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I’ll admit, my life was what a lot of guys would call “enviable”. I’m relatively young at 31, well off, successful, and I’ve got a gorgeous trophy wife to boot. And I’m miserable. Yeah, let me explain.

I’m Mason, 6’1″, decent looks, decent build (thanks to the grind at the gym in my office when I can find the time) with wavy brown hair. I also happen to be the president of a thriving local hotel chain which my father started from nothing and sculpted into the $30 million annual powerhouse it is today. My mother died when I was a child and I have no siblings, so when my father died six years ago from a stroke, his will dictated that the keys to the company were to be left in my hands.

So while I didn’t necessarily earn my place in the world, I like to believe that I’ve certainly risen to the challenge. Our hotel business continues to grow each year since I took over. I have nearly 1,000 employees underneath me who are counting on me to oversee theirs and our company’s well being.

That part of my life I’m happy with; I love the people I work with and coming into work is the best part of my day. Unfortunately, the same can’t be said about my home life. Remember that gorgeous trophy wife I mentioned earlier? Her name is Stacy and we’ve been together for 15 years. Yes, that puts us in high school sweetheart territory.

She was a year behind me, 5’8″, wavy blonde hair and a great body from head to toe which she kept in perfect shape. She didn’t have the biggest chest, more pert and perky than anything, but overall I enjoyed her body. In fact, I enjoyed it as often and as much as she’d let me, but she came from strict Catholic background, so we were pretty limited in what she would do and kept me with blue balls a good bit of the time.

Still, she was the object of most of my friends’ and classmates’ desires and I felt lucky to have her. I have to admit I always took a certain amount of satisfaction when we’d go out and all eyes would be on her.

All that came with a price, unfortunately. She was wildly jealous if I even so much as looked at another girl. She could also be nasty to me at times, even when we were in public, and she was horribly spoiled. I managed to look passed these shortcomings, or maybe better said I simply had a huge blindspot as I focused on her more positive “assets”.

Maybe that’s why my dad never really warmed to her, but he could see she made me happy, so he supported me when I told him I was going to ask for her hand in marriage. We were married as soon as we both finished college. I wanted to go into independent film and be a director to make the kinds of films that I loved, but my father and Stacy put aside their differences long enough to convince me to follow in his footsteps and take up the family business.

I figured I could still find time on the side to put write and devote to film making, but when my father passed, all of that went out the window. As admittedly incredibly naïve as it sounds, I had no idea how much responsibility my father had being in charge of the business. I no longer had time for hobbies and lost most of my friends because I simply didn’t have time to see them, but as I said I enjoyed the work and the people I worked with and was happy continuing what my father started.

Stacy, on the other hand, never had many aspirations beyond staying at home and taking care of the kids, which brings us to where this seemingly picture perfect life begins to fade.

Try as we might (and I loved to try), Stacy and I could not conceive. We went to specialists, took all the pills and drugs you can, tried special diets, and every form of conception involving the two of us you could imagine, but nothing ever took. Stacy refused to believe anything was wrong with her when in reality the sad truth seemed to be that we weren’t a good match in that way.

I suppose I had always wanted kids, but not on the same level that Stacy did. Just about the only thing Stacy ever knew she wanted to be was a mother to her own child, and when I couldn’t accommodate, things began to quickly degrade between the two of us.

She blamed me solely for our troubles and began to treat me like dirt on an increasingly regular basis. She’d never miss a chance to take a shot at my apparent infertility, even once in the company of close friends at a party when she’d had too much to drink. I figure the only reason she stayed with me was because of the extremely cushy life we enjoyed which my place at the company afforded us.

If I was around her more often, I likely would have walked out myself, but being that I had my hands full taking care of the business, I only saw her for dinner on nights she wasn’t out with friends or on an occasional weekend. I knew something had to break, and it was only a matter of time.

That something came from one of the most unexpected places I’d ever imagine.

My secretary (now don’t get ahead of yourself) was due to go on maternity leave at the end of the month for six months. She’s actually the wife of one of my best friends (it was actually at their baby shower that Stacy made the crack at my expense… but I digress) and it just kind of worked out timing wise that when my last secretary quit, my friend’s wife had just been laid off and needed a job.

