A Boss with Benefits

A Boss with Benefits

My virtual assistant is going to find out who’s boss… I own the corporation, but I can’t get decent help… apart from Olivia. She’s been my backup assistant for years, working remotely in the middle of nowhere. I’ll pay her double, give her days off, anything to meet this big deadline. I just don’t need another romantic distraction. I’ve never met Olivia, but I have a feeling that she’s a middle-aged spinster with a dozen cats. Perfect for keeping me out of trouble. There’ll definitely be no temptation. Then Olivia walks into my office, and she’s an emerald-eyed bombshell. I’m in big trouble.

Tags:

Age Rating:18+BillionaireEroticaRomanceBxGFriends To LoversUnexpected RomanceOffice RomanceSecond ChanceBad BoyBossGood GirlWealthySexyRomanticHumorous

Word Count: 32,198

Rating: 4.8

Likes: 20

Status: Completed

Chapter 1 — Ross

Word Count: 2,947

“What do you fucking want?” I barked as my sexy Kansan secretary, Scarlett, entered my office. I shouldn’t have been so crude, and I shouldn’t have shouted at her. But I was tired and out of patience. We New Yorkers had a way of speaking that at times appeared to be crude to the rest of the country, but for us it was natural.

Either way, Scarlett was my secretary, not my wife. I’d made the mistake of fucking her once — and I’d been repeating the mistake over the course of the week.

A man should always learn from his mistakes.

Monday, I should have put an end to it.

Tuesday was too tempting.

Wednesday, it was getting kind of silly… and all the days after that were nothing but plain stupidity and I was paying the price, big time.

Usually, when a woman sees me with a whip in my playroom they tell me to be gentle or they see me with a paddle and demand that I don’t smack them too hard.

Not Scarlett, she was every man’s fantasy in the playroom, boardroom, office, parking lot, and in the elevator, but not in my bedroom. She became too attached from the moment I made the mistake of fucking her in there.

That was when she showed her true colors and none of them were pretty. She killed the fun on Thursday when she asked me to hold her in my bed. That was something that I never do, but while I was carrying her from the playroom to the living room, she asked to lie down in my bed, just for a little while. She’d asked with sweet eyes full of longing and I’d stupidly caved. Somehow, she managed to stay the night. Ladies never spend the night at my place, so I should have called it off right then, but I didn’t. I was a horny fool and after that night I decided that she wouldn’t stay over at my place anymore.

I’d go to her place, fuck her, and as soon as she was sleeping, I’d be out of the door. I always managed to tire her out, so it wasn’t an issue sneaking out.

Big mistake.

I was now stuck with a woman who was…clinging. A shiver of disgust raced down my spine as soon as I thought the word. I glanced up at her as she approached me in my office, a small tear already starting to form in the corner of her eye.

“I just feel as if I’m being used.” She sniffled a little as she got closer to me and I felt my gut twist in apprehension. Here we go…

“Like you just want me for my body and nothing else.” She started to pout, and I could see that she was up to something, because she left the door wide open. We were in my office and she was talking about matters of the heart. Only for me they’re matters of the dick and I could tell that she was up to something. This wasn’t going to go down well, not by a long shot. I knew that she wanted everyone outside to hear. I didn’t need the staff to know that I’d done the same thing.

Again.

The same fucking stupid thing that I’d been warned about too many times already by HR, the CFO, my parents, my friends and even my housekeeper and I still went and did it.

I stood up quickly and closed the door. Then I turned to comfort her, trying to figure out a way to get out of this giant mess that I managed to create, yet again!

Maybe, if she stopped working as my secretary, the huge fuck up that would go away. I shot a speculative glance at her, stalled for time really, then turned away as if thinking over what she had just said. I was trying to come up with a solution, quickly. I could fire her, tell her to get out and not come back, but that could backfire.

If I didn’t let her down gently then she could go to HR and tell them that I couldn’t keep my dick in my pants. The employment agency would be on my case and would shut the company’s account down for sexual harassment and I’d possibly have a lawsuit on my hands. Another employment agency account being terminated, because of my inability to keep my dick in my pants. I needed to think quickly on my feet; I was a fucking billionaire. I was used to doing it all day long. This was no different from a deal, one that I had to crack, or it would break me.

“You need to think about what all this means,” I said.

“What?”

She was right, where was I going with this?

My palms were wet as I tried to find a solution, my voice was raspy from running to close the door and back to her, and my head was fucking spinning out of control. I had an important meeting in twenty minutes. When did life become so fucking complicated and when did I lose control?

What had driven me to make such a stupid mistake again?

“I know you think that I don’t appreciate you.” I stared into her sea-blue eyes, my face a mask of contrition, false contrition, but she didn’t need to know that. I’d play her game, for now, I decided, until after my meeting. Then, I would have time to think about this, and come up with a plan. “But I do. You’re beautiful.”

