Trust Fund Baby Pt. 09

After we hung up, Madison was adamant that proof of negative testing was a sufficient safe-guard for us to subject Olivia to the four of them. I tried to object but she rephrased it as an ultimatum, making it quite clear that if I did not allow the party to continue, Madison would simply relocate the gathering to Steve Baldwin's house.

"Don't force my hand, Pete," she said ominously. "Baldwin loves gang-bangs, particularly non-consensual ones. If you make me leave, I will be gone for three months this time."

We both knew that she had me exactly where she wanted me. I had experienced some profound physical and psychological turmoil the last time Madison stayed at Baldwin's place, and she had only been gone nine days. I would go crazy if Madison left me for three months, and I am not sure if Olivia would emerge from such an ordeal without having a mental breakdown.

"How about we make Liv give Maxwell's three friends a blowjob before they leave?" I countered, hoping that this would be acceptable to Madison.

I feel like she knew that she had me on the ropes, and could have probably extracted more concessions from me, so I was pleasantly surprised when she responded.

"Not just a mechanical blowjob," she said firmly. "A loving, edging, cock-worship session for the three young men, before they leave. A Clarkson special," she added cruelly.

Feeling like I had done a good job of protecting Olivia from the worst, I acquiesced, reluctantly nodding my approval.

"Good boy," Madison said condescendingly. "Now get in there and give those niggers the good news."

I flashed Madison a token look of resistance, but her impassive stare informed me that any pushback was futile.

"Go," she said impatiently. "Now. Make sure Liv understands exactly what is expected of her."

I ran into Olivia in the hallway, and seeing the look of trepidation on her face, I gave her a hug. When we parted our embrace, her anxiety had dissipated, and she actually looked relieved. She smiled sweetly at me, before mouthing the words "Thank you." I could tell that she didn't want any part of this potential gang-bang, and as I looked her over, I felt my resolve weakening, and contemplated taking her to safety at my uncle's house.

To my horror, Madison appeared just outside the doorway, holding the rattan cane in her hand as a reminder to me exactly what her expectations were. I should have held my ground, but as I processed the notion of being whipped by Madison before she left for an extended stay at Baldwin's house, I folded like a pack of cards.

"There's been a change of plans, Olivia," I said quietly. "I am sorry."

"Pete, no, please," she begged me as tears welled up in her eyes. "Don't make me lap-dance for Spider any more."

I think Olivia understood the gravity of the situation when Madison laughed aloud at the lap dance comment. She lowered her voice to a whisper and leaned into me.

"What do you want from me, Pete?" she asked quietly.

"Madison wants you to give each of Maxwell's friends a blow-job," I said weakly, barely able to get the words out.

"Not just a blow-job," Madison interjected firmly. "I want you to orally worship those niggers. What do we call it, Pete?" she added cruelly, putting me on the spot.

"A Clarkson special," I intoned meekly, feeling like a complete pussy being forced to associate the sex-act with Madison's lover.

Olivia looked crestfallen as she lowered her head and processed Madison's expectations.

"Any questions, Liv?" Madison asked cheerfully.

After initially shaking her head, Olivia cleared her throat, and in a barely audible squeak asked for another hit of MDMA to take the edge off. Madison seemed delighted to oblige the younger girl, and poured a healthy dose of crushed ecstasy into the palm of her hand, from a small vial that she had concealed on her.

As Olivia tentatively approached her, Madison lowered her upturned hand to waist level, forcing Olivia to kneel before her to consume its contents. As Olivia ingested the white powder, I tried to calculate how many hits she was taking, but my unfamiliarity with the drug, particularly in its powdered form, ensured that I was left guessing, along with Olivia.

Once Olivia had licked Madison's palm clean, she arose from her knees and followed me into the living room, where the gangsters were waiting.

"Everything cool?" Maxwell asked casually, obviously feeling confident that the negative STI tests would be sufficient for him and his boys to enjoy Olivia. "Are we good to go with Liv?"

Even though I was in the safety of my own home, with my security detail just a phone call away, I felt very nervous as I approached the four black guys.

"Madison and I have agreed to modify the rules slightly to reflect the fact that the four of you all tested negative for STIs today," I began, my lack of confidence evident in my shaky voice. "Maxwell, nothing has changed as far as you are concerned, but we have decided to allow your homies the pleasure of a blow-job, courtesy of the lovely Olivia. I hope this is acceptable to you guys," I added meekly.

