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Business As Usual- Jack's Story (Part 3)

A different perspective on the business of cheating

As the alarm clock screamed, I rolled over and toyed with the idea of just hitting the snooze and going back to sleep. But now that my sweet dreams had been so harshly interrupted, I opened my eyes.

The dream was a becoming a bit foggy and slipping from my mind, but the raging hard-on was not. These are they days I missed my ex the most. We didn’t have much in common anymore, but the one thing we still shared, until she left, was a pretty regular sex life.

Regular, in all senses of the word. I don’t even think we ever actually did it in the daytime, or with the lights on. But a warm body was better than no body, and right about now I would have been happy to prove that.

But, time waits for no man, and no erection. So, after a few minutes of palming myself just a bit, I decided to roll out of bed and jump in the shower. A little soap, some warm water, and the crisp memory of the woman I had met for drinks last night helped me along.

She had been very attractive, in a middle-aged sort of way. But, as with most of the women I seemed to be finding lately, there was that subtle hint of desperation. She seemed to be trying too hard all night. A little too much makeup, the skirt a little too short, the shirt a little too tight. Too easy to laugh at my jokes, and I swear that she had never even read a newspaper. By the end of the night, I found myself feeling sorry for this woman rather than wanting to take her home. So, after exchanging pleasantries and a platonic hug, I walked her to her car and said goodnight.

A few women had made it home with me in the last several months, and it had been nice to have the company. None of those women had been all that remarkable, but a few made encore appearances in my bed. I find it ironic that when you’re young, you buy girls drinks in a bar and beg them to suck you off. Give it ten years, and the divorcees buy them for you, and beg you to let them.

I stepped out of the shower and strolled into the closet. I grabbed my pants, a crisp pastel dress shirt, and one of my many ties. The complete middle management ensemble. This morning I had another one of those interminable ‘coffee with the mayor’ meetings. There’s nothing quite as inspiring as crotchety old men and women with nothing better to do than interrogate you about the goings on in town.

As town manager, I have to make an appearance, even though I am sure my department heads and the mayor could handle it. So I show up, smile, and defer most of the questions to my employees.

I arrived at the building, parked in the back lot, and made my way in. I proceeded to my office, and grabbed my morning cup of coffee before heading off to the boardroom. There, we all took our assigned seats, and I scanned the room. Most of the same faces month after month, with the average age being over seventy-five, as usual. These people really need to find another hobby!

The meeting began, and introductions were made throughout the room. The mayor started reading off his agenda, and discussing all of the events and news for the month. While he did so, I nodded along politely, and my eyes traveled over the audience, trying my best to not look disinterested.

They happened to alight on her. She was looking down at something- probably her phone. I think she is one of the local real estate agents who make an occasional appearance at these meetings. Auburn hair, always dressed professionally, attractive but not obvious. Doesn’t speak up much, but when she does she’s very articulate.

She’s probably not planning on speaking today though, because she’s wearing her civilian clothes. Tee shirt, cardigan and leggings. She abruptly crossed her legs, and the action brings my eyes downward. Knee high boots. Supple brown leather, and laced all the way up the front. Not overtly sexy, but somehow bondage-adjacent. Interesting.

I looked back up, just as she did. Our eyes caught for a moment, and she held my gaze. I don’t recall if we’d ever had a conversation, or even shaken hands. I can’t imagine I would have forgotten those green eyes though….

Perhaps my thoughts bounced around a little longer than I realized, because she appeared to flush a little and look back down. I tried my best for the remainder of the meeting to avoid spending too much time looking her way, and for the most part I was successful. I ran my eyes over her a few times when I was confident she wasn’t looking, when she was distracted and I was in the clear. In between, I answered questions and at least acted professionally!

The meeting officially adjourned. We all stood to leave and I contemplated my exit. When she stood, I quickly noted that she must have spent some time in the gym, because she was curvy but toned. Those pants wouldn’t hide much. As I stood there surreptitiously sizing her up, one of my management team approached her to say hello. She turned to face him, and they shook hands. That ass! Leggings were definitely a flattering choice.

