I played through all the available content and I have a few comments regarding the game's design.
First, it is WAY too grindy. Every stat takes way to long to modify to any significant degree and not only is that extremely tiresome, it leads to noticeable discrepancies in the story. For example, you start sucking off your bully (and get the option to suck off your coach or let him masturbate to your butt) before you are willing to wear a bracelet even. You can buy a dildo and practice sucking it, but can't wear panties under male clothing near the point where you are doing that. It doesn't make sense.
Second, the game is currently less about sissification and more just generic gay content. Yes, eventually you start dressing differently, but you can't wear a female outfit in the current content or utilize any of your feminine traits you've earned in any significant way. All the gifs/videos are just gay sex. Sorry, but gay =/= sissification. I realize this is most likely due to development progress, but you should definitely put a warning. Even for someone like me who LOVES sissification (as my name makes clear I'd think), I don't enjoy regular gay content at all.
Third, the avatar image is atrocious. I see what you're going for, and I love the idea, but until you can pay a real artist to do the avatar art, I recommend switching it to an inventory style avatar that just shoes pictures of the clothing you are wearing. I also recommend using real clothing for that.
Fourth, I understand using a drawn avatar limits the clothing options to what has art, but you should really increase the clothing options. Even if you disregard my previous comment about switching to real pictures for now, doing simply color swaps would be a nice addition and let you add items to "The Closet" store, both male and female.
Fifth, I'm glad you put an Auto-resolve option on (most) the mini-games, because they're long, boring, and there's definitely some difficulty issues. Specifically, the cunnilingus mini-game is far too difficult. I never managed to successfully complete it, whether doing it manually or using auto-resolve, even with maxed out skills. I considered that this may be intentional, perhaps for future content involving you being "useless" to women, but reviewing the games code, that doesn't seem to be the case. Furthermore, in regards to the mini-games in general, I want to specify that when I called them "boring" it isn't because they are poor designs, I actual like what you were going for, but you have to do them WAY too often, which is why they become boring. I also think that if you make your partner cum, there should be a picture for that and a different comment from your partner. The fact that your bully doesn't seem to care if you make him cum or not seems weird, especially since technically I could start the mini-game, never do anything, and get the same result despite technically having done nothing but kneeling and staring at his cock. The same with your girlfriend, regardless of the effort/success of your cunnilingus, she is also satisfied with your performance. With the Buttoncrafts mini-games, I again get what you're going for, but it doesn't make any sense. Sewing is done with patterns, not through memorization. And knowing the difference between bra/pantie types doesn't help in regards to using a sewing pattern. I would recommend completely revamping those scenes to something that makes sense. Also, bras and panties are extremely difficult to sew, particularly bras since they use multiple materials, padding, elastic, wires, hooks, and clasps. So it's strange that your character can do so without having ever sewn before and never practices. Which reminds me, nothing you make in that club is made with Knitting, except MAYBE socks (depending on the kind). It's also sewing, generally with a machine (accept the bracelets, which are just string beads), so you may want to correct that. As for the dish washing mini-game, I don't mind it terribly because it is short, but it doesn't quite work right. I usually have to click on image multiple times to get it to register. Side note regarding that mini-game, it's weird that a mall cafe uses that many plates. It should be pots/pans/utensils since customers would usually be given disposable plates/containers/wrappings at a mall food vendor. Not an actual problem though, just an observation.
Sixth, the days are too short for the amount of things that need to be done. I understand, at least form the appearance of the design, that you want the sissification process to be a slow one, but at the rate possible, it is abysmally slow. Doing something on the computer shouldn't take a third of a day. Literally nothing you do can take that long. You don't Stream long enough, you only watch one porn video, which even if it's a full length movie isn't a third of a day, posting a picture, even including taking it shouldn't take but maybe an hour. Additionally, you have to practice blowjobs and cunnilingus far too many times to max them out if you're also trying to progress the story since each of those takes up a third of a day (and if it takes that long to suck a dick, even with maxed out skills, he's doing it wrong). Seriously, spending that amount of time practicing sucking a dildo everyday is beyond dedication (warranting WAY higher stat boosts and more choices relevant to your willingness to do so). Try it sometime, get a dildo and practice sucking it for the implied 4 hours straight that your protagonist does it. Doing that everyday for that long will kill your jaw. An hour is far more reasonable.
