I think what's going on with an Ety seal and eardrum pressure is that:
1) There should not be noticeable pressure, either negative or positive, from trapped air on the eardrum, or what we seem to feel is the eardrum--these sensations can be deceptive. This should be the case when the transducer and cable are not disturbed and are "at rest" for listening.
(There will obviously be sensations of pressure from the sealing material, foam or silicon, against the lining of the ear canal. In order for the seal to persist there must be some force against the surfaces that make up the seal. If Ety's are uncomfortable to someone, this is one of the reasons; but usually this sensation declines to a tolerable lever or disappears with habituation.)
So, we don't want to trap air "under" the Ety as we push it in place. Some owners wiggle the transducer or pull the outer ear aside as they place the 'phones in final position to vent any pressure.
2) That said, however, if one wiggles or disturbs or, more particularly, pushes and pulls lightly on the transducer making it move in a piston-like fashion slightly into and out from and along the general axis of the ear canal, then--if a proper seal is in fact obtained--there should be a matching motion of the eardrum, a small, fleeting (because the Eustachian is venting and equalizing the pressure from the other side of the eardrum) feeling of pressure, both positive and negative, on what is perceived as the eardrum.
You should be able to feel the eardrum--or something deep within your ear--wiggling along with the transducer. That, indeed, should indicate a stable seal.
Well, did I clarify or muddy the waters--or the earwax?