Trust Fund Baby

I couldn't tell if Madison was genuinely out of it, or if she was fucking with me, but as she continued being evasive, completely avoiding direct answers to my incessant questions, I decided to take a different approach. The half-smoked cigar in the ashtray in my bedroom, and the men's briefs over my shower were not particularly incriminating, in and of themselves. Even the used rubbers only proved that somebody got their rocks off, although with Olivia and Jody both actively working as escorts, it made sense that it was with one of them.

It was little disrespectful, yes, but if someone had fucked Olivia, or enjoyed a blowjob from Jody, before taking a shower and then relaxing with a cigar, it wasn't the end of the world. If I was honest with myself, it was exactly what I would have done had I been left alone in Clarkson's or Baldwin's house, with a hot chick. Those guys were masters at the art of mind games, and so I decided to ignore the not too subtle clues.

That didn't last long, my jealous streak surfacing to torture me, as I kept imagining Baldwin and Clarkson team-tagging my girl in the shower, before one of them relaxed in my bed with a cigar, as Madison sucked him to a second orgasm. Eventually, my curiosity overwhelmed me, and I decided to check out the security tapes from my CCTV system.

Even though I had plenty of time on my hands, I wasn't planning to watch the security footage in its entirety. My condominium had several high-definition 4K cameras situated throughout, ensuring that there were no blind-spots anywhere within my extensive living space. My plan was to fast forward through the tapes, stopping only if I saw something titillating.

Madison was a very manipulative woman, and the thought of her freshening up drinks for the wealthy guys, dressed in a Patriots Cheerleader Uniform, as they shuffled uneasily in their seats, trying to control their erections, was amusing to me. Knowing her, she would get the guys horny, and then offer the two young working girls as an outlet for their release, all the while splitting the tips three ways, as they had agreed.

My first insight into the party was from my front door camera, which had captured the guests coming up my driveway. While I couldn't clearly identify all of the attendees, they arrived within a few minutes of each other, and I recognized a couple of the cars. As I watched Baldwin's LaFerrari pull into my entryway, it seemed like the dick-swinging contest had already started. That prick owned at least a dozen cars, and he had to show up at my place in the car that Madison sucked him off in.

There were a couple of McLaren exotics, Clarkson's bright red Porsche, and another Lamborghini Aventador. As impressive as it was in White, it looked muted compared to my eye-ball searing Arrancio Argos, bright Orange car. Two unidentifiable men arrived in a limousine, and the driver waited in the car as they entered my place. Shortly after that I switched to the interior cameras.

Once all of the guys were seated, Madison, Olivia and Jody emerged into the open living area. To my surprise, all three of them were identically dressed in Trashy Lingerie Cheerleader Uniforms, although while Madison was wearing her brand new Patriots colors, Olivia and Jody had been dolled-up in the Green and Gold of the Green Bay Packers.

Even though Madison totally rocked my world, and I couldn't imagine having a more fulfilling sex-life, I was an eighteen year old boy, and as such, I craved variety. As I admired Jody from afar, I began to imagine getting balls-deep in her tight, teenage pussy. She truly was a stunning young girl, and I found myself comparing her to my girlfriend. Other than the difference in the colors of their respective teams, they appeared to be dressed identically. They looked absolutely phenomenal, every man's dream of how a Super Bowl server should appear.

There was one other difference between Madison's new Patriots' uniform and her old Green Bay outfit, the deletion of the number 69, that had been embroidered in several places in honor of my favorite player, David Bakhtiari. Inexplicably this had been replaced by the number 68, which was of no special significance to me. I still had the program for the game in my possession, and a cursory glance at the roster confirmed that the Patriots didn't have a number 68 on their squad. Jody and Olivia also wore the same number, and Baldwin was the first to remark on it.

"Gentlemen, you may notice the inclusion of the number 68, neatly embroidered on several places of the Cheerleader Uniforms," he began. "Madison's boyfriend initially used the number 69, which was both an homage to his favorite Packers' player, and a lazy double-entendre, which he no doubt felt made him seem more worldly," he added, to a smattering of laughs.

