1st Medal - read the instructions all the way through.
2nd Medal - Click on the K-Fed and Newgrounds links at the beginning.
Walkthrough: Walk left, talk to Jim and Jeff. Walk right 2x talk to Stamper. Pick up Stick. Walk left, pick up gum. Type inventory, combine gum and stick. Walk left, look at gutter. Open door. Walk right 2x, talk to Stamper. Walk left 2x. Talk to Jeff. Walk right 2x. Look at box, type in 936185.93. Pick up water, walk left 2x. Talk to Jim, he gives you KICKPUNCHER code. Walk right, talk to Tim. NOTE: you don't have to hit enter after every word you spell. If you do it correctly, it accepts it and moves on (also, 'kickpuncher' is very necessary so watch your health). Talk to bouncer and you win!
Obviously, I didn't include the 'next' and 'close' commands every time they come up, but otherwise that is how you play this unnecessarily complicated game.
3rd Medal - Kill yourself.
4th Medal - Complete the game.
5th Medal - Lose at Avenue Wrestler (not hard to do).