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“Oh sweetie, you either do this or I tell mom that I keep catching you wearing my clothes, your choice?” She smirked.“O-okay, but, anything but this, please?” He asked, a pleading edge to his voice.“Nope, because giving head is icky, but if I don’t do it she’ll probably dump me and find a new squeeze to lavish with expensive gifts,” she smirked, looking up at him coyly, “soooo, she gets her cock sucked, I get my girlfriend and mom doesn’t find out you’re a cross-dressing sissy slut. Sound fair?”Casey frowned, “....No.”“Well tough, and smile more, you look pretty when you smile. And anyway, if you aren’t convincing, we all lose.” She smiled too sweetly, tucking the last of her makeup gear away, “There. Here, take a look.”She produced her makeup mirror and turned it around. Casey looked down into the reflective surface and blinked, his eyes wide, it was the first time he’d had his makeup done by someone who knew what they were doing, and as he looked between the face in the mirror and. Within the hour he was back in his apartment. He didn't use either the enema kit or the douche, but instead had a good, long shit. Once he'd finished, he broke out the lube and the smallest of the butt plugs in order to get started. He didn't want to show up to Sam's untrained and unprepared -- he wanted Sam to be impressed. He applied the lube to the plug, and then put some on his fingers and worked them in and around his asshole until he was able to insert two of them. He pulled them out and replaced them with the plug. It didn't take much to insert it past the bulge, and soon it was buried in his ass. He pulled up his pants and determined to simply leave it in and get used to it.Through the rest of the evening he did normal, evening things. Made dinner. Ate, Washed the dishes and put the leftovers away. Sat to watch the news and a show or two, all the while aware of the pressure in his ass, and the effect it was having on his cock. He wasn't hard, He was barely inflated. But he was.
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