double gambler

Riding a hooker or ho bareback. fucking her back to front and front to back, gambling on your chances of getting an incurable STD. (2 hole action doubles your chances)

I took the chance and have her the double gambler

The Red Eyed Gambler

You rather mean Yumeko Jabami from kakegurui or Celestia Ludenberg from Danganronpa: Trigger Happy Havoc

person1: Omg, who was the red eyed gambler
person2: Yumeko Jabami
person3: Celestia Ludenberg