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I travel a lot and often engage women for evening companionship. Usually some combination of dinner, drinks and a session. Mostly, I am looking for company, convo and a release. I’m closing in on 50 in a very few years and I wonder about being seen with 20 something women in public places...

I was in Montreal for the first time a few months ago and one of the ladies I sought out for companionship pulled my hair. Just a little and in a playful way. She only did it once...maybe because I was so surprised but it has stuck in the back of my mind. I lightly pull my own hair all the...