Trust Fund Baby Pt. 05

On more than one occasion, by the second or third night, I awoke to a soft tapping on my bedroom door. Acting concerned for their welfare, I would offer to have one of the other female occupants of my house attend to whatever was causing them distress. My altruism was often rewarded by the young woman, who in an attempt to demonstrate her appreciation for my generosity, would suggest that waking up the rest of the household was not the most prudent idea. That perhaps I could alleviate the symptoms of her angst, by allowing her to share my bed.

The young women knew what the deal was, and after a few days in the opulence of my ocean-front mansion, with no concerns about having enough to eat or a comfortable place to sleep, they were more than willing to offer me sexual favors in exchange. As my sexual partners increased, one on one encounters became too vanilla for me, and I struggled to finish without the added excitement of a second, or even third girl. The exception to this was rim-jobs, particularly if the girl was young and wholesome looking.

Some of the teenage runaways, especially from the smaller Mid-Western towns, were incredibly innocent looking, something that I had suspected for years as I followed the "Girls next door" series in Playboy magazine. Some of these angelic-looking eighteen and nineteen year olds, as yet unmolested by the plastic surgery industry, and without the skin damage common in Southern California, were absolute angels. Truly natural depictions of inherent beauty. They had often never been exposed to material wealth, and would enter my mansion in open-mouthed awe, too excited to suppress their amazement, and too naive to know that it made them look unworldly.

Samantha was the first of these innocent beauties to fall into my sphere of influence, and I had fond memories of her kneeling behind me with her tongue in my ass, a huge smile plastered across her face, as she tried to earn the thousand dollars I had offered if she looked like she was having fun.

Jody was the next in a long line of innocent looking girls that crossed the threshold of my home, and even though it was Baldwin and his rich buddies that were enjoying her coquettish charms, I developed quite an erection as I took in the sight of her kneeling in her Cheerleader Uniform, next to Madison and Olivia.

As the end of the first quarter drew to a close, the Patriots had already developed a good lead, and one of the Orange County Performing Arts Center benefactors won the first pool. Twelve thousand five hundred dollars is a significant amount to win on a football bet, but this guy seemed completely unfazed. To my surprise, after he was handed the cash, he fanned the hundred dollar bills, and looking directly at the three young girls as they knelt in the middle of the room, he made a proclamation that changed the course of the evening,

"Which one of you wants to make a shit load of cash for a few minutes work?" he said with a confident smirk, the clear inference being that he was comfortable with the prospect of paying to bust a nut.

Even though the young women had so far presented a united front, kneeling as they were in the center of the room, waiting for their next instructions, the prospect of twelve grand was too much for the two younger girls, and both Olivia and Jody rose from their knees and moved seductively towards the older man. He checked them both out as if trying to decide which one to enjoy, his cock visible in his pants as it stiffened at the thought of getting his rocks off.

"They are happy to share the money," Madison offered cheerfully, as the girls nodded their agreeable affirmations. "We haven't had any requests for refunds," she added playfully, the inference being that he would be more than satisfied with the two of them.

"That works for me, Madison," the benefactor to the Arts responded with a broad smile.

I don't even know what the going rate is for a blow-job from two beautiful, barely-legal girls. Olivia charged me seven hundred the first time we fucked, but she allowed me a considerable amount of latitude in the liberties that I took with her. Jody, at eighteen years of age and with much less mileage on her tight little body, could have conceivably charged more. Even so, that put the price of admission at two grand, tops. Which is why it was such a bold move, and an affront to all the assembled millionaires in the room, when Madison stepped forward and took the entire stack of cash from the hands of the Arts patron.

As the guys looked on in astonishment, Madison relieved the guy of twelve thousand five hundred in cash, and to my amazement he didn't even put up a fight. In fact, in a move that lightened the mood in the room, and set the tone for the rest of the night, he smiled at Madison, shrugged his shoulders and gave her an enthusiastic thumbs-up.

"Easy come, easy go!" he said, presumably referring to the fact that he had won the cash in the football pool.

Madison placed the cash in a large glass jar that sat on the table in the center of the room, and then returned to the visibly excited man.

