1.: First, you need to visit the sex shop in the Red Light District and examine the gimp displayed a mannequin in the middle of the shop. Then talk to the owner(s) George/Georgia about it.
2.: After you did this continue visiting the shop until the gimp disappears. Talking to the owner reveals that she quit – and that the position is open now.
3.: Apply for the job and work at leats one shift as the store gimp.
4.: After that, you can run into Geroge/Georgia when choosing the “hang out” option in the mall. Accept their invitation to the “party”.
5.: After the first party, you can inquire about a new one at the sex shop and start it by visiting the shop on the day it is held.
6.: There are multiple party events and each lets you choose your preferred role during the event. All have to do with latex/rubber, but unlike the first event, you can assume the dominant role during these if you so prefer by choosing to be ‘one of the guests’.