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Office cleaning lady
So the cleaning lady at our office is a cute older woman in her mid 40s. everytime she is prepping her cart in the storage room I have this fantasy of plowing her in that room. I am a 38 year old Profesional and wonder how I should approach her.
The first thing you should do is talk to her. Women are just as uncomfortable as men when it comes to talking. Give her a compliment. Tell her that you like her hair etc. I started an affair with an married older woman in my office just by complimenting her on her feet while riding in an elevator one day. She looked at me and said "you know..your the first man to ever say that to me". I have been fucking her regularly after work for months now.
Approach her quietly from behind...have the chloroform ready