"What is the meaning of 68, you may ask yourself?" he continued. "It is also a play on words, albeit a more sophisticated one. Just as the number 69 depicts simultaneous oral-sex, 68 is a more accurate description of what is on our menu for today. Jody?" he said quietly, leaving the literal translation up to the youngest member of Team Baldwin.

The angelic blonde stepped forward, and with her practiced innocence completed the explanation.

"68," Jody said demurely. "I'll blow you, and you can owe me one."

"Perfect explanation Jody," Baldwin said condescendingly. "Good girl."

Jody was beaming as she went and stood next to Baldwin, and he rested his hand on her ass, and gave it a playful squeeze.

Other than the host, I really had no clue who the male attendees would be at this party. Based on what Madison had told me, there were going to be twelve or thirteen guys that I knew, in some capacity or another. The Newport Beach millionaires are a fairly tight group, particularly the ones with enough time on their hands to be hanging out with hookers on Super Bowl Sunday. A lot of the successful guys in town were happily married, but these guys were perennial bachelors, or married guys that hadn't allowed the sanctity of marriage to prevent them from continuing to be cock-hounds.

As I scanned the room of salivating men, I did recognize a few of their faces, guys that I had met at exotic car shows and at charity functions. Steve Baldwin continued to be front and center, holding court like he owned my fucking place, which was annoying because the last time I saw him, he had commandeered my girlfriend for the night. Right by his side was Clarkson, co-conspirator of this event, which pissed me off.

Evidently not content with a monthly cock-worship session from my girlfriend, he had decided to join the party, presumably to see what else was on offer. Knowing that he was worth tens of millions of dollars made me a lot more jealous of him, and I made a mental note to fast-forward through the parts of the video that he was involved in.

There were a couple of men that I recognized as being very generous patrons of the Orange County Performing Arts Center, their portraits prominently displayed at the venue and all over the website, for their philanthropy. I knew one was recently divorced, and I suspected he might be pushing for extras from the three Cheerleaders.

My next major surprise was seeing the Doctor that had administered my STI tests there. I hadn't seen his late-model Toyota Camry enter my driveway, so maybe he rode with one of the other guys. Any questions that I had about his unlikely inclusion in this exclusive group evaporated once Madison introduced him.

"I hope you enjoyed the limo, Doctor," she said cheerfully, as he shook hands with the guys.

"It was fantastic, Madison, thank you," he gushed appreciatively. "What a way to arrive."

Once I had established that he was there at Madison's request, and had arrived in a limousine that I had apparently paid for, things made even less sense.

He was obviously there in some official capacity, because he was wearing his scrubs. However, as he circulated and made small talk with some of the guys, it was evident that he had an erection. I am not sure what kind of payment plan that he had negotiated for his services, but he was clearly excited at the prospect of what was in store for him. At some point I realized that he had his medical bag with him, and as he kept leaving the communal area accompanied by a single male guest, it occurred to me that he was conducting live STI testing.

I switched cameras immediately upon this revelation, and as I zoned in on my third bedroom, I watched him administer a full battery of STI tests, to an older man that I didn't know. The results were almost immediate, and the Doctor gave the guy an enthusiastic thumbs-up.

"You are good to go, buddy," he said cheerfully, as he stamped the guy's forearm with indelible ink. "You can get balls-deep in whichever available orifice you desire."

I wasn't sure if I had heard that last remark correctly, so I rewound the tape for twenty seconds, and began to question what the expectations were, once I realized that it was exactly what the Doctor had said. I watched two more older guys enter the bedroom, undergo the brief testing procedure, and get the green light.

When I switched back to the footage from the open-plan living area, I was surprised to see that George, the bartender from the patio bar, was there. I guess it made sense for Madison to hire him to dispense drinks, as he was a known and trusted entity, and I didn't have any concerns about having him in my house. My ambivalence about his presence soon dissipated, as the Doctor returned to the main living area, and invited him to get his STI testing done.

