Trust Fund Baby Pt. 05

"Don't swallow all of his load, Madison," Jody implored. "Maybe the three of us can share it after he comes?"

Madison smiled broadly at that suggestion, and grabbing the end of the Doctor's cock, slowly eased him into Olivia's tight young pussy. He let out an audible gasp once he was balls-deep, and Jody leaned in closer to his ear.

"Are you ready for me to eat your ass?" she teased.

The Doctor was done talking, and just nodded his head as he struggled to contain himself. Jody got behind him, rolled over onto her back, and scooted under his nuts, head first. I saw his eyes widen and his mouth fall open, and can only assume that she had extended her tongue and started to pleasure him. The Doctor, understandably under the extreme sexual provocation, began to thrust his hips forward, but Madison put her hand on his chest and arrested his motion.

"Not quite," she said. "A couple of finishing touches for your visual pleasure."

As the Doctor remained motionless on his knees, breathing heavily and starting to perspire from the stress of the anticipation, Madison leaned over Olivia and untied her from the piano leg. Grabbing the handle of the black dog leash, she gave it a tug, which pulled Olivia's head back sharply, and caused her to arch her back. She handed the leash handle to the Doctor, with a smile.

"Take the reins to your bitch," she said cheerfully, "wrap the leather around your fist for greater leverage."

It was Olivia's turn to moan now, as the Doctor tugged aggressively on her leash, pulling her head all the way back.

"How does that feel Doctor?" Madison enquired. "Are you ready to come for us?"

As he nodded his head, unable to verbalize any more responses, I noticed an eerie silence in the room. The raucous cheers and sporadic murmurs of approval, had given way to the sound of twelve men trying to catch every one of the girls' spoken words, as they cajoled and teased the Doctor. All you could hear was heavy breathing and Jody's tongue lapping away at the entrance to the Doctor's asshole.

"You may proceed," Madison announced with some level of theatricality, enjoying her role as ringmaster for this circus.

The Doctor gave another tug on Olivia's leash, thrust his hips forward until he was balls-deep inside the young woman, and turned to kiss Madison. She let him enjoy three or four strokes, and Jody's tender ministrations on his undercarriage, before she told him to stop again. This must have been maddeningly frustrating for the guy, to be so close to orgasm, in his fantasy scenario, but Madison knew exactly what she was doing, and she had to have him almost insane with desire, to exact the highest price from him.

"I almost forgot," she whispered, "we never finalized our fee."

As he teetered on the brink of orgasm, the room fell completely silent. Even Jody had removed her tongue from the entrance to his asshole, as they started to negotiate.

"Two grand," he said shakily. "Two grand extra to finish this way."

"Two grand each?" she countered, "there are three of us totally devoted to your fantasy finish."

"Four grand total," he blurted out, his resistance having been completely worn down by the three young women. "Madison, please," he begged, "let me finish."

"For four grand you can finish," she said magnanimously, "you can blow your load in Olivia's tight young pussy, while Jody wiggles her moist tongue around inside your anus. However, if you want me to participate, you need to pay me too," she added. "For an extra two grand, you can come in my warm mouth, and the three of us will spitball your load."

The prospect of this visual was too much to pass up for Baldwin, and he yelled out in exasperation. "Just pay up, dude. You won the fucking money in a bet. Treat yourself."

The Doctor nodded his consent, and a cheer went up around the room. Apparently several of the assembled millionaires wanted to see the three young women share the Doctor's load.

"An additional six grand," Madison repeated for clarification.

The Doctor stammered a barely audible yes, and as the room fell silent, he gave Olivia's leash another more aggressive tug, and began to fuck her doggy-style. The sounds of Jody's tongue lapping away at the entrance to his asshole resumed, and finally, his whimper and wide-eyed look of ecstasy, signaled her invasion of his anal cavity. I had seen enough edging videos to know exactly what Madison had done, and felt that it truly was a stroke of genius on her part, to keep him on the brink for the entire negotiation session.

Predictably, it didn't take the Doctor long to come under the sustained sexual provocation of three young girls. I watched as his stomach tensed, and he closed his eyes, presumably trying to remember how stunning Jody was, as she wiggled her tongue deep inside his asshole. Right before he ejaculated, he loosened his vice-like grip on Olivia's leash, and Madison put her head on Olivia's ass, facing the Doctor with her lips slightly parted.

In a beautifully choreographed move, on a barely perceptible signal from Madison, Olivia, freed from the constraints of her leash, shuffled forward slightly, allowing the Doctor's pulsating cock to slip out of her warm pussy. Madison grabbed the tip of his cock and guided it between her slightly parted lips, whereupon the Doctor, without losing a single stroke, continued his thrusting motion, effectively using Madison's mouth in the exact same way that he had used Olivia's vagina.

