Since Elena had been turned into a vampire, both Stefan and Elena had agreed that Jeremy should have a safer place to live while Elena transitioned. Damon was a bit annoyed by the proposition but after a while he didn't mind, he was actually quite fond of Jeremy, but would never let him know that, or so he thought. Stefan and Damon had agreed to go help Jeremy pack while Elena had just left with Caroline to school since they had to arrive early to set up for some festival. When the boys got there Jeremy seemed to have most of what he wanted to take with him packed, he just had a couple drawers left but he had to go to school. "Here are the only things in my room not yet packed" Jeremy said directing the boys to the only things not packed. He left in a rush since he was already tardy for school. Damon wasn't very ecstatic about having to pack things for Jeremy but he didn't mind.

Along with Stefan, Damon, began to open the drawers up to start putting them in boxes and such. The first drawer was really only a couple shirts and some pants. As they progressed most of it was just small miscellaneous things that Jeremy didn't want to leave behind in case he got bored at the Salvatore house. After many random drawers and many unnecessary breaks, the boys were down to the last drawer in Jeremy's room. While Stefan finished packing another box, Damon opened the last one and saw that this drawer was Jeremy's underwear drawer. To his exact assumptions, Damon found lots of boxers in Jeremy's drawer. Damon did often find that he thought Jeremy was cute and a bit attractive but Damon had this side to him that really just enjoyed men in underwear, you can call it a fetish. As he picked up the first pair he really inspected them slowly and then brought them up to his nose to smell them, and sadly for him they were completely clean. He did although spring a hard on in his pants just at the thought of him holding what once was on Jeremy. He then realized how his younger brother was packing things just a couple inches away from him. He put them down back in the drawer and was a bit disappointed in the realization that Jeremy only owned boxers, Damon really though that Boxers were the most unflattering type of underwear and that they did Jeremy's body no justice. Then surprisingly Damon realized his brother looking over his shoulder.