Trust Fund Baby Pt. 09

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Madison forces Olivia to service four black guys.
20.8k words
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Part 9 of the 16 part series

Updated 06/10/2023
Created 05/12/2021
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As the day of Olivia's dreaded date with Maxwell dawned, I felt increasingly sorry for the young girl. The morning was heavily scheduled, as a team of beauticians and hairstylists descended upon my home, to completely transform Olivia. When they were done with her beauty treatments, which included a full Brazilian Wax, hair extensions, a complete set of acrylic nails, a massage with scented oils, and a temporary Henna tattoo on her ass that read "Property of Maxwell," she looked phenomenal, and I had an erection that just wouldn't quit.

Olivia took one look at my throbbing cock and glanced nervously towards Madison. The history between them had been turbulent to say the least, and it was clear that the younger girl didn't want to do anything to further inflame the animosity. Despite my efforts to hide it from Madison, she is a very perceptive woman and figured out the source of my arousal immediately.

"Don't worry, Pete," she said dismissively, "you won't be as attracted to Liv once you see what Maxwell has in store for her."

I shot her a confused glance, primarily because I didn't understand her inference that I was going to witness Olivia's ordeal. Madison, sensing my perplexity, sought to clarify the matter, but waited until Olivia was within earshot before she spoke.

"Maxwell lives in the hood," she informed me. "While I feel like Olivia could benefit from a protracted session with the homies, I do need to ensure that she is returned to us in one piece. Our toilets won't clean themselves, will they Liv?" she added, to further diminish Olivia's status within our house.

"No, Miss Madison," Olivia answered respectfully, although her brow was furrowed with anxiety, as she digested her upcoming fate.

Madison had evidently decided that a trip to the ghetto was too dangerous for an unaccompanied young woman. For a split-second I thought Madison might propose sending me with her, which scared the shit out of me. I was quite relieved when Madison told me that she had decided to invite Maxwell to my condo, for his extended apology session.

"While I am sure that Maxwell poses no security risk," she informed us, "Pete will monitor the events of the evening, to ensure Liv's safety is not compromised. Maxwell will be stopping by the sexual health clinic this morning, to submit to a battery of STI tests. I really want to be able to accommodate each and every one of his desires, while still maintaining the health of our house-maid."

I knew better to let her finish before uttering a word, but as soon as Madison was done talking, I voiced my concerns.

"Monitor the events?" I asked with a great deal of trepidation.

"Yes," Madison said emphatically. "As much as I am sure you would like to be in the room when Maxwell enjoys Olivia's apology, you will watch on the security monitors. Any danger to Liv's health and you can intervene, although I caution you that she has demonstrated a high tolerance for pain in the past. For this reason, I only permit you to halt the proceedings if she is in actual physical danger."

"But," I began, before Madison cut me off.

"No more explanation is needed, Pete. Olivia has been given a safe word and has been cautioned not to use it unless it is absolutely necessary. I have made myself very clear," she added firmly. "Do you understand?"

I nodded my head agreeably, having learned to pick my battles carefully when it came to Madison.

"Good," she said, moving on swiftly. "The photographer will be here in the next ten minutes to document Liv's preparation for her big day. Her first interracial encounter," she added, with way too much enthusiasm. "Liv, get your ass into the living area," she barked.

I literally had to double-take when Olivia entered the room. She looked absolutely phenomenal, and I felt my cock twitch as I admired her from a distance. I have always favored blue-eyed blondes and although I have enjoyed a brunette here and there, Olivia included, it is the visual stimulation of blonde hair that I prefer, even when I jerk off. In fact, I hadn't been this aroused by a woman with dark hair since I watched Nicole Scherzinger's, of Pussy Cat Dolls fame, music videos. Those highly stylized, beautifully choreographed and artfully photographed video shoots were designed to elicit sexual response from men, and I was no exception to her sexual allure.

As Olivia moved gracefully across the living area, wearing a bubble-gum pink, stretch Lycra mini-dress with matching garter-belt and stockings, she looked like a total fuck-toy, which of course she was going to be, albeit for Maxwell, assuming he passed the required STI screening.

