Anal/stretch/Remote Controlled Vibe (Lovesense) play stretching sissy ass to its fullest capacity. Wearing plugs for large periods of time, overnight, for a full workday. Start with a small plug and work up to a large one, as Mistress decides. Spreading and presenting of hole for degradation and inspection of stretching progress. Large dildos worn for long periods of time as a task. Heavy fucking using a dildo just long enough for a possible sissygasm. Sissy will beg for more and more stretching of its hole, also, if the penis is a tiny niblet, maybe the asshole can make up for it.