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There are people in that second category, strange as it can sound to people in the first category.
Ultimately, since you can’t know that and this is your boss, I’d err on the side of staying out of that piece of it.
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One time, his wife showed up for a surprise visit to take him out to lunch, and he directed me to lie that the woman who was in his office was there for a job interview.
He also submits expenses from his business trips (where he has traveled alone) and I have to re-calculate everything because he has upgraded the company-provided hotel room to a better one on his personal credit card and bought breakfast for more than one person the next morning.
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He sent me to retrieve it and pay his tab with cash, but the address he sent me to was actually a massage parlor.
I am his assistant, so I know about all his visitors and his schedule.
He is married, but he often has visits from two different women, and he outright told me to never tell his wife about them.
These teen sluts will go above and beyond what it takes to show their fathers how much they adore them, sacrificing their virgin pussies for a sweet taste of papas pecker.
If mommy ever finds out, these girls are grounded for life!
When either of them visit, he locks his door and tells me he is not to be disturbed. He sometimes asks me to book local hotel rooms for an hour or an afternoon, and he sometimes buys jewelry and flowers for the two women he sees regularly.