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I have heard there are more than one size of condoms, because men in some ethnic groups have smaller or larger 'equipment,' but I don't know if those sizes are ever sold together or if just one region gets one size and another region gets another. :) He should be putting it on a non-lubricated penis, and if you are already using lube he can use a lubricated condom, that might help it hold on better. The unrolling is like if you rolled a stocking and put your toe in it and then just rolled it out up your leg. In other words, like unrolling a tube of waxed paper, the "roll" is on the outside. Good luck!