First double penetration - Wife First Double Penetration
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It's something we tend to do very regularly, either with another man or with toys.
What really helped is that I had a fair amount of anal experience and also that I was really into it and relaxed so I wasn't all tensed up and scared.
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I can't speak to pain specifically, but the three of you will just have to take things slow at first, use plenty of lube, and be sure to keep communication open.
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