Should I be hitting on women at work in my position? No. But I probably shouldn’t be ogling them either. I shook a few hands, and slowly made my way out of the room. But I just couldn’t help myself. As I passed by her and my colleague, I caught the light scent of her perfume. I placed my hand lightly on her elbow (That should be a safe enough spot-nothing remotely sexually harassing about an elbow), and said, “Don’t believe anything this guy tells you!” and walked out.

I sat down in my office. What the FUCK was that? Seriously, I’m a little old for being ‘smitten’. Chalk it up to lack of sleep, a little loneliness, and an excess of late night porn and move on. The rest of my day kept me busy, and while she crossed my thoughts a few times, for the most part I didn’t dwell on my schoolboy behavior.

I left work and made the drive home with music blaring in my ears, drowning out any residual thoughts I might have about my work day. But when night time came around, and I sat watching some random television show, she ghosted through my thoughts.

What was it that I found so attractive about her? It’s not like she was a twenty-year-old supermodel or anything. Something had just clicked in that moment when she looked up at me. Even now I could feel myself stiffen a little thinking about her. Something raw and unguarded was in that look, and I couldn’t place my finger on it. It was just, well, unexpectedly hot.

A week or so passed, and I couldn’t let it go. I did a little internet recon and found her email address. It wasn’t very hard to find a valid excuse to email her either. She was a real estate agent, and I had been toying with the idea of selling my house, and perhaps doing a little investing in some rentals. My neighbors were a little too invested in my comings and goings, and I was tired of the questioning stares when women left my home early in the morning. It’s not like I had a press release when I got divorced, so I probably come off as some philandering asshole. Not even close, but I don’t really owe them an explanation. Time to start fresh.

So I crafted a well-written, thoughtfully prepared email that did not include one reference to her leggings or her perfume. Or bondage. And then I waited.

True to her reputation, she replied promptly and inquired about coming to take a look at my house so that she could prepare an accurate market evaluation. After a little back and forth regarding schedules, we settled on Friday afternoon. Nothing in her language gave me any indication that this was anything but business.

But every time I thought about her, I pictured her eyes when she looked at me. I pictured them under me, and looking up at me, and from a dozen other positions. Maybe that was what I saw in her... desire? Or maybe I saw my own reflected. Or maybe I was just a indulging a little flight of fancy with infinite possibilities.

On Friday morning, I decided I just didn’t feel like letting work infringe on the anticipation I was feeling. I phoned in to my assistant and informed her that I would be answering emails and handling a few things from home, but that I would not be coming in to the office. Since I had no scheduled appointments there, and much of my staff enjoyed leaving early on Fridays anyway, it wouldn’t be a problem.

I completed a few reports that weren’t really due until late next week, and then tackled my emails. Apparently the good weather was keeping the citizenry off their computers, which made my life a little easier. I straightened up my desk, made the bed, and ensured that everything around the house was in its place.

My ex and I had bought this house together before we were even married, and it still held some reminders of her. The throw pillows, for instance. No self-respecting man is buying throw pillows for his bed. But they did look nice; I’ll give her that. That, in addition to what I’d already given her: half of ‘our’ furniture and a big check.

I replaced the furniture she took with the help of a local decorator. I wanted classy, but comfortable. Clean lines but not sparse. I like to think that it is like me. I think she achieved it, and I am happy with the look.

I was not really sure what was appropriate to wear for an appointment with an agent in your own house, so I opted for some khakis and a button down shirt. I grabbed some socks, but I never wear shoes around the house really. Honestly, who does?

She rang the bell at just past noon. Show time. I answered the door and greeted her with a broad smile and a handshake.

