Jack Off Stories

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Infinite Scroll

A Day in the Life

by Elizabeth_Cameron on Sep 1, 2017
Group Sex

It was another typical day, nothing extraordinary had happened and Jack didn't expect it to. His life was routine and though sometimes it was monotonous, he enjoyed it. He walked into the usual meeting place, the newly built sports bar entitled Harry's. It sat right across the street from where he usually worked out so it was a convenient spot. "Hey Jack, h...

Office Submission Ch. 04

by EnglishTongue on Mar 5, 2018
Toys & Masturbation

Wednesday "I know Jack, I know. I was looking forward to it too," Anna explained. Jack looked down at the lasagne he had ordered and sighed heavily. The two of them had decided on eating out tonight. Tomorrow they were due to travel up to York for a conference together. Jack was looking forward to a weekend of naughtiness, nakedness and hard fucking whils...

Jack Introduces a New Game

by Mysteria27 on Sep 11, 2017
Erotic Couplings

Brian Keaton had just finished up his last year of college. He was hanging out with his kid brother who was eighteen. He told his brother about a game that they used to play at fraternity parties. Jack was really interested in the game and wanted to try it out with his friends. Jack was a popular football player. Hooking up was very popular at school and Br...

Wife Tied and Blindfolded (MMF)

by easydescent on May 15, 2019
BDSM

I'd known Jack since we were teenagers, although for the last 12 years he had lived on the other side of the country. He had recently moved back to town because of his job and we had been out for drinks a few times but my wife Sara never came along because she wanted us to catch up on old times without boring her. Jack had come to our wedding but as he lived...

A Fond Farewell

by StackedAction on Sep 13, 2017
Group Sex

In 2005 Jack and I both changed jobs and it required we leave our city of 10 years move back to Tahoe. It was a bit sad, but it was a better opportunity for both of us. I had become pretty good friends with my coworkers and they threw us a going away party. My boss, Jane, held it at her house. Jane had a seriously nice place. She had gotten her money throug...

A Most Unlikely Fantasy

by Humpdee84 on Sep 12, 2017
Mature

Jack moved into what he called, his 'closet' right after splitting up with his wife. It was essentially just a bedroom with a kitchen and bath. "Studio" was over stating the situation but since it was all he could afford in a short time period, who was he to argue? He hit it off with the landlord upon their first meeting so the rent wasn't what it COULD have...

Visit to the Lingerie Store

by EnglishTongue on Oct 14, 2017
Toys & Masturbation

Saturday "Well? Will you do that for me? Jack?" He wasn't really focused on what she was saying. Anna was wearing a pair of white see-through small panties and matching bra. Her toned slender figure was accentuated by the flesh coloured high heels she was wearing. Anna was deciding what she should wear for their first shopping trip together. She was str...

Happy Birthday Jinny

by PurpleTroll on Sep 17, 2017
BDSM

Jinny, a very tall and rather muscular Asian woman, was on her hands and knees pretending to scrub a probably imaginary spot on the kitchen floor. She was wearing a black pleated skirt with a number of layers of white fabric that was short enough to expose her white cotton panties in the position she was in. When Jack came in, she turned her face to look a...

Jack in the Lingerie Modeling Salon

by Jackinjillin on Sep 16, 2017
Exhibitionist & Voyeur

Jack trembled slightly as he reached out to ring the bell on the brightly-painted door. He was in a large, humid, damp city in the Pacific Northwest for his annual summer writer's conference, and he stood before this door, in a drab, post-industrial section of the city. It was advertized in the adult newspaper as a "lingerie modeling salon." Their website pr...

Office Submission Ch. 01

by EnglishTongue on Sep 16, 2017
Toys & Masturbation

Friday Jack looked through the mountain of work on his desk, wondering how much of it would wait until next week now. "Thank goodness it's Friday," he said to himself. Then he heard her. He could always hear her before seeing her. Those heels clicking along the floor towards his office. It was a confident, sexy walk - almost a strut along the corridor. S...