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I'm a security guard, so
>Gym is completely dark, only lit by the flashlights patrolling gym apprentices carry
>Instead of fighting gym apprentices you need to sneak past them
>Getting caught by them will send you back to the entrance of the gym
>Need to get to the top of the guard tower in the back of the gym where the leader resides
>Gym leader is sleeping (like me at work), need to wake him to challenge him
>Leader uses Pokemon that are or could be associated with law enforcement/security (so something like Arcanine, Watchog, Bisharp, Stoutland, Weezing and Throh)
>Pre-battle quote: "Whoa! I wasn't sleeping! Huh? You came to challenge me? Man, I oughta fire those . They are NOT doing their job. Between us, they let me do whatever I wanted with this Gym when I got it, so I designed it so to let me do as little work as possible. But, since you're tryin' to make me do my job, I'm gonna go extra hard on you!"
TM would maybe be Bulk Up or Sleep Talk ain't got room for any more shit.