I was happy to step in and offer her the job. She thankfully actually did a great job and was the best secretary I had ever had, but with her set to leave for six months, I needed to find a temporary replacement soon.

I held interviews for candidates among all ages and backgrounds and whittled it down to three finalists. Kent was an ambitious young man to say the least, fresh out of college with designs on starting his own business someday, but he was a bit too much of a brown-noser for my liking, looking to do or say anything to get ahead.

Sarah was probably the most qualified of any of them. She had worked on the desk of one of the higher ups at a rival hotel chain but had quit apparently because of what she referred to as an unprofessional work environment. That was another word for sexual harassment if I’ve ever heard one. She was working her way through college most nights but assured me it wouldn’t get in the way if I hired her.

At 23, she was tall with blonde hair done up and had both the legs and facial features of a model. She was a knockout and reminded me a bit of Stacy when she was younger, but a lot cheerier. Focus, Mason.

Then you had Dawn. At 51, she was easily the oldest of all of the candidates I interviewed. She didn’t have much experience in the administrative assistant field but she interviewed very well and was extremely personable so I decided to put her in the final draw.

With those three in mind, I went home and brought them up in conversation with Stacy over dinner. After I gave her the basic details of the three, she told me rather matter of factly to pick Dawn. I mentioned Stacy had a jealous streak, and when a former female classmate of ours looked me up out of the blue on Facebook a few months earlier, it reignited the watchdog in her.

With that in mind, I was a bit surprised that she didn’t go straight for Kent, but when she quickly followed up her choice by exclaiming “I know you won’t be tempted to get into that fossil’s pants”, her crude thought process was clear.

It was all the same to me, though. With Kent liable to drive me insane and the fact that I frankly didn’t need Sarah as a distraction at work, Dawn was probably the best choice for me. I went out to the back patio to call her and deliver the good news. She was more elated than I was expecting and it took me a couple of minutes just to say goodbye in between the repeated “thank yous”.

That Monday morning, Dawn came in and took over my desk. Other than a few dropped calls or scheduling gaffs early on, she was doing a good job.

I admitted to myself that although she was old enough to be my mother, she was fairly attractive. She was about 5’4″ and maybe about 150 pounds. She wasn’t heavy, but you certainly wouldn’t describe her as a petite woman by any means. She wore the weight well, though. To use a word we don’t often use anymore, “voluptuous” might be a better way to put it.

She had chestnut brown hair which she typically wore up and with little makeup, but for some reason I appreciated that. Maybe the fact that Stacy always went overboard with whatever goop she put on her face turned me off to makeup in general.

Perhaps her best feature was her sizable chest. Not to sound crude but I think I’ve always been a tit man, so I’ve always been attracted to and taken notice of a nice pair when I see one. Not even nice, big is more than enough to get me interested, but it had always been a secret fascination for me out of necessity because that was the one area Stacy was lacking physically. I could tell Dawn was hiding something substantial there, but she dressed very conservatively, so it was difficult to know exactly how substantial.

She typically wore pantsuits or turtleneck sweaters with slacks, in fact I can’t think of a single instance in which she wore a skirt or a dress. She never showed any hint of cleavage or color. Sure it was the wintertime, but her wardrobe seemed to consist of almost exclusively some shade of gray or brown. I started to tease her, asking her if she was familiar with the color “blue” and things like that.

I’d especially make it a point to ask her on casual Fridays, something I decided to institute to shake things up (yep, I’m one of those “fun” bosses), when everyone in the office would dress down but her.

Still, I was only joking and she was a good sport about it, always coming back with a quip of her own. The truth is that she had a great sense of humor and I started to look forward to our interactions as the weeks and months rolled on.

Back home, Stacy decided that if kids weren’t in her immediate future then she would go back to school and get her masters in art history of all things. I’m not quite sure how she landed on that. She minored in art history in college but never once mentioned it until one night at dinner she announced her plans.

