Please let me know what and how I can improve. Im still very much learning within the 3 months ive been working on this.
I tried your game, some things;
1) This needs the gay tag as by chapter 2 you can already work and do stuff in a glory hole. I don't know what specifically because I'm trying to skip out on the M/M content, but between the hugs/kisses at work for men and the glory hole, I'm pretty sure it applies.
2) its very easy to sequence break things. I think for you the order you do things is fairly obvious, but for me, I wound up checking on evelyn who hints and teases about all the stuff she does with John...before even going on the trip with him. There was other instances too, most of them have to do around her trip and when she leaves and comes back.
3) I am assuming the "Fear" stat is to represent how much francis fears he's being cheated on, but I hit the part where she introduces you to the idea of cuckolding with Anna. So now it becomes unclear to me if fear is going to affect her and john or just her messing around in general.
4) Curious stat is actually confusing. It took me awhile to figure out that has to do with the sissification, but its quite broad. It seems to affect crossdressing, being with guys, willingness to cheat, working in feminine conditions, being with guys, etc. It feels like those catergories can be/should be more nuanced if you're trying to hit players preferences (as denoted when you mention cuckolding becomes "disliked" if you refuse ann. But this begs the question: Will francis be able to say he likes/enjoys when its from another woman or will that include John and other guys?)
This is just a side note I guess on "flavor" of sissification, but I kinda thought there would be options to become a housekeeper/maid (really like the idea of your wife turning you into a personal maid at home and renting you out to clean others), a secretary (for the lawyer?), things like that; So far the only jobs I found are for waiter and masseuse. This raises questions I guess about my own personal preferences (I'm just asking, this isn't a suggestion); Both those jobs have interactions with men, via the gloryhole or progressively "earning tips" from the male clients. Is there going to be an option to stick with female clients/futa instead of men (I'll be honest, I don't care if there is a dick or not, I just have to find who its attached to is pretty, and generally its not men, but it does make traps fair to me)? If gay route or M/M content can be avoided, will there be a chance to swap Evelyn away from John for Anna?
There is other things I guess, but this is already a lot and feels intrusive to your writing/style.
edit: one more note since coding is new to you, if you have events that trigger by thresholds of points the player has accumulated in fear/curious/hidden variables, its worth noting its extremely easy to over farm the points, as I suspect that might be what lead to the sequence breaks.