Stories tagged with "MILF"
CEO
Jack signs a pleasurable contract with his alpha female boss.
All men are entitled to their fantasies, however ridiculous asinine or botched, and all men do have their fantasies. Trust me. Erotic costume shops don't come up with some of those get-ups off the top of their heads. You know the ones the schoolgirl with the plaid skirt, the sexy nurse pirate wench hot cop cowgirl, dominatrix teacher, and so on and so on. Sure, I've had my share of fantasies. I've also made a lot of these fantasies come true. In college, I had sex in an ancient pre-Columbian Mexico course, and the professor was really hot. She was from Peru. She had a hot, curvaceous body from centuries of eating maize tortillas, and her father was a diplomat or something. A few months into the course, we got closer and closer to the point where I was basically putting it in her every night. Once I showed up to class first about 15 minutes before it started. We got it on right there in the classroom. I basically finished all over her chest before all the students came rushing in, and she had to button her blouse over my wet come stains. It was hard to watch her every now and then look down to make sure it wasn't seeping through. Luckily, she was wearing a dark shirt. Anyways, the point of the story is that fantasies do come true sometimes. But usually, they remain fantasies, and most people bitch and whine about them never coming true, but not me. Because I'm jack Gary, goddamnit. One of the fantasies I didn't mention before is having sex with your boss, in most people's minds. This fantasy takes place in the boss's office, she's usually wearing one of those grey pants suits, and she has great big tests that are just pouring out of little white shimmies. She isn't too old, not too young, just a classic lady boss from a classic male erotic dream. But my story is in a fantasy. In real life, there are a lot of details and circumstances that only reality can throw at you. You can either stand up to laugh your ass off or cower and run away. My story is a story that really happened. And I didn't even know that being the boss was a fantasy of mine until it actually happened. Maybe it's the sense of power that you bestow when your boss; perhaps it's the feeling of danger or the forbidden aspect of teabagging the boss that gets you off. Whatever it is fucking your boss is something any young gentleman should scratch off his sexual conquest list stat. Unfortunately, most of you will keep this fantasy for the wing tank. That's where all the fantasies live inside your head that you pull out for you beat off. For me, I like to keep my tank empty because I'd like to live life and put my dick in a real policy as opposed to my right hand. A few years ago, I was doing this job. And the woman that hired me was one of the hottest older babes I've ever seen in my life. Before I go any further, I'd like to mention a few things. The classic definition of a boss is someone that hires you and tells you what to do. But in my line of work, people can never tell me what to do. I do what I want when I want, and I get paid for it. Unfortunately, I can't really tell you what I do. Less someone finds out about it and sends an angry letter from a lawyer telling me to stop telling stories about him or her, usually a hurt. So I'll have to keep it vague, and you're going to have to follow along as best as possible with the power of your imagination as to what my occupation actually is in return. I'll try not to bother you with all the unnecessary minutiae and get to all the exciting parts as fast as possible. That being said, I was sought after for my services by a woman who was about 25 years my senior but incredibly gorgeous. It was one of the first times I was sincerely attracted to an older woman, and she happened to be the CEO of one of the biggest companies in the world. We first met at a meeting in an undisclosed city in an undisclosed office about 60 stories in the sky penthouse level shit. I was wearing a suit that distinctly smelled like a young hottie's perfume that left my hotel room that morning. I was exhausted and didn't want to be cooped up in some executive suite on what I could plainly see was a magnificent sunny day, I could clearly remember this woman walking through the door and thinking she was a secretary. Or maybe if I allowed my mom to stretch a little a board member or something. For the sake of this story, we'll call her Beverly. Beverly had dark hair, and although there wasn't a strand of gray, I could tell that she wasn't a day younger than 55; she had sunglasses on, I couldn't really get a glimpse of her eyes. You can't really ever tell what someone looks like until they take their sunglasses off. It's really true that the eyes are the window of the soul. And the reason why TSA makes you take off your shoes when you hand them your ID and boarding pass. Anyways, Beverly takes off her sunglasses and sits at the table. This woman was clearly in charge, but I continued to space off, staring at some window cleaners and thinking about how terrible it would be to hang off the side of the register until she was basically yelling jack at the top of her lungs, trying to get my