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My Mistake with My MILF Boss

Work was always boring. I know I’m supposed to love my job and strive for success, but can we just be real here, it is the place I go to make money. Or it was before she came. It was a day like any other in the beginning. I knew we had someone coming to give a presentation, someone from the New York office, which was where all the big wigs went and the utmost in promotion. They were sending someone down to us to see if they could motivate us to do more and maybe even tempt us with the carrot of wealth and prestige in the big city. I was personally willing to be tempted. My girlfriend and I were pretty much over and I was on a road to nowhere with work here, so it seemed like at least something decent might come out of it.

Walking in that day, I threw my briefcase on the chair and looked around furtively, thinking that maybe I could get a glimpse of them before hand, do a little hand shaking and get a leg up on the other guys at the office who were basically me with different suits and varying names. Wandering around, I saw a gorgeous but mature woman who I just assumed was the hot new executive secretary I’d heard all about. Strolling up to her I smiled and started trying to find out if she was single and if she had any information on the people coming in from New York. She was friendly, but a little rude for a secretary, which lead me to act a little rude myself, asking her something inappropriate and garnering a slight laugh from her, not what I expected. After all I had just basically told her that the boss’s office was empty after 5 pm and if she’d meet me there, I’d happily bend her over the desk. I was a little less graphic, but she got the point and after the laugh, she smiled and told me she would love to! I was thrown and thrilled and grabbed her ass then walked over to my desk.

You Know What’s Coming Next Don’t You?

I should have known too, after all life never runs so smoothly as to have the hot babe readily agree to fuck you after work. However, I was too worried about the executives and too excited about my good fortune to find it odd. Instead I strolled into the meeting a little cocky and ready to impress. There she was, standing at the front of the room, her suit jacket now on over the thin silky blouse I’d seen her in earlier and I knew I had seriously fucked up. She smiled, though not a happy smile, and started talking to all of us. She wasn’t just one of the executives she was the head decision maker and told us that she would be testing out our performance and doing her own personal checks to see how committed to the company we were.

Everyone nodded, including me, ready and willing to do anything at all. I knew I’d have to apologize and after the meeting I walked over, hanging back to get her alone and starting to say I was sorry. She didn’t let me though. She just reached around, squeezed my ass and told me she’d see be after six in the executive offices. Yes, I saw this as me really lucking out! I did not once entertain the thought she wanted anything more than sex with me just like I wanted with her. It never even occurred to me, honestly. I was on cloud nine the rest of the day, cock hard and ready and head set on how things would be in New York when I got there. Maybe she’d be game to fuck me every day. Sex with the boss lady sounded good to me. What it was, was too good to be true, but I didn’t think that.

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MILF in Control

That night I arrived to find her waiting. She smiled and took off her jacket, unbuttoning two of the buttons on her blouse and revealing a sexy lace bra. She motioned for me to come over and then asked me to repeat what I’d said to her earlier. Like a fool I did. She started talking then about taping it and sexual harassment and how she’d hate to have me fired, but that she just loved being control. In fact, she said, she was a bit of a control freak and was hoping to have someone in the New York office who would do anything and everything she liked.

I was her guy! Even if that wasn’t the plan originally in my mind, it became the plan when she told me all about how I’d be servicing her any time she liked and how she’d always had a fantasy of a man under the desk, keeping her satisfied orally while she worked. Then smiled and told me I looked like I had a great mouth.