Doubly na Kanojo ~H na Jonan ka Dou ka wa Sateoki~

The protagonist's life has been nothing but disaster. The fiascos he encounters are always woman-related. Indeed, he has "girl problems". Every time he meets one it's another wild ride. "Here let me take off your pants" = problem Girl wanking him with her hands = problem Girl in sexy school swimsuit = problem Maid uniforms and cheerleaders = problem Sounds like one of them good problems to me!