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I kept hitting her till we reached 36 and then stopped. Only when I stopped I noticed that she was weeping.I looked at her ass and it has turned a red...mess. After that, I took the lube and poured it over her ass and massaged it. I covered my fingers in that lube and inserted my middle finger in her asshole. I rubbed the whole area. She let out a soft moan and tightened her ass.I could feel the pressure on my finger. I started fingering her ass with one finger. She slowly relaxed her ass so I. It may sound bad but I felt I may have a little more control over my assistant, not by way of threatening her employment, rather by just being insistent and getting a feel of the possibility during our prior sessions and if all else failed then yes I intended to hold the job over her head to get me what I wanted.I didn't have to resort to that though, she was a nasty and willing girl inside, she just needed to be comfortable that she could be who she really is inside and I let her feel that. More

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