I'm no expert, but just to emphasis a few things from your link
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Lube: Lot's of it on whatever you are using; toys, fingers, cock.
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If she isn't relaxed don't even bother it wont work.
Lube yes, but I wouldnt put directly on your condom (had trouble maintaining hardon when I did that) instead put on her ass go in a little put more on go a little deeper repeat. Finger to thumb to dick, same process. Go very slowly at first, you'll know when you can speed up. Start this process while doing vaginal k9
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Manicure: If you are worried about whether your finger is going to annoy her with tiny cuts that get painfully infected while healing for days afterward, try after a manicure using the finger on yourself to see if it is comfortable to you. If it isn't to you, it will be unwelcomed by her. Best course of action: Put a condom on the finger. Rim job to get her warmed up and slowly insert with lube. Watch her want more...
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I haven't condom'd my finger beforehand but you definitely need to trim your nails as close as possible and then file them down.