In the submissive to Natasha path, she could use Vacuum Suction Therapy to give the MC small breasts without HRT or surgery, she's already doing something similar but limited to MC's nipples, enlarging them, making them very sensitive (like a girl's), so that would be the next step (a small visual change in scenes with others too, of course, including comments), also, please have her put more feminizing makeup on the MC so he won't just look like a guy with makeup on, maybe make him practice at home too how about she makes him wear stockings, panties and a bra under his clothes at all times, it's still a little inconsistent after all, would wonder what every girl's reaction would be when he undresses, it's actually a miracle nobody has caught him all dressed up in his room yet.