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I've often wondered about that, if I made a tranny cum by pounding her hole, would I feel her asshole contracting and squeezing tighter around my cock every time she squirts her load? And would it put me over the edge until I couldn't hold my cum back and longer, and cause me to dump my entire load deep inside her guts?
If you find the right bottom like me one in a hundred, if you poke and probe his organs deep like that, if you shift and interfere with his innards hard like that you will make him cum and as he ejaculates all over the place the spasms and contractions his sphincter and taint muscles do will milk you, When you fuck me to orgasms as my cum spills out of my body with your incessant thrusting you will fill my intestines with cum, filling my twitching guts till your last drop.