Today’s tale starts in a bank office during the wonderful time of the year when employee performance bonuses are handed out. Despite his great numbers this year, our hero sits glumly at his desk. His manager walks by, gives him a glare, and to his complete surprise, drops an envelope on his desk. Cautiously opening it, he finds an all expenses paid cruise ticket through one of the bank’s major accounts. He’s floored, as he always thought his manager disliked him. Easy to assume given her open dislike of him. He stops by her office to formally put in his time off request for the cruise dates and thank her for the award. She harumphs and says that she practically gets a vacation too knowing he won’t be in the office.
On cruise day, he excitedly hands over his ticket and the porters take his luggage. After the kick-off event and introduction, guests will be led to their cabins and everything will be waiting for him. Having never taken a luxury cruise before, he’s very excited. The boat introduction is cheesy and the staff are too peppy with some forced puns, but it’s all new to him so he enjoys himself, and the open bar for all ticket holders. Stumbling back to his room, he sees a bag at the room’s desk, rinses his mouth to wash away the super sweet taste of the faux tropical drinks, and promptly passes out on top of the bed.
The next morning, he awakens groggy and with a slight hangover. It turns out a fancy room does wonders for recovering from a night partying. He watches the morning sun and the waves as the cruise ship sails on, before heading to the shower. After showering, his skin feels tingly and electric. Then, when drying off, his body hair all falls out. He panics, fearing an allergic reaction at the start of the trip, but on inspection in the mirror, he’s fine. His skin is a bit pink after the hot shower, but otherwise just silky smooth. He washes the shed hair down the drain and wraps himself in a fresh towel. Back in the sleeping area, he takes his clothes bag off the chair but it looks off. It’s the same general size and shape, but the pattern is different and the corners are leather, while the wheels metal instead of his plastic. He looks the bag over and finds a tag for “Ms. Gale Winchester”. Grumbling, he calls the cruise ship equivalent of the front desk, complaining about his lost luggage, already forgetting to ask for new soap. The staff apologize profusely and promise to find his luggage, but everybody is rather busy on the first day of the cruise so they won’t be able to search until tonight. After a pause, they tell him that Ms. Winchester didn’t sign in so she’s not actually on board. She’s a frequent passenger and ships a bag to the boat so she doesn’t have to bring luggage when flying to the cruise each time. Our lead rolls his eyes at the luxury of having that be a concern for yourself. The staff then tell him he’s free to take anything from the bag until his luggage is found, everything is brand new and fresh out of the packaging so it’s nice and clean. Just leave the improper luggage bag outside the door and they’ll collect it in the morning, then drop the new bag off by the time he wakes up.
Grumbling as he hangs up the phone, he does a survey of the clothes. Digging to find the least frilly underpants, he also uncovers some culottes he could pass off as oversized shorts and a plain blouse that would appear to be a dress shirt from a distance. Wanting to make the best of the trip, he tosses the mixed-up luggage bag into the hall, then sets out for breakfast and the day’s events on the ship.
Successfully going about the day without anybody catching on to his unwilling crossdressing, he makes it back to his room and is annoyed to not see his luggage waiting for him. He tosses the day’s clothes on a chair, snuggles into the plush bed, and watches TV as he drifts off to sleep.