The more taboo side of life tends to draw me in like a moth to the flame. My sadistic side loves inflicting pain upon the submissive types. Usually the more pain, the better.
Easier to start them out as a bit of a sissy. Get them all dressed up in a cute dress. Little bit of spanking on that asshole at first to get it nice and puckered up so it feels like a nice tight pussy.
And keeping the cheeks spread apart for a nice bull sized cock to violate said fuck hole. Stretch it out like a rubber band, and pump it full of a nice cum load. Make it ooze out and drizzle like a the filling in a jelly doughnut.
More times I do this, more I want to see how far I can go with other sissies. Maybe even incorporate some cbt while their anal region is being eviscerated by a giant fuck stick. Heard Bengay is a pretty common thing to use…