I really injoyed your novel hope to read more chs soon
Lol Sasuke was really being brutally with Tayuya in this Chapter but she had at least a good meal afterwards. Another woman down or two and good meal at least for the red head. Pretty good day for the Uchiha.
I think in hindsight this is alright to start. It sets up the world appropriately and let's us know all the basic facts. The only thing I'd suggest is that you make it longer and look over it to consider possible character angles.
Set a word count for all chapters in a story to reach. This forced you to go back through a chapter after its 'doke' to add enough detail and meet the count. It pushes you to focus on improved detail and action.
As for characterization I think that Sasuke would be slightly horrified rather than simply embarrassed at getting a boner over Itachi. So there's an angle there that could have been explored in this chapter. Maybe it does come back in later, but we'll first impressions matter.
As always, the smut is gud. Thinking on it though, wouldn't it be more interesting going forward when writing smut to write it as a "carnivore's" journey? I think you did this in Awakening and in the Wanderer Remaster, bit it should maybe be a general plot arc for every harem story. Sasuke gains experience over time and only breaks women level appropriate. Kakashi was his mentor and sensei and so I think even genderbent Kakashi shouldn't break so easily. Instead, she ought to tutor him or they ought to experiment over time and slowly break her that way.
I didn't really care for Fem!Sai the first few times around. She was just kind of there, hit it and quit it. But re-reading this makes me wish there was a little more devoted to her. She could develop emotions through sex, as cheesy as it sounds, and that would be a nice little bit of fluff for the story. My preference is for dominance and ownership but nice cuddles are fine too sometimes.
I had two ideas when reading this. One is more complaining but the other is actually speculative.
First the bitch - I would think that Sasuke could have had a childhood crush on Kushina. So it would have been more interesting to have him fuck her here with that on the forefront of his mind. That fulfillment of childhood fantasy would add more depth.
Secondly, I imagine at some point you might consider finding a cure (otherwise the world is probably doomed to death via inbreeding). So it would be very interesting to see the various conflicts the girls have. Can they be cured or should they choose Sasuke? They will be unable to maintain a mental fiction of simply making the best of a bad business in that case.
I would say this is probably one of the better chapters in the whole fic. It's always a pleasure to see Kushina get plowed, and further down the line it might be nice to see her really get claimed and bred. In fact, if a cure is found that could probably mark the downfall of the whole family. Sasuke impregnates them all one after the other, mocking them for being hid personal breeding bitches.
That's probably why I enjoyed the Kin and Tayuya parts of this. It's just unashamed ownership and conquest. The only thing I think you done get a handle on is the aftercare idea. You can't just destroy your pets, yoy need to reward them with affection. If Sasuke emasculated Naruto for choosing to remain a woman, he should change his tune after Naruto is almost crying from the degradation and build her back up, saying it's fine that she's that way and that he'll accept her as the sissy she is amd take care of her.