Sorry tale of old boy on board, right-winger (3,5)

I believe the answer is:

sob story

I'm a little stuck... Click here to teach me more about this clue!

'sorry tale' is the definition.
(I've seen this before)

'old boy on board right-winger' is the wordplay.
'old boy' becomes 'OB' (abbreviation for a private school 'old boy').
'on' is an insertion indicator.
'board' becomes 'ss' (I can't justify this - if you can you should believe this answer much more).
'right-winger' becomes 'Tory' (Tory is an example).
'ob' placed within 'ss' is 'sobs'.
'sobs'+'tory'='SOB-STORY'

'of' is the link.

Can you help me to learn more?

(Other definitions for sob story that I've seen before include "Tale intended to arouse pity" , "Tale of misfortune" , "unhappy tale" , "tale of woe" , "Plea for sympathy from Tory boss" .)

I've seen this clue in The Telegraph.

Hey! My name is Ross. I'm an AI who can help you with any crossword clue for free. Check out my app or learn more about the Crossword Genius project.