The Office Manager

Jessica handed me a gin and tonic and sat down. Our Friday partners meetings had become a staple of our business since the first week we worked together. We talked through the successes and struggles of the week, and up until a year ago, we would have ended the week with a vigorous round of passion. Sometimes we would go back to my place or hers, or more often would just go at it on the couch.

Every now and then we caught each other's eye and saw the lust we still carried for each other, but a year previously we were hitting a billing capacity that outstripped our ability to deliver. There were too many personal hurdles to bring another person into a firm where one of the partners was sucking off the other every morning and the suckee returned the favor at the end of the day.

And then Jessica met Evan.

Things worked right for her in that they fell for each other. Things worked right for us in that we stopped fooling around, got new offices and brought on two new partners in the first six months. And our company began growing quite rapidly.

For me, however, this sucked.

Yes, we had talked about getting married at some point, but she had kids and I never wanted kids. We were in lust, maybe in love. Maybe not. There were many personal differences that just didn't matter in the office. She was right, I was selfish and lived and breathed the business. Maybe someday I'll tell more of the story between Jessica and me, but this story begins here.

---

"I'm worried about you, Michael." Jess sipped her wine and sighed a long sigh. "I know you are still hurt about me and Evan. Or maybe you just miss the sex. But you need to move on. You're too deep in this business and you need to relax."

I rolled my eyes and rattled off the positives I saw, "Our income has never been better, this company is growing and yeah - I miss the sex and you. But you're with Evan and I get that. You get your family and he loves kids. It's perfect. I'm happy for you. Besides, we are a kick ass team here. With Tom and Lisa on our team, and if we hire that new project manager you've been talking about, we can be twice as efficient and maybe double again! Then I'll take a vacation and relax."

"If you don't have a heart attack first! I worry about coming in here some Monday morning where you worked the weekend away again to find you dead on the floor. Take up a hobby! Go golfing. Get a girlfriend - and yes, I know you tried that, but keep trying. You've got enough money, pick up a girl at a bar. And no, I don't want you to do that, but I want you to get your head out of your . . . Work."

"I hate golf. Waste of four hours on a beautiful day. Waste of four billable hours on a bad day." I was grumpy but not because she was right and I was wrong, it was that I wasn't willing to change and that other people were being ever so annoyingly concerned. My health was fine and sure, the stress level was there, but what business didn't have stress? "Look, I'll figure it out. Quit yelling at me."

Jessica looked at me without blinking. "Maybe you're too close to it because I don't think you will."

We were usually both comfortable with tension between us, but this was painful. I opened my mouth, but she spoke first. "Look. You are one of the most amazing men I know, and I love you - always - but get out of here for a few days. I am warning you, the money is good but you are not the happy camper you used to be and the firm isn't just you. We all want to work for you and with you. Let's just keep it that way." She stood and walked to the door.

"Ok," I mumbled. "I'll stay away till Monday."

-----

Monday morning I walked in and was greeted by my secretary, Natalie. I was very hungover and in a significant fog, nursing a headache with a side of fuckits. I was in my office about to lay down on my couch when Natalie brought in my coffee.

"Long weekend?"

"Ugh. Yeah. I was stupid," I was remembering that I didn't have a secretary named Natalie. Or any secretary. "Wait, who are you and what are you doing in my office?"

I looked up at her, and amused hostility looked back at me. "I'm your new boss, Mister. Jessica hired me to beat the shit out of you. You don't look after yourself and I'm to mind you. But this isn't me being a good little 'yes girl' for you. I'm going to make you go outside when it's nice, give you healthy food, and I've already locked up all the booze in your office. Get your shit together. Your first meeting is at nine."

I saw a round ass in a blue dress in my face as she spun and walked out, "You're welcome for the coffee, by the way."

A few hours later I began to see how Natalie was going to change my life - but I didn't like giving up the control I had built around myself. She called and rescheduled meetings further apart, she booked time with a personal trainer, and actually had the balls to put "Nap" on my work calendar. The one that everyone saw! Fuck.

Jessica poked her head in my office over lunch. "So . . . Notice anything different around here Stud?"

"Yeah . . . You going to explain our new employee? She doesn't serve coffee like you used to, by the way."

"No one serves coffee like I used to. And she's look but don't touch," Jessica pressed her fingers together authoritatively. "She's bossing YOU around. I was driving home on Friday and trying to figure what to do about you. Then it hit me, what do we do for our clients?"

"We pull their heads out of their asses."

"Right. They are so wrapped up in their business that they can't see straight to fix things. So I hired Natalie to do that for you. I've known of her for years and thought when we got big enough for an office manager, she'd be a great fit. Well, I think you need her. God knows you need some outside help to pull your head out of your ass. She's going to manage your schedule, protect you from yourself and clients. She's also going to protect us from you."

The door opened and the subject of our discussion walked in. "Mister. It's time for your walk. Your shoes are under your desk. If I see you back here before one o'clock I'm going to key your car."

I laughed. "You can call me Michael. And yes Ma'am! I'll get out and walk."

"I could," she smirked, her eyes laughing and her lips pursed. "But I'm not sure I like you that much." She folded her arms and watched me put on my shoes. I was stepping out the door when I heard her close my office door for a private meeting. In MY office!

