On Indian bullets (you haven't said which you have yet) there is a paper gasket between the inner chaincase and the crankcase but it is round the outside of the left hand crank seal. The only way I could see that pressure could build up in the primary chaincase is if it was blowing gas through the crank seal into the chaincase. However that is also the only way oil could get from the chaincase into the engine.
So yes, there could be pressurisation of the primary chaincase but this would be an effect rather than a cause. The cause would be the same cause as oil getting into the engine ie. a leaking crank seal
One thing I'd note on the Indian bullets. That crank seal is behind the engine sprocket and the thing that stops it moving out along the crankshaft are three metal tabs trapped under the nuts that hold the inner chaincase on. That suggests to me that there is a historic propensity for the seal to move itself out. So it might be worth having a look to visually check that seal is still in place and those tabs have been fitted in the correct place and the right way round. Also that the engine sprocket spacer piece is in good condition and where it should be. Here's a picture of the one I assembled a couple of weeks ago.
