Should I stop beating my kid?

So me and my son, we play checkers a lot. He really likes to play it and so he makes me do it everyday. But he never seems to get any better at it! I always beat him every single time and this angers him so he throws the board and stomps off.I like to win and I don't understand why he can't try different moves in the game, it's like he wants me to win each time but I don't want to hurt his feelings to much and make him think that he's a loser if I just keep beating him every time we play.. So should I just act dumb and let him beat me so he feels better? or should I just tell him to be man and to do different moves so I can have a challenge?