"What's your name handsome?" she whispered softly, as she moved into his personal space.

"Bob," he stammered, as he realized that the girls were going to take care of him in front of all the other guys. "Bob Matthews."

"Well, Bob Matthews," Madison said gently, "Olivia and Jody love to take care of generous men. How would you like to come?"

"I like blowjobs," he said innocently, before inexplicably adding, "it's been a while though. My wife doesn't like them so much."

"Well, Bob Matthews," Madison cooed, her lips pressed against his ear as she stroked his stiffening cock through his pants. "It's your lucky day. Olivia and Jody love blowjobs, and your recent negative STI test qualifies you for a loving, bareback, two girl suck-fest."

As Madison sucked and nibbled Bob Matthews' earlobe, she motioned for the two young girls to approach him. They moved into his personal space, smiling agreeably and vocalizing their appreciation of his generosity.

"Hi Bob," Jody said with her practiced innocence, "I am so happy to meet you."

"Me too," Olivia said excitedly, "I was hoping you would be first."

I had to hand it to the three of them, they were making Bob feel like the most important guy on the planet, and as they continued to flatter him, I felt myself wanting to trade places with that lucky bastard. Bear in mind that I wasn't even there, I was watching the security footage several hours later, by myself, on my large tv. God only knows how much sexier it must have been to witness it in person, their identical perfume permeating the sexually charged air, Bob's breathing becoming noticeably more pronounced as they teased him, the collective sexual energy as the cocks of the twelve observers involuntarily stiffened.

Jody and Olivia stood before Bob in their identical Green Bay Packers Cheerleader Uniforms, and allowed him to take them in as they smiled agreeably at him.

"Are you ready to get sucked off, Bob?" Madison whispered, her voice barely audible on the tape. "Tell them to kneel."

"Kneel," Bob said shakily, the anticipation clearly getting the best of him and affecting his composure.

The two young girls lowered themselves slowly to their knees in perfect unison, and each extended one flawlessly manicured hand to his zipper, the Green and Gold of their nails contrasting with Madison's nails, which painted in the Patriots colors, were fumbling with the top button of his pants.

As the realization that they were going to suck him off in front of his buddies dawned on the room, you could have cut the sexual tension with a knife. It was a masterful decision on Madison's behalf, to have the blowjob occur in the same room as the football game. You would have expected Olivia and Jody to have escorted him to the bedroom, thus giving him some semblance of privacy. However, in all likelihood, once Bob Matthews had left the room, the remaining men would have returned to viewing the commercials, that on Super Bowl Sunday are wildly entertaining in themselves.

However, by conducting the blowjob right under their noses, Madison successfully engaged the remaining men, keeping them focused on the fact that they too could experience a little bit of nirvana this afternoon.

Once Bob's pants and underwear were around his ankles, Jody looked up admiringly at him, and maintaining eye-contact with him, lowered her teenage lips onto his cock. Olivia began to nibble his scrotum, and as Bob squirmed in ecstasy, it occurred to me that the visual had to be good for future business.

It had, indeed, "been a while" for Bob Matthews and in a scene reminiscent of my first few sexual experiences with Madison, he approached his orgasm with remarkable rapidity. The first clue was his heavy breathing, and then I noticed his legs start to shake, and I knew his release was imminent. Jody continued to bob up and down on his cock, in a steady rhythm, and Olivia disappeared under his nut-sack, presumably to lick his taint.

Bob let out a little whimper, and Madison resumed her verbal teasing, which he seemed to respond favorably to.

"Listen to your body," she whispered. "If you are ready to blow your load, don't fight it. As soon as you get hard again, we will take care of you. Your generous donation entitles you to as many orgasms as you can muster."

You could see the smiles on the faces of the assembled Alphas, as they processed Madison's assurance that any acts of generosity on their behalf would be amply rewarded. As I watched on in awe of Madison's ability to manipulate a roomful of powerful, wealthy men, Bob Matthews cried out in pure delight as he ejaculated into Jody's teenage mouth.

