First shaves are problematic not only because technique issues cause you to question the blade's readiness for shaving, but also because there is no way to have confidence in what you're doing so early into the process.

I think "pushing on" when a blade doesn't seem to be shaving well is a mistake. Keep trying by resetting the blade's angle and use short strokes. If you are absolutely sure your razor is "shave ready", then keep trying. If you're not sure, then send it off for honing and eliminate that variable. There are enough variables to get right in straight shaving, including prep, angles, etc. so it is best to eliminate the ones you can. The first shaves are the most difficult.