Jim Halpert Stories

11,268 results
Orientation
Length
Source
Infinite Scroll

A Hedonistic Vacation

by walterio on Sep 19, 2017
Novels and Novellas

Author's Note: This story is in response to a reader request. The reader vacationed in Jamaica at the Hedonism II resort. He sent me an account of what he did and what he witnessed and asked that I write about his experience. I will call the main character Jim although that is not the requestor's real name. The story is fiction based on the reader's account...

The Education of Jen Ch. 2

by JenJo on Sep 15, 2017
Toys & Masturbation

I'm staring at two raging hard-ons what should I do to make them happy. "Jim why don't you lay down on the bed." I suggested. "Ok Jen." Jim replied. Jim laid down on the bed and I straddled his rock-hard cock and lowered my wet pussy on to his cock. Moving up and down, up and down. "Jen what about me?" Hank asked. "You know what to do Hank." I replied....

A Second Chance at Love Part 5

by rgjohn on Sep 26, 2017
Erotic Couplings

Chapter 1 Jenny could feel the anger well up in her at Katie's insinuation that Jim might be the father of her baby. "You planned this didn't you," Jenny almost screamed. "No, no, no, please, I would never do anything like that," Katie cried. "I thought you were my friend and you do something like this! How could you...how could you Katie!" Jenny said thr...

Pine Tree Loge

by pbon44 on Sep 12, 2017
Erotic Couplings

Jim Cameron pulled up to the office of the Pine Tree lodge; his favorite hideout after a personal crises. The latest stunt ranked high in stupidity. Getting caught in bed with the twenty two year old daughter of his current girl friend was bad. Jessica held a gun permit and he was afraid that she would use it. It was better that he lay low here and let the...

Tyra Takes Control

by magicrub on Sep 16, 2017
Transsexuals & Crossdressers

Tyra: "On your knees, whore," she ordered still fully clothed. Tyra: "A whore belongs on her knees, doesn't she?" Jim: "Yes, mistress." Whack, she smacked him across the face. Tyra: "That's master to you mother fucker. A mistress doesn't have a 10" cock, does she?" Jim: "No master," he replied as she now had his full attention. Tyra: "Better. So, you wi...

A Day In the Country

by camelotbaker on Sep 17, 2017
Loving Wives

Jim and Julie set out for a ride one Saturday. It was mid-May and the weather was warm and clear. They headed for the north Georgia Mountains for the weekend, as they had been busy all week and needed some time to get away and unwind. The Aztec was fully loaded for the weekend with foods and clothing. They had their telescope, camera and other recreational...

I'm Not Jimbo Bond

by GeorgeTasker on Sep 17, 2017
Celebrities & Fan Fiction

Jim stared down into the bottom of his empty beer glass. It had been a shitty day for him and everything had gone wrong. "Same again," he growled to the bartender as he scratched his big beer belly through his grubby flannel shirt. Jim was in his late forties and worked construction, he lived alone and his after work beer at O'Flaherty's Irish Tavern was p...

Christy's Fantasy Come True Ch. 01

by curious_cd on Sep 16, 2017
Transsexuals & Crossdressers

Chris walked through the door of his house Friday afternoon glad the week was over. He dropped his briefcase and coat at the door and headed straight upstairs. It had been a long week and he was looking forward to his usual Friday night ritual to relax. Heading to the bedroom he stripped off his clothes, went into the bathroom and turned on the water. As the...

Jim's Insurance Exam

by JimmyJohnson on Sep 25, 2017
Fetish

This is another work of fiction featuring Jim Johnson (my alter ego). This time, Jim has to go for an insurance physical and his wife Mandy accompanies him to the exam. Just to put a different spin on this story, I tell it from Mandy's viewpoint as she watches Jim's exam. I tried to add a lot of detail and build up the anticipation and embarrassment for Jim...

Mistress Ann - Daughter-in-law Part

by jsexsex on Sep 26, 2017
Loving Wives

Jim sat slumped on the sofa, his cum trickled down his chest, as he reached for a cloth to clean himself, he clicked the remote control to start the second DVD. He was marvelling how this change in his situation had happened so quick! In just a few days. Jim at 5 foot 11 inches was an imposing figure, slightly receding hair with touches of grey, average bui...