I fear it's a bit unclear when interactions are available during night sequences. I've been trying to complete a mission where I grope her ass but the game is very picky on letting me do it, I think I've done it once and have not been able to replicate it
explore, figure stuff out, do things by trial and error
The game let's player find interactions by discovering stuff, it's not another "one-handed" porn game, dev has a different vision, which actually works and people enjoy this concept
The game is not picky about stuff, either you do it correctly or not, you simply didn't shift her legs into doggy position on subsequent trials