George certainly didn't fit the demographic of the rest of the guys at the party, as he was a minimum wage barkeep, hustling for tips. However, as he emerged from the testing room with a big smile on his face, and a visible ink mark on his forearm, I realized that he wasn't there for his ability to make cocktails. It occurred to me that Madison had invited him there, in order to make good on her promise to hook him up, after he fabricated the story about her and the two Asian guys in the limousine.

I didn't understand the need for privacy with regard to the STI testing, particularly as there was some healthy banter going on between the guys. As Madison, Olivia and Jody worked the room taking drink orders and lighting cigars, I came to the realization that the three of them were blissfully unaware that the guys were being tested. This was my first clue that the guys and girls had disparate expectations for the evening, the girls expecting a little frivolity and the opportunity to earn some tips, while the guys were planning on enjoying as many of the nine available orifices as possible.

Even though it was Steve Baldwin's party, in this room full of Alphas, it was anyone's guess as to who would be the first to assert themselves, and attempt something out of line. I had to trust Madison to keep the men in check, although with ten grand each for the girls on the table, I figured that they would cut the guys some slack.

It was a very light-hearted start to the festivities, as the guys enjoyed the pre-game show. Someone suggested a football pool, and everyone wanted to play. I had heard about these before, although I had never participated in one, as they were normally an inter-office affair, and I had never worked a day in my life. Using a board with one hundred squares, each participant purchases one or more of them until they are all spoken for. Typically, one or two dollars per square, the winner is determined by the score at the end of each quarter. Of course, with a room full of wealthy Alphas looking to impress the girls, the betting didn't stay at two dollars per square for long.

In fact, as they sought to one-up each other, the stakes reached five hundred dollars per square, before Madison suggested that there was enough money at stake for it to mean something. All of the squares were quickly snapped up, and even George joined the game, although being in a different league financially than the rest of the guys, he reluctantly parted with five hundred dollars, buying just one square, which put his odds of winning at just one percent.

With fifty thousand dollars available between the four lucky winners, the guys had made their point, and it was the girls who appeared to be salivating, at the ease with which the guys parted with their cash. I watched on fast forward as the girls freshened drinks, flirted incessantly, and generally made themselves available to cater to the wishes of the older men. As the alcohol flowed freely, lowering the inhibitions of the assembled crew, I was aware that they were a bit more touch-feely with the Cheerleaders. Continuing their flirtatious behavior, Jody sat sideways on Baldwin's lap, their prior sexual history removing any awkwardness between them.

Despite their forty year age difference, they were being very amorous, and he kept whispering in her ear, no doubt encouraging her to give him a little extra play. Recognizing that he was one of the Alphas of the group, and having already witnessed his capacity for financial assistance, Jody played along with him, and her hand kept disappearing into his lap, where I assume she was teasing him through his linen pants. He had one hand on her knee, and she offered him no resistance as he moved it slowly up her toned leg, until it disappeared under the hem of her Cheerleader skirt.

She let out an audible gasp at one point, followed by an embarrassed giggle, but still made no attempt to slow his roll. In fact, she parted her thighs slightly to accommodate him, and her eyes widened moments later in response to whatever the hell he was doing. His hand was hidden beneath her pleated skirt, but judging by the look on her face, he was pleasuring her with his fingers. Not in the way that young, inexperienced college guys clumsily finger-bang chicks either, but rather a sustained stimulation of her clitoris that was having the desired effect on her.

She dropped her head to his shoulder, and let out another gasp of pleasure as he continued to toy with her. No-one was paying much attention to Baldwin as he felt Jody up, but as I watched the security footage, I felt like he had her on the road to orgasm. Then, inexplicably, he withdrew his hand from under her skirt, as she lifted her head from his shoulder, and gave him a disappointed pout. He raised his middle finger to her youthful face, and smeared her vaginal secretions across the tip of her cute upturned nose.

As I processed the fact that he had been knuckle-deep inside this goddess, she parted her lips slightly, and took his moist finger into her mouth. It was extremely arousing to watch her suck her own juices from his fingertip, and as she closed her lips around it, he wrapped his other arm possessively around her, as if he was staking his claim.

