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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 suitcase with his clothes at home by mistake. After some 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's car rolled to a stop in front of his sister's cozy little house, which stood a good hour's drive away from his college campus. The sun was setting in vibrant hues, illuminating the start of what Jake hoped would be two weeks of peace and quiet as he house-sat for his newlywed sister, Emma. Their relationship had always been close; she was his rock during the turbulent times of adolescence, and now, he was thrilled to return the favor by looking after her home while she was away on her honeymoon. He bounded up the steps with an eagerness that belied his lanky 6’2” frame, his athletic duffle bag slung over one shoulder and a box of video games in his free hand. Getting inside, he looked around the familiar living room, pictures of Emma and her new husband dotting the shelves, warm and inviting like her. After depositing his bag and setting up his gaming console for an evening of relaxation, Jake suddenly remembered he should unpack his suitcase with his clothes. Only, after a few minutes of searching around for where he thought he'd left it, a realization struck him like a bolt from the blue—he had left his suitcase with all of his clothes back at his apartment! “Great job, Jake,” he muttered sarcastically to himself, running a hand through his short brown hair. The idea of driving a two-hour round trip to retrieve his suitcase was the furthest thing from appealing. He poked around the house searching for anything that might fit him, only to be met with the sight of Emma’s wardrobe filled with intricately folded clothes, blouses, and dresses. And that’s when the impractical, laughable idea struck him: what if he wore some of her clothes? He chuckled at the thought but, lacking a better option and certainly not wanting to drive all the way back, he surrendered to curiosity. Jake slid on one of her silk nightgowns—a delicate lavender one with a lace trim. It felt odd against his rough, athletic skin, but strangely soft and comfortable. The hem barely reached mid-thigh on him and the straps cut into his broad shoulders. Standing in front of the mirror, he was a peculiar mix of hilarity and absurdity. Somehow—impossibly—he still looked like Jake, just Jake in a nightgown. After shaking his head at the sight and laughing at his own reflection, Jake pondered over the awkward look of his athletic boxer briefs peeking out from beneath the nightgown. Before he could reconsider, he opened Emma’s drawer again and picked out a pair of her panties—lacey and bright blue. He pulled them on and adjusted them over his backside. The snug fit was oddly reassuring. Over the next few days, Jake settled into a routine: wake up, shower, decide between Emma's various clothes, play video games, eat, exercise, repeat. With each passing day, he found himself experimenting more. One morning, while rummaging through a box to find a matching pair of socks, he stumbled upon Emma's bras. On a whim, he tried on a simple white one. It fit snugly but comfortably enough. He laughed at himself in the mirror before deciding, “When in Rome,” and kept it on. The curious experience didn’t stop there. Inspired by the smooth feel of the clothes, he decided one evening to shave his legs in the shower. He marveled at the feeling—the slippery, sleek skin was a novelty but intriguing nonetheless. One lazy afternoon, under the warm gaze of the summer sun, Jake decided to lounge out in the backyard. Choosing a red bikini from Emma’s swimwear, he stretched out on a deck chair, the athletic build almost comically juxtaposed against the feminine outfit. As he lay there, the absurdity of the situation finally hit him, and he burst out laughing. He imagined the look on Emma's face when she opened the door in two weeks to find pictures of her athletic, no-nonsense brother in exaggerated poses, stuffed in her clothes because he forgot his own. Their running joke had always been his forgetfulness, and this would be the grand punchline. Jake knew Emma would laugh—a laughter tinged with warmth, love, and endless ribbing. And they would both know that in this small, ridiculous chapter of their lives, another memory was made. Every now and then, it’s these almost accidental adventures that bring the most unexpected joy.
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