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Question: Write a story about a college athlete who is house-sitting for his sister. His sister had just gotten married, and he was very happy to help out by taking care of her house. The first evening there, he realises that while he brought his toiletries and things like video games with him, he must have left his clothes at home by mistake. After a few moments consideration, he spies his sister's silk nightgown. Shrugging to himself, he slips it on, noting how short it is on him, then after a few minutes decides that his boxers look silly with the gown, so he changes into a pair of her panties. For the next two weeks, he wearing his sister's clothes mainly for practical reasons, although he started to wear a bra on a whim, and even shaved his legs just to see what it felt like. One afternoon, he is lounging out the back in the sun, wearing his sister's red bikini, and he just laughs at the image he must make. He knows that his sister will laugh when she sees the pictures of her athletic brother squeezed into her clothes because he forgot his own.
Jake, a college athlete with a chiseled physique and an infectious smile, had always been close to his older sister, Emma. When she asked him to house-sit while she and her new husband went on a fabulous honeymoon, he immediately agreed. It was the least he could do after she had supported him throughout his college and athletic career. Arriving at her house, Jake was in high spirits. He had packed all his essentials—or so he thought. As he started to unpack that first evening, he quickly realized something crucial was missing: his clothes. Amidst his toiletries, video games, and gadgets, there was not a single item of clothing. His closet at home must have looked untouched. Jake chuckled to himself. “Well, this is a new kind of challenge,” he muttered. Embarrassed but undeterred, he sifted through Emma’s wardrobe for any oversized tees or sweatpants. However, Emma did not own athleisure like he did; her wardrobe was filled with dresses, blouses, skirts, tailored pants, and an assortment of delicate nightwear. His eyes landed on a silk nightgown hanging neatly by the bed. Laughing to himself, Jake decided to give it a go. Slipping it on, he felt the cool silk against his skin. It was surprisingly comfortable, though it barely covered his muscular thighs. Glancing in the mirror, he couldn't help but chuckle at the sight: a six-foot-tall, broad-shouldered athlete in a dainty nightgown. As the hours passed, Jake realized that lounging in his boxers with the nightgown looked awkward. He rummaged through Emma's drawers and found a pair of her panties. They fit snugly, and he marveled at how different the fabric felt from his usual briefs. Practicality trumped pride over the next several days as Jake continued to wear Emma's clothing out of necessity. Soon, curiosity got the better of him. He tried on her bras, experimenting to see which styles fit his muscular build best. He even decided to shave his legs once, just to experience the sensation. It was a strange kind of fun—a whimsy he never afforded himself in his regimented life as an athlete. Two weeks flew by, and Jake got used to his unconventional homewear—so much so that one bright afternoon found him donning Emma’s red bikini. He stretched out on a lounge chair in the backyard, enjoying the sun’s warm caress. The image of his bulk snugly fitting into a bikini top and bottoms was too much; he burst into laughter, imagining what a sight he must be. He decided to snap a few selfies, thinking Emma would get a real kick out of them. The day of Emma's return came quickly. Jake had returned everything neatly to its place and was waiting to greet her at the door, back in his own clothes. As they embraced, she looked at him with gratitude. "Everything go smoothly?" she asked. "Without a hitch," he replied, an impish grin playing on his lips. "By the way, I left you a little surprise on your phone." Curious, Emma immediately checked her messages and found the pictures. Her eyes widened, and then she howled with laughter. “Jake! I can’t believe you!” “Hey, it was either that or go naked the whole time,” he joked. Their shared laughter carried through the house, a testament to their unbreakable sibling bond. Jake's unexpected venture into Emma’s wardrobe became a cherished, humorous memory for both—one they would reminisce about for years to come. Though he never thought he'd be wearing a bikini in his sister’s backyard, it was a reminder that sometimes, life’s little misadventures make the best stories.
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