I stroked her long fair hair, thinking that blonds really do have more fun. Once again, I was distracted as my hands moved to her breasts. Those big thick melons that could feed me for a fucking month. They were so damn juicy that I found myself opening up her shirt. Not just fucking opening it, but ripping it open and popping those buttons as my mouth watered and my dick wanted to fuck.

“You’re doing it again. Just looking at my body and wanting to take me.”

My left eyebrow came down and my lips pursed in confusion.

Pardon?

She’d never complained about it before.

My eyes traveled down to the plain white cotton blouse that covered her ponderous globes. Boning, hmm, yes, boning was exactly what I wanted to do right now.

“Shit, your tits, I’ve never had a woman with tits as big as yours…”

I was down to her bra, but it was like she had scaffolding or something keeping them back. Normally she would wear a sexy bra. Not today. She had some contraption that should be illegal for anyone under a hundred.

She pushed me away, but I was like a hungry wolf ready for a feeding frenzy. Shit, she was ready to feed me, whether she liked it or not.

“Don’t do that,” I growled as I moved closer to her.

“See? You only want me for my body. I asked you one question. Answer me, Ross Hamilton!”

She had her hands on her hips and she was not messing around. I had a feeling that my dick was on hold even if it was pointing in her direction.

“Do you love me?”

What?

We’d only be fucking for a week, not a year. And even if I managed to keep interest in her that long…love? Not in the cards for me. Never had been, and it wasn't about to start now.

My cock, which had been fully erect, went down as if a gust of wind had pulled it down and I knew that I had to end this beautiful relationship, big breasts or not. It was too dramatic, even for me.

My sex drive had been killed in the last ten seconds. My heart was racing out of control, debating whether or not to lie, but my mouth did something completely different.

It opened and shut like the blinds in my office did whenever I had company that was half-naked, just like her. Whenever I wanted people to know what I was up to, I would leave them open so that I could spy on them too. When they were closed, that was when it was none of their fucking business. Like now.

I took a deep breath and controlled all my emotions, ensuring that my next words would make everything that had gone wrong go away in the next fifteen minutes, so I could have a few minutes to prepare for the next meeting.

Her eyes were wide open, waiting for my response.

Okay, here went nothing. I was going to say it for the first time in my life. Those three words would stop me from being sued and having to deal with all sorts of shit that I hated doing in public.

I was a billionaire. I had built my company from scratch. I could fucking do this.

She moved closer to me as I smiled. I was about to say the words that she fucking wanted to hear.

Even if it was a lie, she was a woman. She didn’t care about the truth; she just wanted to hear those three little words.

I was going to do this.

I fucking needed to.

My mouth opened one time. I was so close to her that her tits were rubbing on my chest. My dick was on board with the situation again and everything was going according to plan.

“Yes?” said Scarlett, nodding her head like a bobbing doll.

And then I just blurted it out. “No.”

My dick screamed “You fool!” but my racing heart went back to its regular rhythm. The headache that I had was now passing. She lifted her hand and slapped me across the face. She didn’t even bother to button up her shirt. She left my door wide open for everyone to see that I was about to seduce her; that I really couldn’t keep my dick in my pants. I slumped down on my desk, thinking that despite everything, it was for the best. It was the right thing to do.

There was just one problem.

I never did the right thing when it came to matters of the heart.

I must be getting old—or fucking soft—and it sucked!

I patted my pants, where my dick was still half hard, reassuring it that everything was going to be alright.

I whispered, “Down, boy.” I was going to have so many fucking cold showers from now on, it was fucking frightening.

There was only one option, one thing that I could do to get out of this mess, I thought as I closed the door and ignored the looks I was getting. Scarlett was still outside, shouting about me being a liar and trying to get as much attention as possible.

Fuck, she was dramatic!

Then again, that’s what I liked about her in the bedroom. She nearly screamed my damn chandelier down, because she had a set of lungs on her and she should have been an opera singer or a Playboy bunny. Either way, she would have succeeded at both professions.

I soon realized things didn’t need to be that bad. I just needed to think outside the box and see this whole fuckup from a different perspective. I had a lightbulb moment, so I rushed to my desk and I started typing. The words started flowing as my idea soon became a new reality on my screen.

'Dear Virtual Assistant...'

Wait. I couldn’t just call her Virtual Assistant, could I? What the fuck was my VAs name? I realized that I had no clue what her fucking name was, at all. Where was it? Scarlett was really bad at her job as my secretary and the only reason I’d kept her around was to suck my dick and to keep HR happy; both were important to me. She was good at giving head and screaming at the top of her lungs. And being fucking hot to look at, especially when she came to work with no panties.

Shit, I was getting distracted. I needed to start typing fast to get this show on the road before the meeting. I flicked through the emails that Scarlett forwarded to me from her.

