Female led relationships discussion

Hello everyone, I’m looking for some creative suggestions to keep my virtual submissive engaged. Since we are on different continents, meeting up isn’t really an option, and I’d rather avoid using webcams. So far, our communication has been through emails and photos. About four months ago, I published a femdom story online and several men replied. One of them, let’s call him Jack, eventually became my virtual sub. It might seem quite standard to some here, but it is new territory for me. Once he sent his typical nude photos, I instructed him to go to a lingerie store. He needed to get help from a female sales assistant in choosing a particular style of panties and had to confess that they were intended for him because his mistress was requiring it. He followed the instructions and sent back amusing pictures along with an awkward story which I sincerely believe is genuine. I enjoy small penis humiliation, so I also asked him to measure himself. The result showed four inches, but I suspected he might have been erect when measuring and insisted on three inches being more accurate. To settle it, I had him provide proof of taking a cold shower while holding ice packs against his groin before measuring again. His measurement improved slightly over the previous 3-inch figure, yet I still required him to pen an apology for possessing such a tiny member. He also handles cleaning my house in the nude among other duties, but we are settling into a routine. He has requested entering chastity as part of our arrangement, which is one path we’re considering. However, I’m curious if others have different suggestions? He thrives on humiliation and finds female dominance highly arousing. If we lived nearby, there would be endless possibilities, but since we are confined to the digital realm, I wanted to gather more ideas. Best regards, Holly