Losing my [M18] virginity to my crush [F18], the quiet artsy girl at school

Let’s call her Anna.

This happened the Friday night after our high school graduation, in her bedroom at 1AM, while her parents were sound asleep upstairs (her bedroom was on the lower level).

Anna was an artist type, quiet, often spending her lunches alone in the high school library reading a book.

I’d had a crush on her for years, both because I tend to find myself attracted to quiet type girls (I’m a quiet, introspective type myself), but also because her breasts were very large (34H cup, I later learned). Ever since I became interested in girls, I’d always had a (probably unhealthy) fixation/weakness for extremely large breasts.

It’s obvious to me now Anna was insecure about her body, but I loved watching her walk through the hallways at school. Even though she always worse loose fitting sweatshirts/hoodies in a hopeless attempt to conceal her figure, they merely hung like a drape over her incredible, massive bust. I lamented never having a gym class with her where I might’ve seen her with a little less clothing on. She had a cute face, young and girlish with freckles. She wore glasses and no makeup, and I really liked that too – There was something very natural about her.