They do get friendlier with use but unless yours is extraordinarily stiff it should not need any real preparation.
1. Make sure it's pre-threaded correctly except for the last pass. Most buckles have numbers and arrows to guide you. There are plenty of good looking wrong ways to thread the thing.
2. Get it wet, a splash of water will do or you can dunk the whole backside of the BC
3. Have it on a stout surface where you can brace the cylinder with your knee. A stout bench, low tailgate or getting down on 1 knee works.
4. Get the BC on the cylinder
5. Pull the tail taught to remove the slack.
6. While holding the tip of the tail give it a few karate chops to cinch it.
7. While holding the tip rock the buckle half closed, this will hold it in position.
8. Thread the final pass though
9. Rock it closed
10. Set the Velcro tail
That should do the trick.
Pete