guys is actually not that hard... his first time, HE f*cked the gigolo
then at the start of the chapter he says he graduated as was heavily implied last chapter that they were gonna do it (the sister was gonna participate too but got whacked by the fairy guardian)
then he got inception... 'first dream a wet one, then the nightmare of the yandere, where it was then explained that he actually injured himself, but the nightmares where her job, so he "graduated" again to not get another nightmare.
also chapter was clearly a reference to Misery by Stephen King