The Boss


Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, .

Desc: Sex Story: A short story about a mature woman who is enticed into working for an old family friend. Soon she is making a majority of the decisions in the company and when her boss takes her to LA on a business trip, well things change.

I never really thought about Bill being 'the boss', he was really much more of a friend of the family than an employer. My husband Carl and I had known Bill for more than twenty years, hell he had been the godfather to our son and he and his wife Alma were frequent overnight guests at our house ... that is until about five years ago when Alma was diagnosed with breast cancer and from that day on Bill pretty much dedicated himself to taking care of Alma when he wasn't at work. Alma died on a cold rainy January afternoon and Carl and I were there for Bill; helping with the funeral arrangements and making sure that whatever he needed was taken care of. After the funeral we didn't see much of Bill, it seemed that with Alma's death he gave up on any social life and pretty much threw himself into his business.

A year ago Bill called out of the blue and flabbergasted me by asking if I would come to work for him as his personal assistant. I was hesitant, I hadn't worked in years and I kind of enjoyed my freedom but I also missed the socialization process that came with having a job. I discussed the idea with Carl he thought it might be a good idea, if nothing else it would get me out of the house for a while. I told Bill that I would take the job but only if I could start part-time, three days a week, he agreed and that how it started.

Bill was a great boss, he gave me assignments that were challenging and he always took the time to listen to my point of view before making his final decision — and generally he went with whatever I recommended. After the first six months he talked me into going full-time and the following month he started taking me along on his monthly business trips. I was glad to be contributing to society and the money that Bill paid me was just icing on the cake. Carl was very supportive of my working and seemed happy that I was so valuable to Bill; he even told me that he thought that Bill was close to being his old self as he had been in years.

I was sitting behind my desk one afternoon when Bill stopped by and dropped a note off asking me to set up a three day trip to Los Angeles for the following week to finish a huge contract on a project that would be worth millions to the company. I smiled at him and asked if he wanted me to accompany him on the trip and he just nodded his head yes as if it was a stupid question.

"Of course I want you there Cindy, good God I can't afford to make a decision like this without your input."

That compliment couldn't have made me any happier! Carl was headed for a week in Washington, D.C., working on a government contract for his company so the trip to LA was perfect timing.

Bill and I were sequestered in an office on the 16th floor of a building in Century City reading through the documents. I had read the purchase/buy contract umpteenth times then I found what appeared to be a large omission from the contract price and went over to Bills table, leaned over and pointed out the error. He looked down at the document for a second then looked back up at me and grinned. Thinking his reaction strange, I looked down and suddenly realized that the way I was bent over my blouse was gapped and had exposed my bra to Bill's eyes and he certainly wasn't looking away, he was just stared at my bra. Trying to act like a lady I stood up and ignored his gaze instead focusing on the contract. "So here's my take boss, I think you challenge them on this point and when they relent, and my guess is that they will relent, then there is an extra $200k in it for us."

"I think your right Cindy and if that happens I'll make sure that your bonus is even bigger than normal."

"Hell Bill you don't have to do that, I mean that's what you pay me for." We ... well Bill really, signed off on the contract at the end of the second day and the $200k was in the contract. Bill decided it was too late to catch a flight that night so we would stay over and take an early flight the next morning — I made all the necessary arrangements. That night Bill took me to dinner at an expensive restaurant in Santa Monica after dropping $375 we headed back to the hotel for a nightcap. Bill suggested that instead of going to the main bar we adjoin to his suite and use the executive bar in his room. I didn't think anything about it and readily agreed. We arrived at his suite and like the gentleman he is, he opened the door and let me precede him inside. I sat at a bar stool chatting away while Bill went behind the bar and opened us a cold bottle of Napa Valley Chardonnay. He poured two glasses and we sat there, we toasted yet once again, and talked about the contract, the company and then the conversation turned personal, talking about Carl and our son and of course Alma. I had just taken the first sip from my third class of wine when Bill brought what happened at the offices in Century City.

"You know something Cindy I know it's not right but I don't regret looking down your blouse, not one damned bit."

I wasn't sure how to respond to his comment. I hadn't been offended and, after all it had been my fault, leaning over like that, exposing myself. "Uh well Bill there's no need to be all apologetic or anything, it was my fault anyway. Besides it's kind of nice to know that a 52 year old woman can still attract the attention of a gentleman."

"Fifty-two, no shit! That's damned hard to believe Cindy, anyone not knowing you would think that you're years younger."

"Well that's nice of you to say Bill, thanks. Actually I try and work out a couple of days a week. I mean a girl has to look good for her man and I think Carl appreciates the fact that I try to look good for him."

"Hell Carl would be a fool not to appreciate a woman like you. I guess it's just been so long since Alma uh ... well anyway I don't often get a chance to get a glimpse of the breasts of such a beautiful woman."

I didn't know what to say. I took another sip of my wine and suddenly felt sorry for Bill. He was a really nice man and a he was good boss and he had to be hurting from the death of his wife all those years ago, still what could I do? "Well a little glimpse of the forbidden fruit now and again is good for a man, at least that's what I think."

"Really, do you? So what's the chance that you might let me get another glimpse of that lovely body of yours?"

Clearly we were now in uncharted waters! "Oh Bill ... I don't think that would be a very good idea, I mean I am married and you're my boss."

"I know your married Cindy, hell I'm the godfather to your son and I've known Carl for over twenty years and it's true that I'm your boss. Given all of that it would still be a great gift if you would just let me see you again, even for just a minute or two.

Well I could have just said, no! I could have walked out of the suite and gone back to my room, I could have done a dozen of things I didn't but for whatever reason I simply nodded my head yes and began to unbutton my blouse. I mean what was the harm in it anyway and besides it wasn't going to give him much more to look at than he had already seen when I was in my bathing suit. "Okay Bill but just for a minute or two." He nodded his agreement and I finished unbuttoning my blouse and took it off and laid it on the bar. I was wearing a Victoria's Secret push-up bra that emphasized the size of my breasts by pushing them up and out. It was a low-key solid gray colored bra and you couldn't see my nipples or areolas so I felt comfortable sitting there like that. I could tell by his gaze that he was excited and just knowing that excited me too. I mean it had been many a year since anyone but my husband and doctor had seen me without my blouse on and neither of them had ever had a look on their faces like Bill did at that moment. "So I'm guessing by that smirk on your face that you like what you see." I quipped.

"My God Cindy you even more beautiful that I remember. Your breasts are perfect and I ... well I would give a million dollars to see them without your bra."

He had to be joking so in my most teasing voice I challenged him. "Hummm, a million dollars just to see my breasts? Well if you're serious Bill you can make out the check right now." I giggled at my own humor, that is until he took out his checkbook and started writing a check.

"Bill, you stop that this instant! You can't write a check for a million dollars, it's crazy." He looked up at me, his eyes almost pleading with me.

"I would have done it you know."

"You would have written a check for a million dollars just to see my breasts?"

He nodded his head. "Yes I would have."

I couldn't believe it. "Oh for Christ's sake Bill, here." I reached behind my back and unsnapped my bra and took it off and tossed it on top of my blouse. "There you go, Cindy's tits for your eyes only and for free." I rubbed my breasts where my bra had dug into the skin.

.... There is more of this story ...

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Story tagged with:
Ma/Fa / Consensual / Heterosexual /