Are you supporting his ear with the warm rice filled sock? I find that makes it the easiest on both of us...at least Luci for the most part seems to not notice. Sometimes, when I poke the same area too many times she lets me know...and I try to avoid that particular spot for a while. Always use Neosporin afterwards and press the ear lobe gently for a few seconds - that is of course while trying to get Luci to stop eating the Neosporin...she loves the smell of that stuff for some reason Those black ears of hers are difficult to see what's going on but keep trying...it'll get easier with time.
Glad to see Buddy didn't keep you up ALL night...just a part of it...
Have a great day Sandra!