Olivia wore a pink-tinged bronzer with a shimmer unlike anything seen outside of a strip club. It was scented too, and had glitter-flakes embedded within it, creating an image of unbridled luxury. She just looked expensive, the way a Rolls-Royce or a Patek watch does, and had I seen her shopping in Tiffany or Cartier, I would have considered her totally out of my league.

Her raven black hair was absolutely stunning, its length and volume presumably enhanced by the application of hair extensions, as it flowed down her back in long, black waves. Her makeup was flawless, although the bubble-gum pink lipgloss was a little too reminiscent of a bimbo for my liking. Her cheek-bones were frosted with pink glitter, and her long nail extensions were also hot pink. She had a Queen of Spades tattoo visible on her left breast, that I hoped to God was merely a Henna application, as it symbolized a preference for black men. As my eyes roamed across her tight little body, and my gaze moved slowly down her toned legs, I noticed an identical tattoo on her ankle, which also bore a secondary symbol of appreciation for black men, an ankle bracelet that read "BBC Slut."

As stunning as she looked, it was in complete contrast to the look of abject misery that I recognized behind her fake smile. She looked absolutely disgusted with herself, as if she wanted the floor to open up and swallow her. She had gone her entire adult life without any physical contact with a black man, making several decisions along the way that had cost her dearly, both financially and career-wise.

Now as she entered the room, watched closely by her nemesis Madison, who was loving the submissive display as much as Olivia was hating it, she had some very obvious doubts plastered across her perfectly made-up face.

"Beautiful," Madison intoned admiringly, "you are going to make those niggers very happy young men."

Olivia winced at the use of the pejorative to describe the African-Americans, or maybe it was the use of the the word men, reminding her that her initial interaction was to be with Maxwell and his homies, however many of the the poorly-educated gangbangers he had in attendance with him. I felt sorry for her as I could see the inner-turmoil written all over her face. However, as the doorbell rang, and the photographer entered my home, this was not the time for reflection or doubt. This was happening without or without Olivia's consent, and Madison resumed control of the situation, with a new directive.

"Let's start by the Steinway," she informed the photographer. "I want a very artistic and feminine approach to the photos to start with. Then we will turn up the sexual undertones, as this little vixen is entertaining some VIPs later."

"Whatever you wish, Madison," the photographer said agreeably, as Olivia appeared visibly disturbed by the characterization of Maxwell and his homies as VIPs. "I can make the girl appear as angelic or as slutty as you desire."

"Good," Madison responded enthusiastically. "Let's start with a pretty in pink scenario."

To her credit, despite her obvious deep-rooted reservations, Olivia remained passive as the photographer posed her demurely by the grand piano. They photographed her holding a glass of pink champagne to her lips, in a celebratory pose, even though at that exact moment in time, celebrating was just about the last thing on her mind. As she held the Baccarat flute to her pink glossed lips, her feminine, manicured finger nails wrapped around the expensive crystal stem, she looked like the picture of an unattainable, rich man's trophy. The photographer forwarded Madison two beautifully composed pictures, both of which could have graced the cover of Architectural Digest, such was the illusion of refinement they conveyed.

It was out to one of my ocean-front balconies next, for another set of classy poses, Olivia's feminine wiles on display against a backdrop of the bright blue Pacific Ocean. Olivia took a sip of her champagne as the sunlight danced on her eyes, her long-lasting lipgloss refusing to transfer to the rim of the Baccarat flute, in a testament to its claim to be capable of being worn all day long.

The transition from angelic to slutty was slow, but knowing it was happening gave extra meaning to each subtle change, no matter how seemingly insignificant. The first noticeable adjustment was the camera angle, which had thus far been focused solely on Olivia's upper body, in such a way as to create headshots. As the photographer lowered her lens slightly, so that Olivia's tight little ass and toned legs came into view, she also encouraged the display of more skin, along with a more seductive attitude and sultry pose on the bewildered young girl's face.

"Who's the lucky guy?" the photographer asked at one point, causing Olivia to turn up her nose in revulsion at the unwelcome reminder of her fate.

"Guys," Madison gleefully corrected, "Olivia is entertaining several young black guys, today."

After this bombshell was dropped, almost ensuring that all subsequent conversation about this photoshoot would be awkward, I was surprised to hear that the photographer was completely unfazed by the interracial element of the upcoming encounter.

