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If you find yourself clamping, pause, and possibly try to bear-down a little, like you do when you poop, it relaxes the sphincter. My suggestion for lube is to lube anything that will come into contact with something else. Add lube to his shaft as needed.
Also, it's OK to stop if it's not going well. Here are some ground rules before you make a pass at the rear door: And just so you keep it clean — encourage a shower-for-two before you get into bed.
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