This is the definition for context error:
the (...) context for the error is the chain of function calls that led (or may led) to an error.
Look at this example in the Error Summary:

and here are the two error contexts:
So, to answer you question, the number of context refers to the number of functions in where problems are detected.
In the above example, you should read each context error from the bottom-up, and you can identify that both context errors are happening in the strconk
file, in the 100 and 102 lines.
Please, also notice that for each context error, in the Address section, it shows a description of where that error is happening in memory, "0 bytes after a block of size 6". It is a good clue to identify exactly what is causing you troubles.
For detailed information on how Valdrind works, please refer to: https://valgrind.org/docs/manual/manual-core.html
Hope this helps you!