shaved his upper lip every morning three times with, three times against the grain

[Joseph Tracy]

I think it's clearly a fucked up sentence that relies on the impossible double duty of the word "with" and punctuation that doesn't clue the reader to the pauses in a plausible reading . It doesn't approximate speech or thought and is not logically constructed grammar that can be clearly parsed with extra attention. 
What follows is how I think it is intended to be heard/understood. 

> Mucho shaved his upper lip every morning- three times with, three times
> against the grain to remove any remotest breath of a moustache; with new
> blades he drew blood invariably but kept at it.

There are clearly 2  independent clauses here with no conjunction and no semicolon or dash. The word "with" cannot be both a preposition referring to the grain of his moustache, and the start of a different prepositional phrase introducing an additional  clause.  
If this is deliberate, it is almost as if Pynchon is showing how a writer can no more remove certain grammatical indicators completely than Mucho can remove completely a part of his skin. Curiously the semi-colon removed is both whisker and cut-off whisker.
On Dec 28, 2011, at 1:50 AM, Dave Monroe wrote:

> 
> 
> Mucho shaved his upper lip every morning three times with, three times
> against the grain to remove any remotest breath of a moustache, new
> blades he drew blood invariably but kept at it.
> 
> I get the meaning, but the whole sentence is quite unreadable (what
> are, grammatically speaking, those new blades?). It feels wrong. Well,
> it is wrong... at least by any standard known to me. Could with be
> referred both to the grain and to new blades? This is the only
> explanation I could come up with, besides a typo which is highly
> unlikely (what with Pynchon being Pynchon). I mean:
> 
> Mucho shaved his upper lip every morning three times with, three times
> against the grain to remove any remotest breath of a moustache.
> 
> is pretty much clear and doesn't require any explanation.
> 
> Mucho shaved his upper lip every morning three times with new blades;
> he drew blood invariably but kept at it.
> 
> is clear as well, and sounds like something written by a schoolboy .
> The two sentences put together give the meaning I believe the author
> was trying to convey. What do you think?
> 
> http://forum.wordreference.com/showthread.php?t=2321945&p=11658038