Assisting His Assistant

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Chapter 27



For the past two days I heard nothing but this ‘date’, Harper would chime in every so often in between her work and duties. Asking me incessant questions about what she should do and wear.

I was pleased for her finding a date she was excited about. But fuck! I agreed I’d help her gain a love life, but this was crazy. I didn’t sign up for this shit!

That’s all she fucking talks about now.

It was late in the day, and I had just finalized a deal with the most prestige financial institutions in Chicago. The investment strategies I presented at the conference in Miami paid off. It paid off fucking excellent. They chose my proposals, and I was flying on the fucking moon, feeling ecstatic. I was proud I had landed such a huge deal for Bolt Investment. Hoping it would finally please my father and prove to him not only can I do this shit and I can do it well!

A small knock on my door echoed. I looked up to see Harper peeping through, her chocolate brown hair loosely braided to the side. She looked bright with her light pink top and grey pencil skirt. My eyes involuntarily glazed over her legs. She had a new shaped glasses, that fitted her face perfectly. I liked her with her glasses on.

“One more question?” She said with her index finger pointed up. She slipped through the doors and closed it as if we were on a secret mission or something. The corner of my mouth twitched up.

“Sure Harper, why not.” I agreed. The working day almost came to an end, so things slowed down at the office. We both didn’t have much to do. Especially Harper, since her head was zoned in on her date with the IT guy tonight.

“How many glasses of wine should I drink? What’s the cut off limit.” She asked. “Or maybe I shouldn’t drink at all, just in case I confess too much info. I want him to think I’m responsible.”

“Yes, guys wants responsible.” I mocked and blew out a breath. “Harper, no good story started out with a salad. You can have a drink, just don’t get drunk. Unless you want him to carry you to your apartment and get naked with him.”

She gasped.

I smirked, pleased with her reaction.

“I don’t want to get naked with him the first night.” She said, cocking her head up.

“That’s good, I’m glad to hear it.” I agreed, surprising myself.

She bit her bottom lip, that was shaded a rosy pink and fiddled with a charm on her wrist.

“What about if things get heavy and he wants sex?” Harper asked.

“Who cares what he wants! It’s what you would want.” I scolded. “A man hopes to get sex at the end of the night, the woman already knows it.” I smoothly replied.

“True.” She agreed. “How long should I wait do you think?”

I narrowed my eyes. I had to think about this one. “Usually the third date is good, so at least it won’t be a hit it and quit it situation.”

She nodded in thought, her brows creased. What’s going on in her head when it comes to sex with this guy? I shuddered at the thought and didn’t sit well with me.

“Or... in your situation, I advise 3 months. You know the 90-day rule and all.” I said and averted my eyes to some documents on my desk.

Her eyes snapped to me, the look of disappointment. “Why so long?”

I sighed, suddenly feeling slightly awkward. “Get to know the guy first. You lasted 5 years without sex, I think you can survive another 3 months.”

She crinkled her nose. “I guess, maybe.” She said unsure.

I gave a firm nod in approval.

“Obviously, there might be a kiss? If the evening is going good.” She sang smugly. “I least I can look forward to that.”

I leaned over my desk and looked over some contracts. My head turned to Harper still daydreaming about her damn kiss.

“Kissing...” I grimaced.

She tilted her head. “Oh please, you kiss your ‘models’ all the time, I’ve seen it.”

I scowled at the thought. “I’m not a fan of the act.”

“Why not?” She asked confused.

“It’s too intimate.” I explained. “So is spooning with a woman and sleeping over. No thank you. I’ll rather avoid it all together. It’s my rules I’ll never break.”

Harper pulled her mouth. “Ugh, you’re hopeless, honestly.” She shook her head.

I chuckled and shrugged. “You break the rules, and next thing you in a committed relationship. I told you Harper, I just fuck!”

She closed her mouth taken slightly aback at my frankness. I didn’t even mean to be that blunt.

“Do you even have sexual chemistry with the guy?” I asked. “How do you know if he even wanted to kiss?”

She frowned. “I’m sure he would. I don’t know. I-I- we’ll just see where the evening takes us.”

I smirked. “Do you know how to flirt Harper?”

Harper popped her eyes briefly open. “Flirt?” She repeated, holding her hands on her hips awkwardly. “Yeah! Sure, I know how to flirt.”

“Oh? Why don’t you show me? I’ll let you know if it works.” I suggested. Her nervous laughter amusing me.

I sat against the table, my arms folded as I listened intently to what she was about to do.

She seemed uncomfortable. “Right now? Here in front of you?” She asked hesitantly.

I nodded in earnest and smirked. “What better way to practice than with me Harper. Get you ready for the game you know. I’m the king of flirting. Let me see what you got.”

I gave her a cheeky wink. But my words and action seemed to unnerve her more. She was pulling stiff again and her eyes seemed to look like a deer caught in headlights.

Harper cleared her throat and stared at something on the office carpet. Her dark brown eyes snapped to mine. “Okay! Let’s do this.”

The corner of my mouth hiked. “Excellent! Pretend I’m the I.T. guy.”

Harper rolled her eyes. “His name is Jake.”

“Sure, whatever.” I said. “We’re standing in front of your apartment building.” She nodded. “The evening went well, and he says – I really enjoyed my evening with you, I would like to do it again. What do you say?”

My eyes locked onto hers intently as she gulped.

“Well, I had a great time with you too Jake.” She said plainly.

I pulled my mouth, not impressed. “What’s running through your mind?” I asked playing the ‘Jake’ part.

“Your cute butt.” Harper struggled, while wiggling her eyebrows. “I just want to binge-watch it all day, like Netflix!” She blurted.

My eyes popped and I stifled a laugh. What the fuck was that!?

I was momentarily lost for words. “I said flirt, not talk dirty. If that was even dirty talk? You failed horribly.”

Harper breathed a dejected sighed and smacked a palm on her forehead.

I rolled my eyes. “Fuck Harper, you over thinking this as usual. You can’t take notes on things like this okay. The rules of flirting are simple. Just use friendly body language, like giving him a coy smile or a playful hair flip. Touch his arm lightly and give compliments. It would show that you’re interested.”

I knew this well, how many flirtatious smiles, winks and hair flipping had I seen. And that was just on a bad day.

She nodded, her arm reaching for the notepad she placed on my desk.

“Don’t you dare take notes on that.”

“uh-uh, I wasn’t planning to.” She lied.

A thought snapped into my mind. “Harper, when last did you even kiss a guy?” I asked, afraid of her answer.

She blew out a hot breath. “About 3 years ago, I think.”

Fuck me, why wasn’t I surprised. “Of cause.” I said sarcastically.

The poor girl was going to be lost at tonight’s date. It was my moral duty to prepare her.

I came closer to Harper. “You know what, I’m in a giving and helping mood.” I said in a low tone. “Why don’t you sharpen your skills and break the draught with me?”

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