My girlfriend is iffy about anal. When I get it its like a treat. What I have to do is pretty much get her into a sex coma. I get her off a few times and then pull out the vibrator. usually she likes to play with herself with "her little friend" and I finger her. Then I will rub her ass and ask if she wants it or where she wants it, and if she says anywhere then I will finger her ass a little and ask if it was ok, if yes, then I go for it but if no then I just fuck her again lol.
But I would say use lube and get a vibrator! It is very important, and try licking it a little or lick the skin between her ass and vagina. If its a go then start with one finger and gently move up to two. I like to stick the vibrator in her vagina and while I have to fingers in her ass I push on the vibrator towards her g-spot and she goes crazy. After you play around with the two fingers in her then try your penis, but always keep her in mind. If it starts hurting STOP, and dont go in all the way, pump the head in and out and then work it deeper till she cant take it any further. I can only go halfway with my current gf so be careful, the last thing you want to do is hurt her.
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