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Question: Write a story about a college guy who wakes up with a bad headache after a party the night before. He realises that this isn't his dorm room, it's his sister's, which is clear across campus. Not only that, he's wearing his sister's pajamas, which are very short on him revealing that he's also wearing his sister's underwear too. When he shuffles out to use the bathroom, one of the other women in the dorm calls him by his sister's name, and he realises that they think he's his sister. After cleaning up, he heads back to her room, puts on a clean pair of panties and a bra, before slipping into a soft dress, not trusting that he'll be able to get into a pair of her jeans. A little bit of lipgloss and mascara are enough for his reflection to look close enough to his sister to pass muster. He puts on a little bit of her jewellery, squeezes his feet into her flats and grabs her purse to head across campus to his own dorm room. Hopefully his sister stayed there and is dressed in his own clothes.
Jake slowly opened his eyes, groaning as a sharp pain pulsed through his head. He squinted, trying to make sense of the unfamiliar surroundings. This wasn’t his dorm room. The posters on the wall, the neatly arranged makeup on the dresser, and the pastel-colored bedding told him all he needed to know: he was in his sister Emily’s room, clear across campus. Confusion turned to panic as he felt the tight constriction of clothes that were definitely not his own. He glanced down and his face flushed. He was wearing Emily’s pajamas—short, floral-patterned shorts and a tiny tank top that barely covered anything. His horror increased when he realized beneath the pajamas, he was also wearing her underwear. His head still pounding, Jake forced himself out of bed and shuffled to the small mirror by the closet. His disheveled hair and groggy expression mirrored how he felt. He needed to get to the bathroom, freshen up, and figure out what had happened. Just as he stepped into the hallway, a cheerful voice called out, "Morning, Emily!" Jake looked up to see one of Emily’s dorm mates smiling at him. In his sleep-deprived state, he automatically responded with a half-hearted wave and nodded, hoping it would be enough to avoid suspicion. Locking the bathroom door behind him, he splashed cold water on his face and took a deep breath. Maybe, just maybe, Emily was in his dorm room, wearing his clothes. He'd confirm that once he got there. For now, he had to play along. Wiping his face dry, Jake went back to Emily’s room and opened her wardrobe, searching for something—anything—that might help him blend in. Seeing the clean panties and a bra, Jake hesitated for a moment before putting them on. It felt odd and uncomfortable, but the urgency of the situation gave him little choice. Next, he picked out a soft, loose dress. It seemed forgiving enough for his frame, though it still fit snugly in places it shouldn’t. Jeans were out of the question; he was sure he’d rip them. Steadying his hands, he applied a bit of lipgloss and mascara, hoping they'd be sufficient for him to resemble Emily closely enough. Looking in the mirror, he was surprised at how convincing he looked. Some of Emily’s jewelry and her flats completed the ensemble. Squeezing his feet into the shoes was a challenge, but he managed to make them fit. He grabbed Emily’s purse, threw in a few essentials, and took a deep breath. Walking in Emily’s shoes, both literally and figuratively, was an experience he didn’t need to repeat. He tiptoed out of the room, cautiously making his way through the dorm halls. Heads turned, but no one seemed to suspect anything as he made his way out and across campus. His heart pounded, urgency driving him forward despite the odd stares. Finally, he arrived at his dorm, slipping inside and praying Emily was there. Relief washed over him when he saw Emily sitting on his bed, scrolling through her phone, dressed in his clothes. She looked up, an eyebrow raised, then burst into laughter. "Well, this is a sight I never thought I'd see," she teased. "Emily!" Jake said, exasperation and relief mingling in his voice. "You have no idea what I went through to get here." Emily’s laughter died down, and she grinned at him. "Let's get you out of those clothes and back into your own." Jake nodded, grateful. This was an experience neither of them would forget, but Jake hoped it was one they'd never have to repeat.
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