It's not even close - Blue wins

You thought your losses to Blue went by fast, but this battle seems to be going for the record. A lot of new trainers like catching a Mankey because its unrivaled speed catches other newbies off guard. This challenger seems to be using that exact strategy.

Blue is obviously ready for it, though, as he orders Squirtle to unleash a series of Water Gun attacks that overwhelm Mankey before it can even close the distance to unleash its flurry of attacks.

The next Pokemon to face Squirtle is a Caterpie which Blue's opponent seems much more unsure about. This time Squirtle switches to an aggressive stance, attacking Caterpie with successive Tackles and Bites while periodically retreating into its shell to avoid counterattacks.

The whole thing ends up over in less than three minutes. The loser falls to his knees, obviously not expecting he'd actually need to pay up that much money. Blue steps up to him holding his hand out, waiting for his payment to be handed over. He finally pulls out his wallet, taking an excessive amount of time to count his bills. As he finally hands over the money, he stares at you with resentment. You smirk at him, knowing if Blue beat you so badly twice this morning, this wannabe didn't stand a chance. Regardless, he doesn't take his eyes off of you until after Blue counts all his winnings, puts them away, and turns to continue on to Viridian City.

Wait, no no no! You come to a realization as you follow Blue up the path again. You shouldn't be acting so smug when Blue wins! You need to focus on yourself and trying to get free from being Blue's Sex ****!

You are still arguing with yourself in your own head when Blue announces to you, "All right, we're finally here, Viridian! I really feel like a real trainer now!" If only you could say the same about yourself. "All right, busy day, let's get going!"