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“What are you going to do?" Just relax. I think maybe you'll enjoy it." He went into the kitchen for the gloves and then collected lube from the bathroom. When he returned to the bedroom, I put on the gloves and instructed him to get down on his knees and bend over the side of the bed. Thus, his rosy red ass was exposed to me in all it's glory. I applied a good amount of lube to my index finger and proceeded to rub it all around his anus. Once it was slippery all around his asshole and his butt crack, I gently inserted my finger. He moaned as I poked gently in and out. "Does that hurt?" "No, not really.”I pulled my finger back out and applied more lube and spread some over my other fingers. I gently inserted my finger. But, this time, I pushed it in a little further and then pulled it back out repeatedly. After a few minutes of this, he was moaning. "Are you okay?” “Yes, I’m good,” Joe answered but he was breathing a little harder. And I got a big, "ahhhh," when I added a second. If it panned out thenshe would get something that Tom would regret saying for a very longtime; and if it didn't then it would still be a great mind-fuck on herpart.Tom wanted to wear makeup to make himself unrecognizable or at leastless recognizable, but he knew he couldn't just come out and say so orPrincess Dee refuse to allow it. He had to convince Princess Dee that heactually wanted to wear it to show that he really was a sissy."I want to wear makeup so I can be a good sissy for you on webcam," Tomstated."Why?" Princess Dee asked him again."To do what you want me to do for you on webcam," Tom answered.Princess Dee smiled, so far this was playing out as she was hoping itwould. "What is it I want you to do on cam my little sissy?" she asked.Tom was getting frustrated with the questions. It was almost liketalking to a three year old who was playing the "Why?" game that allkids of certain ages find so amusing. This did not seem to be going assmoothly as Tom was hoping it would. "You.
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