This achievement is when you start Duel of Speed. Credit to the Walkthrough guys for a description:
After the cut-scene you will be confronted with a racing track.
Avoid the first fence by moving right.
Avoid the second fence by moving left.
For the third fence, move right once more.
For the fourth fence move left.
When you reach the fifth and sixth fences, move right so you are in between the two.
Move either left or right around the Hay Bales.
For this section we will be jumping over obstacles by pressing Y, remembering to press it as soon as possible, otherwise you will not make it.
Do this twice, then quickly move to the right to avoid another fence
For the next fence, avoid it by moving left.
Avoid the next fence by moving right, then quickly press Y to jump the horizontal pole.
After the cut-scene, Whisper will be completely blind, so we will have to give him directions, here they are in order:
Left
Right
Right
Left
Left
After another cut-scene, we will now be riding Kyle and Larry. This is by far the slowest part of the race.
Press Y to jump over the first three obstacles. Choose any of the answers for the first two questions, as it is too late to win.
During the next part of the race, we must use our common sense and choose an answer that we know will result in Whisper failing to complete the obstacle.
We will see Whisper riding towards an arboretum, say 'Standing on your hands', and he will smack into the tree. Letting us over take him.
As we ride up to the two guards with the Hay Bales. choose 'Backwards' so Whisper falls over them. Remember to press Y afterwards, so you can jump them yourself.
Finally, when you pass the bleachers, choose 'And talk to a guard' to distract Whisper and win!
Here is a video of the achievement. Credit to Fringe Show for the video.