We need to work on getting rid of all that hair!!! Shaving just irritates the skin but epilating combined with spot waxing should help speed his feminization along nicely! Hir total emasculation will take time before she becomes a real sissy!
I would go to a very public nail salon and make it real obvious he is now a true sissy! If the subject of preparing for a date should arise, She definitely should have the opportunity to chime in that they are getting matching pedi's of Her lover's favorite color to admire!
Polish his toenails to match his pink panties! If he agrees to keep them polished all the time so they are always on display to Your lovers, he might earn an orgasm as a reward,...maybe!