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As has been mentioned, use a lot of lube. I have also had best success with this after dildo play... and lots of lube. Speaking of lube, the whole area needs lubed as well as your entire hand, not just the labias. One mistake is to try to insert the thumb after you have worked up to four fingers when you actually want to fold the thumb across your palm before forming a fist to finally gain total insertion. I want to mention again, use a lot of lube.
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