A Female CEO’s Secret Life Pt. 01

As a busy CEO, work often gets stressful. I am constantly faced with strict deadlines, difficult decisions and managing people with complex personalities. I have to do it all with a positive attitude, showing a calm but commanding disposition in order to get the best out of my team. As a woman executive, I am also always under a microscope. While the world has been moving more toward equality, it is not quite there yet. With all eyes on me, I must always remain diplomatic and conduct myself in a professional way. The boardroom is a place to be confident yet conservative in my appearance and demeanor.

This has always been a struggle for me, as it is the exact opposite of how I am in my private life. In my college years, I had that rare ability to take care of business while walking on the edge a bit in my social circles. I enjoyed the power I possessed over men with being a bit promiscuous at times. I would often wear slightly suggestive clothes and think nothing of bringing that catch of the night back to my place for a little fun. It was always on my terms though and it is amazing to see the power I can have over men when I am in complete control. I know how to push the limits and have them on the edge of their seats eagerly anticipating what may or may not lie ahead.

As I rose through the ranks in my professional life, I did it the hard way through my work ethic and merits. I suppose I could have slept my way to the top, but then it would be hard to keep that a secret and to be respected and taken seriously. Like I said, I have been under the microscope for many years, so I have had to be creative in finding a way to feed my insatiable desire for passion and promiscuity.

We just got through a rough stretch in our fiscal calendar and delivered a stellar earnings report. After a month of early mornings, late nights and intense meetings, I decided I needed some "me" time. As a successful single woman, I have the luxury of being able to travel to wherever I want, whenever I can slip away. It was time to take advantage of that. This was the perfect remedy to decompress and relieve the stress of work. I checked the Cyber Monday fares and booked the next flight out to Maui, where I could go in anonymity and enjoy some time to myself doing whatever and whoever I want.

These solo trips are a chance to really let my hair down. No pants suits and ankle length skirts make it into my luggage on these trips. This is a chance for me to cut loose and release the inner slut inside of me. If it tells you anything about my wardrobe for these trips, I can fit about 10 different outfits in a small carry-on bag because there simply isn't much to these skimpy get ups.

I always make sure to pack a full variety of pleasure toys. You see, I don't always count on meeting a man on these trips. If it happens, it happens, but I am there for me and at the very least, I always know that with toys in hand, I can satisfy myself. So, into the bag went a variety of vibrators, keagle balls, butt plugs, dildos and lube. When I head out on my own, I make sure that I come back well satisfied. I am like a caged animal ready to be let out.

My first stop was to the Fairmont. This was not my first rodeo with these "Me" trips. Since money was not an object, I always booked two rooms at neighboring hotels. One room was for fun, and one was for lodging. I learned a long time ago that mixing the two was a recipe for disaster. In the first room, I would store my suitcase with all my naughty toys. That way I could have a place with easy access for my sexual encounters. This was a place to get it on and get myself off and at the conclusion, I could simply head back to my other hotel room without regret. One of my close friends back home laughed when I told her of this strategy. She said it was almost like I created my very own walk of shame. I told her, "Honey, there is no shame in these trips for me. I either go in and go to town on myself or pick a man and have unbridled wet and passionate sex with no strings attached." The ability to walk away was key in avoiding uncomfortable extended stays from my partners should they start to feel attached. So, I dropped off my suitcase of toys and headed to my next stop.

The Grand Wailea is one of the most expensive and exclusive resorts on Maui. I booked myself a Villa so I could be away from the other guests and not attract much attention as I exited and entered the property in my promiscuous attire. When I got to my room, the first thing I did was draw a nice refreshing bath. I wanted to make sure to pamper myself a bit before heading out for the evening. As I stripped out of my airplane clothes, I could already feel the anticipation of the evening building. My plan was to venture to the Fairmont and sit at the bar and enjoy a few cocktails while I surveyed the land and plotted my next course of action.

As I began to think about this, I began to feel a wetness between my legs. I slowly pinched my nipples and rolled them ever so gently through my fingertips. I stepped into the bath and continued this light petting as I refreshed myself from the long flight. I had to stop short of getting myself off though. I had a long night of pleasure ahead of me and it was important to pace myself and build the anticipation.

I stepped out of the bath and did my hair and makeup. At work, I am constantly in conservative mode and typically wear my hair up with a basic makeup job. These trips are different though. I always wear my hair down, so it is flowing over my shoulders with just the right amount of curl. Then I applied some sensual red lipstick. Nothing screams sexuality like a pair of pouty bright red lips.

Then it was into the wardrobe closet to pick out just the right outfit. I was feeling a bit naughty this evening, so I felt that leather was in my future. I grabbed my favorite pair of tight leather pants with a flared boot cut at the end. Then I found my naughtiest leather bra that accentuated my 36DD breasts. I always try and size down as much as possible as I find it incredibly sexy to be spilling of my bras exposing my ample cleavage. There have been times that I would just roll with this as an outfit if I was in Los Angeles or Vegas, but in Hawaii, I decided that a sexy sheer black blouse would be the perfect complement for this ensemble. Then it was time to hit the shoe closet. A pair of 5 inch red "Come Fuck Me" pumps seemed to be in order.

Panties are simply never part of my wardrobe on these trips. I want to be free and always have easy access. As I began to lotion up, I slowly slipped a finger into my pussy. The juices were already flowing, and I could tell this was going to be an exceptional night. I slowly caressed myself, circling my clit with my delicate fingertip. Tonight, was about me and about power. I was going to be in control. I grabbed my butt plug and applied just a touch of lube so it would nestle nicely in my ass. I recently discovered how pleasurable butt plugs are. It provides that feeling of fullness while being my own dirty little secret. Whenever I guy discovers it, he knows just what a nasty little slut I can be.

