Oh so many questions.
My answers:
Personally, I don't fetishize butt plugs per se; I see them as tools to allow repetitive anal penetration from partner sex or masturbation to occur sooner and with less 'warming up'. And that's pretty cool, because I wish I had a self-lubricating pussy. I own 1 butt plug.
One of my best sissy memories was going going to a sex shop in the local gay village as a college freshman, buying a butt plug, putting it in inside a nearby cafe washroom, and then getting stoned and walking around the gay village with it in.
I've had female partners who were able to quickly have vaginal sex with me in public. If I had a 'butt plug goal' (lol, things said only on c/sissy :) it'd be to be able to do that myself with a butt plug. That is, I'm out with my man, we're feeling frisky, I'm already plugged, I take it out (and am hopefully quite lubed up), and I get a quick shag on a beach or something ;)