Trust Fund Baby Pt. 01

I never really realized how fortunate I was until I turned thirty. By this time in my life my social circle had morphed from close childhood friends and High School buddies, into one of men that could afford the things that I liked to do. I had nothing against my old circle of friends, it was just tiresome hearing them complaining about being broke, and how much they hated their jobs. It was also getting old picking up the tab, every time we did anything, so it was not surprising that I surrounded myself with wealthy guys, who had a lot of free time to do fun shit.

I was a trust-fund baby, and I was fortunate enough to get my first dividend on my eighteenth birthday. With little parental guidance, and the restraint of a typical teenager, I bought an ocean-front condo in Newport Beach and a bright orange Lamborghini. My car insurance was eight thousand dollars per year, but I just didn't give a fuck.

I did have access to a financial planner, and after I met with him a couple of times, he assured me that the way my trust was set up, would make it virtually impossible for me to run out of money, unless I got heavily into drugs or gambling. In addition to a huge monthly stipend, the trust stipulated cash payouts at five-year intervals, until I turned fifty years old, at which time the balance was available to me.

I didn't spend money because I enjoyed spending it, or even because I enjoyed the lifestyle it provided me. I spent money, solely to try and get laid. Which is why my Lamborghini was fluorescent orange, and my condo was a breathtakingly modern panty-dropper.

I hadn't always been a confident kid, even though I grew up in an affluent neighborhood, and I was reasonably good-looking and athletic. My confidence soared when I had money, especially as I quickly realized that women viewed me differently, once they knew I was rich.

I had a very wealthy uncle that I had always been close to, and after my parents died, he tried to mentor me. His advice often seemed counter-intuitive and off the wall, but the more I followed it, the more I got laid. He was in his late forties, and always had a different young woman hanging from his arm, so it seemed like any advice he gave was probably worth following.

My uncle sat me down shortly after I got my first trust-fund disbursement, and advised me to get a really flashy car, a panty-dropper pad, and a vasectomy. What the fuck? I had just turned eighteen, and he wanted me to get the snip? When I gave him some pushback about the idea, he sat me down and made a compelling argument for it.

"First of all," he began, "I love you like my son, and I would never intentionally give you bad advice. A lot of what I am about to tell you, will make sense when you are thirty. Women are going to want you to have sex with them, because you are good-looking and very wealthy. However, their end goal is for you to impregnate them, so that they can claim child support. If you eliminate that possibility, you can have casual sex with as many women as you desire. In fact, you can tell them that you want to have their babies, and they will let you fuck them more often."

This made no sense to me, at the tender age of eighteen, but I trusted my uncle implicitly.

"What if I meet someone that I want to have kids with?" I asked.

"Then, there are specific steps that you take, in the right order," he advised me. "First of all, you get married with an iron-clad pre-nuptial agreement. Once you are married, and have enjoyed all of the practice sex that you can handle, you get a reversal of your vasectomy. You will need to wait three to four weeks after the procedure to have sex, so schedule a business trip to avoid any unnecessary embarrassing conversations."

"This seems like a bit of a hassle," I said, naively.

My uncle was quite a patient man, and took the time to explain to me how much hassle having unwanted babies with a gold-digger was, compared to his scenario. His last piece of advice?

"Don't have any physical contact with anyone, unless you are one hundred percent certain that they are over eighteen."

One month later, with my vas-deferens severed, and a very realistic fake-ID, I started trolling the bars of Newport Beach in my Lamborghini, with varying success. I had learned much through trial and error, but also took any feedback that was offered, particularly from guys that had game.

For me, I operated at my best level when I was sober and appeared busy. Most socializing in Southern California is done outside, and many bars have outdoor patios, utilizing overhead heat-lamps in the winter months.

I would drive to a bar or nice hotel that had such an outdoor patio, ensuring that my arrival was viewed by the majority of the patrons. I avoided the upscale places, as I wasn't looking for women that were used to dating wealthy guys. They had their own game going on, and it was expensive. I was looking for beautiful women with regular mundane lives and jobs. Airline hostesses, beauticians, nurses, waitresses, women that would view me as a potential way out.

