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You situate the position first and the guy to enter cunt goes in first. It's difficult to enter in pussy if the ass is already full. The physically stronger guy on the bottom is called the anchor. I remember guys discussing with each other over who'd anchor. Any porn people here correct me if I'm wrong. I answered this to the best of what I remember.
If there was one thing I was good at as male talent it was riding anchor, I'd put my popeye forearms in the small of her back and squeeze. The ass pops right up 
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