Confirmed.Yes, that's how the cock stare skill works. Use it enough times on different enemies (so not the same guy in a fight repeatedly) and you'll start unlocking passives which change the dialogue Karryn uses and enemy reactions to it.
Cock-Curious passive is awarded after 15 successful cock stares and it increases cock desire instead of diminishing it.
Cockwatching is my Hobby (more than 42 cockstares used) further improves that ability and also Karryn's cock desire grows with each erect member present in battle.