Tonight, I thought it might be nice to try a bit more than just my butt plug. I decided to try out my newest toy. A vibrating egg that would slip into my pussy that I could operate with a discrete remote control. I can't begin to describe how sensual it feels to start your evening in a pair of leather pants with a leather bra and both your pussy and ass filled. I could barely contain myself as I walked out the door.

The Uber driver picked me up and kept adjusting his mirror to get a great view of my tits in the back seat. I could tell this ride was going to remain in his highlight reel for a long time. He dropped me at the Fairmont, and I proceeded to head to the bar. It was just after sunset and the mood was set, I walked into the room and got many glances from the guests ranging from the wanton approval of the men and a bit of jealousy from the females whose men couldn't take their eyes off me. I was on full display, and I loved every second of it.

I grabbed a seat at the bar and ordered a Sex on the Beach. I always make this my first drink just so I can see the bartender's reaction as I sat in my slutty outfit with my breasts on full display. As I waited for my drink, I surveyed the land to see if this was a solo night or if I would find a mate. I made brief eye contact with a handsome man that appeared to be in his forties in the far corner of the bar drinking alone. He looked back and smiled, but I quickly looked away. Let the seduction commence as I began my routine while remaining in total control of the outcome.

I discretely turned my vibrator on the lowest setting, just to get that rush of pleasure brewing between my thighs. The moisture began to build, and it felt wonderful with my bare pussy against my leather pants. The bartender brought my drink over and began making small talk. He asked me my name and where I was from. I love when this happens because I always make up an alter ego and let the story flow. Today I became Alexis from a small town in Nebraska. I was recently divorced from my high school sweetheart who was the quarterback on the football team. He never grew past his high school glory in our hometown, so we drifted apart and split up. I was out here on a solo trip to find myself, clear my head and rebuild my life.

As I talked a bit, I decided to amp up my vibrator to the next setting. As I made up this fictious life, I wanted to really feel the pleasure building so I could lose myself in the character. Sex on the Beach is also the perfect drink to alert the others in the bar that I was potentially open for business. Everyone can clearly identify that bright blue liquid and know that this scantily clad girl had sex on her mind. The straw serves and important purpose as well. I start by being slightly seductive with my lips as I suck on it and then amp it up as the night goes on. The bartender was nice enough, but I always found that picking them up was too easy. It also meant you had to wait around until his shift was over, and tonight, was not the night to sit around and wait. I needed to start planning my first orgasm and it sure wasn't going to be at 11:00 PM.

Meanwhile, I had paid no attention to my forty-something across the bar. He decided to make his move and called for the bartender. They spoke quickly while I reapplied some more red lipstick. I made sure to exaggerate the strokes of the lipstick tube as I pressed it against my lips. I also subtly adjusted my breasts just so I could brush against my own nipples and make sure that I was looking my best while on full display. The bartender came over and told me that the gentlemen wanted to buy me a drink and asked me what I wanted. At this point I switched over to a nice glass of Sauvignon Blanc. To many glasses of Sex on the Beach would be too sugary and leave me feeling bloated. I had to stay in my lane and get just a slight buzz working without going overboard. Again, it was important that I stayed in total control.

I made sure to press my lips firmly against my wine glass, so it left a clear outline of my lips. I found it sexy that gentlemen could glance at my glass and fantasize about what it would be like to have my red lips wrapped around their cocks. I could see a couple of the gentlemen adjust in their seats, surely a sign that things were heating up below the belt.

I slowly sipped my glass of wine and began the tease. I circled my lips with my pinky finger and smiled to myself as I pretended to check my phone. I wanted my admirers to think I may have a pre-arranged rendezvous set up. I increased my vibrations in my pussy by another level. At this point, I could literally feel my juices begin to run down my thigh nearing my ankle. I threw my hair back a bit as a shimmied through my first small orgasm of the evening. I had grown quite adept at being able to have a small one right there in public without anyone suspecting a thing. At this point, I had to decide how my night was going to go. Would I continue to pleasure myself with my vibrating egg accentuating my butt plug that began to tingle in my ass, or would I make my move and send a signal to my George Clooney type in the corner. I decided to dial back my vibrator, because tonight, I was going to open my legs for full pleasure and let this man take me in ways I could only hope to imagine.

With my vibrator back at the base level, I asked the bartender to bring me my check and a napkin. As I settled my bill, I took out a pen and wrote, "Come to room 1032 at 9:00 PM. Be ready to..." and then I drew an arrow to the inside of the napkin. I took out my red lipstick and wrote "Fuck Me" in bright red. Then I slipped my extra room key in there. I called over the bartender again and slipped him a $100 bill and said, "Give this to the gentlemen in the corner in about 15 minutes please". He grabbed the note and began to walk away. As he read it, he did a double take, stopping in his tracks. He turned to come back to me, no doubt hoping to convince me that he should be my prey for the evening. But I had already gotten up and strutted my stuff out of the bar as a flipped my hair back, leaving all the men scrambling to hide the bulges in their pants from their wives.

My Uber Black pulled up. It was a sleek Mercedes Benz with dark leather seats. It was the perfect complement to my leather pants and bra. I slid into the car feeling the squish between my legs. "To the Fairmont", I instructed the driver, as I kicked my vibrator up one notch and threw my head back on the headrest in anticipation of what was to come.

The End of Part 1...