It's rubber boy's milking day! I've only gotten this one into chastity last week, so it is time to milk his cock before putting it back into a different-sized cage of a better fit. This is a good opportunity to train his tight little asshole to cum from my cock! I claim his ass as Mine both inside and out: first a little spanking to redden his ass before I stretch that hole and stuff it. Fingers, plug, strap-on, stroking—he's going to blow this pent-up load so hard for me! Soon, he'll be my weak rubber butt boy, begging me to fill and fuck his ass more and more.

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