will wanting to wear dresses/skirts/make up in intimate moments, but obviously his access to these items is very limited, he's only ever gotten to try some that el discarded for maybe being too old or not her style anymore, but because they were hers first and he's trying them on secretly he can never bring himself to use them in the situations he'd want to most. he very very nervously opens up about this to his boyfriend after months of dating, terrified of his reaction--jock BF is a bit confused because this is hawkins and he's never heard of such a thing, but he's open to try it because it's rare for will to express he wants/likes something openly, and honestly, wouldn't will look so pretty in those anyways. so he uses his straight-passing privilege to go buy these things for will in the guise of "it's for my girl." all the store clerks are charmed by how dedicated this guy is to buying gifts for his girlfriend, by how carefully he chooses the fabrics and the colors because "she has the softest skin it's very sensitive," "it has to match hi--her eyes," etc.
