Not exactly the best at writing fan fics but I'll give my best shot
Summary:
After Luigi breaks his arm due to a plan not working, Bowser takes him in and learning just how broken he is. They start to bond with one another and each helps the other to resolve their repressed issues.
Chapter 1
The entire Mushroom Kingdom was in a state of panic. Bowser and his army had begun an attack on the kingdom and they were almost at Peachs' castle. "We have to get the princess to safety!" Toad yelled brandishing his frying pan as a weapon. "Can't Mario save us?" "No," the Princess sighed "He fell ill this morning. He can't fight." "Then we shall have to get him to safety along with you" Toadsworth stated as he hurriedly guided Peach out of danger. "What about me? Can't I help?" A voice rang around the room. It was Luigi's. "Hmmmm... you're much too cowardly and weak to defend us..." Toad said thinking of how Lu could possibly be useful. "...but, you ARE the perfect size for another plan." Toad ran across the room and harshly pulled Luigi into Peach's closet "Toad, what's happening? What other plan??" Luigi asked, conused and a bit frightened. Toad didn't answer or even seem to hear Luigi's pleads for answers. He forced one Peachs' spare dresses over Luigi's clothes and messily dumped a wig onto his head. Toad finally shoved a mask on his face and started pushing him towards the balcony. " Toad whats going on??" Luigi cried, even more confused than he was before. But that didn't matter. Because Lu felt a sudden shove from behind him, causing him to topple over the edge and fall to the troops below.
He understood now. His friend had, quite literally, thrown him to the wolves.
After an incident at his highschool prom, Luigi lost ALL confidence he had to wear dresses in public.
But when he and Bowser start to bond, the Koopa king and Junior help him rebuild his confidence and when he's rescued and taken back to the mushroom kingdom he is more comfortable and starts wearing dresses at some events.
P.S: Bowser thinks Luigi looks really cute in a dress but you didn't hear that from me!