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Chapter 23
by
jonjacobs64
Should we explore a bit further?
First contact!
My right hand shook as I reached for Charissa's left breast. With my gaze fixed on her closed eyes, monitoring for any sign of wakefulness, I gently cupped her boob in my palm. It felt glorious, as plump and firm as I imagined. I held her from underneath, feeling the weight of her D-cup tit, and ventured a gentle but extremely arousing squeeze.
Charissa was still out like a light, so my journey continued. I brought my left hand forward to match my right and soon I was fondling both of Charissa's tits through her tank top. I kept my hands fairly still, relishing the forbidden contact while planning my next move.
After a minute or so of feeling her up through her shirt, I knew I had to go further. My dick wouldn't have it any other way! I had puzzled out what I figured was the gentlest approach. First, I took her right hand in my own and softly and gently lifted it off her belly, placing it on the touch beside her. She didn't stir. Then, with my left hand, I lifted the bottom of her shirt, making a kind of tent, and I reached under the bottom of her shirt with my right hand. I was flying a little blind, and I startled myself when my hand made contact with her bare breast. My penis twitched, and my hand rested calmly on her flesh. I cupped her breast again, making skin-on-skin contact, and I swear I almost drooled on the couch.
It felt too risky to put both hands beneath her shirt, so I used my right hand to play with each of her tits. I slowly--oh-so-slowly--rubbed her nipples with my fingertips and sucked in an excited breath to feel them involuntarily stiffen. Charissa remained completely relaxed as I continued to play with her breasts, stroking, lifting, folding, and rubbing--all the while feeling as though I were in a paradisiacal dream.
My left arm started to feel tired holding Charissa's shirt aloft, but I couldn't make myself part ways just yet. I decided to try to see those beautiful breasts I'd had so much fun playing with. So I pulled out my right hand, stationed myself on my knees on the carpet in front of her, and used both hands to gently lift Charissa's shirt away from her body.
There they were. The objects of my lustful fantasies, revealed before my eyes. Round and firm, the nipples still prominent from my stimulation. I held my breath as I watched her breathe, entranced by her magnificent breasts as they rose and fell before me. I don't know how long I stared, but eventually, my left arm really did need to rest, so with considerable ****, I replaced her shirt, checking again that Charissa was still fast asleep. She did make one of her sleepy little whimpers but otherwise seemed to still be completely out of it.
The movie was almost over, and I honestly didn't know how long I could push my luck. This experience had been a dream come true, and if Charissa woke up while I was groping her, everything would come crashing down. Could I risk any more contact?

Should we push our luck just a little further?
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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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