Trust Fund Baby Pt. 08

I tried to talk Madison out of forcing Olivia to entertain Maxwell, once it became evident to me that it was really pitting Olivia against her deep-rooted, life-long convictions. She had grown up in an all-white, segregated community, and while she had never consciously tried to be racist, the mere fact that she wasn't around black people, shaped the way that she felt about them.

She felt a combination of fear and distrust anytime she was around African-Americans, but this quickly elevated to palpable disgust when it came to the thought of any physical interaction between the races. Olivia had been an escort for several years by the time she was forced into her tryst with Maxwell, during which time she had turned down numerous black men, based solely on the color of their skin.

Even when she had worked briefly at a massage parlor, right out of High School at the tender age of eighteen, she had refused to service a couple of black customers. In fact, it was this perceived discrimination that had caused her to lose her job after just a few months. Since that day, she had vowed not to have any physical contact with black males, and she had managed to avoid even casual conversation with any men of color. It was difficult for me to watch her inner-turmoil as she came to grips with the fact that she was going to be on her knees, orally servicing Maxwell.

Madison, however, was adamant that the interracial blow-job take place, and took great pleasure in informing Olivia of the upcoming date. Olivia had three days notice, and at the time she confided in me that she considered just moving on, leaving the state and putting her legal woes behind her.

I tried to imagine something that I would struggle with so much, that it would force me to uproot and leave town, but I came up empty. When I tried to talk some sense into her, tears welled up in her eyes and she hung her head, as if she was being asked to do the most despicable thing imaginable.

"Olivia," I said, trying to put things in perspective, "you allowed me to urinate all over you and then make you chase crumpled-up dollar bills, like you were a little dog. Surely, that is worse?"

"I would rather have a dozen white guys piss all over me, than kiss a black man," she said, sobbing uncontrollably at her impending fate.

Madison in contrast, was having an absolute field-day, even going so far as to schedule a conference call between her, Olivia, and Maxwell, the day prior to the scheduled suck-fest.

"I want you there too," she told me. "You need to learn Liv's place in our relationship."

As the time of the call approached, Madison gave Olivia some explicit instructions.

"Shave your pussy, girl," she said condescendingly, "and present yourself naked for inspection, when you are ready."

Olivia looked horrified as she processed Madison's orders, returning several minutes later with no clothes on, and no visible pubic hair.

"Kneel," Madison barked. "Put your hands behind your head and spread your legs."

Once the younger girl was on her knees, Madison retrieved the rattan cane from the mantle-piece, where it was kept in plain view as a reminder to Olivia of the importance of obedience. Olivia feared the cane almost as much as her upcoming dalliance with Maxwell, and as Madison ran the tip of it across her buttocks, I could see Olivia trembling. She had intertwined her fingertips behind her neck, and this posture forced her breasts forward.

As Madison stood behind her, she slid the cane under Olivia's pussy, and I saw the tip of it emerge from between her legs. Tapping the cane against her inner-thighs, Madison conveyed the message that she wanted Olivia to spread her knees further apart, and the younger girl obeyed without hesitation.

"I am not sure if Maxwell will want to switch to FaceTime," Madison said deviously, as Olivia bit her bottom lip. "Either way, you will appear more deferential if you are naked."

Olivia looked to be on the verge of tears, but as Madison traced the tip of the cane between her labia, as she slowly withdrew it from between her thighs, Olivia inhaled sharply. It was at this point that I noticed that her nipples were erect, and that she was breathing heavily.

"The bitch is getting herself worked up," Madison said dispassionately. "She claims that she thinks interracial sex is disgusting, yet she self-lubricates at the prospect of offering herself up to Maxwell."

I wanted to defend Olivia, but as I observed her clear signs of arousal, there was nothing that I could say that would negate her incontrovertible signs of excitement.

"When we call him I expect an elevated level of respect on your part," Madison began. "You may refer to him as Mr. Maxwell, and only speak when you are spoken to. If he has questions for you, focus on providing him the answer that he wants to hear, and don't be overly concerned with your internal biases. When he is done, I have prepared a brief closing script for you."