Seventh, the sissification "route" doesn't make sense. You can go along with everything and be willing, but you don't progress fast enough for you seem willing outside of responses and thoughts. I only played through once because of how long it took, but given the choices possible, it seems like you can be unwilling, but I don't know how this style plays. Is the intention to allow you to become masculine? If so, that's fine, but with the current content and rate of progress that seems like a pretty boring route since you basically wouldn't have anything to do other than disagree with everything that happens.
Eighth, the protagonist has a strange understanding of penis size. He seems to think his is normal, but he watches porn and is old enough to have seen other people naked at various points in his life (whether catching a glimpse of the guy next to him at a urinal or changing in a gym locker room). Given that, how one earth could he think that he has anything remotely close to a normal sized penis? I would recommend that he have a more normal sized one, but once taking the testosterone blockers, it begins getting smaller, or instead you revamp dialogue/thoughts to make more sense.
Ninth, your girlfriend being supportive of you being a cuck and sissy is fine, but her personality takes some pretty huge swings. She goes from not wanting to sleep with other girls because it's "borderline" cheating (nothing borderline about it by the way, it's straight up cheating) to sleeping with the teacher as often as possible overnight. She also goes from "would you be okay with me doing collaborations for StarApp Plus?" to literally devouring dick right in front of you immediately. Is she a supportive, loving girlfriend or a straight up slut? Either way, how and why was she ever with the protagonist? If she's with him because her goal from day one was to turn him into a cuck and sissy, why does she drag it out so much? Instead of saying that she likes that you wear panties, why not require you to wear them because she thinks it's sexy (If she's trying to sissify you)? I just don't understand her as a character, she makes no sense. Also, requiring that you have to let your boss fuck your girlfriend to get a promotion doesn't make a lot of sense. Being able to get a promotion implies that there is a position that needs to be filled, so him waiting the potential weeks to months for you to progress to the point of having an open relationship without filling that position is nonsensical. Instead, why not make it possible to get the promotion after training to bake, and then make it possible to get a raise by letting your boss fuck your girlfriend.
Tenth, the restricted internet is a ridiculous idea. Your character lives in an apartment, not a dorm (according to the text) so he isn't using the school's internet. Phones have a data plan, when not on WiFi, you can do whatever you want, it's that simple, so the StarApp Plus restriction doesn't make sense either. If you want to put a restriction on internet, it's an easy fix. Change "Apartment" to "Dorm" (and we'll assume the protagonist doesn't have hot spot capabilities, though adding that as something you can buy for a monthly or even weekly expense would make sense as a method of getting around needing vouchers) and for StarApp Plus, make it require a registration fee (requiring more money) or a minimum followers (requiring more photo shoots).
Finally, there are way too many pointless locations. The grocery store has 4 options, and 3 of them are quickly removed (Why do you not already own a comb? Also, if you're going to make me by a new razor every week, but other life-sim requirements in too, like groceries, laundry detergent, shampoo, soap, etc...). The adult store has 2 options, both of which are one use (You could add more dildos of varying length that you have to use to get better at deepthroating). The clothing store has 2 options, again both of which are one use. The hair salon has 1 option, since apparently the only hair styles your character is willing to use are "Short" and "Shoulder length" (judging from the avatar art at least). You can't dye your hair (which again, even if you keep the current avatar style, is a simple to "draw" (ie, use the bucket tool) and code) and you can't actually change hair styles (even with long hair, it looks like a male haircut). Rourke's house is used like 3 times, but is always available for you to walk into for no reason. I bring this up because I constantly checked every location for new story/items/content after pretty much every event. Either add stuff to the locations or add messages saying when new things are added/available at a location (Like maybe a "thought" when you're in your bedroom saying "I should go to X for Y". Also, on the weekends, there should be a "Go to work" button in your bedroom just like "Go to school" on weekdays.
I hope I didn't come off as too harsh. I love sissification games and I hope to see yours improve and grow. I appreciate the effort you've put in so far as well, I just hope my comments help you improve the game.
