In retrospect, my sexual encounters with Madison and Olivia were kind of a baptism by fire. Within forty-eight hours, I went from having had very limited sexual experience to checking off nearly all of the items on my sexual bucket list. As an eighteen year old boy, my sexual fantasies were shaped by my exposure to pornography, and revolved around the standard adolescent male dreams of blowjobs, doggy-style sex and threesomes.
Years later I would come to learn that there is a continuum of increased depravity as far as sex goes, but as a sheltered teenager, I couldn't really imagine anything further than my current desires. It didn't go unnoticed though that despite my rapidly expanding sexual experience, the one thing that I dreamt about was Madison getting used in the back of the limousine by two paying customers.
It was this image that kept me rock-hard all night, and when I jerked off in the morning, it was the thought of her on her knees on the plush carpeting of the stretch limo that made me blow my wad all over her silky panties. I had cuckold fantasies without even being aware that such a sexual proclivity existed.
Even though I had enjoyed a fantastic night with Olivia, my thoughts always returned to Madison when I was alone. Maybe it was because she was my first experienced sex partner, or perhaps because I found her so fucking irresistible, but I found myself fantasizing about her whenever I masturbated. When she didn't appear on the patio of our bar for three nights running, I decided to show up at her work and see if she had any interest in dating me.
I felt the ten-year age difference every time I saw her. She just seemed completely out of my league, so much more worldly, sophisticated and mature than me. I know that the outside world saw me as a catch for her, inclined as it is to focus solely on the financial component of relationships. When I pulled up outside the Tom Ford store in my orange Lamborghini, there was a palpable stir in the valet-parking area. The upscale men's clothiers attracted wealthy clients, but a Lamborghini Aventador is such an overt display of success, that it took things to a different level.
I felt nervous as I approached the entrance to Madison's work place. I saw her the second that I approached the store front, an impeccably groomed woman on her knees, adjusting a distinguished looking man's hem, his erection clearly visible in his three thousand dollar suit.
To the uninitiated, it appeared to be the typical power dynamic between a wealthy man and a beautiful sales clerk. However, I knew Madison deserved better than this. Part of me wanted to storm in there and break up this unsettling visual, but Madison would have been pissed at my intervention. Her submissive persona around the wealthy men who could afford Tom Ford suits undoubtedly increased her commissions, but it was being the object of their desire that floated her boat.
Madison would never have admitted it, but she loved seeing an older man develop an erection as she adjusted his collar like a dutiful girlfriend, or knelt before him to hem his pants. They all desired her, wanted to possess her, even if for just one evening, but she just wanted one of them to impregnate her, and most were wise to her game. Surely, she must have noticed, as word of her hidden agenda circulated around Newport Beach, that these older wealthy locals were only interested in oral or anal-sex with her, as they tried to ensure their lineage wasn't extended by Madison.
When I entered the store, she looked up, and we locked eyes, albeit for a few seconds. Madison's achingly beautiful blue eyes peered up at me through her perfect blonde bangs, and she smiled at me. Seconds later, she averted her gaze, concentrating her attention back on her wealthy client. After she had pinned the hem of his pants, she made no attempt to get up from her knees, remaining demurely at his feet, with her palms flat on her lower thighs, as she looked up at him adoringly. They spoke like this for several moments, Madison hanging on his every word, before he finally extended his hand and invited her to stand, thereby controlling every part of their interaction.
Once she was on her feet, standing way too close to him for normal social contact, he placed one hand on her lower back and she allowed him to escort her to the cash register. She rang up an impressive array of suits, shoes, shirts and accessories before he handed her a Black American Express Card. His hand rested on the small of her back, just above her upturned butt-cheeks the whole time.
"Thank you, Mr. Clarkson," she said seductively, as she took the coveted Black card from him, her perfectly manicured nails highlighting her femininity.
"You are welcome babydoll," he responded condescendingly, seemingly enjoying her submission to him.
His hand had moved to her ass now, and I watched jealously, wondering if he could tell she was wearing a garter-belt under her bespoke suit.
