It says get r*ped 15 times by Jackys and reach wave 10, that means in a single game, the way to do this is to kill all but 1 Jacky in a wave, press 'S' so you give in, and immediately hold ⬆️ so you get out of it's grasp without much stamina or pleasure damage received, repeat that 15 times, then survive until wave 10, and voila!.