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Currently you are able to watch "Oreimo - Season 1" streaming on Crunchyroll Amazon Channel.
There are no options to watch Oreimo for free online today in Canada. You can select 'Free' and hit the notification bell to be notified when season is available to watch for free on streaming services and TV.
Living in the shadow of his talented younger sister, Kyousuke Kosaka conducts a normal lifestyle until he accidentally finds out that she hides a secret. In addition to being smart, pretty, and popular; Kirino Kosaka is also an obsessive consumer of anime and eroge (adult computer games). What will Kyousuke do? Will this tear their already rocky relationship apart or bring them closer together?