A compression board apparatus of a generally planar surface has an insert that compresses to a position that is flat or flush with a top surface of the board, when a load is applied to the top surface of the board. When the load is removed, the insert releases, thereby expanding to a released position. The insert is arranged to both extend above the top surface of the board and extend below a bottom surface of the board. The insert may be secured by at least locking mechanism and enables a user who applies a load to the top surface of the board to maintain contact with the board's surface, even in an airborne position and when the board is in a non-planar position.