Jack And Jill Stories

359,762 results
Orientation
Length
Source
Infinite Scroll

All Dolled Up

by Flashlight7.5 on Sep 13, 2017
Erotic Couplings

"What do you think?" Jill asked, running her fingers through her hair. "Your hair looks great." Jack smiled from the bed. "But you need some lipstick, I think." "What kind?" She started searching through the vanity drawer. "Some sort of red would be the most appropriate, don't you think?" Jill didn't answer. She found a good color and slowly rubbed the...

Jack Fucks Jill's Mum Ch. 03

by Jack1107 on Oct 22, 2019
Mature

Jack received a message just after five from Sheila, it read, "Dear Jack, thank you so much for the time you spent with Jean and me last night, I appreciate it, last night was a learning experience for me, I'm convinced the wedding will be excellent, you have an excellent way with words, this is why I'm writing to you. I would like you to help me write my sp...

The Girl Next Door

by JerseyCop on Sep 13, 2017
Erotic Couplings

I can hardly believe nearly forty years have passed since I was a rookie cop in New Jersey. I was just 22 when hired in early 1969. I was just out of college and was, in fact, the first member of my department to have a college degree. This is quite likely my final story for Literotica as I am anticipating moving to Europe where I expect to languish on a Med...

Jen's Birthday Pt. 05

by tailfin on Jun 5, 2018
Group Sex

Jeff woke in the dark with an urgent need to pee. He was on his side and his cock was very hard and pressed against Jen's soft bottom. He could feel Stacey's bottom pressed against his own. Glancing over Jen he spied the alarm clock on the bedside table which showed it was 2:30. He could not believe how hard his cock was after what had transpired several hou...

Retirement Community Pt. 01

by Joeehartley on Sep 14, 2020
Mature

Joe E Hartley January 2020 Jack unpacked the final box the moving company had delivered. He surveyed his new home, this was to be his last move, at least while he was still upright. He now had fewer possessions, no garage, no power tools, and no garden. What he did have was a small two-bedroom apartment where one bedroom had no bed, but did have his easel...

Didi and Ken Throw a Party Ch. 04

by oldhippie1949 on Aug 31, 2017
Group Sex

The Party Continues Sheila and I lay on the aft deck for a while. We drifted off to sleep for a little while nestled comfortably in each other's arms. It was Cheryl's voice that roused us. "Oh, there you are! I've been wandering around the boat looking for you. I was afraid you'd jumped overboard." "No, sugar, we were just resting for a bit. What's up?"...

Choices Ch. 08

by johngalt47 on Sep 15, 2017
Novels and Novellas

My thanks to my editor adetaildiva. Without her this would be a poorer story. After her any errors are mine. * On Friday, I was able to slip out early and miss the traffic to my house. That gave me time for a quick game of catch with Bobby before I took off for my date with Nan. I liked spending time with him. I was a good athlete in school, but I never ha...

Vision of the Spirit Ch. 04

by wilderness on Sep 16, 2017
Novels and Novellas

Exhausted by Friday's adventure, Tom's dreamless sleep lasted well beyond dawn. When the sun finally touched his subconscious, he rolled away from the light and opened his eyes. Satisfied warmth surrounded him, as the memory of the previous night replayed. He sat up with a start, realizing Hannah wasn't pressed against his back. She was nowhere in sight. His...

Wild Photo Session Pt. 02

by LaceyDresser on Aug 24, 2020
Mature

Prologue: Obviously this is a continuation of Wild Photo Session, which I suggest you read first. Although it's a bit shorter than the first part, I chose to end it where I did since it was a good breakpoint between installments documenting the evening's activities. And as you can surmise by the ending, another chapter is in the works. Unfortunately it migh...

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...