As you said above, the word "bob" means fencing and you want to know how this can have a double meaning related to homophobes.
This is what I see the 2 meanings as:
1. fencing, as in taking out your fencing sword
2. take out your penis, as penis would be another word for sword in plays/books such as the one you're reading - this would be relating to gays if the convo was btwn 2 men
Portraits are being compared to a beautiful, elegant sunset.
The speaker is saying that a portrait is much more fine and beautiful than other faces one sees throughout the day, and a typical evening's sunset is, similarly, not as beautiful as a shiny, smooth-looking sunshine.
JFK's Inaugural Address was given almost 60 years ago. It was an inspirational speech which addressed what is to be an American. The main themes were freedom, peace, God's role in our lives and service to others or personal accountability.
They use words that create imagery and set the tone simply because that is their jobs as poets.