James has two choices for a shemale little sister who will generally be easily directed around; Cindi and Bonnie.
Cindi the dickgirl is more than a foot shorter than James, and compared to his averagely lithe build, she's what some would call 'a dainty-footed cherub', and others would call 'a fat bottomed shortstack'. With her light, easily burned skin, messy blond hair pulled into two loose pigtails and her blushing, dimpled cheeks, she's certainly rocking that naïve, exploitable underclassman look. For all that she wears a skirt her chest's barely there, and if it weren't for her fiercely puffy areola and proudly straining nipples harshly tenting her shirt you'd wonder if she was just a crossdressing boy.
For all that she's tiny, her wide hips and heavy ass look completely at home on her, as she needs all that meat for the monster that springs from her loins. More than a foot and a half of thick, almost puffy cock thicker than your arm droops down past her skirt's bottom and nearly reaches the floor with its heavy hanging, even with Cindi standing. Her cock's fist-sized pink head has a large, visibly protruding urethral slit, leaving you little doubt that this little sister really likes to explore her cock. Not to be outdone, her crotchless underwear strains to comfortably let an enormous pair of testicles spill free, each nearly the size of a basketball. Despite their great size, they're strangely snug in the dickgirl's large sack, and stay close to her body. Similarly, her testes seem to softly give way quite easily to the movements of her legs.
Cindi is the sort of freshman that plenty of people would bully or even abuse - and from the look of her she might like that sort of thing.
Bonnie the shemale may be noticeably shorter than James, but she definitely outweighs him. With more than a touch of puff to her limbs and a soft belly that manages to overhang her skirt's clasp, she manages to make her weight look good by being absolutely stacked from top to bottom, plumpness or no. With skin the shade of milk chocolate, a shockingly precise afro and archetypal beauty mark mole all on top of her relative size and fearless-seeming demeanor, she comes off as lazily personable, and confident in who she is. For all that she's clearly wearing one of the school's largest shirts, her broad frame and bountiful chest are so demanding that the garment's hem is hiked up, and soft inches of belly-flesh are exposed pretty much all the time, recessed navel and all. You can't help but notice the strained fabric over her nipples looks oddly warped - just how bumpy are her areola, if you can tell from the far side of a shirt?
Big gal or no, Bonnie's not packing anything particularly impressive. With a visibly phimotic dick that only barely meets school standards and a pair of balls that, while adequately sized and bulgy still don't look all that mature, her genitals seem to scream of inadequacy the rest of her doesn't feel. With her skirt back on, there's nary a bulge between her particularly wide hips and thick thighs to show that she's not a 'real' girl. Well, other than the ever-growing cumstains front and center over her groin. Even so, for all that she can rock a classically feminine look more ably than most, her body language is pretty free and loose, the very opposite of coquettish.
Bonnie is the sort of freshman that most people can get along fine with - and with how little care she's giving her soiled junk, she's probably quite blasé about all things sexual.
Does James end up with tiny Cindi as his little sister, or plush Bonnie?
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