Final answer:
Winston spent his afternoons escorting younger students home, often those with appealing sisters or hospitable mothers, to maintain good relations important for his subsistence.
Step-by-step explanation:
Winston spent many childhood afternoons convoying smaller students home, interacting with those who had attractive sisters or kind mothers.
He ensured to maintain good relations with his pupils and their families, as his livelihood partly depended on the hospitality of his students' families where he would board and lodge.
The passage implies that beyond his role as an educator, Winston's afternoons were invested in fostering community ties, likely to augment his social and economic standing within the neighborhood.