is the following a) possible, b) legal

let us say I want to sell my KXL shares at as large a loss as possible and to sell the same shares to my son who has minimum income. So could I arrange a trade of 20,000 shares let us say at 40 cents so that I sell and my son buys at 40 cents and nobody else get the chance of getting them instead of my son.

this could be good for capital gains taxes etc; what is legal and what possible from a practical point of view?