All characters depicted are 18+.
"I have to go into the office now, Kaitlyn! And now, thanks to you, I don't have any suits!"
I was supposed to be starting my vacation when the call came in. One last piece of business before the holiday started. Kaitlyn was in charge of all the details and she'd insisted that I didn't bring anything business related! She thinks I work too hard.
Kaitlyn just smiled that high-wattage smile that normally made my knees get wobbly. Of course, today I was a little bit annoyed so this time it didn't work. "Stop smiling!", I said as angrily as I could muster. But given that I was in my underwear and my girlfriend was quite a bit taller than I was so I had to look up at her, it may have come across as cute instead of angry. She gave me those little 'Oh so cute' eyes. That only made me angrier!
"We only have a 24 hour window to match offers! And they said I have to be there in person, I can't do an e-signature!" As I stomped my little feet, again I didn't see the desired result as she visibly stifled a giggle. Then she spoke to me like an amused mother.
"Nicholas, honey, relax! I know you needed at least one suit for our vacation and I knew none of your old suits would be good, so I had one special made for you." It took a moment for what she had said to penetrate my panicked angry brain, but when it did, I exhaled so hard it was almost violent.
"Oh thank goodness, Kaitlyn. Why didn't you tell me you had a suit!? I was all worked up over nothing." She walked over to her closet, shaking her head before she pulled out a suit bag. She unzipped it. At first I was happy to see a suit, black and white by the look of it. But there was a flash of pink? I craned my neck to get a better look and saw it was like some kind of bodysuit? I wish I'd noticed the little smirk she had on her face as she was pulling it out... But I was just in a hurry to get dressed. Still I had to ask.
"What's that? A suit has a dress shirt, trousers and a jacket. That doesn't look like..." Kaitlyn opened up the back, bent over and held open the leg holes for me. "But that doesn't... That's not..." She shook the garment at me, the universal command every parent does to get their child to put a leg in and I just reflexively put a foot in one of the leg holes. Once it was in, I put the other leg in... And then suddenly I was off the floor, in the air!
Kaitlyn had immediately yanked me off the floor, pulling the 'pants' up over my legs. In shock I was lowered to the floor, and while I was still off balance, Kaitlyn was putting my arms into the sleeves like you would when you were dressing a toddler. She was already buttoning up the back before I started to regain my senses. I realized I was wearing some kind of skin-tight leotard with arms and legs. Oh wait, I think those are called unitards? Kaitlyn began explaining as she continued doing up the buttons. There seemed to be a lot of buttons.
"A dress shirt and trousers? Then you're always worrying about your shirt becoming untucked! Attach them and you never have to worry", Kaitlyn explained. What I was processing was that it was so snug it was really pulling me in, acting almost as some kind of shape-wear and giving me a tight little waist. But what was really concerning me was that there appeared to be some frills attached to the unitard. I reached down to grab the frill at my waist and give it a little tug. I realized that despite this material seeming light, it was actually a lot tougher than it looked. I wouldn't have to worry about tearing these clothes. But I looked at Kaitlyn, holding the frill with a questioning look on my face. "What the...", I started. My girlfriend just gave me a look like it was obvious.
"Nikki, you know I wouldn't send you to work in an outfit that didn't have a little flair! You know I want my boyfriend to be the most cutest, most adorable head-turner in the room!" Kaitlyn held open a suit jacket and I slid my arms in. Like the unitard, this jacket was extremely taunt, but I had to admit it did look the part... If you overlooked the frills, bows and pink accents! She tapped my chin to get me to look up, and I did as she wrapped something around my neck. I had assumed some kind of necktie, but it wrapped all the way around my neck and she was lacing it up behind my back? I patiently stared up until she was done, even though I was getting more and more worried. I reached up to feel some kind of posture collar around my neck forcing me to hold my head high? This certainly wasn't the necktie I was expecting!
