I LOVE these games. I discovered them randomly surfing Newgrounds last week and have kind of been obsessed since.
I like the ideas previously discussed about a DILF and/or in public. I know this would be more involved than anything before, but I was thinking to increase options perhaps "You", the main character, has recurring dreams that your crush comes over to your place in different fantasy attire (punk, sailor, cowboy, DILF/suit, elf, etc.) and after your erotic dream, you wake up to him knocking on your door. This gives the player multiple clothing options, in addition to dialogue choices catered to that fantasy. Each toolbox would have more toys to play with as well.
Anyhow, I'm rambling and I know there are other projects needing attention right now, but the possibilities of future T&T games is exciting.