Pretty much anywhere I rolled up to, would end up valet-parking my Lamborghini right up front, which meant I had an audience both when I arrived and when I left. I stayed sober for several reasons. First of all, my car was my conversation starter, and I needed to be able to drive it. Secondly, I found that while alcohol lowered my inhibitions and made me a little more talkative, it also lowered my standards, and I was trolling for tens.

As I mentioned, I had varying amounts of success when I first started bar-hopping. I had no trouble attracting the attention of young women, but most of them were so obviously gold-diggers that it was very off-putting for me. I also got propositioned a couple of times, young girls working their way through college, offering sex in exchange for a few hundred dollars. I had only ever been with two women before, and the financial component, coupled with the expectation that a hooker would have way more sexual experience than me, made the prospect very intimidating. For this reason, most nights I would buy a few drinks for various hot chicks, before leaving alone.

I have fond memories of my first successful night out, even though it was baptism by fire. I didn't have tons of game, hadn't worked out my back-story, unaware that everyone in Southern California had one, and wasn't sure of the etiquette in a bar, having just secured my fake-ID. After I entrusted my Lamborghini to the High School age valet-parking attendant, I even asked for my keys back, such was my level of naivety.

I entered the patio with my phone glued to my ear, having followed my uncle's advice to always appear busy. Like I said, I wasn't brimming with confidence, but I noticed several of the women in the bar were checking me out.

One of them made a move right away, a great-looking older woman, well, relative to me. She was probably in her late twenties.

"I love the color of your Aventador," she opened with, instantly impressing me with her knowledge of exotic cars.

Most women in the Newport Beach area understood the correlation between exotic cars and wealth, some could even tell a Ferrari and a Lambo apart. However, it was rare to find a woman that could identify the model of Lamborghini, without seeing the nomenclature. I was impressed.

I moved my phone away from my ear, and responded.

"Thank you for noticing, you have great taste in cars."

She smiled at me, a smile I would later learn to recognize, signaled availability. After abruptly terminating my phone call, I asked her if she wanted a drink. Her proof of age dilemma was solved by the bartender, who immediately asked us both for ID. Even though I had used my fake ID successfully a few times before, being only eighteen, I handed it over with some trepidation.

Fortunately for me, my ID passed his scrutiny, and after a cursory check of my companion's driver license, the barkeep acknowledged her with a friendly greeting.

"Hi Madison, great to see you this evening."

"George," she said sweetly, confirming my hunch that they knew each other.

We made our way over to the patio, and selected a table in full view of my Lamborghini. Although this was inadvertent, after a post-date debrief with my uncle, he advised me to incorporate this accidental coincidence into my future encounters.

"Rub your wealth in her face," he advised me, "it is why she is sitting with you. Imagine if Madison had sat down opposite you with her legs wide-open, displaying her shaved pussy," he added. "Would have been an incentive to stay focused, no? Keep your eye on the prize, as it were."

We made small-talk and as I got more comfortable, I began to check Madison out. She shared with me that she was twenty-eight years old, originally from Kansas and worked in the Tom Ford store in Fashion Island. I didn't understand the significance of most of this, but after about an hour, during which we consumed two drinks and became significantly more touchy-feely, I excused myself to call my uncle.

"I need to take care of some business," I lied. "Be back in a few moments. Can I get you another drink?"

Madison graciously accepted my explanation, and I went to the bar and freshened-up her drink. George was my barkeep, and in a spontaneous move, which I later incorporated as an integral part of my recon, I tipped him twenty dollars. Well, to be more accurate, I held a twenty dollar bill extended between my fore and middle fingers, inviting him to take it. As he reached out to grab it, I asked him a question, making it clear that the two were related.

"Is she a regular?" I asked, as he tentatively grabbed the end of the twenty.

"In here every night," he responded. "Drinks water until someone offers to buy her something stronger."

I released my end of the bill, ceding possession of it to George. Reaching into my billfold, I extended another twenty dollar bill in his general direction.

"Any other tips?" I asked.

"She is always looking to upgrade her situation," he added, now that I had primed the pump. "She will sit with anyone who is buying drinks, until a better offer comes along. I have only ever seen her leave with two or three guys, wealthy guys, like yourself."

