Do these sentences sound natural?
'What age exactly does your voice break?'

'My voice broke when I was in middle school!'

'He sounds like his voice never broke!'

Question

Do these sentences sound natural?
'What age exactly does your voice break?'

'My voice broke when I was in middle school!'

'He sounds like his voice never broke!'

Answer

- At what age exactly does your voice drop?
- My voice dropped when I was in middle school! 
- 'He sounds like his voice never dropped!

By 'Voice break,' I'm assuming you mean the deepening of the voice that occurs during puberty.

Answer

"At what age..." otherwise I see no problems.

Answer

These are natural-sounding sentences.