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IMHO it’s less about position than about preparation. it should never hurt. you should feel confident with your partner and eager to find a good way to get going. there’s quite some guides/tutorials/how-tos online
this seems to be a good one: https://www.pornhub.com/view_video.php?viewkey=646c77b364ae1 but i was actually thinking of this: https://www.pornhub.com/view_video.php?viewkey=ph5e1ad234109e5
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