I am not sure how much extra-curricular activity Bob Matthews had enjoyed in his life, but if he had ever paid for a blowjob before, I was certain that it hadn't ended the way that this one eventually did. After he came, Bob backed up and reached down for his pants, resting as they were around his ankles.

"Take your time, handsome," Madison whispered, as she continued to suck his earlobe. "The girls will clean you up. Just relax."

As Bob released his grip on his clothes, and they fell back to the floor, Olivia emerged from under his nut-sack, and in conjunction with Jody, began to clean him up with their tongues. As much as Bob had clearly enjoyed his two-girl blowjob, he was really loving the tender ministrations of the two young women, as they licked all traces of his ejaculate from his softening cock, using tender motions of their soft, eager tongues. They appeared to be in no hurry, switching to wet-wipes after they had teased him for several more moments.

It was Madison who deemed him sufficiently clean after a cursory inspection, and at this point Jody and Olivia pulled Bob's underwear up over his cock, giving him a quick nibble through his briefs. Once his pants were around his waist, the two of them zipped him up, and fastened his top button. It was a fantastically attentive service, eclipsing anything I had ever seen, either in person, or in pornography. Bob looked completely and utterly satisfied, shocked almost at the tenderness that they had shown him, a total girlfriend experience combined with the fantastic visual of two young women working selflessly in tandem for his pleasure.

"Let me know when you are ready to go again, Bob," Madison whispered gently in his ear, which now bore the marks of her lipgloss all over the lobe.

I had a hard-on just watching her in action, which is pretty incredible considering that I got to fuck her numerous times a week. As the three women left the room holding hands to freshen up, Bob flopped into an oversized recliner, the experience having wiped him out completely. I switched cameras at that point, in order to watch the girls enter my master bedroom, to try and gauge their reaction to the blowjob they had just given Bob.

"Nice work girls," Madison opined, as Jody spat Bob's load into my sink. "Twelve grand in the pot already."

As the girls high-fived and congratulated each other on their windfall, I had to admire Madison's artful manipulation. It was a given that she was a master at influencing men, but it was amazing that she was able to extend this skill to coerce women too. Madison had just earned a touch over four grand without getting her hands dirty, so to speak. It was awe-inspiring, and I was very proud of my girlfriend as she corralled the young girls, and the three of them reentered the living area.

Mathews was still ensconced in my large recliner, probably reflecting on his world-class blowjob. He didn't seem to give a fuck about the twelve grand, an indication perhaps of his wealth, or at least his disposable income. As the game entered the second quarter, the girls knelt together in the middle of the room, having first ensured that everybody had a fresh cocktail. I googled Bob Matthews as I fast forwarded through the second quarter, learning that he was a retired business owner, and a Legacy Member of the Orange County Performing Arts Center, a distinction reserved for individuals who had donated more than two hundred and fifty thousand dollars to the organization. No wonder the twelve grand meant nothing to him.

As the second quarter came to a close, the young women asked the guys if they needed any drinks or snacks, and then announced the winner of the second quarter football pool. As luck would have it, George won, and as the other guys congratulated him on his unlikely stroke of luck, I could see the look of resignation on his face, as he weighed up the prospect of getting some action from the girls, against keeping, what for him was a much needed twelve thousand five hundred dollars. As he struggled with his decision, the girls left the room quietly.

"Enjoy the half-time show," Madison said cheerfully, as she exited the room behind the others.

As the guys settled in to watch Beyoncé perform, Madison was engineering a half-time show of her own, and as the first song came to its conclusion, she asked Baldwin to mute the television.

"Gentlemen, I present to you, for your visual delight, my bitches," Madison announced with a certain amount of theatrical flair, as she strode into the room with two long, black leather leashes trailing behind her.

I am assuming that Madison selected extra-long dog leashes for the additional anticipation that they provided, as it was several seconds before her bitches emerged from my hallway. Stripped from their matching Cheerleader Uniforms, and now dressed in skin-tight latex catsuits, they trotted along behind Madison, in the playful gait of a pair of puppies. They each had a black tail wedged into their assholes, presumably attached to a butt-plug. The way the tail entered their butts through a small hole in the rear of the catsuit, made it apparent that anal sex was on the menu.