I had brought up the idea of adoption, but neither of us had really done much to look into it which was a combination of her wanting to have her own child rather than someone else’s, but also our subtle way of admitting that neither of us was particularly happy with our situation.

After three months, my friend’s wife/my former secretary called me and told me she wouldn’t be coming back and because of a substantial promotion my friend got at his job, she had decided to stay at home and to take care of their new baby full time. I thanked her for her service and wished her the best before I hung up.

I called Dawn in my office after I got off the phone and told her that if she wanted to stay on full time then the job was hers. She caught me off guard as she rushed over and gave me a big hug.

“So… do you want the job?” I teased.

“If you’re still offering after that display of mine, yes” she smiled as she said.

“Welcome aboard then, glad to have you” I replied.

“I want to celebrate, can I take you out for a drink after work, or would that be crossing some HR line?” she asked, still consumed with excitement at the news.

“No, I’d like to, but I have dinner reservations with Stacy tonight. Rain check, though?” I asked. I groaned in my mind as I remembered the dinner plans I had. I would have much rather gone out for a drink with my 51 year old secretary than meet my conventionally gorgeous wife for dinner at a fine restaurant. Definitely not a good sign, I thought, as I felt myself frowning at the thought of my unfortunate situation.

“Sounds good, and thank you again…” She smiled and lingered for a moment before turning. “Well I better get back to work”.

“You and me both” I said and smiled once more as she left my office and returned to her desk.

The rest of the afternoon was uneventful until at about 5:30 when Stacy called to apologize, saying she had just remembered about our reservations but had already agreed to go out to dinner with some grad school classmates that night so she wouldn’t be joining me (is that how that’s supposed to work?). In any event, she asked if I wanted her to cancel the reservations but I told her no, I’d take care of it.

This was one of the most popular restaurants in town and there was nearly a one month waiting period just to get a reservation, so I figured why let it go to waste. I saw Dawn through the glass in my office gathering her things to go home so I went out to catch her before she left.

“So bad news and good news” I told her. All good news, I thought to myself. “The bad news is Stacy can’t join me tonight, so the good news is I’m free tonight, that is if you’re still interested”.

“I’m sorry to hear that, is everything okay?” she asked looking concerned.

“Yeah, just something came up at the last minute” I replied.

“Well, I’m definitely still interested, where shall we go?” she asked.

“I’ve still got the reservation for La Sandros if you’d care to join me, my treat.” I offered.

“That place is too expensive, I couldn’t let you do that.” she pleaded.

“We’re celebrating, remember?” I reminded her.

“Well, if you don’t mind going out to dinner with an old woman, then I’m in.” she chuckled.

“Don’t be silly, it would be my pleasure. We’ll have a good time.” I assured her.

“Okay, well I’ll meet you there, then? I want to go home and change.” she said.

“That’s true, they have a strict ‘no gray or brown clothing’ policy.” I casually joked.

“I’m sure I can find something.” she said grinning, almost flirtatiously.

“Okay, the reservations are for 7 o’clock so I’ll see you then.” I said.

“See you then.” she nodded and smiled as she turned and went for the elevator.

I didn’t think much of it. I was just a bit relieved how the night was turning out as I figured I was sure to have ten times a better time with Dawn than I’d have with Stacy at the restaurant. We’d actually have something to talk about, for one.

It would take me a half hour to get home in rush hour traffic and another half hour to get to the restaurant, so I figured it wasn’t worth it to make the trip home to change and I just stayed late at the office and got some things done. I wasn’t trying to impress anyone after all; I was just going to meet my coworker for a bite after work. When 6:30 rolled around I gathered my things and made my way to the restaurant.

I got there a few minutes early so I waited out front of the restaurant for Dawn. I messed a bit with my phone between glances around for her while I waited. After a couple of minutes I looked up to see Dawn hurrying up the block. I had to do a doubletake to recognize her. She was wearing a dress for the first time since I had met her, and this was definitely worth the wait.

It was a blue sleeveless dress with a bit of a shine to it and came just passed her knees. It wasn’t especially tight, but it was low cut in the front and gave an ample view of her cleavage. My suspicions were confirmed; she had wonderful tits which looked to be double D cups with admittedly a bit of sag from carrying them around over the years, but like I said, I’m just a fan in general. In fact I had to catch myself as I was beginning to stare.

