It also says that Aletta's KP are lower than 50. So possibly, the event will happen if you fucked the two on two separate occassions within the space of a week and one of them (not both) is not kinky enough. Remember to unlock Aletta's submissuve side as well, which is quite easy - just chat with her a lot at work, making sure to provide her with the right answers to her questions. It's faster that way than spending an hour a day on the silly rough cunnilingus scene, which grants you two kink points with Aletta, to eventually take away one, if Mike shuts his mouth quick enough to evade her squirt.Shiori's kinkpoint is 100 and I triggered the event names 'aletta&shiori showdown'. But wiki says one of its prerequisites is shiori's kinkpoint less than 50.
To sum up, the best strategy playing this game in order to score as many female characters in a single playthrough as is possible is to be very patient and relatively sex avoidant in the early game, concentrating on self-improvement first and then slowly corrupting the girls with smooth talk, 'accidental' butt-slaps and dubious gifts rather that 'hot coffees'. Hot coffees are usually triggers to events which may have unpleasant consequences, if the girls are not prepared LP/KP and bisex-wise. As riduculous as it may sound, some of them can be turned into sex slaves with Mike not fucking them even once. Thus, he can become an ultra alpha-stud collecting regular rackets from desperate women, at the same time being a faithful boyfriend or a chaste single. So far, the silly girls say nothing to the fact that half of the town's female population wears collars. There are just a few scenes at home where either Sasha or Bree will react negatively to the other wearing a collar or walking naked at home, when they themselves are not. You'll lose a few lovepoints which are all to easy to gain back and then they'll shut up about it.