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Take time to relax her properly. Make sure it's properly cleaned and lubed. Apply pressure, not force. Give it time to relax. Don't expect gaping pornstar anal the first time around. It takes time for the ass to get used to anal sex and it needs to be trained often to stay used to it.
Cock size (or whatever is being inserted) has alot to do with it. But cleanliness in my experience is the most important factor for both parties.
To put it bluntly, look at the size of some shits girls & guys take. Most guys don't compare to that.
This is all if you want her to receive any pleasure from the act. No idea what the mindset is of the initiating party.
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