I am running portable everything... so I guess the first question is does the monitoring support things like firefox
Portable Firefox could be a terrible mistake if you are concerned about secure deleting of your activities.
I have in the past tried the Portable version from PortableApps
http://portableapps....irefox_portable
At that time, and very probably even now, it was basically a NON-portable variant which used the STANDARD FIREFOX user profile for all user data,
and the "portable trick" was to take a "INSTALLED-SNAPSHOT" of the user profile and then restore to that profile any previous LAST-USER-DATA,
and then Firefox runs and updates this "common" user profile with your current user data.
When Firefox is closed then PortableApps will copy your latest user data from your user profile into the LAST-USER-DATA ready for use then next time,
AND ADDITIONALLY will clean up all OBVIOUS traces in the STANDARD FIREFOX user profile by copying back the "INSTALLED-SNAPSHOT".
I strongly suspect that OBVIOUS traces are simply deleted and instantly recovered by RECUVA.
If you are concerned about security you should consider Portable Palemoon which does NOT create or use a standard user profile.
Palemoon is based on the same open source software as Firefox and can run the same Add-ons.
http://www.palemoon.org/
They have an active forum and most questions are answered very quickly.
N.B.
I believe that :-
Portable Palemoon is so portable that two separate instances may run simultaneously with separate profiles and no conflict;
Portable Firefox had no such capability when I tried that in the past.
Incidentally, I never feel the need to Secure wipe and remove my traces,
but I gave up Firefox (installed) and went to Palemoon (installed) because every other day the CCleaner forum was unreadable with Firefox and its rabid update cycle,
whilst Palemoon never let me down.