"That will work for me," Spider said enthusiastically. "Can she finish my lap dance first?"

I turned briefly to look at Olivia to try and gauge her reaction, and was greeted by the sight of Madison entering the room, enthusiastically. It appeared that she didn't want to miss one second of Olivia's disappointment at the constantly moving goalposts, and she began to direct the quivering young girl.

"Liv would be delighted to be your private dancer, Spider," she said cheerfully. "What kind of music would you like us to play while she entertains you with a lap dance?"

Predictably, Spider was into rap music, and as Madison fired up some of his favorite tunes, Liv approached him apprehensively. It looked as if the extra hits of MDMA had further lowered her inhibitions, because she started to sway seductively to the new rhythm of Kendrick Lamar. Spider had been erect for the last hour and was done with the dancing, unless it was performed in the close proximity of his lap.

As Olivia shimmied towards him, her arms outstretched to showcase her breasts, he grabbed her by one hand, and pulled her into his recliner. Olivia let out a cry of surprise, and I looked to Madison for guidance.

"Let him enjoy himself," she cautioned me. "That slut has been teasing him for the better part of an hour. It's time for her to put out."

Spider seemed emboldened by the fact that we were not intervening, and wrapped his muscular black arm around her slim waist. As he held her tightly in place on his lap, he began to grope and fondle her, completely ignoring her obvious disapproval and attempts to fend him off.

I had only been in a strip-club a couple of times by this point in my life, and both times were in a non-alcoholic gentleman's club, into which eighteen year olds were permitted entry. I am not sure if it was the younger crowd, intimidated by the bouncers lurking everywhere, or the lack of alcohol flowing which undoubtedly lowers inhibitions, but I witnessed a very respectful interaction between dancer and patron, at all times.

Maybe things are different in the hood, but Spider's aggressive manhandling of Olivia would have earned him a beat-down in most strip-clubs, and possibly a charge of sexual assault. He was simultaneously trying to pull her top down to expose her tits, French-kiss her, and stick his hand up her ridiculously short dress. Olivia fought him off the best she could, but a few moments later her breasts were poking out of the dress and Spider was showing the rest of the crew her Queen of Spades tattoo.

Moments later, he had succeeded in wedging one of his thick black fingers inside her, and Olivia's eyes opened wide with horror, as her worst fears about being intimate with black men were realized.

"Please, Spider," she begged at one point. "Slow down, you are hurting me."

A better friend would have interceded at the first sound of her distress, but Madison leaned into me and whispered ominously, "Let him have his fun. It's just a blow-job."

Finally, as I watched on in disgust, Olivia stopped fighting him and began to negotiate his preferred method of sexual release. Spider eased up a little on the physical attack, and as he verbalized his desires, she got between his legs and sank to her knees in front of the recliner.

Spider talked a big game, as she unbuckled his Walmart belt and slid his shorts down around his ankles. However, even though he had a huge cock and a filthy mouth, as soon as she lowered her glossed lips to his cock-head, he closed his eyes and began to whimper.

Maxwell had been quite candid about his lack of experience with white bitches on the night that Madison and Jody had sucked him off in my Lamborghini. As I watched Spider approach his orgasm with alacrity, I realized that he too was probably enjoying his first blow-job from a white woman. He ejaculated about two minutes after she first began to fellate him, and Olivia's experience enabled her to know exactly when he was coming, and divert it, so that he blew his load all over his Tommy Hilfiger shirt.

Recognizing that her commitment to Spider had been fulfilled, she arose from her knees and sashayed over to Trigger. Spider was trying to compose himself, and seemed embarrassed by his lack of stamina. After wiping his semen from the front of his shirt, he excused himself to smoke a cigarette, and that was the last we saw of him.

Olivia seemed much less intimidated as she approached Trigger, and I wasn't sure if it was her realization that these guys weren't going to last long, or if the alcohol and MDMA were finally kicking in, but she ended up blowing the other two guys in quick succession. Trigger was actually very respectful, at least compared to Spider. He didn't really grope Olivia as she knelt before him, and was silent when he blew his load a couple of minutes later.