"Thank you, George," I said with true gratitude. "In the future, whenever I order a drink, please make mine alcohol-free."

"You got it," the barkeep responded. "Have a fun night."

I returned to the lovely Madison with her drink, and a bottled water for myself. She was no longer alone, two handsome Newport Beach wannabes, having swooped down on her, the moment I left. I placed her drink on the table, and indicated I would be right back. The two guys barely acknowledged me, intent as they were on picking up Madison. For her part, she was flirting incessantly with them, trying to figure out what they were about.

At first it felt like an affront to me that these two handsome guys were muscling in on my territory. I would later learn that having "game" involves such brazen moves, and that ignoring, or even disrespecting, other men was part of the bar scene. As the two guys leaned in and put the moves on Madison, I called my uncle for an update.

Once I explained my predicament, including my rookie mistake of asking the valet-parking attendant for my keys, he summarized my options for me.

"I will be brief," he assured me. "Listen carefully."

As I listened intently, my wise uncle shared the following tidbits with me. Madison was a classic Newport Beach troll, a beautiful woman with her biological clock ticking, in search of an appropriate father for her first kid. The future strength of the relationship was unimportant to Madison, she just needed a wealthy sperm-donor. The fact that she worked at Tom Ford was probably not coincidental, as selling expensive men's suits would expose her to wealthy potential suitors. The fact that she was from Kansas could also be construed as a positive thing. She probably had no safety-net in California, in terms of family. This might force her to do things that she would not consider in her home town, out of financial necessity. Also, the lack of familial pressure might inadvertently lower her defenses, and make her less virtuous. Don't worry about the Newport Beach guys, unless they suddenly pull out the keys to a Bugatti Veyron, and slap them on the table in an overt show of one-upmanship. Madison has selected her mark for the evening, and you are it, he assured me.

"Anything else, uncle," I asked, soaking up his advice like a sponge.

"Well, ordinarily," he continued, "I would avoid women that can identify exotic cars or Rolex watch models from a distance. They are typically materialistic, often times complete gold-diggers. However, as you are relatively new to the bar scene, enjoy whatever play the lovely Madison gives you. Now is the time to get your keys out," he added. "Cut your losses before you spend any real money."

I wasn't really sure if he meant that it was time for me to leave, or it was time for me to get my keys out, as if to signal my intent to leave. Either way, it was time for me to get back to Madison, and as I approached her table she was fully engaged with the handsome Newport Beach guys. One of the guys was in full cock-block mode, having taken my seat and having placed his hand on Madison's wrist, in order to display his Rolex.

I felt completely out of my league, an eighteen year old boy, in a bar amongst seasoned players. However, I trusted my uncle implicitly and followed his direction.

"I should probably get going Madison," I said politely, as I extracted the keys to my Lamborghini from my jeans pocket. "I have a busy day tomorrow."

I placed the keys to my Aventador on the table, and picked up my bottled water to finish it up, before I left. Lamborghini keys are not particularly distinguishable from other exotic-car keys, but my two male table guests observed the raging bull insignia emblazoned on the front of it, gave each other a nervous glance, both reflexively eye-balled my orange Lambo and threw their cards in. As if to acknowledge a losing hand in a high-stakes poker game, they folded and said their goodbyes.

The younger one, broke from his persona of a player for a few seconds, to ask me about the color of my car.

"Arancio Argos?" he asked me, looking every bit like a fanboy instead of a successful Newport Beach businessman.

"Good eye," I said, throwing him him a bone, in the form of a compliment. "You know your exotic cars."

Turning my attention towards Madison, I extended my hand to help her out of her seat.

"Shall we?" I offered, my heart beating as I stepped out of my comfort zone. "Are you up for a nightcap?"

To my relief, particularly as my sticking my neck out had an audience, she started to rise from her seat.

"I would love to," she said graciously.

As her slender, toned frame got up from her seat, I observed her with a critical eye for the first time. Make no mistake, short of discovering a penis between her legs, or a hairy chest, there was no way I was going to change my mind, but it was reassuring to me that she appeared to be a spectacularly put together woman. Madison was about five feet nine inches tall, maybe one hundred and twenty pounds, perfectly sculpted from hours in the gym, and a borderline starvation diet.

