Retry penalties are ONLY for failures, NOT for successes. The +5 dc increase retry penalty for Intimidate is only if you fail, NOT if you succeed.
Imagine it like when you fail to pick a lock and break the tool off inside it, or fail to move silently and have the guards alerted to possible intruders. If you tried to be scary but your voice cracked and you tripped over your cloak and fell in the mud, all your subsequent Intimidate checks would be harder.