See your method works way better than what I was thinking. But what are you thinking would be the best way to implement this if you did? Tie it to a "Confidence" stat, or make it an option from the get go? Would it be an optional change in when Jenny and Debbie find out about his small dick size depending on progression in their storylines? You are a damn smart cookie, so figure you have something in mind. If not that's cool too, spitballing is fun.
Also having only started playing recentlyish, about as long as I have been replying here, Jenny could potentially invite over, say, Jane to embarrass Anon randomly. Endless potential for whatever characters you want to write for. Jane originally had more content on earlier builds of the original, right? DC deciding to rework it?