All men are entitled to their fantasies; however ridiculous, asinine or debauched. 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 on and on. Sure, I’ve had my share of fantasies. I’ve also made a lot of those fantasies come true. In college I had a Sexuality In Ancient Pre-Columbian Mexico course and the professor was really hot. She was from Peru, 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 cum stains. It was hot to watch her every now and then look down to make sure that it wasn’t seeping through. Luckily, she was wearing a dark shirt. Anyways, the point of this story is that fantasies do come true, sometimes. But usually they remain fantasies and most people bitch and whine about them never coming true. Not me, because I’m Jack Gary goddammit.
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 bosses office. She is usually wearing one of those grey pant suits and she has great big tits that are just pouring out of a little white chemise. And she isn’t too old and not too young – just a classic lady boss from a classic male erotic dream. But my story isn’t a fantasy. In real life there are lots of details and circumstances that only reality can throw at you. You can either stand up to and laugh your ass off or cower and run away. My story is a story that really happened and I didn’t even know that banging the boss was a fantasy of mine until it actually happened. Maybe it’s the sense of power that you bestow in your boss. Perhaps it’s the feeling of danger or the forbidden aspect of tea bagging your 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 wank tank (that’s where all the fantasies live inside your head that you pull from when you beat off). For me, I like to keep my wank tank empty, because I’d like to live life and put my dick in a real pussy, 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 all 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, lest 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 her). So I’ll have to keep it vague and you are 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 minutia 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 every 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 hotty’s perfume that left my hotel room that very morning. I was exhausted and didn’t want to be cooped up in some executive’s suite on a what I could very plainly see was a magnificent, sunny day. I can clearly remember this woman walking through the door and thinking she was a secretary or maybe if I allowed my mind 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 grey, I could tell that she wasn’t a day younger than 55. She had sunglasses on and I couldn’t really get a glimpse of her eyes. You can’t really ever tell what someone looks like until they take off their sunglasses. It’s really true that the eyes are the window of the soul and the reason why TSA makes you take off your shades when you hand them your ID and boarding pass. Anyways, Beverly takes off her sunglasses and sits at the head of 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 buildings all day cleaning up bird shit. That’s when the Beverly’s voice hit me through the haze of my daydreaming. She was calling my name and it didn’t fully 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 imagined her in all types of banal office settings ripping off my clothes and taking me as she swiped off pencils, staplers, papers and pens off desks. But Beverly was also married and gave off the impression that she was impenetrable to any kind of friendly, let alone romantic advances. Beverly was strictly business, but I refused 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 pilgrim slave, if only for a night. After the meeting and over the next few days all I could do was think about was Beverly. The boss fantasy took a hold of me like the SARS virus. Beverly was in my wank 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 about all 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 whole host of ulterior motives. Apparently she had the same motives.
The plane had your classic company jet décor. 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 reach 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 paper work so I filled my time by flirting incessantly with the flight attendant. But after some uncomfortable 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’s ass. I almost didn’t want Beverly to say anything or ask 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, albeit all-expenses-paid trip, and I started to doze off. That’s when Beverly interrupted my day dreaming, again. She had developed a habit of doing that. This time she put her paper work down and her hand on my thigh. I knew where this was going and in 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 unbuttoned her blouse and her breasts literally fell out. For a moment I thought that they she should have checked her tits at the gate they were so big and we were going to crash Aaliyah style into the ground. Then I remembered 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 peculiarly not wearing. Then I thought about her tits again. She looked really 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 wanted, right penis? I kept asking myself and there normal, ethical answer would be a big no, but my penis was already signing the contract. It was a big yes. Before I new 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 seed like a seasoned pro and to my astonishment went back to her paper work. Over the course of the next couple of days she would give me one amazing blowjob 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 once of those experiences that you can’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 just fine of course – with a great story to tell. Beverly, if you are reading this: you had great tits (hopefully they haven’t sagged too much over the years) and you gave a great BJ (if your husband can still get it up, he is one lucky man).