Let’s start again with a very simple case, full electronic keyer operations.
The figure shows the Dot Contact Closure (red) of the paddle and the relating side-tone signal (yellow) of 600Hz. There should also be the Dash Contact Closure, say in green, but my oscilloscope has only two channels. You need to use your imagination by considering the movement of your fingers when you are sending the letter R.
To generate the second dot, the last element of the letter R, you only have to keep your thumb in position until you hear the start of dash, because most modern keyers have both dot- and dash-memories, and due to those memories the side-tone signal perfectly meets the timing rules of morse code (as far as a single letter is concerned).
Any questions so far?