The last guy, Snake Eyes, or Snake as he asked everybody to call him now that he considered us his homies, definitely didn't get his nickname from playing dice, but rather from the considerably sized snake that resided in his pants. I noticed it immediately, an impressive looking member throbbing against his shorts, as he stood before Olivia.

"Kneel," he ordered her as she extended her dainty hand towards him.

Olivia shot Madison a confused stare, and as my girlfriend nodded her agreement that Snake was running the show, she dropped to her knees. Olivia must have telegraphed her surprise to him as she lowered his boxers, because he immediately offered up an explanation.

"There was another guy in our crew called Snake," he offered without any prompting. "I have been known as Snake since I was a teenager, but took the street name, Snake Eyes out of respect for the fact that he was there first."

"I see why," Olivia said with some trepidation, "holy fuck."

Unlike the sex depicted in pornographic movies, in which well-endowed men are always blessed with unearthly stamina, Snake was a very easy come. For all their bravado, it was apparent that these gangsters didn't get much play, at least from beautiful, young white girls. Snake blew his load very quickly under Olivia's oral ministrations and Olivia allowed herself a barely perceptible smile, as she realized that most of her work was done.

Or so she thought. As she went to stand up, Snake rested his hand on her shoulder, effectively holding her in place. With his other hand he grabbed his huge cock and smeared the tip of it across her cute, upturned nose, thereby transferring some of his seminal fluid to her face. Even though she had a look of shock on her face, Olivia didn't voice an objection, thereby emboldening Snake, who began to wipe the excess semen from the tip of his cock, onto her stunned face.

Madison had done a good job of adequately conveying the rules to all parties involved, but whether or not it was done intentionally, she had neglected to mention the use of cell phones. As Snake wiped his cock all over Olivia's face, he grabbed his iPhone and started to document his subjugation of the young girl.

"Please don't take any pictures, Snake," Olivia implored the increasingly aggressive gangster, as he hung his mammoth cock across her face, to showcase its impressive size.

Olivia's pleas fell on deaf ears, and by the time Snake was dressed and heading out of the door, his large black nuts were completely drained, and he had the photographic evidence to prove that he had been blown by a white chick.

After the three gangsters left, the vibe mellowed considerably, and I no longer feared that the party could get out of control. Maxwell had thoroughly enjoyed watching Olivia's submission to his homies, but was ready for his turn with the young girl. As he arose slowly from his chair, his erection was clearly visible in the front of his Nike basketball shorts.

"Kneel, Liv," he said firmly, as he stood in the center of the room.

Liv was trembling as she lowered herself to her knees, which caused the hem of her micro-dress to raise up her thighs, exposing her shaved pussy. I took some satisfaction from the fact that I had already blown my load inside Olivia, but Maxwell wasn't about to go down on her, which would have been the only way to find out. It was quite evident from his demeanor and body language, that today's encounter was going to be all about his pleasure.

"Crawl to me," he ordered, as Liv knelt before him biting her bottom lip, and looking like she was about to burst into tears.

As she obediently approached him on all fours, he began to taunt her.

"I knew you would offer yourself to me," he mocked. "I want you to blow me first, on your knees as a sign of respect."

I am sure it took a lot for Olivia to kneel before this cocky, black gangster and release his cock from his Nike shorts, particularly as he had shown disrespect towards her by neglecting to shower after his physical exertion on the basketball court. However, as he took a large swig of his Heineken, she lowered the waistband of his athletic gear, and moved her lips to his cock.

I imagine that she was emboldened by the tale of Jody and Madison's encounter with Maxwell, in which he had blown his load within just a few moments. However, as she kissed, nibbled and sucked his cock-head, he stood there impassively, unmoved by her best efforts. Even when she moved to his frenulum, which is a sure-fire way to accelerate a man's release, he was stoic, leading me to believe that he had been given a little pharmaceutical help when he visited the Doctor this morning.

That would have been right up Madison's alley, prescribing Maxwell something to delay his orgasm, so that Liv would have to work harder to please him. Madison was enjoying the show so much, that I dare not ask her.

Once Maxwell had enjoyed an extended cock-worship session from Olivia, he removed his clothes and sat in my recliner. Knowing that he hadn't showered after his physical exertions made me less than ecstatic about him sitting naked in my chair, although as he raised his feet onto the leather seating surface, I was just grateful that it wasn't me who was going to eat his ass.