I waved her in, and she proceeded into the foyer. I closed the door, and turned to take her full measure. Wow. That little fantasy I had been entertaining in my head had not done her justice. For as good as she looked in her casual clothes, it definitely added an element of ‘forbidden fruit’ to see her in her business attire. She wore a green blouse that set off her eyes, a black skirt that ended just at her knees, but clung at just the right places, and black heels. The peep toe heels allowed her dark red nails to be just visible. All together, it fell somewhere between naughty librarian and Vogue ad

“Thank you for coming,” I said. “I’m thinking that I may want to put this house on the market and move to one closer to the water. I would also like a little bit more privacy, as my neighbors are just way too close.”

“Not a problem,” she said. “I was very flattered that you contacted me, and I am looking forward to servicing you”.

Hold up… servicing me? There is no way she really meant that as I heard it. My mind raced at all the lewd innuendo I immediately attached. Okay, be a gentleman.

“When would you like to start?” I asked. “Do we need to look at the market reports you brought first, or contracts, or did you want to walk through and see the house?

She advised that perhaps she could take a look at the floor plan and any improvements, and then we could talk. She was carrying a black shoulder bag, and I motioned for her to drop it in the family room to her left. She did so, and I walked her through the house.

She remained at a comfortable distance, and as we walked through she commented on room sizes, wall color, etcetera. I received a warm smile here and there, a few joking comments, and we shared small talk about the weather, the neighborhood, and what I might be looking for in my next home.

We ended our tour in the kitchen. She walked to the patio door and placed both hands on her hips as she surveyed the yard. Yes, definitely naughty librarian.

“So, what do you think? Do I need to make any changes, fix anything, hire a decorator…?” I asked jokingly.

“No, it’s a lovely house. I think that if you decide to move forward you’ll do well. You have good taste and I can’t imagine it won’t sell quickly.”

“Well, with you in charge I can’t imagine it wouldn’t be fast.” It was out of my mouth before I realized how it sounded. Granted, I meant it just exactly as it sounded. But, I was walking a fine line here!

“I’ll need to go back to the office to put together the proposal on price and marketing, but if you’d like, I’d be happy to show you the reports I brought and we can talk about the process,” she stated matter-of-factly.

Not a welcoming reception on that comment evidently.

“I have plenty of time. I’m playing hooky from work today,” I replied. “I think I’m going to grab a drink first. Can I get you something? I have a great bottle of wine in the fridge.” A little alcohol never hurt to break the ice.

“You know what? I’ll take you up on that offer,” she said.

I pulled out two large glasses and opened the wine. It was a favorite of mine, and I always kept some in the house. I watched as she tipped her glass, and she seemed to relax a little. I was encouraged to see her glass empty quickly as we chatted about window coverings and desirable neighborhoods in town.

“Goes down easy, doesn’t it? Can I pour you another glass?” I solicited.

“You were right. It is a great bottle of wine and I don’t want to deprive you of it. So I’ll pass. But thank you for offering,” she replied.

Obviously she had enjoyed that first glass, and there was at least one more bottle in reserve. So I refilled my glass, and then attempted to do the same for her. Unfortunately, she chose that exact moment to raise the glass to her lips for the one remaining sip. I managed to get the majority of the wine I poured into her glass, but also managed to spill some into her cleavage.

She jumped a little as the cold wine dripped down. I was a little embarrassed, and a lot amused. I quickly grabbed a towel from the counter and handed it to her.

“I’m so sorry!” I told her.

She was daintily pressing the towel against her cleavage attempting to soak up the errant wine. My eyes followed the towel as she did so, and I am sure my interest was now evident.

“Well, now you’ve got me just a little wet,” she remarked.

That got my attention. I apologized once again for my clumsiness.

“It’s fine. That’s the joy of white wine: no stains,” she remarked. “I left my bag right inside the family room. Shall we move into there or would you like to keep the meeting in the kitchen to prevent more spills?”

I laughed under my breath and followed her to the family room. She bent over to grab the bag she had placed on the floor and appeared to catch her heel on the carpet as she did so. She let out a little squeal. She looked a little unsteady, so I stepped behind her and placed my hands on her hips to help her regain her balance. And then I clearly lost mine.