"This is a joke, right?", I said thinking she was going to laugh then pull out my real suit. But instead she pulled out a pair of shoes. I didn't really get a good look at them, but she guided me forward to step into them. Suddenly I was a good half a foot higher in the air. I thought I was stepping into dress shoes, but these were platform high heels. "High heels?!", I said with a little squeak of disbelief. "I can't go into the office with high heels!"
"Nikki, you are always complaining you wish you were taller. Well, there you go, your wish has come true. And you're complaining?", she said, now a little annoyed. As I tried to process what she'd just said, Kaitlyn turned me to face her. Even though I was a lot taller on the heels, I was still looking up at her as she finger combed my hair back and placed what felt like a hairband on my head. "There! Now you are perfect. You go into work, you sign your silly little contracts and then you hurry home so we can go on vacation!". She was all earnest now. And with that, she turned and left the room. I watched her walk away. I was going to say something but seeing her feminine stride and her... umm... Assets on display, I forgot my protests and remembered why I was so infatuated with that woman. She was perfection. I could only stare as she strode off. That's my girlfriend!
Once I remembered where I was and what I had to do, I knew I had to get a look at myself in the mirror. I started to walk forward, but I was so very awkward on the platform heels I had to step carefully. I tried to kick the shoes off, but it didn't budge at all. Weird because I only stepped into them but now they felt strapped on? It was only a short distance to the mirror so I was soon there.
Looking into the mirror, I had a shock. I was wearing the girliest 'suit', I'd ever seen! It was some kind of frilly unitard, decorated with hearts and frills and ribbons. Perched on those platform heels, I would be a laughing-stock! But what really stood out was the feminine little tiara perfectly balanced on my head! A TIARA?! No, no, that was not happening. I reached up to pull it off my head. To my surprise, it felt stuck. I applied a little more force. Nothing. Finally I reached up with both hands and did my best to rip it off. It didn't hurt... But it felt like the tiara was actually part of my head. It was like trying to pull your arm off your shoulder. As ridiculously as I was dressed, this was something way weirder. This was something I just couldn't compute.
"Kaitlyn... Why can't I take this tiara off?!", I said with just a tinge of alarm.
---
Nicholas
I should introduce myself. My name is Nicholas Windsor. Nick to my friends. And before you ask, yes, my father was Alec Windsor founder of Prestige Global. Like my father, I'm a bit on the smaller side. Standing at 5'1"/155cm and weighing just under 100 pounds/45kg even at 18 years old, I've always been the smallest kid in every class I've been in. My fair-skinned complexion complements my somewhat longish brownish hair and pale green eyes. Growing up in wealth, I've had the privilege of a life filled with opportunities and luxury. While I was lucky being born well-off, I've been far less lucky in the realm of love. Not that I had a lot of opportunity. I went to all-boy private schools growing up, so I didn't really get to meet many girls. And I just didn't know how to approach girls directly myself. I was far too scared and shy. I've always wondered if my mother, she passed away when I was an infant, would've been able to give me advice on the romance front. My dad certainly couldn't. His life was nothing but work. So you can see I was never close with my parents. I never had the opportunity.
I will never forget the day I found out my father had passed away. I woke to the sound of my phone buzzing incessantly on the bedside table. Groggy and disoriented, I fumbled for it, squinting at the bright screen. The caller ID flashed "Dad." My heart sank even before I answered.
"Nicholas, it's Javon," came the deep voice on the other end. My father's longtime assistant rarely called directly unless it was urgent. "There's been an accident. Mr. Windsor... your father, Alec Windsor, he didn't make it."
The words hit me like a freight train. My father, the formidable Alec Windsor, head of Prestige Global, gone in a helicopter crash. My mind raced, struggling to comprehend the weight of the news. I was barely eighteen, just planning to start college, and suddenly thrust into a world of corporate chaos. Within hours, reality slammed into me harder than I could have imagined. Lawyers, executives, and condolences poured in. I was now the heir apparent, expected to manage a multinational corporation when I could barely manage my own homework. Javon became my lifeline in those tumultuous days.