"I do a lot of interracial boudoir photography sessions," she responded cheerfully. "Black guys like to show off their white bitches to their homeboys," she added. "It's a cultural thing I guess, although it does sound like you are allowing your man to bring his crew with him to experience your sensuality first hand."

Olivia nodded demurely, although the notion that she had invited Maxwell's homies to watch her dance for him, couldn't be further from the truth. However, as the photographer moved on, Olivia merely obeyed her instructions, hiking up the hem of her stretch Lycra dress, so that it rested across the bottom of her ass-cheeks.

"Perfect," the woman said as she snapped busily away. "Now lean your upper body over the top of the Steinway."

My gloss black Steinway was an imposing looking addition to my living area, and whereas it would have totally dominated a regular-sized living room, it looked in perfect proportion in my massive open-plan condominium. I didn't even play any musical instruments, but luxury Newport Beach homes nearly always had a Grand Piano on display, along with the obligatory telescope, so I followed suit.

My financial advisor's brokerage had leased it for me after I signed an exclusive agreement with them to manage my finances. I didn't even interview other agents, choosing to utilize the same guy that had guided my uncle financially over the last forty years. I signed a long-term agreement, which terminated on my thirtieth birthday, although there were other ways I could exit the contract, my uncle assured me, if certain performance expectations were not met.

I didn't understand the financial component of my trust fund, nor did I desire to. I knew that barring multiple divorces, or an unexpected unfettered drug or gambling addiction, I couldn't possibly spend all of the money, the way that it was due to be disbursed. I had a quick look at the numbers, and could comprehend the fact that I was to receive one hundred and sixty thousand dollars per month, starting on my eighteenth birthday, increasing to two hundred and twenty five thousand dollars per month when I turned twenty-one. However, beyond that, as my monthly allowance increased exponentially with each passing milestone, the magnitude of the numbers was too difficult to understand. It was easier to turn over the management of my funds to the brokerage, and as a token of their appreciation, they leased me the massive piano.

It was a Type D too, which meant absolutely nothing to me when it was craned into my condo shortly after my eighteenth birthday. However, with every passing acknowledgment of its grandeur, it became apparent to me that among the myriad of ways that the Newport Beach wealthy used to establish the pecking order amongst themselves, the size of your piano was one of them. In fact, I felt a surge of pride every time a first-time guest to my home remarked upon it.

"Beautiful piano," they would begin. "Type D Steinway. You have impeccable taste young man."

Initially my surge of pride would be followed immediately by a feeling of panic, as I prayed that they didn't ask me to play something on it. However, as I became slowly indoctrinated into this wealthy enclave, I realized that despite the ubiquity with which these opulent shows of wealth were displayed, no-one could actually play them.

In fact, every single Steinway that I encountered within the opulent living spaces of my neighbors, still had the protective cover affixed to the top. This see-through, Invisi-shield wrap, similar to that which is applied to exotic cars to protect the paintwork, allowed the Grand Pianos to be used for more realistic purposes, without fear of any damage. The 3M proprietary application served as an adequate defense against indentations from stiletto heels, as nubile young females danced atop the nine foot by five foot impromptu stage that the huge musical instrument provided. It also protected the lacquered gloss finish from minor scratch marks, when partygoers used razor blades atop the perfectly flat surface to apportion their cocaine. I was grateful to my uncle for his advice to leave the wrap protection on, as I later learned that while a Steinway serves a purpose for a multitude of fun activities, playing a rendition of Beethoven's Moonlight Sonata is not one of them.

After a few pictures of Olivia leaning provocatively over the Steinway, her black hair cascading down her lean back as she looked over her shoulder signaling her complete availability, the photographer told her to climb on top of the piano.

"This is the point where people are grateful that they left the cover on," she remarked with a knowing smile. "Although I do carry large black silk sheets with me, just in case I encounter a household where somebody actually plays," she added.

Safe in the knowledge that Olivia's sky-high, bubble-gum pink, fuck-me pumps posed no danger to my Steinway, I watched enthusiastically as she climbed atop the glossy black instrument. She looked equal parts dumbfounded and humiliated as she waited patiently on the top of the piano.

"Okay, let's get you up on all fours," the photographer suggested cheerfully. "Men always appreciate the inference that this position provides."

Olivia hung her head briefly, before swallowing her pride and assuming the doggy-style position.

