You're doing something wrong.
MC's roll to ambush Esther is random every day, so it can't happen every day (unless you're "lucky"). Second: you have (almost) full control of if you want it to happen or not: click "safe route" several times to almost never get caught (unless the initial roll was VERY high and you had bad luck).
No, you should NOT spank Gloria each and every day for 2 Lewdness. That's the worst option and it's said in the game.
You only spank her for disobeying the rules (she removed her butt-plug). Force her to wear it and wait when she disobeys you, spank her, repeat. Visit Carl and progress the subway subquest for extra Lewd points. Simply spanking her (especially from the start and EVERY day is the best way to turn the game into a nightmare grind). Later more options will unlock for you.
Congrats, you've found the worst way to play the game
I understand where it comes from - you have a bitch on your plate (and a dick in your hand
![LUL :LUL: :LUL:](data:image/gif;base64,R0lGODlhAQABAIAAAAAAAP///yH5BAEAAAAALAAAAAABAAEAAAIBRAA7)
), why not abuse the shit out of her, right? Nope. Patience, young padavan.