I'm assuming that insurance will require legit FAA loggable time. In a part 91 ASEL, that means PIC.
a) If you are not current in ASEL it is not loggable in the FAA sense, period. I know, I know, you can log anything you want but I would not pollute your logbook with something you will have to explain later...and will not be easily explainable.
b) Not on your life. If you were doing the landings out-of-currency with a pax on board, you are in clear violation of part 61. Another (non-CFI) pilot is just a pax in most ASEL.
Basically he is the PIC, and you are going for an airplane ride. Or you are the PIC, and violating part 61 by carrying a pax.
You need to stop everything (don't log a thing) and go get ASEL current. THEN (and only then) go fly you 25 hours with the guy. Since most ASEL doesn't require type training, you can log it even if you really don't know what you're doing as long as you're current (that's what the other guy is there for).
Might want to read up on the insurance requirements...the other guy CANNOT log PIC if you are going to do so. So you might be in violation (ie uninsured) while building time. Maybe get a letter from them saying that supervised PIC is OK.