when the rear naked is applied properly, it should:
have the trachea in the crux of your elbow, this isn't an air choke, its a blood choke, the pressure should be on the arteries on the side of the neck.
if you're doing it right handed, your right arm should be around his neck with your hand on your left bicep. Then, your left arm should be bent (trapping your right hand) with your left fist behind the guys head. Your head should then be leaning against his head like your cuddling on the couch, with your right cheek pressed firmly against the rear-left of his head.
Once that is on, that's the basic choke. Now, you should press your elbows together horizontially, as in, east to west, like your trying to make your elbows switch sides of your body from left to right, right to left.
at the same time, as with most holds and chokes, you should then sorta arch your back, pressing your chest out, and at the same time squeeze your shoulderblades together (but don't pull your elbows apart). You gotta be able to squeest those elbows together and at the same time pull your scapula's back with your back muscles.
try those things and see what happens.
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