Yeah its supposed to but whenever arousal maxes out during a stream or someone on it pays for a vibration with one of the toys it does a Willpower check, which my character always succeeds at to stop it from happening as they have max willpower.
Update: I managed to do it, in order to masturbate and orgasm during a stream you do need to have NO toy currently equipped that take up the vagina/Anus slots. Otherwise you are block from doing anything with it and are stuck unable to orgasm if you have willpower.