desensitizing anal lube

Yes. You need to relax while inserting; try taking a deep breath and relax while exhaling and exerting steady, gentle pressure on the Aneros. It may take several breathes but it should slip in.

You need those nerves sensitized for the Aneros to work, plus, how do you know if you're doing damage if you can't feel anything?

I find it easier to insert if I use some kind of desensitizing anal lube along with a H2O lube. does this hinder the process?

Agree with Badger on the lube. Aneros insertion shouldn't be a painful process that requires a desensitizing agent. (Which may become a session killer.)

-- Build some mental anticipation and desire by resting the Aneros on a buttock or thigh for a few moments before insertion. Focus on "wanting it" (perhaps contrary to your prior opinions about anal penetration.)
-- If you believe that your anal sphincter isn't easily opening (dilating) as you push from the outside, briefly 'bear down' from inside (like you were ejecting a BM). That brief move will dilate you. Once the head slides in the rest is easy.

After a few sessions, you'll develop near automatic reflexes to accomplish all this. Some guys suck in a Progasm in one step. For others it's a two step process.

-- Make sure you're getting the p-tab positioned on your "sweet spot." ...enjoy 8) 😛 ❗