He seems very comfortable manhandling my girlfriend, I mused, before terminating that train of thought. Whatever history Madison and I had, she definitely wasn't my girlfriend, nor was I about to allow that to happen. Madison and the older guy were flirting incessantly now, stoking my jealousy as I watched her playfully engage with him. He glanced at me a couple of times, seemingly trying to size up my relationship with Madison. Her relaxed demeanor towards me, coupled with the fact that she had made no attempt to engage me as customer, was a clear indication that I was either a current, or potential, boyfriend. Once he had signed the receipt, he asked her to help him carry his purchases to the car.
This seemed a little unnecessary, as he only had four or five bags of newly acquired clothing, but Madison seemed delighted to help. There were no other customers in the store, which is fairly typical for high-end men's clothiers, that often work on an appointment only basis. Besides, I was there, and could greet any other customers that happened to walk in. Madison and her older friend walked towards the front door of the store with his packages in tow, and he held the door open for her, as if they were on a date.
She flashed him a broad smile and he made eye-contact with me and smirked at me. Then he followed right behind her, casually resting his hand on her ass as they walked towards his car. I watched intently to gauge the level of intimacy in their interaction, but also because I was very curious what car he drove. They ended up standing next to a beautiful Lipstick Red Porsche Cayenne SUV, and even though it was brand new, as evidenced by the Newport Beach Porsche dealer inserts in the license plate holder, it felt like a victory having pulled up in my Aventador.
In fact, part of me wanted to go out to my car under the pretense of getting something from it, just to let him see that I was a bigger baller than him. Years later, as my wealth increased exponentially, from both the continued access to my trust-fund, and some phenomenal investments that I was advised to make by my financial consultant, I realized that the overt display of wealth through cars, boats, watches and other similar accoutrements, was something that older guys often grew out of.
However, at the tender age of eighteen, with my self-confidence growing daily, my car was a huge part of my identity, and a bright Orange Lamborghini Aventador clearly trumped a Porsche SUV. This confidence that I was the better man because I had the more expensive car, was one of the reasons that it felt like such an affront when I saw them flirting incessantly within the open driver's door of his SUV. He whispered something in her ear, which made her throw her head back and laugh. Then Madison leaned in and kissed the older man. It wasn't a Euro-style kiss on the cheek either, but rather a very sensual open-mouthed kiss on the lips. She made no attempt to hide it from me either, and if I hadn't know better, I would have thought it was designed to make me jealous.
Truth is, it was an attempt on his part to make me jealous, and he was succeeding. He was leaning against the side of his driver's seat and she had moved herself between his open legs. They appeared to be dry-humping as they made out, although I didn't think that Mr. Clarkson was going to blow his load in his tailored pants the way I would have done under her sensual advances. They parted lips after several moments of passionate kissing, and he looked over her shoulder and smirked at me, enjoying my jealous reaction. Clarkson whispered something in her ear and she looked directly at him and nodded her agreement.
Then in a move that was equal parts sexy and flirtatious, she slung her handbag over her shoulder, and walked around the rear of his SUV, getting in the passenger seat, as he looked smugly at me. After she closed the door he entered the vehicle and pulled his door tightly closed. The rear three windows of the SUV had a light tint applied to them, but in the bright Californian sunshine, I could clearly make out their silhouettes. I watched in despair as they leaned towards each other and continued to kiss.
There were still no customers in the Tom Ford store, so I had moved towards the front door to gain a better vantage point. A few seconds later I recoiled as I saw Madison's head disappear from view, slowly descending into his lap. What the fuck? Were they messing with me?
Unfortunately, I got my answer almost immediately as Clarkson put his right arm around the passenger head-rest, and reclined his head back on his own leather support. If I had any doubts about what was happening within the cabin of that sumptuously appointed Porsche, they evaporated as the car began to rock gently. Madison was apparently giving the older man a blowjob, and he took way longer to come than I did when Olivia had performed fellatio on me.
Madison sucked the older man for several minutes, until he finally threw his head back and grabbed the passenger head-rest with his right hand. After he ejaculated, she remained in his lap, hidden from my view for several moments more, until her silhouette finally reappeared in the rear window of the SUV. She didn't seem in any hurry to leave his car either, as she used the vanity mirror to reapply her lipgloss. Finally, after several minutes of post-orgasmic small talk, her car door opened and she emerged from the Porsche looking picture perfect.
As she walked back towards the Tom Ford Store, she had her handbag in one hand, and a large La Perla shopping bag in the other, presumably a gift from Clarkson. She never looked back as she walked seductively into the store, and she approached me to greet me.
