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My girlfriend and I want to try anal and have read all the advice given but have run into a problem. For the last month or so, we start out with vaginal sex while I use a finger to massage around her anus, it drives her nuts. It's well lubed and insert a finger, most of the time I can only get it in to the first knuckle and she says it hurts. I try more lube and it doesn't help. We do this every time we have sex and it doesn't seem to loosen up at all. Seems as if we have hit a dead end.
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