"Arch your back, Liv," the photographer instructed, using Madison's preferred name for the young girl. "Look straight at the camera and blow a kiss to what's his name."

"His name is Maxwell," Madison offered. "Liv's boyfriend is Maxwell."

Over the next several minutes, as the photographer manhandled Olivia into a succession of increasingly lewd poses, I felt myself get erect again. Madison noticed immediately, and walking over to the fireplace mantle, retrieved the rattan cane from its resting place. As she walked directly behind me, she ran the tip of the cane across my buttocks, as a sort of warning shot before I got myself into any trouble.

"Don't fucking embarrass me, Pete," she whispered ominously, "or I will punish you in front of the photographer."

As if to transmit my obedience to her, I left the room in silence, willing my erection to subside. Unfortunately for me, at this point in my life I was still a teenager, and once stimulated, nothing short of ejaculating was going to suppress my hard-on. I did find a small pair of swim trunks in my closet, and I put them on under my briefs, hoping that if I couldn't will my erection away, I could at least hide it.

When I returned to the living area a few moments later, the transition from angelic to slutty was complete, and it was a different Olivia that cavorted atop my Steinway. Under guidance from the photographer, and encouraged to play along by Madison who stood right next to the piano wielding the rattan cane, Liv had lowered the top of her skin-tight dress to reveal her perfect tits. The black, Queen of Spades tattoo on her left breast was now visible to anyone who got to view the photos, and this had clearly rattled Olivia, as the smile had disappeared from her youthful face.

"Fetch some ice and the wet-wipes," Madison ordered me, as I scurried into the kitchen.

It hit me the second I opened my oversized Sub-Zero freezer, and was assaulted by the visual of my "special" ice-tray, which contained numerous frozen cubes of Clarkson's semen. Did Madison want a regular ice-cube or one of the special ones? I didn't have time to contemplate, so I grabbed a regular cube, placed it inside a glass, and hurried back to the living area. In the few seconds that I had taken to follow her less than explicit instructions, Madison had forged a startling transformation in Olivia's attitude, as the younger girl was now in a much more sexual stance, and had a huge smile on her face.

When I saw the rattan cane resting against Olivia's upper-thighs, I realized quite how this adjustment had occurred, although judging from the lack of welts on Olivia, the threat of a whipping had been sufficient to induce her cooperation.

"Get her nips hard," Madison instructed me. "I want Maxwell to think that she is hot for him."

The ice-cube felt uncomfortably cold as I retrieved it from the glass with my fingertips, and I wanted to apologize to Olivia before I placed it against her nipple. However, under the watchful gaze of Madison, there was no time for pleasantries, and I held the ice-cube firmly against her left breast, as it hung beneath her.

Immediately upon impact, Olivia let out a gasp and drew in a sharp breath from the shock of the cold. She tried to recoil but as she arched her back, Madison reacted swiftly by withdrawing the cane from the back of her thighs, and placing it on the small of her back. Two gentle taps was all it took, before Olivia lowered her breast obediently onto the ice-cube. A few moments later, as she struggled to control her breathing under the sustained assault of the freezing cube, her nipple hardened completely, jutting beneath her like a pencil eraser, and giving the impression that she was highly aroused.

"Wipe the excess liquid from her breast with a wet-wipe," Madison instructed me. "I want her desire to look natural."

The photographer wasted no time documenting such obvious arousal, and as Madison used the tip of the cane to position the younger girl, I watched on with my erection fighting against the confines of the two pairs of underwear I was wearing to hide it. Occasionally, Madison barked instructions at me.

"Put the ice-cube back on her nipple," she ordered. "Arrange her hair so that it flows evenly down her back," she added, turning me into a de-facto photographer's assistant.

Once Olivia's compliance was assured using the threat of a thrashing, Madison made Olivia hold the cane in her mouth like a puppy holds a newspaper. This inference of submission was very erotic, and it also invited Maxwell to punish Olivia when he finally took her reins. Once the photographer signaled her satisfaction with those demeaning pictures, Olivia was positioned facing away from the camera, still in the doggy-style pose. Her Lycra dress was still hiked up over her tight ass-cheeks, although the photographer, increasingly comfortable with Olivia's compliance, reached under her and slowly lowered her matching pink, thong panties.