Javon
Javon and I couldn't be more different. Towering over me at well over six feet, his imposing frame and deep voice were a stark contrast to my own slight stature and quiet demeanor. I was slender, he was thick and muscular. I had pale skin and hair past my ears. Javon had skin of deep umber with a meticulously shaved head. Yet despite our differences, Javon was my guide through the labyrinth of board meetings, financial reports, and endless decisions. Prestige Global was my father's life's work, and now it rested on my shoulders. The pressure was suffocating. Meetings blurred into late nights poring over documents I barely understood. Every decision felt monumental, every mistake potentially catastrophic. Javon's presence was a reassuring constant. He navigated the corporate world with ease, shielding me from the sharks circling for any sign of weakness. His calm demeanor and unwavering support steadied my nerves, reminding me that I wasn't completely alone in this new, daunting role.
Now while Javon was invaluable in those first weeks, as I began to understand the company better and see my father's vision, Javon and I weren't quite on the same page. As the weeks turned into months since my father's passing, tensions began to simmer beneath the surface as we started to disagree. The weight of responsibility hung heavy on my shoulders, and with it came a growing realization. I had ideas about how to lead the company forward, ideas that differed sharply from those of Javon Brooks, my father's trusted assistant.
Javon, with his experience and a pragmatic approach honed by years at my father's side, advocated for continuity. He believed in maintaining the status quo, focusing on steady growth and solidifying the company's current market positions. His arguments were grounded in realism and caution, citing historical data and market trends to support his stance.
On the other hand, I saw an opportunity for innovation. Fresh into this world of business, I was filled with youthful optimism and bold visions of transforming Prestige Global into a leader of technological advancement and sustainability. I envisioned bold investments in green energy projects, aggressive expansion into emerging markets, and a complete overhaul of our digital infrastructure. To me, these changes were not just necessary but imperative for staying ahead in a rapidly evolving global landscape.
The first real clash between Javon and me came to a head during a strategy meeting. Voices rose, tempered arguments turning into passionate debates. Javon's deep voice reverberated through the conference room as he argued for caution and incremental progress. I struggled to keep my high-pitched squeaky voice under control, trying to project my determination without sounding like a whiny kid.
"Javon, the world is changing. We need to adapt, to innovate. Our competitors are moving forward, and if we don't take risks now, we risk falling behind irreversibly", I said, leaning over the boardroom table. I eyed Javon levelly, realizing that with me leaning and him seated, we were about the same height.
"Nicholas, we can't afford to gamble with the company's stability," he insisted, his tone firm but not unkind. "Your father built this empire on solid foundations. We must respect that legacy." Javon visibly stopped himself and took a deep breath. His irritation disappeared. "Look, I know you are about to take a vacation with your new girlfriend. Maybe some time off would be good for both of us. Why don't we table this, reconvene when you return and see what a break does for our views."
I knew there was no way I was going to change my mind on this matter. But I did smile at the thought of my upcoming first vacation with Kaitlyn. Who was Kaitlyn? My new girlfriend! I know what you're thinking... "I thought you said you'd never had a girlfriend?" Kaitlyn was my first! It's amazing what can happen when you're suddenly in charge of a multinational corporation! As I'd mentioned, my biggest issue was being too shy (and a little scared) to approach women. Kaitlyn approached me! I smiled at the memory. But more on how we met later.
"All right, Javon. We'll pick this up when I get back," my mood now much lighter. The tension was immediately defused, and Javon was back to his less stern, more relaxed self.
"I understand you're going to Lolligag Island?" Javon asked. I nodded in the affirmative and asked him if he'd been. Javon smiled with those perfect white teeth of his, clearly enjoying a memory. "I've been there several times. It's one of my favorite places. Who knows, I might swing by and visit while you're out there with Kaitlyn." He paused, suddenly serious. "But I promise, no talking business while we're there". Then he broke into laughter like he'd told a joke. I smiled more out of reflex than finding it funny. I'd had to deal with the funeral, taking over the company and starting a relationship with Kaitlyn just in the last year... It had been a long time since I'd had a break and I was so looking forward to this one. Especially since Kaitlyn had hinted that Lolligag island would be where I'd finally say good-bye to my virginity!