She was wearing a large and what I would normally describe as a gaudy necklace, but it looked nice on her somehow. She also had on more makeup than she normally wore, but she wore it well and it made her look ten years younger. Maybe I’ll have to rethink my stance on makeup, I thought to myself.

All in all she looked ravishing. Maybe it was because of the age difference, but I felt comfortable letting her know, like it was coming from an old friend.

“You look grea…” I gushed but caught myself. Don’t need to go overboard I thought, let’s pull it back a step. “You clean up good.” I said to her more casually.

“Hopefully this makes up for all those grays and browns as you put it. And yes… I have heard of ‘blue’.” she teased.

I grinned at her like an idiot as she smiled at me, clearly enjoying the palpable effect she had likely hoped to achieve from a younger man.

“Shall we?” she asked.

“Yeah let’s go in.” I said as I snapped out of my trance.

I went over to open the door for her but one of the restaurant’s hosts beat me to it. We walked up to the hostess station where the hostess greeted us.

“Hello, I have a 7 o’clock reservation for dinner”. I felt like an idiot as I realized that last bit of what I had said, but luckily no one seemed to notice. Dawn’s transformation had caught me off guard, I guess.

“What’s the name?” the hostess asked.

“Mason Cowell.” I replied.

“Right this way, your table is ready for you.” the hostess replied as she picked up a couple of menus and led us through the crowded restaurant. I let Dawn go ahead of me so I could treat myself to a nice view of her from behind. My how quickly my thoughts on her have “evolved” I noted to myself as I felt myself shaking my head.

I looked around to find a number of men looking at the two of us. I was wondering if they were checking Dawn out, as well, or if they were just trying to take guesses at our relationship. Whatever, I thought to myself. Let’s just have a good time like we came here to do. As we arrived at our table, I pulled out the chair for Dawn. “How chivalrous of you.” she said as I smiled back at her.

I relaxed as we ordered and had some wine. Dawn was always easy to talk to in the office, and this more casual environment was no exception. We started with some idle chitchat and a bit of gossip about our coworkers while we ate but the conversation eventually turned personal as the wine began to have an effect on the both of us.

I told Dawn the various details of my life up to that point. I confided in her that despite being the boss for six years I still was nervous about how everybody we worked with viewed me, and if they even liked or respected me behind my back. Dawn assured me that everyone had only nice things to say about me which was nice to hear, even if I didn’t fully believe her.

I went on to tell her about my father and how he started the company, and when he died I took over. I told her I still missed and thought about my father every day and hoped that I was making him proud. I found myself getting a bit choked up when I said that which I guess comes from both drinking too much in addition to not really talking about it since he died.

Dawn smiled and said “I know he would; you’re doing a great job and you’re a wonderful man. He would be very proud of you today, Mason”. I managed a smile as Dawn looked at me thoughtfully. After a moment she switched gears and asked me if I had any children. Not wanting to get into that whole headache, I quickly answered no and deftly turned the question back on her. She explained that she had a son who was in his third year at college.

I knew she was single from overhearing a part of a conversation she had with a coworker awhile back about a date that she had gone the night before once, but didn’t know anything beyond that.

She told me that her husband of 25 years, Stan, had died suddenly in a car accident a couple of years earlier. After the funeral it came out that he had been keeping a mistress on the side and had given most of his money away to her over the years, leaving Dawn and her son without much to live on and forcing her to go back to work just as her son was beginning college.

She made it a point to assure me that she was doing fine now financially and that she “didn’t want me to think she was grubbing for a raise.” she said with a smile.

The smile left her face and she got emotional as she told me how crushed she was when and how her son had found out about her father’s affair. She had meant to keep it a secret when she dragged it out of her late husband’s estate lawyer that he dictated a number of things to be left to the other woman. The other woman called up drunk one night and Dawn’s son happened to pick up the phone and learned about the whole thing right from “the whore’s mouth” as Dawn put it.

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