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Many years ago in my college days, while working at an animal shelter as a trainer, I would go to adopter's homes for in home training sessions. Because I worked during regular 9 to 5 business hours it was common for me to show up when only the lady of the house was home alone, the husband would be at work and the kids were at school. Often I would show up for these sessions to be greeted at the door by very attractive middle aged women in moderately revealing outfits that showcased their bodies and then some.
As the youngest guy in my section at 19 years old, I would do my best to keep my professional demeanor and focus on the job, but it wasn't always possible with some of the clients, especially the ones who requested additional sessions and dressed more provokingly and seductively with each visit.
During one such session, one of the ladies took a 'kong' dog toy and put on a show with it I will never forget, as it lead to events that required me to reschedule all of my other appointments for that day. She became a regular on my schedule every two weeks after that day, and occasionally in between sessions off the clock.
In the years and the jobs that followed I used a lot of what I learned at that job in dealing with people and those sort of situations.
Nothing is more tricky especially in this age but reading the signals before you start is essential, then you can start.
Years ago when working as a move service engineer I used to get sent to one client as the service manager felt intimidated by the owner. A very down to earth lady, I gave back as good
as I got when it came to banter and complaints about her contract with us. They sealed a new deal and expanded their vehicle fleet and I was invited along to their celebrations as keeping the fleet of vehicles serviceable was essential to winning the contract. Drink flowed, dancing happened, touching commenced by her, it had happened before while working, I responded that it was ok. We ended up back at her place and the inevitable happened, from then on I used sensual times to secure a bigger servicing contract with her until we looked after the whole fleet.
Back when harmlessly flirting with a co-worker didn't get one an instant trip to HR, I had a few instances where business turned into pleasure. I don't think I ever crossed the line into creepy, more or less tested the waters for any interest in me, and backed off if what I was hinting at, like dinner or a drink, was unwanted. A few female coworkers did go into the creepy toward me. One was a stalker.
I this day and age, doing so is walking a tight rope.