Jack And Jill Stories

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Jack and Jill

by Historynut on Sep 17, 2017
Non-Erotic

Jack and Jill: The Awakening of Priapus and Venus Jack Manly and Jill Comfort sat across from one another at a table in a dimly lit bistro, holding hands, gazing deep into one another's eyes. Their voices were low and becoming throaty as they talked quietly. The flickering candle light added subtle highlights to Jill's (Dare I use the cliché?) peac...

Jack and Jill Meet Melonie

by Flashlight7.5 on Sep 1, 2017
Group Sex

It was a swinging reception in a grand hotel with a funky DJ and great food. Jack had been dancing most of the night and Jill had been teasing him with glances and touches for most of the time. Jack had moved to the large fruit bar and was helping himself to some grapes when Jill came quietly up behind him. "Hi," she purred. "Hi." He fed her a grape. "Did...

Jack and Jill Ch. 3

by millieteases on Sep 1, 2017
Group Sex

NOTE: This is an adult story. If you are not a legal adult in your jurisdiction, please do not continue. If frank depictions of human sexuality offend you, please do not continue. Otherwise, please enjoy. Together to Learn - Jack and Jill "Well, I think we need to do something more," said Mitsy. "I mean, the other night was tremendous, but there's got to b...

Jack and Jill Jack Off

by Gunnsinhosen on Sep 13, 2017
Exhibitionist & Voyeur

Background This is a work of FICTION – nothing more than an expression of mutual physical attraction (LUST) between two friends! So the chatting and flirting went on and on, getting ever closer to outright "sexting" or "cybersex", but not going the entire way. That was until Jill texted Jack about seeing a man who looked like him holding a melon and brin...

Jack and Jill's Parallel World Trip Ch. 01

by MeatBeat117 on Jul 4, 2018
Sci-Fi & Fantasy

*All characters who have sex in this story are over 18* *** Jack was pissed off. It was the middle of summer and he was supposed to be at Lyla Banks's house maybe getting laid for the first time but instead he was off to see his boring as hell step-sister. "What's wrong, honey?" Asked his mother. "Why do I have to do this? Jill is so boring and I'm gonn...

Jack and Jill's Parallel World Trip Ch. 02

by MeatBeat117 on Jul 10, 2018
Sci-Fi & Fantasy

After they had both cleaned themselves, Lyla made her way to go out the door without a stitch of clothing on. "Shouldn't you get dressed first"? Lyla laughed "you're gonna have to get used to life outside the church soon dude," she said, walking out. Jack reluctantly left his clothes behind and walked outside and was greeted by another surprise. Everyone...

Jack and Jill's Parallel World Trip Ch. 03

by MeatBeat117 on Aug 14, 2018
Sci-Fi & Fantasy

Jill held down on his wrist and a holographic screen shot out of it. "Alright so here's your phone and the app is down here," said Jill, pointing down. "Ok," said Jack, tapping on the app that said "Malone". A bunch of different options turned up on the screen such as viagra, pubic hair, cum taste, and many more. Jack tapped on viagra and a tick appeared...

Jack and Jill's Parallel World Trip Ch. 04

by MeatBeat117 on Jun 5, 2019
Sci-Fi & Fantasy

Editor's note: this story contains scenes of incest or incest content. ***** Jack woke the next morning to the smell of pancakes and made his way downstairs to find his sister cooking naked in the kitchen. She smiled as she saw him enter and sat two plates down at the table. "So he's finally awake!! Dig in bro," she said, smiling. Jack sat down and start...

Jack and Jill Pt. 01: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

Dinner was almost ready when the doorbell rang. He turned down the stove and went to answer the door. She was taller than he expected, broader too, but she was undeniably a very attractive black woman. 'Hi,' she smiled 'You must be Jack, I'm Jean, it's nice to finally meet you.' Jean was Jill's colleague from work, he had heard about her many times over t...

Jack and Jill Pt. 06: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

They had been trying for a baby for some time and had come to the sad realisation that it wasn't going to happen without some intervention. The doctors wanted them to use donated sperm and have insemination, but it seemed so clinical. Jean had told them about a breeding club that she had worked in and they both liked the sound of it, but as she was walking t...