As she placed one hand on the wall, the other rubbed her ankle. I took a small step forward. I don’t even think I did it on purpose. Her position was just too inviting. I was very aroused, that much was clear now to both of us. What was I doing?

I stood still, not moving one inch. I silently awaited her reaction. A rebuke, a slap, indignation maybe? What I honestly didn’t expect was the sigh that came next.

She stood up slowly, and I remained stock still. To diffuse the potential fallout I asked, “Are you OK? Is there anything I can do for you?”

Then she plainly answered, “Well, I am still a little wet.”

Once again something clicked. With one sentence she touched the dirty part of me that lurked in the corners of my mind.

My hands slowly brushed down over her hips, to her thighs, to the hem of her skirt. I grasped the hem and brought it up to reveal what was underneath. She did not disappoint. Black lace panties were now on full display. I reached down with one hand and moved it between her legs.

“A little?” I said. She was so wet, and I wanted her right now. I had the fantasy of her stalking through my head for at least a week and here she was in front of me.

My free hand found its way around her chest and pulled her even closer, while the other remained tangled in lace. I was enjoying rubbing my engorged cock against her ass. I could feel her body responding as she subtly moved with me.

There were a million things I wanted to say, but what came out was, “Put your hands on the wall.”

She hesitated, and I wasn’t sure if maybe I had misjudged the situation. But I was committed to it now; my hand was on her panties, so I don’t think there was any question of my intent.

“Put your hands on the wall so I can fuck you,” I said more directly.

And she did just that.

As good as that skirt looked on, I wanted it off. I took a step back and pulled it down to gain access to the zipper. I unzipped it and watched it fall away. I took in the moment, pausing to appreciate the view. And it was certainly a fine view.

She tuned slightly, and looked at me over her shoulder. That look was all desire. And it echoed the one we shared the day she came to that meeting. But it was a lot more intimate in a room alone with her.

I decided to confess. “You have no idea how much I wanted you. I was so hard at that meeting I wanted to take you to my office and bend you over my desk.”

In response she turned to face me. She held my gaze, but didn’t say a word. I watched as her hand found each button on her blouse. When they were all undone she shrugged it off her shoulders and let it fall. I was rewarded with more black lace, artfully holding in ample breasts.

I reached forward and cupped them, grasping hard nipples and not relenting. In response she reached forward and finally touched me. A light graze across my tented crotch, and then she turned her attention to removing my shirt. She ran her nails down my chest and took stock of every muscle.

Once my shirt hit the floor, joining hers, she turned her attention to my pants. As she removed them, her hand once again ran lightly over my cock. It was now aching in response. She turned her eyes up toward mine and then slowly, deliberately ran her tongue over her lips. My hand was immediately drawn downward, and I wrapped it around myself. I couldn’t ever remember being this hard, and I was sure I could not be any harder. And as if she had read my mind and wanted to disprove that, she raised her finger to her mouth and inserted it. She then removed it ever so slowly and ran it across the glistening head of my cock still in my grasp. And when she was satisfied that she had my full attention she placed it back in her mouth.

I lost any self control that I had left. I promptly turned her to once again face that wall and stepped in closer. With one movement I was inside her. She was warm and tight, and so wet I had no doubt that she wanted this too. I continued to thrust into her hard, pushing her firmly against that wall. In return I felt the familiar clench of muscles surround me, as she undoubtedly reached her climax.

But, I was not even close to done. I slowed my pace a little to allow her to fully enjoy her release. When the aftershocks stopped, I began my pursuit again, intentionally pulling almost all the way out only to watch as I slid forward to slam it home again. And once again, she came-- so hard this time that she seemed to stumble a little.

So I wrapped my arms around her and we moved to the couch. I held her tight, and remained inside as we sat down. The act of sitting brought me even deeper, and she seemed to find another orgasm. I can’t complain; the feeling of her muscles massaging mine was only driving me further toward the edge. But, there was no way I wanted to come yet. This was much too delicious to rush.

Just as I was about to begin again, she leaned forward and I unceremoniously slipped out of her. What was going on?