Olivia shuffled around uncomfortably on her knees as she processed what was expected of her. Madison lifted the cane skyward, and walked around in front of the younger girl. As she absentmindedly traced the tip of her cane across Olivia's ever-hardening nipples, there was a brief moment of unspoken understanding between them, and Olivia nodded her head, as if to assure her tormentor that she would follow the script.

I watched on intently as Madison toyed with Olivia, relishing her anticipation of the dreaded phone call, while also enjoying her elevated level of arousal. I am not sure if being naked in front of us turned Olivia on, or if it was the rattan cane, being used as it was to stimulate her erogenous zones, rather than as an instrument of torture. However, as Olivia let out a quiet moan, it was obvious that Madison was getting to her.

"Fetch me two pillows and Liv's vibrator," Madison instructed me. "It is in my bedside drawer," she added. "I can't trust her to have it in her room."

We were still at the stage in our relationship where I obeyed Madison without question, and I scurried off to follow her commands. When I returned moments later, Olivia was in a high state of arousal, thrusting her pelvis forward lewdly, as the tip of the rattan cane rested against her clitoris.

"Prop the vibrator up on the pillows," Madison instructed me. "Place the tip of it against her clit," she added, removing the rattan cane, the end of which was slick with the signs of Olivia's arousal.

I tried to give Olivia some acknowledgment of apology, but she had her eyes closed as if she was trying to blot out her humiliation. She jumped reflexively as my knuckle brushed her pubic area, trying to position the vibrator perfectly. Once the tip of the vibrator was resting against her clitoris, Madison told me to hold the pillows in place, and ordered Olivia to slowly lower herself. There were a couple of minor adjustments to be made, and when Madison was satisfied that the vibrator was perfectly positioned, she fired it up.

Olivia let out a whimper as the vibrator worked its magic, and I could tell that she was going to climax very quickly under this stimulation. A few moments later Olivia's stomach tightened, which was Madison's cue to immediately cease the stimulation. Olivia let out a moan of frustration and then looked nervously at Madison, as if to seek permission to have some release before the dreaded phone call.

"My bad," Madison said cheerfully, "wrong speed."

Olivia and I knew exactly what Madison was doing, and as my girlfriend selected a lower setting, Olivia slumped her head, fully aware that this was to be a teasing session, not some much needed release.

"If I am satisfied that you were sufficiently obsequious to Maxwell, I will let you have one orgasm after you guys hang up," Madison said magnanimously, leaving the vibrator resting on Olivia's clitoris, the diminished power rendering her not quite capable of release.

"Let's call Mr. Maxwell," Madison said enthusiastically, reminding Olivia of the respectful way she needed to address the young black man.

I felt sorry for Olivia as she knelt naked with the vibrator stimulating her clitoris, with insufficient speed to bring her to climax. I am not even sure when the last time was that she had an orgasm. Madison kept the younger girl naked at all times, so that it was easy for her to keep tabs on her arousal. She wasn't even trusted to have her vibrator in her own room, the sex-toy residing in Madison's bedside drawer for safe-keeping.

Now as Olivia writhed around on the end of the personal massager, trying desperately to get some release before her impending phone call, I had no clue how she was going to concentrate on the task at hand. Her eyes were closed, her head was lowered, and she seemed totally focused on her orgasm. By contrast, Madison was in her element. She dialed the number and I heard the dial tone over the speaker.

Maxwell's deep voice jolted Olivia out of her trance, and she waited patiently as he rambled on about his expectations. He was being quite impolite in the way he addressed her, both in his tone and the graphic nature of the call.

"I am looking forward to watching you suck me off," was the last thing he said, before finally allowing her to speak.

Olivia was so engrossed in her path to self-gratification that she missed her cue, prompting Madison to flick the tip of the rattan cane across one of the younger girl's erect nipples, which elicited an anguished cry, and spurred her into action.

"I can't wait, Mr. Maxwell," Olivia said, her affected, cheerful tone belying the disgusted look on her face. "I shaved my pussy for you."

"Good girl," he said condescendingly. "Send me a photo of it after you hang up."

"Yes, Mr. Maxwell," Olivia responded agreeably. "Whatever you want."

Olivia fell silent as Maxwell continued his graphic depictions of his desires, her revulsion evident as she absorbed his lewd expectations.

"Do you like rim-jobs?" he asked at one point. "Giving, of course," he added, unnecessarily.

