Shelby Greene couldn’t believe his luck. On a whim, he had entered some sweepstakes for a scholarship to this school on the west coast, and he had actually won! He and his single mother were both very pleased with this, packing their things and driving all the way to Suncrest Academy.
When they arrived, Shelby and his mom joined the throngs of other students moving their things into dorm rooms. During this, a few students had lifted his skirt up, pantsed his mom, and they both dealt with more than a few comments about their rears. Shelby would just roll his eyes; his round butt was something he picked up from his mom, and was already used to comments about it!
At last, the unpacking was done, and the two Greenes stood together in the dorm. “Now, I want updates everyday,” she told him. “Keep up with your studies, and don’t spend all your time goofing off.”
“Alright, I’ll be careful with my time, and I’ll call you every day,” replied Shelby, smiling as he and his mother hugged.
However, during this hug, she slid her hands down to his skirt, gripping his waistband and yanking up high! Shelby gasped in surprise as his lucky underwear-a pair of white granny panties with yellow stars-were pulled beneath his shoulder blades.
“One more thing,” his mom teased, “if I hear that you’re being a bully, I’ll give you a wedgie you’ll never be able to pick!”
“Alright, alright!” he laughed, once he had pried his underwear from her grip. “I’ll just relive your college years, get my head dunked in toilets and hang on flagpoles.”
“Attaboy,” she teased, letting his waistband snap back down. “I’ll text when I get back home.”
As she left, Shelby looked back at his underwear with a slight pout. Unlike most guys his age, he wore granny panties-that fact, combined with his soft features, shoulder-length brown hair, and wide hips, meant he was often mistaken for a girl. He didn’t particularly mind it, nobody was actively malicious about it.
The femboy closed the blinds on the window before reaching back and digging the panties from his butt. While he was picking, he heard the bathroom door open, blushing as he realized his roommate was about to see him like this!
Turning his back away, he got a good look at his roommate. To his surprise, it was Dakota Williams, a close friend of his from high school. They had been left in a hanging wedgie from the same fence, and since that day they had been pretty close. She confided in him her love of wedgies, he told her his dream to be a writer, and the both of them generally told each other everything-everything, that is, except that they were going to the same school.
“Shelby?” she spoke first, a bewildered expression on her face. “What are you doing here?”
“Uh… this is my dorm,” he responded. “I didn’t know we’d be roommates.”
“Oh, trust me, it’s not just you. How did you even get enrolled?”
“What are you talking about? I got that scholarship. Wait…” Shelby put a finger to his chin, the gears in his head turning. The fact that Dakota was surprised to see him, the abundance of girls he had seen around campus. “Is this a girls' school?”
“Uh, duh!” Dakoto laughed, but it was more out of confusion than humor. “Hey, listen, I won’t tell anyone about this mixup.” Shelby let out a sigh of relief, before Dakota lifted a finger. “But…”
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