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Babysitter Diaries 3. Kendra and Ally: Kendra is fed up with babysitter Ally. When Kendra catches Ally and her boyfriend in her bed she thinks of a good way to punish them both.. Chastity Lynn: Jay's wife recently passed away and newly hired babysitter Chastity is there to take care of the children. jay can't resist Chastity's tender love and care!. Ella Milano: Alec arrives home to find his wife and lover Ella sitting in the same room. When he finds out that Ella is the new babysitter he knows he is in for some trouble.. India Summer: A last minute cancellation leaves India in a bind. As a last resort, the babysitter's boyfriend, Michael, is there to fill in for more than just a few hours.. Lexi Bloom: Babysitter Lexi isn't much to look at..or is she? Christian just can't keep his hands off the real babysitter..