Even with the most casual observation of the scene, one would have quickly established that with three young girls and thirteen men, there would be no staking claim this evening. A certain amount of sharing was inevitable, particularly because Madison was solely there to stoke libidos and facilitate the sex-acts, rather than to actually participate herself. Right before kickoff, Jody scooted off of Baldwin's lap, and after a final refresh of the drinks, the three seductively attired Cheerleaders knelt in the middle of the floor awaiting further instructions. The change in their attitude was palpable, almost as if they were conveying a unified message that the complimentary flirting was over, and any future contact would need to be paid for.

I fast forwarded the security footage through the first quarter as the action in the room didn't warrant a second look. The Cheerleaders remained on their knees, arising periodically on request to fetch ice, or replenish snacks. Given the choice I would have taken Madison, as our chemistry is off the charts and she embodies everything that I find sexy in a woman. However, Jody was an incredibly beautiful young girl, a lithe blue-eyed blonde with an undeniable sex appeal, and as I watched the way she moved, I began to fantasize about her sucking my cock.

She was one of those rare women that had the natural foundation to be an absolute goddess. In fact, if one of these millionaires had taken her on as a project, and was willing to invest the money into her surgical improvement, she could have been a Newport Beach ten. She had a great attitude too, being an out of state runaway, with diminished expectations and a willingness to please a man, in exchange for a roof over her head.

Years later, after I dumped Madison, Jody was exactly the kind of girl I gravitated to. Blonde, young, recently arrived in Southern California, with no family, friends or safety net, often fleeing an abusive partner or toxic family situation, and just looking for a soft place to land. I offered that in spades, my ever-improving financial situation affording me the opportunity to spoil young women, in exchange for unlimited access to all three of their holes.

Even though I always stayed right on the water in Newport Beach, as my monthly trust-fund disbursements increased, I upgraded my living arrangements numerous times, until by the time I was in my late twenties, I had a fifteen thousand square foot mansion sitting on the sand. I often had two or three eighteen year old runaways crashing there, and found that allowing multiple girls in my house simultaneously, reduced the demands on me for my time, as they tended to amuse themselves as a group. However, after the sun set over the Pacific Ocean, and bedtime loomed, healthy competition ensued, and I would find myself getting promised all kinds of delights in exchange for sharing my bed with one of them.

I was in my late twenties, a multi-millionaire, my self-confidence having grown from years of positive affirmations from young women. I had my premature ejaculation under control and considered myself a capable lover. For this reason, even though I listened to their impassioned pleas with open ears, most nights I simply invited all of them to join me in my massive custom-made bed. I was still an aficionado of rim-jobs, and having three young women in my bed afforded me numerous options to bust a nut, while having a young girl's tongue buried in my asshole.

Olivia remained a close friend of mine for much of my twenties, although we stopped having a sexual relationship by the time I was twenty-five. I still took care of her financially, her relatively simple needs costing me less than four thousand dollars per month. For my fifty grand a year investment, I got access to her wealth of experience dealing with the endless stream of teenage runaways that flooded into Southern California in search of fame and fortune. The Golden State has done a fantastic job of marketing itself as the land of opportunity, and this endless self-promotion induces thousands of young women each year to relocate to this sun-kissed paradise, often arriving with little more than the clothes on their back.

Olivia knew the places that they gravitated to, and as a twenty-something goth chick would quickly gain their confidence. Of course, I was competing against numerous charities that actually gave a fuck about their welfare, but these places required the young women to abstain from drugs and alcohol, in order to be admitted. By contrast, I only required the women to be cute, and as the predominant lure of Southern California was show-business, which attracted models and aspiring actresses, there was no shortage of beautiful women knocking on my door.

I let them in unconditionally too, offering them a welcome package that included a toothbrush, some female sanitary products, and some ridiculously expensive LaPerla silk pajamas. After a good night's sleep, which for the majority of them was the first in months, I joined them for breakfast, where I would make it abundantly clear to them that I wanted absolutely nothing in return for my largesse. That they were welcome to stay with me until they got back on their feet. That I wanted nothing more than their well-being.