The top picture shows the steering column wiring. The only thing you need to worry about is the red highlighted wires. These are in that brown 6 pin connector. To add pins to the connector on the truck side, there should be a red plug and when you remove that you can remove the pins (after you move a little tab, should be able to see this).
The black/yellow wire can be jumped to the Grey/Yellow wire. As long as the black/yellow wire has 12v, the servo thinks that the pressure switch is there and the brakes aren't applied. But you do have the actual brake switch on the pedals to turn off the cruise.
BTW on a Ranger for your year your cruise control buttons most likely won't light up. Your steering column wiring is wired for this, but it is the truck side that isn't. You can add an extra pin on the truck side to match the LB/RD wire on the column side.