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I don't see what's wrong with going more than once, I have decent stamina and can do kegels but if it's been a week since I got some 5 min is an epic feat. And 4 months, I can't even imagine...
I just don't see the point of jerking off beforehand unless you just can't get it up again for some reason. That first time goes pretty quick yeah, but after that you'll be able to last much much longer.
Bonus if you are into moneyshots, depending on how long you've gone without that first load can be HUGE.
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