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nail Jell-O to a tree 

to do something difficult or impossible, especially when there is no real point in doing so
To eat a spoon full of cinnamon by itself would amount to nailing Jell-O to a tree. (example of nail Jell-O to a tree)

Nail his/your pecker to a fence post. 

Means one of two things.
1:Something one guy tells another to make a point.
2:A type of crucifixion where you are tranfixed to a fence post by having your pecker nailed to it where you will have to stay till you die or someone comes along to rescue you.
1:Hears the keys to my car.Put a dent in it and I a nail your pecker to a fence post.
2:There's that queer again.Lets nail his pecker to a fience post.
And that is the meaning of nail his/your pecker to a fence post.