I believe that V transitioned before Vergil and started hrt and stuff (in this au where V is also here cause ,...reasons ?). Vergil is afraid to transition not because shes afraid of oppression or acceptance , its because its an unknown territory for her. Its hard to admit she isnt in control.
Dante transitioned somewhere before dmc3 and Vergil although she had suspicions back then she found it foolish to want something more from her human vessel. Admitting she cares about gender presentation is admitting shes human. Humanity is weak, therefore those desires are to be ignored. Thats why Dante transitioned early and Vergil post dmc5(therapy in form of committing acts of terrorism).
Her gender presentation had more to do with imitating her dads elegance and even though it is a part of her now , shes didnt experiment much.
Holy yappppp!! Anyways heres the script for my fuck ass hand writing
V: if you are so interested in makeup , you can just ask , no need to hover
Vergil : i want no such thing
V: you are smarter than that , you know you cant lie to me
I know your true desires , i was you
What are you so afraid of?
Why wont you make the leap ?