(Part 2) I think "bleak" is a misprint for "beak." (Yes, John thinks so, too). "Beak" is British slang for "a judge," especially a low-ranking local judge. Again, this is the language Bertie Wooster would have used. "Cheek" means boldness, like an impertinent teenager who "talks back." For example, suppose a parent says "Please eat your vegetables, they're good for you, there are starving children in Zambia who would love those vegetables," and an eleven-year-old boy retorts "And I would love to send my vegetables to them." That's "cheek." In more straightforward English, "Bertie Wooster, the foolish aristocrat P. G. Wodehouse wrote about, seems to be forever pulling practical jokes, like stealing policemen's helmets off their heads, and then having judges let him off with almost no punishment, for being obnoxious."

P. G. Wodehouse (pronounced "wood-house") wrote dozens of comic stories. They are famous. The central characters are the foolish Bertie Wooster and his intelligent butler, Jeeves. The stories are not realistic. They are comically exaggerated, like characters in an animated cartoon. They are set in Edwardian England, about 1900-1910. Wooster is rich. Wooster is an adult, but he acts like a 14-year-old boy. Wooster speaks colloquial English of the era. I think the person who wrote your sentence is trying to be clever by imitating that language himself. A "buffoon" is a fool. "Buffoonish" means foolish. An "aristocrat" is someone who belongs to the upper classes. "Jape" is an out-of-date word for a joke. In the case of Bertie Wooster, it means a practical joke or prank. For example, in "The Ordeal of Young Tuppy," we learn that Tuppy Glossop pulled a practical joke on Bertie. In revenge, Bertie wants to sneak into Tuppy's bedroom at night and puncture his hot-water bottle--a rubber container of hot water used to warm beds--so that Tuppy will wake up in a wet bed. "Charted" usually means making a diagram or map, but it can mean to make a plan or a record. The straightforward phrase would be "wrote about." "To pinch" can be slang for "to steal." Bertie Wooster speaks informal English, and he almost always uses the word "pinch" for "steal." "Pinch" suggests something minor--like borrowing somebody's scissors without asking permission. Apparently in those days it was fairly easy for a bold prankster to pull the helmet off a policeman's head. In theory this would be a serious offense. Traditionally, in schools, schoolchildren were punished for minor offense by being "rapped across the knuckles," hit with a ruler. It is an idiom for "a minor punishment." In the US we sometimes say "slapped on the wrist." For example, "He should have gone to prison for five years, but the judge only sentenced him to thirty days. That's just a slap on the wrist."

It means Bertie Wooster is always being reprimanded by "A beak" not bleak . "beak' = old word for a Magistrate.