Y/N has always been different from everyone Damon Salvatore has known. Innocent, kind, and untouched by heartbreak, she has never dated, never kissed anyone, and has never experienced love. When Damon discovers this at the Salvatore Boarding House, he expects to tease her, but instead, he finds himself captivated by her sincerity and innocence. For the first time in over a century, Damon wants to protect something rather than destroy it, and he finds himself wondering if he could be the person worthy of being her first.

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