Trust Fund Baby Pt. 02

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.

"Nice Porsche," I said, lost for words but trying to stay cool and to contain my jealousy.

"Brand new," she taunted, as if she was trying to get under my skin. "But it's not an Aventador," she added with a giggle as she approached me and hugged me warmly.

My body reacts a certain way to Madison, and there is nothing I can do to prevent it. Today was no exception, and as soon as I smelled her pheromones, my cock hardened. She noticed immediately, and chastised me.

"You are such a little boy," she said condescendingly. "No control of your bodily functions."

"Hi Madison," I responded, "nice to see you too. How have you been?"

"Living the dream," she joked. "I just made four hundred dollars commission for spending fifteen minutes on my knees in front of a wealthy older man."

I knew she was joking but her attempt at humor stirred my jealousy immediately, and it didn't feel good at all. Particularly as she seemed to gloss over the fact that she had given him a blowjob in his brand new Porsche.

"I looked for you in the bar," I said weakly, laying all of my cards on the table.

"I heard," she teased. "George told me that you came in the next night and were a good boy. However, when I wasn't there two nights in a row you left with that skank Olivia?"

I shuffled around uncomfortably, feeling a mixture of guilt and stupidity at my decision to fuck Olivia.

"It's okay, baby," she assured me. "Relax, you are a wealthy young guy, you should play the field."

I wanted to tell her that I loved her and I didn't need anyone else, but we were in different phases of our life, and she apparently didn't feel the same way.

"Did you lay the pipe to Olivia, too?" she asked. "How much did she charge you?"

I must have had a confused look on my face, because Madison laughed and started back in on me.

"Everybody knows she is a working girl, baby," she said. "You have the pick of Newport Beach, and you choose a hooker," she taunted me.

Madison and I continued our flirtatious banter, interrupted only by the arrival of her boss just before noon. She informed me that she was about to go to lunch, if I wanted to join her. I accepted immediately, asking her where she would like to go, but she told me to follow her, and we ended up in the employee lunch room.

Employee lunch room was a bit of a misnomer, it was actually a store room, with a microwave in it, which was adequate for that particular branch of Tom Ford, as it only had two employees, Madison and the Store Manager. I was very comfortable with Madison, and I sat on one of the dining chairs by the microwave, as she bent over at the waist and rooted through the fridge.

Madison knew I had the hots for her, and never missing an opportunity to tease me, she hiked up her skirt, and lowered herself onto her knees by the fridge. Looking over her shoulder she asked seductively.

"Do you see anything you fancy?" knowing full well the spell she cast on me.

I arose tentatively from the dining chair, my erection tenting in my pants, the curse of being eighteen years old, and perpetually horny. As soon as I reached where Madison was kneeling she turned to face me, her lips inches from my cock. For a few moments, I fantasized about her blowing me, but then I remembered our disparate agendas, and her desire for me to impregnate her. I felt guilty knowing that we were about to fuck, Madison undoubtedly hoping that this would be the time that I inseminated her, while I was safe in the knowledge that my vasectomy would prevent such an unwanted occurrence.

Madison must have seen the lust and desire written on my face, because she cut me some slack, on her knees in that lunch room. She extended her dainty fingertips to my crotch and caressed my throbbing erection through my pants. I let out a whimper of pleasure, which she took as consent. She moved her manicured nails towards my zipper, and slowly undid my jeans.

Knowing that she had just blown Clarkson made me stiffen involuntarily, and Madison looked up at me for clarification.

"Can I suck you off, baby?" she asked with a practiced innocence.

I wanted Madison to give me a blowjob more than anything at that moment, but my uncle's words of wisdom about using protection to prevent catching a sexually transmitted infection were ringing in my ears. Before I could censor myself I blurted out my concerns.

"Do I need a condom, Madison?" I began. "Clarkson..." my words trailed away.

"I don't have unprotected sex with other guys," she assured me. "Clarkson wore a condom so that you don't have to. You never have to with me," she continued, "for oral, vaginal or anal."

