Trust Fund Baby Pt. 07

I should have just let her beat me first, but as soon as I realized that she considered us "baby" and "Olivia", I failed the test.

"Olivia comes before Pete," I countered weakly, hating myself the second I threw my friend to the wolves.

"Pussy," Madison spat out, the alcohol seemingly having increased her disdain for me.

I felt the rattan cane being removed from my butt-cheeks, and I closed my eyes in anticipation of the first strike. My heart was thumping in my chest, my ears were ringing from the stress and anxiety, and I was sweating profusely under the threat of physical pain.

I heard the swooshing sound of the cane as it was driven swiftly through the air, followed almost immediately by the crack of the rattan as it made contact with human flesh. I jumped reflexively, but evidently there was a slight delay between impact and the resultant pain.

I didn't realize until I heard Olivia's pitiful shriek of pain, that she had received the first stroke. She cried out in anguish, and then immediately began to offer her own alternatives for punishment, in lieu of the cane.

"I will take care of Maxwell," she cried, "apologize to him for my rudeness the first time we met, and make amends to him."

"There you go, Liv," Madison said condescendingly, "thinking outside the box. I like that idea. I know you think you are too good for black guys, so this is exactly the kind of meaningful sacrifice that I am looking for. You are excused. We will call Maxwell later tonight and you will offer him your humblest apologies and set a date for his retribution."

I thought I might piss myself as I knelt there with my forehead pressed against the stone floor. Olivia was weeping as she exited my living area, the pain from one blow having been sufficient to break her life-long resolve against dating black men, and reduce her to a blubbering mess.

"I will call Clarkson," I offered, trying to mimic Olivia's suggestion, in the hope of walking free.

"And?" Madison said, as she relished extracting her pound of flesh from me.

"I will tell him that he has my full support for his monthly suck-fest," I added.

"That's a start," she responded, as she traced the tip of the cane across my lower back.

I had no clue what she wanted to hear, so in an effort to avoid my stroke of the cane, I blurted out all kinds of concessions.

"I will prepare you for his enjoyment," I offered. "Help you get dressed up for him, rub aromatic oil into your skin so that you are soft and scented for him. I will shave your legs for him, get you wet to facilitate his entry, lube your anal-passage for his use."

She allowed me to beg and grovel for several moments before she finally let me off the hook. I felt the cane lift from my lower back, and she placed it back on the mantle piece.

"You will write a list of the concessions you are prepared to offer Clarkson," she instructed me. "When you are done, I want you to call him and let him know that you have had a change of heart, when it comes to our friendship. Now, go to your room."

Later that evening, after Madison had luxuriated in the soaking tub, she told Olivia and I to join her in the living area. She hadn't given me permission to get dressed, so we were both still naked as she forced us to kneel on the stone hearth, the stress-creating position hurting my knees almost immediately.

"Liv first," she ordered, handing Olivia her iPhone, to which she had severely restricted the young girl's access. "Call Maxwell on speaker."

I knew that this was a difficult call for Olivia to make, for several reasons. Not only had she steadfastly refused every single offer ever made to her by a black man, but she was philosophically opposed to interracial relationships. As I got older and enjoyed the services of more escorts, I came to realize that some of them had things they just didn't want to do, but it could nearly always be resolved by throwing more money at them. Olivia had turned down a large sum of money from a black man, on more than one occasion, and seemed resolute in her decision not to date or engage with them sexually.

As Madison observed, with a satisfied look on her face, Olivia suppressed her deep-rooted revulsion of African-Americans, and turned on the charm. As soon as Maxwell answered the phone, I knew that he had been prepped by Madison. Ostensibly, Olivia was calling him to offer her apologies for refusing to blow him on Super Bowl Sunday, based solely on his race. By his own admission, he had never been with a white woman prior to the game, so as she offered to make it up to him, he should have been pleased with her change of heart. However, he made her virtually beg him for permission to suck his cock, and by the end of the telephone call, she had agreed to give him a rim-job by way of apology.

"I will let you know the day before," Maxwell informed Olivia. "Send me some pictures of you in a few cute outfits so that I can decide what I want you to wear."

"I will coordinate things with you, Maxwell," Madison said cheerfully, "Liv currently has very restricted phone privileges."

