The only time I messed with mine was as a teenager, and that was actually to make it more feminine (was born with a classic male hairline complete with widow's peak, probably perceived it as more masculine than it actually was due to seeing myself as male, was self-conscious about presenting as female with obvious male traits, so I plucked the offending pointy part.) I stopped doing that when I cut it short, and I have to say having an obviously male hairline is probably one of the characteristics that contributes most to my passing.
As far as having a stylist masculinize it: I understand that it's fairly common (standard?) for black men who get short haircuts to have their hairlines adjusted/defined in the process. I haven't heard of/seen it being done for white/Asian/Latino guys. Presumably the process would be the same, but if you have dark hair on fair skin like in your avatar it might not be as successful because your hair could show through the skin and create a "shadow" effect even if it's shaved smooth in the adjusted areas. That's something to check with your stylist. But if you can get a good effect, then I'm sure it's worth whatever trouble it takes to get it, short of waxing or plucking.