I was rock hard and pointing skyward as she turned and kneeled in front of me. I silently breathed a sigh of relief, and leaned back to enjoy the show.

I watched intently as her tongue found its way around the underside of my shaft. She teased up and down a few times, before taking it fully into her mouth. Her hand snaked around the base and gently twisted just a little, and the total sensation was unbelievably intense. She looked at me with a mischievous glint in her eye, and I knew that she was enjoying the control. As she began moving faster I started to tense a little, and I could feel myself getting ready to come. She then slowed things back down again and moved her hands and her tongue down to my balls. It was nice, but I really wanted to be back in her mouth, and she finally relented.

She resumed sucking me as deeply as she could, teasing me with her tongue, massaging me with her hand. I was so close. An uncontrolled groan escaped and my breathing was unsteady. I wanted desperately to come in her mouth, to feel her relish her work.

But instead, she stood up and removed her bra. Then she did something I’d only actually seen happen in a movie. She raised her breast while looking me straight in the eye, and slowly licked her nipple. Who is this woman?

She moved forward until she straddled me, and then impaled herself. She watched every expression on my face, gauging my reactions, adjusting her speed for maximum effect. As I took in all of this, watching her, she sped up her efforts until she was bouncing off my cock and I finally found my release. It pulsated for what seemed like forever, and it took a while for me to come back down.

When she was satisfied that I was satisfied, she moved off my lap. She then moved around the room retrieving her clothes as I observed. It was a lovely sight, because right now she was wearing only those black peep toe heels. Without even realizing it, my hand wandered down to my semi-erect cock and began stroking it. I have no idea how, but I was suddenly at full attention again. And I wanted those heels back on my couch.

I watched her eyes follow my hand, and observed her breathing get a little quicker.

“Are you coming or going?” I asked as innocently as I could muster.

“You think you’re pretty funny don’t you? But I’ll give you this: you are pretty witty and you certainly keep things interesting.”

“Well, it takes two. That’s why I prefer smart women. They are pretty sexy. But you apparently don’t even have to talk to get me hard. Bonus.”

“Coming.”

“What?”

“That’s my choice. But you don’t have to talk to accomplish that. “

She promptly dropped the clothes onto a nearby chair and returned to the couch. When she stood before me, I leaned forward and kissed her lightly between her legs. My tongue followed, and her answering moans told me she was right at the precipice. But I wanted to feel her come again while I was inside her.

I took her hand and pulled her down onto the couch, placing myself between her legs. I didn’t enter her, I just remained enveloped in her wetness, the warmth, the intimacy and the anticipation. I leaned down and kissed her for the first time. It struck me that of all the things I had perpetrated with this woman today, a simple kiss seemed to hold the most anxiety. Maybe because it had been so easy to objectify her, especially if I didn’t make this connection. She answered my kiss, soft at first and then more demanding.

As our lips parted, I pushed into her, watching her face as she had watched mine. I controlled the movement, the progression, the act. Soon I felt that familiar pull, and I knew she did as well. My pace increased and we both reached a final salacious release.

I directed her to the bathroom so she could freshen up a little, and I went the upstairs facilities and did the same. I grabbed my clothes on the way and threw them back on.

She had not, and when I returned she was just picking them up to dress. I reached out and grabbed the black lace panties. Kneeling down in front of her, I slid them over her heels and up each leg until they were back in their rightful place. I took the bra too, and placed her breasts lovingly back into their support system.

Before I could take too much time gawking at her lace trousseau and heels, she slid into her skirt and replaced her blouse.

“See, no stains,” she remarked as she buttoned up.

“Next time I’ll make sure you are properly un-attired before serving the wine,” I commented with a smile.

“Really? And who said there would be a next time?” she asked coyly.

“Well, you are my Realtor, so we’ll need to meet to get my house ready, sign papers, and look for a new one. And I may be considering some investment property too. So I’ll need lots of servicing.”

Yes, servicing. I’m guessing Freud knew what he was talking about, given the day I’ve had.

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