"Sounds good," Maxwell responded. "Make sure the bitch shaves her pussy," he added as an afterthought, as Olivia contorted her face in disgust.

"That went well," Madison said with a giggle, after they hung up the phone with Maxwell. "Looks like you are going to get your first taste of black cock, Liv," she added contemptuously. "Go to your room."

As Olivia shuffled silently out of my living area, Madison turned her attention to me.

"Your turn, Pete," she said cheerfully, "are you ready to call Clarkson?"

Faced with the prospect of having to call that prick and ask him how my girlfriend could improve his monthly blow-job, I was never going to be ready. Madison sensed this and put down her phone.

"Here Pete," she said, as she offered me a pillow on which to kneel. "Let me at least get you comfortable."

I felt much better once I had some fabric between my knees and the rough stone hearth, and Madison seemed to soften her stance towards me.

"What are you going to offer him?" she taunted. "I already give him a total cock-worship session. I do my absolute best each and every time, and I am not sure if I can improve."

As much as I hated her for rubbing this in my face, it was also a source of intense arousal for me, and even though I tried to fight it, my cock started to twitch. Madison noticed immediately, and predictably used my excitement against me.

"Pete, you can't really offer him any concrete tips for improvement, if you have no clue what I currently do for him," she said. "Why don't I give you a Clarkson blow-job, and you can critique it and offer suggestions for the next time I blow him."

In my heart and soul, I didn't want to go down this road, but as Madison continued to taunt me, I am ashamed to say I got erect. I tried to block out her intoxicating scent, the glint in her eyes as she mocked me, and the sight of her garter-belt straps peeking out from beneath the hem of her tailored skirt, but it was to no avail, and after a couple of tender caresses I was completely hard.

"Be right back," she said seductively, as I knelt on the pillow with my nuts churning, and pre-cum forming around the tip of my cock.

When she emerged from the master bedroom a few moments later, she had removed her skirt and was wearing just a tiny pair of thong panties, a matching garter-belt and stockings, a half-bra that pushed her tits up into the sky, and her ubiquitous Louboutins.

"Thank you for your generous purchase today, baby," she whispered, immediately role-playing as if I was Clarkson. "I don't know what I would do without you."

It should have pissed me off that she was so obsequious towards him, but as she got into my personal space and began to nibble and suck my earlobe, I decided to go with the flow and enjoy the orgasm. Madison moved tantalizingly slowly down my body, kissing every square inch of my chest and stomach before she grazed the tip of my cock with her glossed lips, causing an expulsion of pre-cum as she did so.

Recognizing that I lacked the self-control and stamina that her lover possessed, she moved away from my shaft and began to nibble my scrotum.

"Does that feel good, baby?" she teased. "Your nuts feel very heavy and swollen. Are you going to come in my mouth today, or do you want to blow your load in the bag and have me take it home to Pete?"

Madison chose her words masterfully, and as she continued to address me as though I was Clarkson, I found myself desperate for release. She sucked my nuts for a while, her baby blue eyes glinting as she looked up adoringly at me. Without warning, she disappeared beneath me and I felt her tongue graze my taint. I let out a whimper of pleasure, and was rewarded with Madison running her tongue across my nuts and up the length of my shaft, until she reached the glans, and closed her moist lips over it.

Reflexively I began to pump between her slightly parted lips, fucking it the way I would a pussy. One of the things that made Madison completely indispensable to me was the unrestricted access to sex that she provided me, twenty-four hours a day. There was a considerable amount of teasing and foreplay, but when I was ready to blow my load, she always was willing to accommodate me.

Her role-playing today however, wasn't about indulging me, but was rather an exercise to soften me up, before I made the call to her lover. She let me enjoy four or five pumps between her soft lips, before she parted them and removed her mouth from me. I let out a sigh of frustration, and she spoke up immediately.

"Take your time, baby," she implored me. "Don't come too quickly. I only get to do this once a month, so please don't rush me."

She gave me a frenulum massage next, flicking her tongue across the hyper-sensitive area in slow, delicate strokes, which caused my nuts to tighten within a few seconds. When she sensed I was close, she abruptly stopped the stimulation, lowered her head and resumed nibbling my nuts. This prevented me from blowing my load, but as she continued to tease me and demonstrate a variety of techniques, she kept me right on the boil.

