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The only true meaning of bobcatting is the following one.
a few guys go stand in a circle and each of them jerks off the guy on their left. (or right whatevs)
Mostly used as an insult
guy A "you heard the news about these guys? They were bobcatting all weekend"
guy B "thats disgusting"
The action of attempting to insert a flaccid object into a tight hole.
"Dammit Billy, I'm trying to thread my tippet into this indicator and it's a total Buttery Bobcat going on over here."
"I was at the brothel last night and was so drunk I totally did a Buttery Bobcat"
When one sleeps on their back with a knife or forearm clutched closely to their chest in anticipation of a predator awakening them.
I got real tired on my camping trip so I took a quick bobcat nap.
A cougar that used to be a man.
She's got and older. A Bobcat I hear. Go for it.
A male homosexual that frequently seeks out the company and affections of much younger men (e.g., homosexual male version of the often used "Cougar" describing an older woman that is attracted to and dates much younger men).
My 45 year-old next door neighbor is quite a Bobcat, there is always a steady stream of 20 something guys going into his 1 bedroom house after the clubs close, and then appearing for the walk of shame as they scurry to an Uber in the morning.