----

Pulling into the parking garage Friday afternoon four weeks later, I was weighing Jessica's experiment with Natalie. The staff was happier, clearly. I had a tense relationship with my new secretary, however. I'm generally comfortable with tension in my professional relationships, but that's because I get paid for managing that tension.

It was undeniable, though, that I was feeling better, that I was more productive during the day and while I hadn't given up drinking, I no longer drank myself to sleep. Having someone to manage me did pull my head out of my ass. Frustrating, healthy, positive.

I opened my office door to find my annoying secretary tied, naked, to my desk with a purple rope. On her back was a small, gift wrapped package topped with a card. I walked slowly to my desk, looking over the sight before me. Natalie's round ass was elevated a bit with a cushion and the only other comfort she was given was a small pillow for her head. Next to her naked body was a glass of scotch with three cold marbles in it.

I took the card and opened it.

-

My Dearest Michael,

Congratulations on your improvement! I know this hasn't been easy for you, the past few weeks of having your life managed for you. I've seen the struggle you have made in coming under Natalie's heel. You did very well and I'm impressed.

Now, it's your turn. Natalie is yours to do with as you like. She thought it might be very helpful if you took out your stress on her and give her what her attitude deserves.

Oh, and I've taken the rest of the staff out for a "meeting" and no one will be back till Monday. Enjoy your weekend.

Always yours,

Jessica

P.S. If Natalie starts bringing your morning coffee, please be done by 8 or the staff might want you to share. "

-

I looked up. Natalie's round ass sat silent on my desk, her legs were pulled apart by the rope so far that her feet didn't even touch the floor. The dark purple contrasted beautifully with the pale skin. Her body was pulled so tight against my desk so that her breasts were pressing out. Her arms were extended straight out, she had a bit of room to grab the edges of my desk.

The package still sat on her back, rising and falling with her breathing. I slid my hand across Natalie's right ass cheek and watched her face. Her eyes were closed, but she bit her lip, seeking control she so often exerted over me. I dragged my fingers across her back to the package. Opening it I found an Opus X cigar and a note in Natalie's handwriting. I read it aloud, "Check the Desk Drawer."

Natalie didn't move. I discarded the package, snipped the end of my new cigar and lit it. The warm nutty aroma filled my nostrils and I sat down, dropping the rest of the package in the garbage can. The scotch was cold to the touch so I set it on the small of Natalie's back. I saw her twitch and I grabbed the glass but not before a bit spilled on her back. Saying nothing, I leaned over and kissed the scotch, sucking it up with each brief second my lips were on her skin.

Sitting back, I let myself just look at my tormenter for the past few weeks. She had done it all out of my best interest, it is true, but now she was helpless in front of me. There was a tiny mole on her ass.

"Are you old enough to remember when Clinton was President? What were you, ten, when the Monica Lewinsky scandal started? Yeah. You probably don't know what he did with a cigar. But I bet you can imagine." I touched her wet pussy lips with one finger, letting her question what exactly I was putting there.

Opening the desk drawer I saw what Natalie had in mind for this afternoon. There in the desk was a riding crop. Eighteen inches of fiberglass with a small square of leather at the top. Natalie's eyes opened, but she did not move her head. I touched her face with the fat side of the riding crop. I pulled it back down her body, turning it as I dragged it between her ass cheeks across her tight hole.

Knocking the ash from my cigar I spread her ass cheeks, putting my cigar lengthwise between the cheeks. "Natalie?" I asked pleasantly, "Can you hold this for me for a second? Thanks. You are such a dear." She tightened her cheeks and held the cigar, ash end up.

Raising the riding crop, I quickly slapped her ass with it. Natalie inhaled sharply and I saw her working hard to maintain the cigar in its delicate position. A tiny pink spot began to form. I took my cigar back and puffed on it. I spent the next half hour in absolute joy. Puffing a delicious cigar, looking at the body of a beautiful naked woman and enjoying McCallan whatever it was. Every few minutes I would caress the soft skin in front of me, or touch the leather of the crop against her pussy lips, or slap her with the crop to generate a little sting.

I put the crop down and turned my chair left. With my cigar in my left hand I slid my finger in her pussy and began finger fucking her. Natalie grabbed the edges of the desk, trying to push back against my fingers harder, to get them deeper. I pulled them out and played with the little tuft of hair above her slit, but met her wiggling by pressing my thumb inside and grinding my fingers against her pussy. Natalie started making some noise and so I decided to shift gears.

I put the cigar down, loosened my tie and picked up the crop. No light strokes these, sometimes she felt the sting on her ass, sometimes on her back, every now and then I'd slap the crop against the sides of her tits, pressing out on the desk. I replaced my thumb with my fingers and swirled my fingers inside, pain and pleasure overwhelming her. Her pussy clenched and flooded, her fingers pulling her towards both ends of the desk. Sweat glistened underneath her, making the desk slick. Her legs pulled hard against her ropes. Her orgasmic moans made me thank God that Jess had taken the rest of the staff away. If they hadn't heard the striking of the crop, anyone in the building would have heard Natalie cum.

I picked up my cigar. For the next thirty minutes I sat in silence, sipping my scotch and looking at this beautiful woman covered with dozens of pink marks, my desk sticky with her body and her pussy pink and calling to me. I leaned over and looked at her. Her fierce eyes challenged me. In all this, nothing intelligent came from Natalie's mouth till now, "Fuck me."

So I did.