"Feel good, baby?" she whispered. "Let me know when you want to fuck my tits."

I let out another whimper, as I processed her acknowledgment that Clarkson's monthly car-date included a Russian finish, if he so desired. I had a feeling that he tit-fucked her occasionally, as the lacy chest of her lingerie was splattered with his semen once in a while. However, hearing her verbalize it was both a kick in the nuts, and a significant boost towards my impending orgasm.

"I am close, baby," I said through my gritted teeth. "I am really close."

I guess that was all Madison needed to hear, because she crawled out from underneath me, grabbed her phone, put it on speaker and started dialing.

"Liv, get your ass out here," she shouted, before turning to me.

"I will finish you off after you make your call," she said with a giggle. "Give me your pillow."

I reluctantly removed the pillow from under my knees, and gingerly tried to find a comfortable kneeling position on the rough-hewn tiles. I was hoping for some privacy for my call, but as Olivia entered my living area naked, and on Madison's signal, knelt on the stone hearth, I realized that she was going to witness my humiliation, just as I had witnessed hers. After the third ring, I was praying for it to go to voicemail, but then a deep authoritative voice answered.

"Hi Sugar lips," he said, presumably under the assumption that Madison was calling.

As soon as he answered, I realized that I didn't know Clarkson's first name, and I cursed myself for neglecting to ask Madison. In a split-second, I addressed him the only way I knew how.

"Mr. Clarkson," I began, the deference of using this respectful title, making me feel sick. "It's Pete."

Clarkson knew exactly who I was, but as I squirmed uncomfortably in front of the two young women, he acted like he had no clue.

"Who?" he asked, as Madison started to giggle.

"Hi baby," Madison whispered seductively. "It's Pete, my boyfriend. He has a huge favor to ask of you. Are you feeling generous, baby?"

"Always around you, Sugar lips," he replied. "What do you want from me, Pete?"

As I look back now and try to justify my behavior, all I can come up with is that I would have promised just about anything to have been spared the rattan cane. Olivia's blood-curdling scream was awful to have to listen to, and the welts all over her body from her previous session with the instrument of torture, were an indication of the long-term suffering she endured after her whipping.

I was an eighteen year old boy, scared shitless at the prospect of corporal punishment, and even more traumatized by the thought of losing Madison. For this reason, I acted with much obsequiousness as I responded to Clarkson's question.

"Um, Mr. Clarkson," I began uncomfortably, "first of all I want you to know that you have my full support when it comes to your friendship with my girlfriend."

"Good to know, Pete," he said cheerfully. "Not that I really need it. And it's not really a friendship is it? How many of your friends suck you off once a month? Is that the reason you called me? I am a very busy man."

"Well, um," I stammered, really struggling to get the words out of my mouth. "Actually I called to see if there was anything I could do to make it more enjoyable for you?"

"Let me get this straight," he said with a chuckle. "You want to make maximize my pleasure from my monthly suck-fest with your girlfriend?"

"Yes, Mr. Clarkson," I responded with as much reverence as I could muster.

"Go on," he instructed. "I am liking the sound of this proposal. What do you have in mind?"

I was hoping to get a little more feedback from him, so that I could satisfy Madison's perverse desire to humiliate me, but apparently I was on my own. After a few suggestions, he did finally respond, and it was clear that I was barking up the wrong tree.

"To be honest, Pete," he began, "I am not sure that you can do anything to improve on my experience. Your girlfriend has sucked my cock once a month for the last four years, and while it has always been enjoyable, she finally has perfected the art of a loving, edging blow-job. She puts her heart and soul into each and every encounter, and although I am never shy about giving her constructive criticism, it is becoming increasingly more difficult to find fault in her performance. The whole experience is just about perfect, and I doubt I will ever tire of it."

"Nor will I," Madison added enthusiastically. "Sucking you off is the highlight of my month, and until Pete marries me, it will be firmly etched on my calendar."

"There must be something I can offer you by way of improvement," I said meekly, trying to avoid the rattan cane.

"How about an extra girl?" he inquired, telegraphing his interest in a monthly two-girl blowjob. "That would be fun."