"Lick my balls," he ordered Olivia, as she knelt in front of the recliner.

To Olivia's credit, she was doing an admirable job of suppressing her disgust and disdain for black men, and appeared to have a smile on her face, as she lowered her tongue to his undoubtedly sweaty nut-sack. Maxwell sat in this fairly unorthodox position for several moments, as Olivia lapped away at his black scrotum.

"Taint," he added firmly, as she lowered her head further beneath his under-carriage.

Finally, after several more moments of her worshiping his nether regions, he grabbed his ankles, and in an impressive display of strength and flexibility, held his legs aloft, thereby exposing his asshole. He didn't need to issue any more mono-syllabic commands, as Olivia knew exactly where this was heading.

I felt sorry for her as she extended her tongue, and began to lap gently at Maxwell's sweaty ass-hole. Despite having spent her entire adult life in a pay for sex environment, starting out in the massage parlor, moving onto the gentlemen's clubs as a dancer, and culminating as an escort in Newport Beach, Olivia conducted herself with a certain amount of pride, considering her circumstances. Now, however, as she abandoned her life-long commitment to avoid interracial dating, she was reduced to eating a black man's ass. Not just any black man either, as there were a few successful, well-groomed African-Americans in South Orange County. No, Maxwell was a gangster, a poorly groomed, financially disadvantaged man, for whom the term "nigger" could not have been more appropriate.

In addition to a dirty ass, he also possessed a dirty mouth, and he rained a torrent of insults upon the young girl, as she engaged in her first interracial encounter. I saw her wince a couple of times, and I couldn't tell if it was because of a particularly insulting comment, or from the unpleasant scent of his sweaty ass. Finally, after several minutes, as she stuck her tongue inside his asshole, and simultaneously jerked him off, he let out a guttural moan, and ejaculated all over the side of her face. Olivia recoiled the second his semen landed on her cheek, and as she knelt before him, the large glob moved slowly down her face.

"Get me another beer," he said firmly, as she tried to clean his seminal fluids from her face. "Let my come dry on you," he added.

I feel like Maxwell had really got under her skin, but by the time she returned with his ice-cold Heineken, she had gathered her composure, and she excused herself to freshen up. By the time Olivia returned to his chair, his cock began to twitch and he spoke up, loudly enough for Madison to hear.

"Can I fuck her now?" he asked. "I will be ready in just a few minutes."

Even though I hadn't envisioned an extended, multi-orgasmic encounter between Olivia and Maxwell, Madison signaled her consent for the young black man to continue, and as he slowly hardened, he made his wishes clear.

"Doggy-style," he informed Olivia, as he got more and more comfortable with mono-syllabic instructions.

This was where the rubber met the road for Olivia, and I half-expected her to throw in the towel. Oral-sex is not really considered sex by my generation, but rather is viewed as foreplay, comparable to heavy-petting or a hand-job. However, as Olivia shuffled nervously into position, on all fours, she was about to experience actual penetration, by a black man.

I don't think she was completely sure which hole he was going to violate, as he applied a liberal dose of Anal-Ease to his fully erect cock. Once she was in his desired position, he sidled up behind her, seemingly unsure himself whether he want to fuck her vaginally, or anally.

Switching cameras so that I could see the look on her face, she appeared disconsolate as he probed both of her orifices, trying to make a decision. I could tell that Olivia was very perturbed by the prospect of sex with Maxwell. She had managed to go her whole life with minimal contact with black men, even refusing massage service a few times, based solely on the color of the man's skin.

Now she was seconds away from getting her first black cock inside her tight wet pussy, or maybe her anal-passage, as Maxwell continued to probe the entrances to both. Finally, after what must have felt like an eternity to the poor girl, he eased forward into her tight, wet pussy.

"Property of Maxwell," he said dispassionately, as he read the huge Henna tattoo on her lower back. "Nice touch, Liv."

Maxwell eased his way inside the young girl, pausing only once he was balls-deep. Judging by the look on her face, which had changed from disgust to surprise, I think he may have been deeper inside her than she had ever experienced before. She involuntarily let out a little gasp of pleasure, and I watched as she immediately cursed herself for doing so.