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A planned masturbation session, usually referring to "jacking off." The planning part is what makes a jack sesh different than simply masturbating.

Quick Jack Sesh guide:
1)Mise En Place!- Have lube, paper towels (enough for both catching semen and wiping hands so that you can continue to search for porn/switch videos without getting your keyboard all sticky) and a small plastic bag near by.
2)Make sure you have plenty of time and space. Enough time and space to jack as hard and loud as you want with moderate to loud pornography without head phones. This is important, as headphones detract from the overall masturbation experience. This means each room must be searched to ensure that absolutely nobody is in your dwelling, and you must know when people will be returning. Even if you live in a place where nobody cares if you loudly masturbate, this rule must be followed. A Jack Sesh is a holy, personal experience. A Jack Sesh must not be tainted with the presence of another person.
3) Take your time. Enjoy your Jack Sesh. Go slow at first. Find a hot video, one with a bit of a kinky story. Give yourself at least 30 minutes before you go to your go-to video and blow a massive load.
I can't wait to have a Sunday morning Jack Sesh while everyone else is at church.
by Weeaboo_Starshine March 09, 2018
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