I have done it, depends on frame as to whether machining is required.
I have an iron horse MkIII and bought the Nuke Proof headset
http://www.chainreactioncycles.com/Models.aspx?ModelID=60615
To allow me to fit tapered Rock Shox Revs. For my frame the lower cup was too big, it had a 20mm flange and my frame would accept 10mm of insertion. I got the machinist at work to pop it in the lathe and he took the outside edge of it down to 10mm and tapered it up as per the original design. It took him 5-10 minutes max, cost to me was a packet of chocolate biscuits.
At some point in the future I believe Nuke Proof will be selling the non-oversised flange models but I have no idea when.
One thing I would advise getting is a set of digital callipers like these from Lidl on sale from tomorrow so when it comes to you taking the parts to a machine shop you will have accurate, measurements for them to work to.
http://www.lidl.co.uk/cps/rde/xchg/lidl_uk/hs.xsl/index_19198.htm