Wildly enough, Anko’s path to Orochimaru isn’t a simple tale of hero meets master — it’s messy, dark, and shaded by the Cursed Seal that defines so much of her backstory in 'Naruto'. In the flashbacks shown in the series, Anko was a child who crossed paths with Orochimaru during the height of his forbidden experiments. He was already fascinated with the limits of human bodies and jutsu, and some kids ended up as unwilling subjects. Anko survived one of those encounters and, as a result, carried the mark Orochimaru left: the Cursed Seal of Heaven.
From how I piece it together watching the episodes and rereading scenes, Anko became his student under very complicated circumstances. There’s a mix of coercion and twisted mentorship — Orochimaru both experimented on and trained her, so she gained skills but also trauma. Later scenes make it clear she didn’t become his lifelong follower out of trust; she escaped or broke away, and her time with him left psychological scars as much as ninja ones. That’s why when she returns in the storyline she’s so wary, bitter, and yet capable — all those traits point back to Orochimaru’s influence.
I’ve always felt for Anko because she’s emblematic of how 'Naruto' handles grey morality: powerful people leave marks, and the young survivors have to rebuild identity. Her complicated relationship with Orochimaru, flavored by experimentation, survival, and the cursed mark, makes her one of the more tragic but intriguing figures in the series — it’s a storyline that still gives me chills.