|Lovely story. I think you are like me in that you see an incredible richness and detail in ordinary everyday situations that others either don't notice or don't bother responding to. Your descriptions of Phillip are very vivid and I grew to hate him quite intensely, so was glad to know you'd taken it upon yourself to do him in!
You described him so well that at some point I could actually smell him.
I'd beware of putting too much detail in, because there are times that I got the feeling that there was a bit of repetition. Some self discipline can give your writing much better impact. For example, both para 2 and 4 describe how loud he was.
A couple of typos:
"My first impression of Phillip was THAT he was blessed with ignorance." Bad mistake in your first sentence!
"...pure embarrassment of having heard one OF his asinine insights or observations ..."
"..was the Phillip Alan Randolph III.." "The" sounds funny - I'd leave it out, or if you must spell it thee, or I think you can use an apostrophe to signal "thee" ie. the' .
"no choice but to kill Phillip Alan Randolph the III."
I would definitely take that last "the" out, and have "Phillip Alan Randolph III."
I didn't realise the narrator was a male until quite far into the story. Initially I even thought "she" was developing lesbian feelings for Trudy. Might be a good idea to make this clear early on.
What could work very well too is to really play on the male contest thing. In a way this story positions the narrator as a little saint. You might want to play on the angle that the story is actually about a beast AND a weazil. Trudy is in fact being maneuvered upon by two predators. .. . Just an idea . ..
Hope to read more of your writing. I love office politics and intrigue. And you clearly have a wicked sense of humour.