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1) tell him whining is profoundly unattractive and never get him where he wants to go. 2) tell him flat out it ain't happening with you EVER, and ask if he wants to leave. 3) read up on how to do anal (gently and with lots of lube) and try it once. you might like or hate it. but if it doesn't turn you on, you can truly say you gave it a fair shot, and he can't complain you didn't try. 4) tell him you'll try it once, but ONLY if you can fuck him up the ass with a dildo once first. that shuts up an aspiring anal explorer. 5) (last resort) break up and tell him this is the reason why. In some circumstances #3 is the way to go. However, the fact that your guy is whining endlessly, and can't take no for an answer, suggests that he's rarely or never performed anal and won't be good at it. If a can't make his woman really anal penetration if he doesn't know how to warm her up to the idea that there are some yummy nerve endings back there, and it's not about just plunging in to a tighter forbidden hole he's seen used and in porn then the chances are her muscles tense up and it hurt like the dickens.
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