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#1
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first time isnt so bad if you just relax, if your tense then it will hurt esp if when they pull out. As far as cleaning your hole it is a good idea but not that necessary. But it is a great feeling!!
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#2
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Cleaning your hole is more than a good idea. It's better for your health and that of your partner ... not to mention that it is a sign of respect for the pleasure your partner is going to bring you by putting her cock in your ass.
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