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Update: Managed to fist my friend (31M 38F). Thanks BDSMAdvice.
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This is an update on my original post. I(31M) was trying to fist my friend (38F), but we were stuck at the knuckles. After trying some of the advice received in our original post, yesterday night I was able to fit my whole fist inside her. The nitrile glove and further stimulation of her clitoris definitely helped a lot. We also switched from doing doggy to having her with one leg on the floor and the other propped on a table. Thanks to everybody who commented on the original post.
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