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His hand squeezes your ass, pushing on it not yet ready to blow his load sliding out so only hiss tip is inside you while he tries to catch his breath and refocus his mind. You can feel both his hands squeezing your ass pressing you down more into the pillows for what feels like an eternity, before you feel his hands squeezing your ass he plunges back into you, filling you up again. Your eyes roll into the back of your head, your hands squeezing at the bonds holding you now as you want to grab and hold himself deep inside you. Your legs fight as well now, your mind wanting to make him fill you. The bindings holding firm as he begins to pound himself into you. Feeling him start to slide out of you, you let out a soft whimpering sound again, not liking the feeling of your pussy being empty. Before you can raise your head to beg, to urge him to fill you pussy with his hard cock again he drives himself deep into you. As he does you let yourself be shoved deep into the pillows, a moan. Before standing back up, I quickly flick the switch on the plug's baseto the ON position. I then snatch my phone off the side table and standback in front of my son. With one hand on my hip, I browse through thephone with my other, trying to find the correct app.Me: Ah here it is! This prostate milking tool comes with its own app, soit, in theory, can be controlled from anywhere. Let's begin!With my free hand, I pull my panties out of his mouth and throw themaside. At this point, I can't tell whether my sissy looks scared orrelieved.Me: Are you ready?Him: Do we have to do this mommy? I cum so rarely anyways...less thanonce a month. Can't we keep doing it the same way? (He swings gentlyagainst his bondage as he speaks.)Me: But those milkings give you pleasure. I know they do. I can see yourface every time you spurt your cum through your chastity cage. I can'thave that anymore.Before he has a chance to respond, I tap the green button on the appthat says "START". A little timer starts.
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