Hours later. Back at the hotel
Olivia’s POV
"Wow, Oliver, when did you start wearing designers? These clothes are a far cry from what I’m used to seeing you wear," Maxwell said as he went through my suitcase, looking for the perfect clothes for me for the dinner with Diane.
I gritted my teeth in anger as I watched him rifle through my belongings. "Sir, you don’t have to help me with an outfit. I can pick an outfit myself."
"Oh, Hopton. We both know you have zero fashion sense. Have you looked at yourself after dressing up? I’ve never seen you in fitted clothes. They’re always all loose and baggy."
"I’m not complaining, sir. I love my comfort."
"Not when you’re here with me. You’re not going to embarrass me with your poor fashion sense."
I took a deep breath, trying to stay calm. "I don’t... I don’t have poor fashion sense, Mr. Wellington." The words came out strained as I tried to curb my anger.
"Yes, you do."
As I watched him dig deeper into my suitcase, my heart began racing - not just from anger, but from pure terror. What if he discovered my feminine items hidden beneath all those carefully placed suits? My chest binder, the makeup I used to contour my face more masculine, the...
Just when his hands were going down... down... down... I jumped forward and grabbed his wrists.
"That’s enough, sir!" I stopped him, perhaps a bit too forcefully.
He stared at my hands wrapped around his wrists, then looked back at me with curious eyes. "Your hands are so soft, Oliver. What hand-care products do you use?"
I immediately snatched my hands back, hiding them behind my back as if they’d betrayed some terrible secret. "Nothing, sir."
"It’s okay if you don’t want to share," he said with an amused smile, turning back to my clothes. "But seriously, they’re softer than most women’s hands. You sure you’re not secretly getting manicures?"
My face burned. "I’m sure."
Maxwell chuckled and continued his inspection, but mercifully stayed in the upper layers of clothing. Then he stopped, carefully folding my clothes back and looking thoughtful.
"You know what? I think I have the perfect outfit for you."
He moved away from my suitcase - thank God - and headed toward his own luggage. I kept protesting: "It’s fine, sir. Really, it’s fine, sir." But at the same time, I found myself craning my neck to see what kind of outfit he had in mind.
Maxwell opened his suitcase and pulled out a pair of dark jeans and an expensive-looking button-down long sleeve shirt in deep blue.
I stared at him, mouth agape. "You want me to wear jeans?"
"Yes. Diane isn’t the type to go for five-star hotel restaurants. You both would probably have a casual dinner and maybe a walk in the park while eating ice cream."
"How do you know what she likes, sir?" I asked suspiciously.
"I know Diane," he said simply, but something in his tone made me think there was more to that story.
"I really don’t want to do this, sir. My girlfriend will be pissed if she finds out I’m going on a dinner date with another woman."
Maxwell looked up at me with a glint in his eyes. "What happens in Chicago stays in Chicago, Oliver."
I grabbed the clothes from him, holding them against my chest. "Fine. I’ll change."
As I headed toward the bathroom, Maxwell caught my arm. "You can change right here. We’re both men."
My blood turned to ice. "I... I prefer privacy when changing," I stammered, yanking my arm away and practically sprinting toward the bathroom.
"Modest, aren’t we?" Maxwell called after me with amusement. "You’re full of surprises, Hopton!"
I slammed the bathroom door behind me and leaned against it, my heart pounding so hard. This was getting more dangerous by the minute. I quickly began changing, making sure my chest binder was secure and my disguise was still intact.
The jeans were... different. More fitted than anything I usually wore as Oliver, and it actually brought out the curves of my bum a bit. Thankfully, the shirt was long and covered it perfectly. I caught myself in the mirror, and I almost looked very attractive.
Just then, I noticed something behind my Jean pocket. I pulled it out and gasped. It was a wallet, heavy with cash inside it. Maxwell probably slipped it in when I wasn’t looking.
Well, it’s good he thought of funding this date. After all it was his idea, and u have no money.
Just as I was adjusting the collar of my shirt and checking my appearance one final time, Maxwell knocked on the door.
"Oliver! Diane is here!"
Shit.
I took a deep breath and opened the bathroom door.
And there she was.
Diane stood in the hotel room looking absolutely stunning in a simple blue dress, her hair styled in soft waves. But what made my stomach drop to my feet was the way she was looking at me - really looking at me, like she couldn’t wait to eat me raw.
"Well, well," Maxwell said with satisfaction, "don’t you two make a handsome couple!"
Diane’s lips curved into a smile, "Hello, Oliver. It’s so nice seeing you out of a suit."
Her voice sounded casual, but her eyes suggested that she would prefer seeing me out of any clothes and naked.
"It’s nice seeing you out of a suit as well, Diane." I managed to say, not wanting to look timid in front of her.
"Oh, come now, Oliver," Maxwell chided, "you can do better than that! Look at this woman... she’s absolutely gorgeous! At least tell her she looks beautiful."
My face burned with embarrassment. "You look... very nice," I managed.
Maxwell threw his hands up in exasperation. "Very nice? VERY NICE? Oliver, this is exactly why you have bad taste in women. ’Very nice’ is what you say about a decent sandwich, not about a beautiful woman!"
Diane laughed so hard, she had to hold on to Maxwell for balance. "It’s alright, Max. I think Oliver is just a bit reserved. Some men are like that, you know."
"Reserved?" Maxwell scoffed. "I wouldn’t say that,’ but reserved works too."
This was already a disaster, and we hadn’t even left the hotel room yet.