Chapter 2 Dinner With The Boss

Winona's POV:

Before leaving, I paused to check my reflection in the mirror. Satisfied with how I looked, I grabbed my keys and headed out to the car, ready to meet Davidson.

I wore my favorite red top with a pair of jeans and slipped on some high heels. My hair was pulled back into a neat ponytail. I didn't want to overdress and send the wrong message, but I didn't want to look too casual either.

Getting to the restaurant didn't take long. Even though Davidson offered to pick me up, I told him we should just meet there. Anything else would have felt too much like a real date, and that wasn't the impression I wanted to give.

"Hello, ma'am, do you need a table?" the receptionist asked with a warm smile as soon as I walked in.

"Someone is already waiting for me. Mr. Davidson," I said, smiling.

"Of course, he let us know you'd be joining him. Right this way." She smiled.

"Thank you," I responded, matching her smile.

She led me through the main dining area to the back, where the booths were tucked away in a quieter, more private space. It had a VIP feel- exactly the kind of place Davidson would choose.

He was already there, sitting back with a glass of whiskey, scrolling through his phone, probably buried in work emails as usual.

"Good evening," I said, catching his attention with a smile.

As he looked my way, he took a long moment to study me from head to toe. His tongue slipped across his bottom lip, and it seemed he was completely unaware of the habit. When he finally settled his gaze on me, a slow smile appeared.

"Good evening, Winona, you look beautiful tonight," he said, his tone warm and gentle.

My cheeks turned warm at his compliment, and I gave him a small nod as I thanked him. He looked as handsome as ever. I had always seen him dressed in sharp suits, so it felt odd to find him in jeans and a simple shirt. After I thanked the receptionist, I walked into the booth and faced him.

"Would you like something to drink?" he asked.

"I'll just have water. I'm driving tonight, so I can't drink." I smiled.

"That's a smart choice," he said, letting out a laugh.

A server came by, took our drink orders, and brought them back a few minutes later before leaving the two of us alone. I could not ignore the uneasy feeling that crept in. Honestly, I had spent countless moments alone with him before. This time, though, felt completely different. We were not at work, and there was nothing professional about this meeting at all.

Davidson took a slow sip of his whiskey, then looked over at me.

"Do you have a dress for the Gala?" he asked.

"I have a few dresses, but nothing that would work for an event like this. I'll find something," I replied with a small smile.

"That's unnecessary. I'll pick one out and have it sent to you," he responded, grinning.

"You have no idea what size I wear or what style I like." I laughed.

"Size 38," he answered, giving me a confident wink.

How did he even know that?

"How do you know my size?" I asked, raising an eyebrow in curiosity.

"I can tell just by looking at you," he muttered, giving me a playful wink. "Honestly, your curves make it pretty easy to guess."

I laughed and shook my head, feeling my cheeks grow warm with embarrassment.

He must have taken the time to really notice my figure if he knew my size that easily. The idea left me both amused and a little uneasy. Had he actually been paying that much attention?

"Were you checking me out?" I asked, raising my brows and trying not to smile.

"Yes, of course. Come on, Winona. I might be your boss, but I'm still a man. I notice beautiful women, and I notice their bodies, just like anyone else would. But honestly, it's only been in the last two months, after Leona left," he added.

I shook my head and nervously bit my lower lip. His eyes were on me in a way that felt different from before. He ran his tongue over his lower lip and glanced away. I let out a quiet breath, feeling a bit unsettled since I was not used to this side of him. He was not joking like he always did. He was truly flirting with me, and I had no idea what to do about it.

"So, tell me, do you like red or black? And what about the length-would you rather wear something that hits at mid-thigh or do you want it to fall to your knees?" He leaned forward, shifting back to the topic of the dress.

"You really don't have to go out of your way. I'll pick out something myself. Buying a dress for me is not necessary," I answered, trying to sound light.

"Winona, don't make this difficult. You're doing me a favor by going with me. The least I can do is make sure you have something special to wear. Please, just answer the question for me." His voice took on a firmer edge.

I knew there was no point in trying to talk him out of this. I had known him long enough to realize that once he decided on something, he was not going to budge. I rolled my eyes and pouted a little, which only made him laugh.

"I'm still waiting for an answer, Winona," he said with a grin.

"Fine. I like red, and I'd rather have the dress at mid-thigh length. Thank you," I stammered, glancing at him.

"No need to thank me. This is just my way of showing how much I appreciate you helping me out," he remarked, still smiling. "Now, are you ready to order some food?"

I shook my head and picked up the menu, pretending to study it for a moment. After Davidson and I placed our orders with the waiter, we picked up the conversation again.

"If Leona asks about us, just tell her we've been seeing each other casually for a few weeks," he muttered, lowering his voice.

Seeing each other for a few weeks? I had thought this whole thing was just to get under her skin for one night.

"Why would you want me to say that? And what exactly do you mean by 'seeing each other casually'?" I asked, frowning.

"If we just say you're my date for the evening, she'll figure out the real reason I brought you. When I say 'seeing each other casually,' I mean going out together, hooking up-casual sex," he answered, almost too matter-of-factly.

Was this really just going to be a web of lies?

"Are you serious right now? What am I supposed to say if she flat out asks me? Should I just admit that you and I are sleeping together?" I blurted, instantly regretting the words as my face went hot.

"Exactly," he said, giving me a mischievous wink. "Who knew you had such a dirty mouth, Winona?" His voice carried a teasing, almost wicked edge.

"Oh, just be quiet. But fine, I'll play along." I laughed as I shook my head.

"Thank you," he replied, flashing me a wide grin.

Davidson went over all the details I needed for the Gala that weekend, making sure I understood exactly what to expect. He made it sound like it would actually be a fun night, and for a moment, I forgot about all the lying. Even so, I could not help but feel nervous. I had never gone to an event like this as a guest. Every time I attended something similar, it was always because I was working for him, making sure everything ran smoothly. The thought of just relaxing and having people wait on me felt unfamiliar. I also knew there would be people whispering and staring, because everyone would recognize exactly who I was.

How predictable.

The boss and the assistant.

Maybe agreeing to this had not been the best decision after all.

But it was too late for second thoughts, and backing out now would only make things worse.