Train My Ass Miss Dia, Plllllease!

Dean Strong is such a little bitch. He has been sucking up to me for weeks begging to come back to The Armory for training. Since his cock has proven to be completely worthless in the past he specifically requests that we humiliatingly clean out his ass and stretch and train it with graduated butt plugs. Miss Dia slaps a chastity belt on this little ass fucker and he can barely keep any of the plugs in without them popping out. Miss Dia cleans him out with enemas, plugs his ass up, paddles it hard, hangs weights from the butt plug and it just keeps slipping out. She gets fed up and and does a reverse pile driver on his ass. Plugging him up with a strap on that has a buttplug on one side and a dildo for her to fuck on the other. Every pump of her pussy on the dildo pushes the plug deeper in his greedy little fuck hole. Cheers Dean! Hope you got everything you asked for!