attention. When she entered the room, Beverly didn't even offer a hint that she was the boss. But now, I could clearly tell that this woman was in complete control. And for a moment, she had my full undivided attention until I started to feel like that age-old familiar sensation, arousal. I was attracted to Beverly; she had one of those rare alpha female-type personalities that immediately makes you think about what they would be like in bed. I thought about this for the remainder of the meeting. I imagined her pinning me down on a desk and ravaging me. I imagine her in all types of banal office settings ripping off my Close and taking me as she swiped off pencils, staplers, papers, and pens off desks. But Beverly was also married, gave off the impression that she was impenetrable to any kind of friendly, let alone romantic advances. Beverly was strictly business, but I refuse to believe that I couldn't plant a jack Gary flag somewhere somehow. Even though her husband was the CFO, and she had a diamond the size of Plymouth Rock on her finger, I was determined that I was going to be her filthy pilgrims' slave if only for a night after the meeting and over the next few days, all I could do was think about Beverly, the boss fantasy took hold of me like the SARS virus. Beverly was in my wink tank, and she was drowning. After about a week, Beverly called me and asked me to join her on the company jet to an office in another city. Apparently, I was doing a really great job not doing anything I was supposed to be doing. Or maybe she was looking me up and learned all about the jack Gary legends and wanted a part of the action. I said yes. And the next morning, I was on a tarmac with my weekend bag and a whole host of ulterior motives. Apparently, she had the same motives. The plane had your classic company, Jet decor, fancy wood paneling, plush leather seats, and large plasma screen TVs. Our flight was only going to be an hour-long, but I couldn't imagine what we could actually talk about within that timeframe. I started to have doubts about why she wanted me there in the first place. Did I let some stupid fantasy drag me along on some boring business trip? Where was my dick leading me this time? As we reached cruising altitude, the gorgeous female flight attendant offers us breakfast and beverages. It was nice and relaxing to lounge around after a busy few weeks. Beverly was busy with paperwork, so I filled my time by flirting incessantly with the flight attendant. But after someone comfortable turbulence, the flight attendant crawled into a secluded room and shut the door. I was left there twiddling my thumbs while Beverly was next to me, working away. Breakfast was finished, and the drinks were gone. I started staring off at the sky through the little circular windows getting rather cozy in the leather seats that smelled like a baby camel his ass. I almost didn't want Beverly to say anything or asked me anything because I was sure this was not going to be one of my fantasies come true. So I relished in the leisure of being on a private jet on a short I'll be an all-expenses-paid trip, and I started to doze off. That's when Beverly interrupted my daydreaming again. She had developed a habit of doing this. This time she put her paperwork down and her hand on my thigh. I knew where this was going. And at this moment, I knew why I was 25,000 feet in the sky with the CEO of one of the biggest companies in the world. Beverly on a button, her blouse, and her breasts literally fell out for a moment. I thought that she should have checked her tits at the gate. They were so big, and we're going to crash Leah style into the ground. Then I remember that we were on a private jet, her private jet. I also thought about her husband and the rock on her finger that on this day she was oddly not wearing, then I thought about her tits again. She looked great for her age, and her nipples weren't too big as I expected them to be. I thought that the big nipple thing was going to be the deal-breaker, and I was going to be saved, but alas, this is what I want it a right penis. I kept asking myself, and their normal ethical answer would be a big no, but my penis was already signing the contract. It was a big Yes. Before I knew it, she was sucking me off. She had years and years of experience, and it was a great BJ. When I was done, she gulped down my seat like a seasoned pro. And to my astonishment, she went back to her paperwork. Over the course of the next couple of days, she would give me one amazing blow job after the other, once in the company boardroom, twice in her expansive office, and three times in the elevator. She was also apparently a boss at sucking dick in the end. It was one of those experiences that you couldn't wait to write about. I ended up not working for the company shortly after the dick-sucking escapades. She ended up marrying her boring husband, and the company collapsed after the financial crash. And I'm fine, Of course, with a great story to tell. Beverly, if you're reading this, you had great sets. Hopefully, they haven't sagged much over the years, and you gave a great BJ if your husband can still get it up. He is one lucky man.
Rating: 4.9/5 (total: 27)
