first time using a brush / (by extension) first time doing something / (slang, by extension) man losing his virginity

Same as above

a brush, a pen, a writing or drawing implement / the mark made by a brush or pen / writing or drawing with a brush or pen

a writing brush, a painting brush, a pen / the act of writing / something written / handwriting, how someone writes

(obsolete) same as for fude above: brush; pen; writing

(obsolete) same as for fude above: brush; pen; writing

brush / writing brush / paintbrush / pen

good at writing

good correspondent, someone who can easily write compositions or letters

Kyūjitai form of 随筆 (“essay”)