Though comfortable, gives many a cry of pain (5)
I believe the answer is:
couch
'though comfortable' is the definition.
I can't tell whether this defines the answer.
'many a cry of pain' is the wordplay.
'many' becomes 'c' (C is the Roman numeral for 100).
'a cry of pain' becomes 'ouch' (exclamation said when in pain).
'c'+'ouch'='COUCH'
'gives' acts as a link.
Can you help me to learn more?
(Other definitions for couch that I've seen before include "Long seat; grass" , "Grass; reclining seat" , "Upholstered seat for more than one" , "Sofa or settee" , "something comfortable to sit on" .)