Eh, panties are just briefs for women, if she's not asking you to parade yourself in them I don't see that one as all that big a deal, but yeah the rest of it is just crazy. I really like that early bit though, we see that he was a complete slut even before any of the girls got their hands on him, it's hilarious the things he'll do for one of Riley's blowjobs. I wish there was more games like that, where the guy crossdresses and things not because he's forced to, but just because his girlfriend likes it.
While I'm here, can I ask quickly about the different sex options (shemale, female, futa), when would you say is a good point to switch from the default shemale route? I remember in previous versions doing so as soon as it's an option would lead to missing some things being unlocked in the salon and clinic, but the unlocking has been overhauled this last version, with a lot of the options being open really early. Is it OK to go for female or futa as soon as that's unlocked now?