Just as it appeared that Olivia had reached the end of her rope, Madison increased the speed of the vibrator, causing Olivia to moan out loud from the sustained stimulation. Maxwell picked up on her verbal cues and responded before she had a chance to answer the question.

"I will take that as a yes," he said with a chuckle. "I have never had a white woman eat my ass," he added. "Aren't you the lucky one?"

I thought that Olivia might throw-up as Maxwell demeaned her on the speaker phone. After ensuring that she was going to send him a picture of her freshly-shaved pussy, he dropped another bombshell.

"I am bringing two of my homies," he informed her, making zero attempt to get her consent. "Don't worry, I am not expecting a gang-bang," he added. "They will split after you dance for us."

I could see the revulsion on Olivia's face as she processed his expectations. However, as Madison looked on approvingly, the younger girl resisted the urge to push back, and remained silent. Madison couldn't contain her glee at the new revelation, and agreed to Maxwell's request with far too much delight in her voice.

"Olivia would be honored to dance for you and your friends," Madison said cheerfully. "I will bring some dollar bills so that you guys can tip her if you like what you see. She loves to give generous guys lap dances."

I could tell that just the thought of having to give Maxwell and his homies a lap dance was so demeaning to Olivia, but as Madison nudged the younger girl and mouthed the words "thank him," she was spurred into action, and began to speak with much more enthusiasm than she was feeling.

"Thanks for the opportunity to serve you, Maxwell," she said, struggling to verbalize Madison's pre-written script. "I can't wait to see you guys tomorrow."

"Wear something pink," he ordered, just before he hung up the phone, "at least for our lap dances."

If Olivia had seemed dejected during the conversation, she was positively disconsolate as Madison posed her for the picture that Maxwell had requested. She remained naked on her knees as Madison cheerfully snapped some shots, before selecting one that she deemed sufficiently humiliating. The vibrator had done a great job of arousing Olivia, and there was no way to hide her apparent excitement from the camera. Her nipples were erect, she was visibly flushed from having been kept so close to orgasm for several minutes, and there were traces of vaginal secretions all over her inner-thighs and her labia, which themselves appeared puffy and swollen.

Madison sent two of the most compromising photos, with a text that read, "Your bitch can't wait to service you. Check out the evidence of Olivia's arousal at the thought of rimming you."

I empathized with Olivia as her situation closely paralleled mine. We both were caught up in Madison's web, although I kept reassuring myself that I was free to leave at any time, even though I knew that I was just as ensnared as Olivia was. In the light of day, I truly detested being cuckolded, and yet I had my most powerful orgasms under the taunts of Madison, as she described her trysts in excruciating detail.

Olivia, for her part, was absolutely reviled by the thought of interracial coupling, and yet being submissive aroused her intensely. She was very conflicted when Madison offered her some release, but as the vibrator brushed against her clitoris, her defenses broke down, and she lowered herself upon it.

Olivia closed her eyes in an attempt to block out Madison's constant verbal taunts, but the prospect of an orgasm after having been kept on the brink for so long, was impossible for her to resist.

"Maxwell is going to want to watch you masturbate for him and his friends," Madison whispered, as she knelt by Olivia's ear. "I expect you to do the right thing if those young guys get hard."

I recognized her internal struggle as she tried to walk the line between her desire to get off, and her deep-rooted contempt for the black men that she was expected to service. Sex is a very powerful motivator, capable of overriding even the most ingrained biases in our psyche, even if just for a few moments as we approach orgasm. As Olivia ground her clitoris against the throbbing vibrator, and Madison whispered a continuous stream of taunts in her ear, release was inevitable, and quickly approaching.

Of course, with Madison nothing is ever as easy as it seems, and so I wasn't surprised when she lowered the speed of the vibrator, which denied Olivia her much anticipated orgasm. In retrospect, it was a masterful move on Madison's part to lower the setting rather than to turn it off completely, which would have given Olivia a much needed reset to gain her composure.

Olivia was now willing to do whatever it took to get release, and looked up at Madison with pleading eyes, as if to convey her intent to obey.

"Say it girl," Madison said condescendingly, "whatever is on your mind."

"Please Miss Madison," Olivia stammered, overwhelmed with desire. "What do I have to do to get some release?"

