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When I started out I found the whole strop tension/blade pressure/contact and oh, don't cut your strop thing to be a "pat your head, rub your tummy" moment.
So I got out a trusty spring clamp and and clamped the swivel end of the strop to the top of the counter with the strop laying flat on top and parallel to the edge.
Maintaining a grip on the handle end for a little tension (it does not take much - set up with the handle off the edge of the counter) I could concentrate on the razor and my results improved immediately.
Learning how to shave with a straight razor requires lots of new skills.
This is why those first shaves take 45 minutes or longer (some times a lot longer)
For me the counter trick allowed me to break that process in to steps that are a little easier to master.
Smooth Shaving...
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I would agree cupping being the issue. is it a 3" strop? X stroke with the heel leading might help and a little slack in the strop, not drooping though, and a very light touch.