Higher circular orbits are indeed slower than lower ones. The shuttle goes around the earth in 90 minutes, the moon takes 28 days. Geosynchronous orbit, where one orbit takes one day, is in between.
What's confusing about transfers is that elliptical orbits are orbits where your velocity varies based on where you are in the orbit. Your speed is highest at perigee and lowest at apogee. In fact, your speed at perigee will be higher than the speed of an object in a circular orbit at that altitude. The reverse is true at apogee; your speed will be slower than an object in a circular orbit at the same altitude.
So if you and your docking target are both in circular orbits, and you increase your speed in order to catch up, then you will simultaneously be raising the other side of your orbit, half a turn away. The difference at your current location will be minute, but will grow every continuously over that half a turn. If you're docking in the next few seconds it won't be a problem (the docking mechanism will handle a small offset, and it equalizes your speeds provided the difference isn't too much). If you're still several minutes away, however, you might find that the extra radial velocity means that you fly over the top of your target.
If you miss and continue to follow your new orbit you will indeed find that your overall time to orbit is now higher than your target's. It may be many orbits before you again have a close approach with your target, although if the difference in speeds is small then it may appear from your perspective that you are in fact orbiting your target.