Where were those emails? I asked myself as I started to lose patience and already, I’d thrown in the towel, certain that I’d never find one in time, but after carefully looking I found one.

Bingo!

Her name was Olivia. So, I deleted the 'Dear Virtual Assistant' greeting and sent a more personal email. I didn’t want to scare her over email, I just needed her to come into the office.

Subject: Employment in the Office

Dear Olivia, I am sorry to send this at such short notice.

I need you to stop being a virtual assistant and start working in the office for just six weeks. That’s all I require, it’s just that Scarlett is temporarily unavailable, and I really need your assistance in the office.

I would appreciate it if you could be in the office by nine tomorrow morning, so that we can get started.

Ross Hamilton, CEO.

Hamilton Investments I wasn’t expecting her to reply straight away. Even Scarlett never did that, and she sat just outside my office. I was surprised when, within two minutes of me pressing the send button, she had already replied to my message. She was that good! Olivia had been with the company for over two years but had never stepped foot inside this building. I thought it was strange, the fact that she had never come in, and the fact that I even needed her when I paid someone else to be my secretary, but HR had suggested a VA was just what I needed, so I hired one.

Even some of the ladies that worked from home full-time made an appearance in the office once in a while, especially when it came to the office party, but Olivia? I’d never set eyes on her before. I didn't know if that was a good or bad thing and right now, I didn’t care. I had to find a replacement and the next six weeks would be enough to seal the deal and make sure that HR didn’t get on my case about not only losing the contract with the employment agency, but possibly having a sexual harassment law suit on our hands, because of this situation with Scarlett.

Employees would complain about working all day long, but the moment they were given something for free, like at the company Christmas party, they didn’t hesitate to come to the office - free food and drink, with music. No one passed on that opportunity, especially in this office.

Re: Employment not in the Office.

Dear Mr. Hamilton Thank you very much for your e-mail. I must say that I was surprised to receive an e-mail from you and not Scarlett, because I think that she’s been your most long-standing assistant to date. As you well know, I work not only for your department, but also for the whole company.

Do you mind if I assess my duties for the week, prior to committing to coming into the office tomorrow?

Regards, Olivia Watson.

Virtual Assistant, Hamilton Investments.

I re-read her email and stared at it blankly. She must have thought that I was giving her an option to come in tomorrow or even the next day. There was no fucking option, it wasn’t a request. She needed to come to the office tomorrow. I was the CEO, whoever else she had work for, they needed to wait. I didn’t care, it wasn’t my problem. I only had one issue and that was I needed a new secretary in the office tomorrow!

Subject: Not an Option!

Olivia, Be in my office at 7am tomorrow.

Ross.

I didn’t wait for a response. It wasn’t a debate: she had to be in my office tomorrow morning, or she would be out of a job. I didn’t know her situation and I had to get to this meeting. They say that time flies when you’re having fun; I never understood the saying, because it never seemed to fly when I needed it to. I buzzed for HR to pass on the details, confident that tomorrow I would have a secretary by my side. Judging by Olivia’s lack of enthusiasm for the change of arrangements, I was confident that it would be all work and no play. She had to be a hermit or something. I had been messing around with girls on the playground instead of getting in touch with real women. Experienced ones that were in control of their emotions. I was thirty-five and it was time that I started acting my age and only go for women my own age, after all, not all of them wanted a ring on their finger after the first week.

It was a good thing that a hermit like Olivia, with probably one too many cats, was coming into the office. One thing was for sure, it was unlikely that I would be tempted by her, which meant for once I’d keep my cock in my pants. She had to be a spinster, otherwise she would at least make an appearance at the office party. Instead, she liked to stay at home, but her time working from home was over for the next six weeks and she’d better get used to it.

Chapter 2 — Olivia

Word Count: 1,435

My finger hovered over the keyboard, ready to tell him that I couldn’t come to the office. The point of being a virtual assistant was to stay at home. What didn’t he understand about that?

I had to look after my mom, and I couldn’t afford to hire a nurse to help her. The company paid me well, but they didn’t pay that well that I could afford a nurse. I hummed over the idea of asking for a raise over the next few weeks, so I could pay for one.

That could be an option.

Scarlett knew about my situation, which led me to work more hours than if I was present in an office. The time that I wasn’t helping my mom, I was working. I used to be a top executive, but the moment Mom started suffering from dementia, I started working from home. At first it was fine getting a nurse to look after her part-time, because she would have good and bad days, and I could be in the house and get a lot more done during office hours but lately she’d been getting worse. So, bad that the strain of working and little sleep was starting to get to me.

Since I’d been at home, she’d spent most of her time with me in the room. Sometimes she read the same page over and over again with little concentration. Other times, reading became too much for her and she would sit like a zombie in front of the TV.

