

by andy_charles on Sep 16, 2017
Novels and Novellas

Tales From Sechs City -- welcome to Sechs City, a wealthy, middle-class costal area of Western America in the state of California. A gorgeous, quiet largely uneventful place, people move to the city to follow their dreams, to live their day-to-day lives. It's almost too perfect to be true... * "Honey? Lianne?" Lewis was full of excitement as he charged th...