Please don't list this on a work's page as a trope. Examples can go on the work's YMMV tab.
Tear Jerker: Song at Dawn
Estella'sfirst experience with sex is painful to read. Not only does the physical experience sound traumatic but her ideas about romance and ballads are trashed.
Alis' torment at the hands of Raymond de Toulose. It takes a special kind of twisted mind to even think of that, let alone carry it out with such nonchallance. The poor thing is broken emotionally and her life steadily gets worse from then on.