Alkene Electrophilic Addition Reaction Stereoselectivity When Two New Asymmetric Centers Form
Stereoselective becomes a hand-wavy term as soon as you may end up with more than one type of stereoisomer. If you want to actually state what is going on, you would most likely use either of the terms enantioselective (selects for a specific enantiomer) or diastereoselective (selects for a specific diastereomer; this may or may not include both enantiomers of the diastereomer).

In the first case, there is only one selectivity that can be observed; you can only get diastereomers, no enantiomers. Therefore, there may be some reason in shortening the term to stereoselective. In the second case you should not resort to using stereoselective because it is not specific enough — and that is irrelevant of the question whether stereospecificity is observed or not.

The second reaction would likely indeed be diastereoselective to a certain extent while definitely not being enantioselective (because the product is symmetric). So calling it diastereoselective — and thus, by intrapolation, stereoselective — may be justified.

In practice, the selectivities of both reactions would be so low that no practicing organic chemist would call either ‘selective’.