HammerFall,
I don't have a milling machine. So... a whole lot of work! I made fitted filing jigs by hand:
1. Took 2 chunks of 2 by 2 by 1/4" 1095.
2. Drilled 3 matching holes in the two plates. Tapped one plate and drilled a little bigger in the other.
3. Cut a curve.
4. Took 2 more chunks of 1095.
5. Drilled holes again. (but didn't tap - used nuts - I learned).
6. Cut matching curve and spend hours fitting the curves together. File, drummel, coat with ink, rub together, more file, drummel, hold together and put against a strong light, more filing.....
7. Hardened the steel to +64HRC
After that things got easier. I cut to shape the 2 bolster sides. Then clamp in the jigs and file smooth. Then the same with the wood using the matching jig. Lining up the wood in the jig actually takes longer than filing!
If you are just making one, then fitted the jigs isn't any benefit. However I had 4 bolsters to fit!
There is another method I found here:
http://www.robbrownknives.com/tutorials/bolsters/
However, now that I have reusable filing jigs I'm set.
Does that help?
Steve