Jack And Jill Stories

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A Place to Call Home Pt. 04

by JackandJilldo on Oct 13, 2020
Erotic Couplings

Dozens, if not hundreds, of results popped up on the monitor, and I had no idea where to begin. Most were links to her videos, and there were a ton of them! Jill placed her hand over her mouth as I scrolled down page after page. After page. After yet another page. "Oh my god!" she gasped softly, dropping her head in shame. "That's really me?" "Looks like y...

Intersexed Man Fucks Girlfriend Ch. 02

by freewritter on Sep 12, 2017
Fetish

The morning brought Jill and I into a lazy Saturday morning. She woke up rolling over and messaging my penis, while spreading my skin with her fingers to gain access. My dick was semi hard from the regular morning hard on, and as she began to wet her finger with my dripping of pre cum, she rubbed the head of my penis causing my shaft to begin enlarging. At t...

Jack and Jill Pt. 05: Thailand

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

The decision to move to Thailand was a big one, but Jill was glad that they had done it. Here they could live out all of their sexual fantasies in total freedom, without judgement or harassment. She had completed Jack's feminisation by insisting he had breast implants when they arrived, but that was months ago and they were all healed now. She loved to grab...

A Journal of Truth Ch. 09

by Dlicious_49 on Sep 12, 2017
Group Sex

I didn't go home for the weekend as had been my usual schedule. No, this weekend, I stayed in town because hubby was at a manager's conference that weekend for his firm. Since he'd be gone, I chose to spend that weekend in Denver where I had been commuting to as a consultant to my old employer. The plan was to catch up on some paperwork and, perhaps, a whole...

My Journey into Sluttiness Ch. 03

by snowbunny1978 on Sep 15, 2017
Loving Wives

Preamble Reading Chapter One will place this in context Bill's lessons were finished with no more contacts between us. Jeff and I had two more love making encounters where one took place over several hours on a night that John was out of town. Being with Jeff, cheating more and having awesome sexual pleasure I was becoming more comfortable with myself and...

The Incriminating Dots Pt. 03: Discovery

by Cuckoldjim on Sep 17, 2017
Loving Wives

Jack had been sitting in yet another lonely hotel room on yet another lonely evening, lamenting the escalating demands of his career that compelled him to travel so often when the fateful text arrived. His most recent business trips had been even lonelier than usual because of his lingering anxieties about Jill's recent business trip. He could vividly recall...

Fairy Tale Fuck Fights 05

by markydaysaid on Sep 25, 2017
Sci-Fi & Fantasy

NOTE: This story is a sequel to Fairy Tale Fuck Fights (3 or 5 depending on the website): Little Bo Peep versus Baba Black Sheep. # STORY TILL NOW: Little Bo Peep is the most badass pimp in her little kingdom, hooking up every prince and pauper with the penises and pussies of their choice, but recently another badass pimp has been muscling into her territo...

Jen's Birthday Pt. 06

by tailfin on Aug 14, 2018
Group Sex

[I appreciate all your constructive comments. It is difficult to find time to write and your encouragement is motivating] * Jen awoke cuddled next to Stacey under the covers. She briefly wondered where Jeff had gotten off to, but began focusing almost immediately on how amazing Stacey's soft voluptuous body felt next to her. Jen nuzzled up to her and spoon...

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...

A Place to Call Home Pt. 01

by JackandJilldo on Mar 2, 2020
Erotic Couplings

I live out in the country, with several dozen acres of land that overlook a small mountain chain. It's a beautiful view from the top of the ridge where my house is, with sweeping views of the valley, and the mountains extending for twenty miles or so before terminating. Aside from that, it's mostly wooded and very private; sitting in almost a half mile from...