"I am not sharing your magnificent cock with anyone, baby," Madison cooed seductively. "However, I have a rim-job girl at my disposal that would be delighted to eat your ass, while I suck you off. We just need to change locations as the front seat of your car is not the most conducive to a simultaneous blow-job and rim-job."

"How about upstairs at your work?" Clarkson asked, without skipping a beat. "If we do it before your Manager arrives, Pete can watch the store."

I hated this idea with a passion. Not only was I less than enthralled about my forced participation in this sordid monthly ritual, but the thought of having to actually be there, filled me with dread. However, a swift kick from Madison, as I shuffled uncomfortably on the jagged tiles of my hearth, made me focus on the task at hand, and I heard myself responding exactly the opposite of how I felt.

"That is a fantastic idea, Mr. Clarkson," I said meekly. "Olivia and I would be honored to help increase your enjoyment of my girlfriend."

Clarkson knew he had me on the ropes, and because he is an asshole, continued to push for more concessions. By the time the excruciatingly humiliating conversation was finally over, he had ground me down and I just wanted to get the hell off the phone.

"Why don't you give Mr. Clarkson a quick recap of our new program?" Madison said cheerfully.

As I stuttered and stammered my way through the new routine, Clarkson interjected occasionally, seeking clarification or making minor adjustments, in order to get his session exactly the way he wanted it. By the time he dismissed me, he had crafted his fantasy scenario, and I had an appointment on my monthly calendar that I genuinely dreaded.

Even though it had only been a few days since his last monthly blow-job, he didn't want to wait three weeks to enjoy his new program, so he informed us that he was moving the date forward. Of course, in typical Clarkson style, he presented it as a win for Madison.

"I am in need of a wardrobe revamp, Madison," he announced. "I need several new suits, shoes, and all the accouterments. Let's meet at Tom Ford on Thursday morning. Does that give you enough time to prepare?"

"Yes, baby. Of course. Whatever you want. Thank you so much," she gushed appreciatively, focusing solely on her commission rather than what the three of us were giving up to accommodate him.

"Good girl," he said condescendingly. "See you bitches on Thursday."

After he terminated the call, the disparate look on our faces told the story. As emasculating as it was for me to offer up my girlfriend for another man's enjoyment, Olivia had given up the most. Not only had she been forced to break her life-long commitment to avoid sexual relations with men of color, but she had begged Maxwell to allow her the privilege of sucking him off. In addition to that debasement, she had been tossed in as an afterthought to sweeten the deal with Clarkson. Once a month, for the foreseeable future, or at least until Madison and I got married, Olivia was going to be eating an old man's asshole, as my girlfriend sucked him off.

I hadn't fared much better. In addition to the demeaning phone call that I was forced to make, I was now obligated to watch the Tom Ford showroom on Thursday morning, while my girlfriend escorted Clarkson upstairs and thanked him for his wardrobe revamp purchases. Predictably Madison had emerged unscathed, with the prospect of hundreds, if not thousands of dollars of commissions awaiting her on Thursday morning, plus the assistance of Olivia to get her lover off, which would presumably reduce my girlfriend's work load.

"That went well," Madison announced, ignoring the fact that I had a huge hard-on and had leaked all over the hearth on which I had been kneeling for the duration of my phone call.

Madison made me wait until bedtime for release, the final part of my punishment for my perceived indiscretions with Olivia. I would have been a very quick come under normal circumstances, given the fact that Madison had edged me to the brink of release earlier that day. However, as she lubed up her tits and invited me to straddle them, I knew it was going to be over as soon as it started. It wasn't until I felt Olivia's warm breath on my ass-cheeks, that I realized that I was going to get a simultaneous blow-job and rim-job treat.

"This is how we are going to get Clarkson off on Thursday," Madison taunted me, as I fast approached orgasm. "At least for his first pop. Clear a hole in your schedule for Thursday, Pete," she added. "Clarkson has a much longer refractory period than you, so we may be upstairs for a while."

I just couldn't control myself around Madison, and ended up blowing my load in her mouth as she teased me verbally. Olivia's tongue felt amazing wiggling around inside my asshole and I had a phenomenal orgasm. Immediately after I gathered myself, I withdrew my softening cock from between Madison's lips and Olivia disappeared. I sensed her withdrawing down my hallway, and shortly after I heard the pocket door to her tiny room slide close.