I recognized Olivia's black collar from the night that I dominated her, and a smile crept onto my face as I recalled her scampering around my home chasing wadded up fifty dollar bills. Madison swept into the room, brought her bitches to heel with a single sharply issued command, and then led them on a couple of laps of my living area to demonstrate their complete submission to her. As the guys cheered her on, she made them sit, beg and roll over, Jody all the while smiling, as if she was having the time of her young life. Olivia for her part, remained cheerful, although when I paused the footage and zoomed in on her face, I could see the resentment in her eyes.

I knew the dynamic between Madison and Olivia well enough to recognize that the resentful look was not aimed at the men, but rather at Madison, the two of them having had quite a checkered history. I knew that one day it would culminate in an ugly confrontation, but for the time being, Olivia remained on all fours as Madison paraded her around the room on a leash, like she was trying to win a "Best in Show" prize.

Finally, as the laughter and merriment reached a deafening crescendo, Madison led her bitches into the center of my living area, and with a forceful tone, commanded them to "Sit." It was an awe-inspiring sight, to see my girlfriend stood there owning the room, a dozen or so men applauding her ability to control the bitches, while Olivia and Jody knelt silently on their haunches, either side of their mistress.

Madison even gave them a treat. Reaching into a small plastic bag, she retrieved several M&Ms, and after placing them in the middle of her outstretched hand, she allowed her puppies to lower their faces into her palm, and eat their treats. This elicited a second round of applause from the men, and another noticeable flash of resentment from Olivia, at the unnecessarily disrespectful treatment.

Madison handed the leashes to George, announcing his ownership of them to the entire room.

"Your prize, my friend. Enjoy!"

George wrapped the leashes around his fist, and in act of bravado for the other guys, gave them a sharp tug as he moved slowly around the living area, his bitches in tow, on all fours. As I watched the security footage, I could see a certain amount of trepidation, regret even, on his face. This was where the rubber met the road for him, one of the more difficult decisions he would have to make in his life, as he weighed up the prospect of butt-fucking the two young beauties, against keeping the twelve thousand five hundred dollars, which more than any of the guys in the room, he needed the most.

Madison decided to let him off the hook, and followed him to the center of the room. Leaning into him, she whispered softly, in a voice that was barely audible on the security tapes.

"Take your bitches into the master bedroom, George, I will be right behind you."

There was a resounding applause as George led his two newly-acquired puppies from the room, and I switched security tapes to my bedroom, as Madison followed in behind him. The four of them assembled by the side of my bed, and Madison patted the King Size mattress, which was the cue for the two leashed girls to hop up on it. She swiftly removed their tails, and as they wiggled their asses invitingly, George looked on in awe, licking his lips.

"Really?" he said, his voice quivering in excitement. "Both for me?"

"Two tight, Grade A, American asses, ripe for the taking," Madison assured him, as the puppies continued to wiggle seductively.

"As desperately as I want to do this," George said dejectedly, "I need the money more. I hope you guys can understand."

Of course, they understood. All four of them were hard working people just trying to make a living. Even though Bob Matthews could drop twelve grand on a blowjob without thinking about it, that represented three months pay for George, and he had bills to pay.

"We understand, George," Jody said sweetly. "We are all in the same boat, financially," she added, climbing off the bed and giving him a hug before looking directly into his eyes as if she was contemplating offering him a freebie.

"Well," Madison said quietly, "the other guys don't need to know what happened behind closed doors."

"Thanks for offering to save face for me," he said shyly. "The other guys will have a million questions for me."

"And we will have the answers for them, won't we girls," Madison added gently.

George excused himself to take a quick shower, and as soon as he left the room, the vibe changed.

"Well that show of dominance was a little excessive, don't you think, Madison?" Olivia said tersely, presumably referring to the way Madison had run them through a battery of obedience tricks.

"I just wanted all of the guys to see you as the bitch you are, Olivia," Madison responded coldly. "Before any more money exchanges hands."