Jack Off Stories

334,850 results
Orientation
Length
Source
Infinite Scroll

The Slave's Roommate

by holly_b on Sep 13, 2017
BDSM

Jack was half shaft deep in Sara's ass when he paused to admire his handiwork. Sara was standing, bent over her bed with her head mashed into a pile of pillows. Her jeans and panties were bunched around her ankles, leaving her standing in a precarious toddle. They were both breathing heavily, and there were several red hand prints across the tan flesh of Sar...

Brother Fills In For Absent Sister Ch. 02

by walterio on Sep 25, 2017
Mature

Sally came home early on Friday afternoon and she spotted Jack's car in the driveway. She wondered if Jack and her 18 year old son were having sex again. She had only seen them together that one time but she suspected there was a reason that Jack was spending more time at her house lately. Sally decided to be quiet when she entered her home and secretly hope...

Finding Their Kinks Ch. 07

by SexyAdventures on Mar 3, 2020
Fetish

Jack woke up from his deep slumber in their hotel bed to the sound of the shower running. He yawned and stretched, assisting himself in his change of consciousness from sound asleep to slowly rolling himself out of bed. He put his two feet firmly on the floor, steadied himself, yawned once more, and walked slowly to the door separating their temporary bedroo...

The Summoning

by GoldenCojones on Sep 13, 2017
Group Sex

Alice took the book from its glass topped case on the pedestal sitting beside their bedroom dresser. Its weathered leather cover, inscribed with a pentagram pierced by a phallus, exuded age. "This belonged to my great-great-great grandmother," she whispered in a reverent tone. She stood holding the book, intent green eyes locked on the cover. Her raven hair...

Djinn in the City Ch. 03

by svenjolly on Sep 12, 2017
Sci-Fi & Fantasy

I'd like to thank everyone for your comments and votes, this has been a great experience. This is the last chapter of the Djinn in the City series, but I do have some ideas to continue the story if you all want more. Comments appreciated! * The next morning was hectic. Fedex delivered a mass of Amazon orders in the morning, including the much-awaited elect...

Jack's First Time

by bi_cpl_with_crossdresser on Jul 13, 2020
Transgender & Crossdressers

There were no secrets between Jack and Marcy, hell when you have been married to the same person for almost 24 years and together for even longer there was no need. Marcy had professed to Jack well before they were even a couple that she was bi and soon after they were dating Jack confessed he was a Crossdresser, a few years later he also said he thought h...

The Sex Toy Store

by EnglishTongue on Oct 14, 2017
Toys & Masturbation

Saturday Jack stared out at the sets of endless red brake lights shining through the rain. He slowed his car to a stop and waited. His mind drifted - as it often did at the minute - to the events of the past fortnight. He had been involved with Anna for just over two weeks now and their relationship was growing. They hadn't kissed or even slept together....

Sex Lessons with Jack

by CaseyMathis on Feb 4, 2020
First Time

In a typical street in the nicer part of town, sits a row of almost identical well-kept houses. The residents are generally well off retirees or families with high paying jobs and nannies to look after their kids. In the end terrace lives a man who's done very well for himself given that he's only 31. Jack works in IT. While we was at uni he successfully d...

Office Submission Ch. 03

by EnglishTongue on Oct 12, 2017
Toys & Masturbation

Monday Jack stared down at the keyboard. He was struggling to finish his report. His mind was elsewhere and he was beginning to wonder if he would meet the deadline for tomorrow. Jack was finding it hard to focus at work lately. He had so much to do and it kept him incredibly busy but his mind constantly wandered as he remembered the things that had been h...

Coming of Dawn

by Mystery_Meat on Sep 17, 2017
Mature

Just a few hours earlier, the clear blue sky had been thick with hot lead and flak. The American B-17 bombers struggled to maintain formation despite the onslaught of Focke Wulf 190's, Messerschmitt 109's, and deadly flak. However, the bombers were far from sitting ducks. They weren't called 'Flying Fortresses' for nothing. Top and bottom machine gun turrets...