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Chapter 20
by
jonjacobs64
Was this a one-time occurrence?
Thankfully not! Here's the daily routine.
As we moved into the second week of our arrangement, the family settled into something of a routine. The kids were having an absolute blast with their babysitter each day, and Charissa seemed to be enjoying the arrangement as well. I also settled into a routine, but it was much more ... strained.
Each morning, I'd be up by 6:00 to hear Charissa go out for her morning run. I'd make my way to her bedroom, snoop around, smell her sheets, just enjoy "her" space during her brief absence, and then I'd scoot back up to my own refuge. I'd listen for her to get into the shower, and then I'd go into the kitchen. I'd return her cheery "good morning" as she walked past in just her towel, and I'd enjoy her casual company as the four of us ate breakfast. I'd recommend some activity for the day, send them packing and then raid her room once more.
I spent hours rummaging through her computer, leafing through her bible, and looking at her clothes. And I summoned all the patience and diligence of a man with a PhD in English literature and set myself to reading her diary from the beginning, page by page. I learned all about her faith--and her doubt. I learned about her complicated relationship with her parents, especially her overbearing dad, and about her various boyfriends over the years. I learned about Amy, who became increasingly more adventurous over the years and whose recklessness Charissa grudgingly admired. And I learned about that old boyfriend, Jason, who had pressured Charissa past her comfort zone and who she had dumped when he asked to touch her breasts.
I held myself back from reading her recent entries, slow-rolling the research operation to maximum effect. I was thrilled by the challenge presented by learning such intimate secrets about her and not letting on. For instance, I feigned surprise when she lit up with delight to see that I had bought her favorite cereal (old-school Life), and I knew I'd scored some points when she returned to the house one day and heard me listening to Coldplay.
Each night, after the kids went to bed, Charissa and I hung out. We talked for a while about her day with the kids and then also about each other's lives. I told her a little about my relationship, even going so far as sharing that one of the reasons my ex and I broke up was that we weren't meeting each other's needs sexually. (I had needs; she wasn't sexual!) She hinted at some private details of her life, such as mentioning vaguely that she didn't have a boyfriend "anymore," but refrained from really opening up about that.
And then we'd always head to the basement for some TV. We watched more Game of Thrones, of course, which I loved. She agreed to watch one Marvel movie of my choice (Iron Man, obviously), and I agreed to watch one Left Behind movie (she picked the original). I always offered her an alcoholic drink; she always declined. Whenever anything sexy happened, the usual silence descended. Otherwise, we were light and friendly and just having a great time.
And finally, finally, the highlight of the night. After Charissa brushed her teeth and closed her bedroom door, I would listen at the top of the stairs. Inevitably, the TV would turn on, and I'd overhear her watching something very raunchy. I would patiently wait for the program to end, listen for the faint sound of her door closing, and then sneak into the basement. Without fail, from the other side of her bedroom door, I'd hear her fapping away with that plain dildo I fondled every morning. My imagination ran wild, and after overhearing her inevitable, stifled climax, I'd pad back upstairs to blow my own load.
I knew I couldn't go on like this. I needed more. And the next Saturday night, I was finally able to take the next step.

What's the next step?
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Babysitter Moves In
A summer of fun with a recent college grad
Charissa babysat my kids all four years that she attended the Christian college down the road from us. She needed a place to stay after graduation, so I made a deal: Free room and board in exchange for nannying all summer long. Neither of us could predict where this new arrangement might lead...
Updated on Jun 2, 2026
by jonjacobs64
Created on Mar 1, 2024
by jonjacobs64
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