Madison looked at the younger woman with amusement, before increasing the speed of the vibrator, seemingly throwing Olivia a bone. Olivia closed her eyes, and began to grind against the massager with renewed vigor. She was so engrossed in her impending release that she never even noticed Madison pick up her phone and make a call.

"A little preview for you Maxwell," Madison said cheerfully, as she turned the camera to face Olivia. "Smile for Mr. Maxwell, Olivia."

Olivia opened her eyes and seemed horrified to see Maxwell smiling, as she was forced to perform for him. I could only imagine how difficult it must have been for her to have to masturbate for his visual pleasure, but she was too close to orgasm to care about anything else, and as she got to the point of no return, Madison continued to bark instructions at her.

"Smile, girl," she mocked. "Let Mr. Maxwell know how happy you are to perform for him."

"My friends are here too," he said joyfully. "Work it baby. Come for us."

I marveled at Olivia's ability to suppress her disdain for this young, black man, and paste a huge smile across her face. I am not sure if she was driven by fear of the rattan cane, being wielded as a tool of intimidation by Madison, or by her desire to be rewarded with an orgasm, but either way she made Maxwell feel like a revered and honored guest, as she licked the two middle fingers of her right hand, and lowered them to her pussy.

As Olivia began to toy with herself, for the visual delight of Maxwell and his homies, I knew that the pleasure she was experiencing, was not faked. The evidence of her self-lubrication was two-fold, both visible on her inner-thighs in the form of vaginal secretions, and audible from the squishy sounds her rapidly-moistening pussy was making. Her nipples hardened and her stomach muscles tightened as she worked her clitoris with her fingers.

I felt myself get erect too, both from the erotic, live sex-show I had front row seats to, and the humiliation that I knew Olivia was experiencing, from being forced to be a black man's toy. As she approached her release, Maxwell spoke.

"Get in the doggy-style position, Liv," he directed, using the abbreviated form of her name that Madison preferred. "Face the camera."

The impromptu change in position interrupted Olivia's approach to her orgasm, causing her to sigh with frustration. However, after a quick admonition from Madison, the smile reappeared on her young face, and she stuck her fingers back between her thighs and began to masturbate furiously.

"Lick your lips, bitch," Maxwell ordered, "make yourself available to us."

It was around the fourth time that they made her change sexual positions, that I realized exactly what they were doing. Each time she got tantalizingly close to her release, they abruptly terminated her stimulation by ordering her to change her pose. Doggy-style facing the camera, changed to her facing away from their watchful gaze, during which time Maxwell and his friends made lewd comments about the obvious signs of her arousal.

I couldn't disagree with their assessment, her vaginal secretions even more obvious as she turned her ass to the camera. As her dainty fingers furiously rubbed against her clitoris, Maxwell issued her more demeaning commands.

"Shimmy that ass, girl," he ordered, as his friends laughed along in the background. "Let's see you shake your money-maker."

Olivia did shake her ass for the young men, and even as I watched the smile disappear from her face, her enthusiasm to please the black guys, didn't seem to diminish.

"I want to fuck her, Madison," Maxwell announced. "Is that going to be a problem?"

Even though I knew that this was going to be a monumental problem for Olivia, who prior to this demeaning showtime had never had any sexual encounter with a black man, Madison made the decision for the younger woman, without any consultation, or attempt to secure her approval.

"Liv disrespected you Maxwell," Madison began. "She has signaled her commitment to provide you with an apology that rectifies the wrong she did to you, whatever you feel that this might entail."

"Can I fuck her ass then?" he countered, pushing for more concessions as Olivia approached release.

"If that is what it takes for you to feel justly compensated for her disrespect," Madison said. "She will be available to you for whatever you deem reasonable retribution," she added ominously.

Maxwell finally instructed Olivia to lay on her back with her knees elevated, and her feet planted firmly on the floor.

"Splay your legs apart," he ordered, "and use the vibrator to finish yourself off for us."

I had been in this exact same predicament before, fast approaching orgasm and wanting nothing to delay it, and yet under less than ideal circumstances as Madison taunted me about her extra-curricular sexual activities. I knew that Olivia was right on the edge, and that her orgasm was inevitable, especially with the introduction of the vibrator. I could also see how disgusted she was going to be with herself, after she came.