Well I can turn a parallel OD but do sometimes get a tapered bore, I put it down to additional flex due to the distance the cutting edge is from the toolpost.
When turning an OD I seldom get any material removed when I wind the tool back to take the next cut unless I’m taking heavy cuts. But when boring the tool will usually leave the tell tale spiral on the bore as it is wound out quickly.
The only thing I can see that is different is that I may have 100mm from the toolpost when boring but 10mm when turning.
That cylinder I showed above had some taper but I know how to deal with it, either by using the brake cylinder hone or in this case as it was a bit more pronounced I used the Emery method. Does not seem to be a problem, this is the engine quickly assembled and as you can see there is a good bounce when it comes up to compression. I should say that for this video I had not yet fitted the Viton O ring, no gaskets fitted, no springs on the valves and I even had the valves in the wrong way round so they had not been lapped into their respective seats. Squeaks a bit as the air get spast my fingers which are covering the plug and valve access holes.
I don’t tend to bore cylinders on the mill as it is hard to feed consistantly so prefer to use the lathe either with the part in the chuck if it’s a small engine or bolted to the cross slide if large and use a between ctrs bar. The later does not produce a taper so again it suggest the problem is specific to using boring bars in the toolpost.