"Ashleigh makes going to the movies an experience Jack won't ever forget."
Picking up where Part V ended, Ashleigh and I did sleep well that night – as you can imagine. I remember waking up in the same position I fell asleep in, and Ashleigh was still lying on my chest. She...
"Jack is unexpectedly asked to join a threesome with a coworker and her boyfriend."
By June 2018, I had a slight reputation amongst a few women at my store. I didn’t mind, but the past year had been very adventurous thanks to Ashleigh. It was the anniversary week of Ashleigh and I’s first night...
"Jack finds out the outcome of what Ashleigh and her boyfriend, Andy, discussed."
Ashleigh had found someone to take her shifts on Tuesday and Wednesday so she and Andy could spend time together, meet her family, and talk. Andy had dumped a lot of information on her the Thursday prior. I could only...
"There was more to Ashleigh being upset last Friday, and now she confesses them to Jack."
If you read the previous story in this chain, “Supervisor and Cashier Part III: A Shoulder To Cry On,” then you may have predicted what was coming next with Ashleigh and me. Then again, you maybe didn’t.I had gone over...
"Ashleigh asks Jack to come to her house to comfort her after a fight with her boyfriend."
It had been a regular Thursday at the grocery. I had arrived for work at 2:30 p.m. to be the second shift self-checkout attendant. These shifts either went well or who a complete cluster show. I remember that day wasn’t...
"The Office"
‘How do I get myself into these things?’ she thought absently as she spread her thighs even further apart.Sarah Jones was sitting on the edge of her desk with her skirt hiked up and her hose on the floor alongside...
"Abby had befriended Ashleigh and heard stories about Jack. Now she wants an evening with him."
Three weeks had passed since Ashleigh left to go back to school in Illinois, and I was sitting in a meeting for what was essentially a “customer first” group (follow the Supervisor and Cashier stories for more on Ashleigh). This group’s...
"One week after their first night together, Jack returns to Ashleigh's to spend the whole night."
- The third week of June, 2017 -It had nearly been a week since I followed Ashleigh back to her townhouse last Saturday night. I never worked Sundays, and she didn’t work the following Monday, but we had texted back...
"A divorced cashier is curious to find out if her younger supervisor lives up to his reputation."
As you may learn from future stories, Ashleigh went back to school in Illinois in mid-August. We met up a number of times in the two months prior and apparently, she didn’t keep some details about us to herself. That...
"My amazing relationship with Natalia is all over, so I end up fucking a coworker."
That rainy afternoon, I was sitting with Natalia drinking some coffee, trying to settle some issues that had arisen some weeks before. We were in one of the university cafeterias, one that was not so close to Science School, the...