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It shouldn't change. Are you checking the air preasure with Harley's pump/gauge? It has a least one check valve built into it. I am not one to buy Harley if I can find the manufacture that builds for them but....
I thought I was loosing preasure and even replaced the fittings that connect the plastic air lines only to find the gauge I was using was allowing air to escape each time I checked it. The gauge I was using was a quality gauge but did not have a check valve in it.
If you feel that your shocks do leak, they would be leaking all the time. If that is so I would pump about 20# into the shock and do a soapy water test on the fittings, both with and without any rider/passenger weight on the bike. If they leak you will know it with the soapy water.
I got the HD pump, it's small and has the check valve. I found that; 1) either all the air had leaked out from the time I bought it or 2) air was never added. I suspect #2, I put 10 PSI in and checked it a few weeks later and it was 10PSI.
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