It had been nearly three years of working for Hamilton Investments and I didn’t want to change it. I used to have other clients, and it was easy to juggle them around because I could get so much work done. I could work for the other clients at night or in the early hours of the morning such as overseas clients, but, lately with Mom's added confusion, I’d resorted to sticking to the one client, Hamilton Investments.

“I need to tell him the truth. Maybe he’ll be reasonable?” I suggested to my laptop, psyching myself up to pick up the phone and just have a conversation with him. Emails were so impersonal, and he was human after all, he would understand if I spoke to him.

Mom shouted out, “Who, dear?”

“My boss.”

She shook her head. “Who are you?”

I was just about to answer her, when I could see the confusion in her eyes. The confusion that appeared from time to time whenever she hadn’t taken her pills.

“Shit!” I shouted as I headed to the kitchen. One thing about Mom, especially when she was this confused, was that she wouldn’t get angry. If anything, she would cry about her confusion.

“Who are you?” she demanded, and as I stood up, I turned and saw her. She hadn’t been this bad for a while.

I was disappointed because we’d had a good day yesterday, and it made me think that maybe the doctors were wrong. They warned me that she would deteriorate, and I refused to hear the words from their mouths. I’d sought different opinions, but they’d all told me the same thing. I’d read online about others that had found relief through diet and had managed to turn things around for themselves. Sure, they hadn’t been cured but their diet and medication had slowed down the process and I thought that if I put in the time and effort then, the same thing would happen for Mom.

Yesterday, we went to the park and she’d reminisced about the good old days; not as if she was living the old times which she did on occasion, but remembering it as if she had tapped into her long-term memories and was telling me about her childhood. It had been as if she was her old self and she not only talked about her childhood but mine too. Sure, she thought that she was talking to a stranger, but it gave me hope. Warmth. Knowing that some part of her memory remained, that somewhere up there in her brain my mom still existed. The one I had lost nearly three years ago. Once in a while she would come back. Sometimes, those moments nearly broke me because they served as a reminder of what we were both losing to her disease.

“I’m here to help you.” I started to breathe slowly, trying to get her to focus. It was a technique that I’d learned when I took a course in order to learn about taking care of a relative with dementia.

Her dark eyes were filled with tears as she looked over at me. I knew the next stage was coming soon. I think she sensed it too. “I just don’t remember. I don’t know who you are. I don’t know where I am. I don’t remember anything.”

She looked down and I saw that her pants were soiled. I had to change her and get her into bed. I had seen the generous financial offer that Mr. Hamilton had sent with his final email demanding that I go to the office, as if he’d read my mind. I couldn’t turn it down; because I’d taken a big demotion with this job and I couldn’t afford to turn up my nose at the idea of getting some help even if it was only a couple of days per week.

I had to go into the office, there were no two ways about it. I took a deep breath as I smiled at Mom, trying not to take my frustration out on her. I’d run big corporations and I used to get stressed all the time, but it was nothing compared to having to look after Mom. The emotional strain took its toll on me at times and I had to remind myself that it was natural. I was only human; it would get to me. I used to go to a support group, but then I stopped going, because most of the time all we would do would be to get together and cry. I had my aunt come and look after Mom for a couple of hours whenever I went there; but then I found it was too depressing to continue, so I stopped. Besides, the bills needed to be paid and having a social life didn’t seem that important anymore.

“Bath time?” she asked me with hope in her eyes. She got excited about the idea of taking a bath. It was a little too early in the day to have a bath, but we both needed a distraction. Usually, I did it at night when she became restless and didn't want to go to bed.

I decided to take her up early and let her do something she enjoyed. As soon as I took Mom up for her bath, and added the bath salts, she smiled at me.

I loved seeing her smile.

She looked over at me with a beaming smile of joy. “It looks so nice.”

I nodded in agreement and helped her climb in the tub. She sank into the water with a sigh and it was as if all her worries were washed away as the warm water surrounded her.

I wished that I could climb in there with her, as I started to get anxious about having to go to the office. After Mom had her bath and after I had her safely ensconced on the living room couch, I cleaned the kitchen, and then got on the phone to my brother.

It would take two weeks for my first increased paycheck to come through and then I’d be able to get a nurse. Ross did say it was for only six weeks. I assumed that things would go back to normal after that. Until then Brett, my brother, would have to take care of her. A visit once a month when he only lived five minutes from the house wasn’t good enough. I was sick of acting like the only child and taking on every single responsibility. For once in his life he would have to stop living off his minimal paycheck from Starbucks. He only worked there on the weekend, That was all he needed to do to pay for the room that he lived in and he could survive on that. My brother wasn’t ambitious and always got by, by doing extraordinarily little in life. He would have to do something meaningful with his life, which at this point included looking after Mom.