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Ever dream of being feminized by me then fucked by and cummed on by a bunch of guys and trans girls? While attending a college party, I overhear the class stud Silas bragging about how he's going to bang me... so I decide he needs to be knocked down a peg by fucking his cute guy friend Caleb instead! But when I get this unassuming sweetie up to the bedroom, I confess I'm only into pretty girls and masculine guys -- neither of which describes poor Caleb! But when I take a closer look at him... I realize: hey, he'd make a pretty cute girl! So with my kiss I lower his pitiful defenses, and the next thing he knows he's slipping out of his grungy guy threads and into some soft, silky panties, padded bra, and pretty pretty dress! A little eyeliner and lipstick and suddenly, "Caleb" is now "Cailey"! I break in this pretty new thing with my girlcock, fucking her mouth and spanking her soft little butt to confirm my suspicions: she is a natural born slut! So why not show off my new discovery with our friends? I drag her by the hand back to the party and ask the group, "Who wants to FUCK my pretty new friend?" In less than a minute the orgy begins, with little Cailey at the center and me, her proud mentor, watching over her as we both suck and fuck all the dicks available to us. And her reward for being such a good girl? ALL the cum pouring directly from those cocks onto her pretty face! While we all pant and sweat I stroke her hair and kiss her messy face, asking her, "aren't you happier as a girl?" "Yes," she replies with a jizz-soaked smirk. Come live your fantasy with Cailey Katts and Kaela Luna, both 2026 TransErotica Award winners!