Madison was wearing a skin-tight stretch-satin dress in a beautiful shade of peach, that perfectly accentuated her curves, and was extremely flattering on her. In her high heels, which I would later learn were Christian Louboutins, she was actually taller than me, which my uncle had already warned me I should get used to, as a wealthy playboy. Her long blonde hair was perfectly straight, and judging by the length of it, had the addition of hair-extensions. Her make-up was impeccable, professionally done for sure, accentuating her youthful appearance and at the same time making her look very desirable. She had scented herself just as we left the bar and smelled intoxicating.

Under normal circumstances, this woman was way out of my league, but as we headed towards my car, it was evident that our vastly different agendas were on a collision course.

My Aventador looked very intimidating, parked front and center with the fog-lights on. To my surprise, Mr. Cock-block and his friend followed us over to the valet-parking area, and asked for a photo next to the car. For the first time that evening, I felt like a baller. Not only had I had vanquished my competition for the lovely Madison's attention, but they had followed me to my car, like a couple of fanboys.

I allowed the two young Newport Beach guys into my Lambo, and Madison and I embraced as we watched them like kids in a candy store. Once the photos were taken, Madison couldn't help kicking the Rolex guy in the nuts.

"Do you go to Tijuana often?" she asked, "I recognized the Rolex from the Mexican watch guy."

"Ouch!" his partner in crime exclaimed. "I told you the Newport Beach babes would see that your watch was fake."

With that, our two wannabes bailed, and Madison waited by my passenger door, to be let into my car. The valet-parking attendant came round to where she was waiting and fumbled with the door handle trying to open the scissor door. After a couple of failed attempts, I started around the hood of the car to show him how it was done. Before I got there however, Madison reached down, pressed the door-release button, embedded within the handle, and pulled directly upwards, thus opening the scissor door.

I reached her right as she was leaning forwards to get into the car, and we exchanged a knowing look, as I realized that this was not her first ride in a Lamborghini. Getting into a Lambo is not as easy as it looks, and in a skin-tight dress, it is a challenge to look graceful. Madison, extended one of her shapely legs over the low door-sill, causing her satin dress to cling tightly to her lithe frame and expose the straps of her garter-belt.

I hadn't been around a lot of women in my life, a few girls maybe, but none of them had been as sophisticated and alluring as Madison. I didn't want to stare but I couldn't help myself, and as she shimmied to get into the low-slung exotic car, I was treated to the sight of her tiny thong, nestling between her tight buns, under her satin dress. My cock responded to the visual treat, throbbing in my pants with desire.

As the dress was stretched tight over her lithe frame, I had fantasies of bending her over the hood of the Lambo, and fucking her doggy-style in her lingerie. Once Madison was safely ensconced in the deep bucket-seats, she flashed me a broad smile, her perfect white veneers contrasting with her tanned skin, and gave me the thumbs-up signal. I closed the door behind her, and got into my side of the bright-orange exotic.

As much attention as the car garnered when it was sitting in the front of the restaurant, once I fired it up, a small crowd circled around us. The car was so loud, modified as it was with an Akrapovic exhaust, that magnified the cacophony of the V12 engine. Even in Newport Beach, where millionaires are ubiquitous, the sight and sound of a brightly-colored Lamborghini still evoked a response from the predominantly, young male crowd of onlookers. Several of them had their cell phones held aloft, documenting the scene of a young man leaving with a breathtakingly beautiful woman, in a tight dress.

Madison was lapping it up, enjoying the jealous stares of the late-teen and early twenty aspiring models, who thought that they deserved to be in the car with me. That night started me on the road to total self-confidence, and it all began with that first successful foray into the bar scene. As we pulled out of the parking lot, I looked across at Madison. She looked flushed, excited even, the prospect of a life without having to work seemingly flashing through her mind. She had hiked her dress up, under the pretense of entering the low-slung car, but it also served to let me know that her garter-belt and her panties were the same shade of peach as her dress.