Like I said, the thought of getting a blowjob from Madison was top of my list of priorities, and as soon as the perfunctory objection was voiced and responded to, I was good to go. I nodded my head meekly and she removed my erect cock from my underwear.

Then, as I looked on in adoration, Madison took my cock-head between her lips, and started to gently suck my cock. Her mouth was warm and inviting, and the way she bobbed her head ever so slowly up and down my shaft, as she looked up at me with her baby blues, made me want to come almost immediately.

"Madison, I am not going to last long," I whispered hoarsely, "You are just too beautiful for me to resist."

Madison smiled up at me, as if to give me consent to come in her mouth, and a few seconds later I erupted with a roar, and blew my load between her lips. My legs were shaky beneath me as I emptied my nutsack, and I looked down admiringly at Madison as she fulfilled one of my fantasies. After I composed myself, she arose slowly from her knees, adjusted her skirt and gave me a peck on the lips. I watched to see if she spat my semen into the sink, but she had already swallowed my load.

We ate a light lunch of cheese and crackers, and before long, our conversation took an embarrassing turn.

"That reminds me," Madison began, "I left a pair of La Perla underwear at your house. Can I pick them up after work? I don't want a skank like Olivia stealing them. That is a $135 pair of panties."

"I took them to the dry-cleaners," I lied, embarrassed that I had jerked off on them multiple times. "I will pick them up tomorrow for you."

"Ok, don't forget," Madison instructed me, "I only have a few pairs in that color."

"A few pairs?" I asked incredulously. "How do you afford underwear that expensive, Madison?"

"First of all," she said, "you shouldn't ask questions that you might not want to hear the answer to. That said, my La Perla underwear, like almost everything expensive that I own, were gifts from men. You, young man, should only have one question when it comes to my underwear," she teased, pausing for effect.

"Which is?" I asked, my cock twitching in my pants, as I considered the only reason why a man would buy a woman underwear.

"Do I have enough sexy underwear that you and I could fuck every day, and you would never see the same panties twice? And, the answer is yes," she said with a giggle.

That was all I needed to hear. Madison was a sexy bitch and she knew how to get into my head. She reached over and grabbed my cock through my jeans, and upon learning that I was hard again, she reached under her skirt, grabbed the waistband of her panties, and pulled them down over her knees. As soon as her panties hit the floor, she handed them to me.

"Dry clean these too," she told me. "Blowjobs make me wet."

I took the silky panties from her as I processed her words. I would have preferred to hear that giving me a blowjob had made her wet, but the way she had phrased her physical reaction to oral-sex, made me question whether blowing me or Clarkson had made her self-lubricate. She seemed to enjoy keeping me in the dark, as far as her true feelings towards me.

Madison scooted forward until she was up against a pile of boxes, that extended from the floor to about waist height. She leaned forward, supporting her weight on her forearms, and wiggled her ass.

"Hike my skirt up," she invited me, "and blow your load inside me."

I ended up fucking Madison from behind, over a box of Tom Ford shoes. I am not sure how comfortable she could have been bent over the way she was, but to my surprise she ended up having two very vocal orgasms.

Hearing her squeal and cry out with pleasure did wonders for my self-confidence and I began to wonder how I compared to some of her other lovers. Even though I was just eighteen years of age, I was apparently blessed with a large cock and the ability to get Madison off whenever we fucked. As sexually inexperienced as I was, I was just beginning to discover what turned me on. I closed my eyes and recalled the image of Madison's head disappearing into Clarkson's lap as she thanked him for his continued patronage.

As I pictured her sexual encounter with Clarkson, I felt a tingling deep in my nuts. To my horror, the idea of her with another man aroused me, and I involuntarily shared my thoughts.

"Does Clarkson have a big cock too?" I asked shyly.

Madison was a seasoned courtesan and wasn't going to be shocked by the inner workings of my mind, no matter how depraved. She had seen and heard it all before, and knew instantly how to react to my fantasy.