I heard a faint humming sound emanating from beneath the Doctor, and realized that Jody had added the additional stimulus of vibration to his already otherworldly impending orgasm. I am not sure if Baldwin had taught her that trick, but to my knowledge he was the only other man that Jody had rimmed, and I am sure he had his own specific requests when it came to that sexual act.

The Doctor tensed up, opened his eyes to take in the visual component of his fantasy scenario, and then with a guttural moan, blew his load between Madison's slightly parted lips. Jody continued her low pitched humming as she wiggled her tongue around inside his ass, and Olivia turned her head back towards the Doctor, and began to egg him on.

"Unload your nuts, baby," she encouraged him. "Make enough for us to all share."

Right after he came he seemed to be in a suspended state of bliss. It lasted several seconds too, as he threw his head back, closed his eyes, and began to whimper. I wasn't sure if it had been a particularly long time since he had last ejaculated, or if it was the effects of whatever performance-enhancing drugs he had taken, but it was a stupendous orgasm, enjoyed almost as much by the onlookers as by the good Doctor.

Even though I know Madison to be an enthusiastic swallower of semen, she made good on her promise to share his load with the other girls. By the time he had finished unloading into her mouth, it was full of his come. She waited until he was done thrusting too, her overriding priority appearing to be his enjoyment of his release. As he slumped forward, he triggered a domino effect of motion from the three girls.

Madison lifted her head from Olivia's ass-cheeks, and scooted over to the center of the room, where she remained on her knees. Jody emerged from the Doctor's undercarriage with a proud smile on her face, as if she had just contributed to one of the most significant orgasms in history. The Doctor looked back over his shoulder when she came out from beneath him, as if he wanted one more look at her angelic face to assure himself that this innocent looking goddess really had just been underneath him with her tongue deep inside his asshole.

I had to double-take too, inconceivable as it was that such a stunning young girl would be rimming this older man. Jody crawled over to Madison on her hands and knees electing to remain in her submissive role. The two of them waited expectantly for Olivia, who was moving a little slower than the two blondes, thanks to her protracted ass-fucking. She limped gingerly over, before sinking to her knees next to her fellow Cheerleaders.

I had seen the occasional snowball video on Pornhub although it wasn't really my thing. However, with three such beautiful women involved, one of which was my girlfriend, it was sure to be an erotic sight. As Madison parted her lips, revealing the milky contents of her mouth, the two younger girls descended upon her like starving nestlings waiting to be nourished. It was an incredibly exciting visual to watch Madison lower her mouth to theirs, and allow the semen to flow into their willing orifices, in much the same way that a bird feeds its young some regurgitated offerings. They passed his load freely between them, stopping occasionally to kiss or touch tongues.

Several moments later, as the volume of semen had diminished through attrition and ingestion, they knelt together and holding hands in solidarity, looked straight at the Doctor, and simultaneously swallowed the remains of his load. There was an impromptu round of applause from the rest of the guys, and the three young women remained motionless on their knees for a few moments more, their lips, noses and chins coated with his seminal fluids.

Madison arose first, and once again, having issued a barely perceptible signal, was followed out of the room by the other two, Jody skipping along without a care in the world, as Olivia limped gingerly behind her.

It was the Doctor's turn to slump in the chair now, thoroughly wiped out from his three girl orgasm. The fact that he hadn't paid yet was not lost on Madison, and she returned to the room shortly after she left, to extract the cash from his hands. He gave it up very reluctantly too, and I suspect were it not for the peer pressure of the rest of the guys to settle his debts, and pay the eight thousand one hundred dollars he had committed to, he would have probably tried to renegotiate.

His reluctance to pay was not lost on the other guys, for whom eight grand was chump change. In fact, he lost respect in the eyes of a lot of them for being a "cheap Charlie" as they say in Thailand. Possibly only George, who had elected to keep all of his cash and forgo the pleasures of the flesh, would have understood the difficulty the Doctor was having parting with his cash.

After he handed her the wad of cash, she counted it in front of him, seemingly to rub it in his face that they had extracted so much from him, for one orgasm. It was only going to be one orgasm too, for the Doctor, his reticence to pay assuring that he never got the promise of unlimited releases, the way the first lucky recipient of the two-girl blowjob did, after he willingly parted with his entire winnings. You could see the wistful look on the Doctor's face after he recovered from his orgasm, like he regretted getting caught up in the moment. He was no match for Madison, and had he known that an hour ago, he would be eight grand richer.

With the game having apparently been decided, the guys started to lose interest by the start of the fourth quarter, and with their inhibitions lowered by the alcohol, sex became the focus of their attention. The three Cheerleaders returned to the room having just freshened up, and began to circulate to see if the guys needed anything. Madison seemed delighted when the Patron of the Arts informed her that he was ready to go again.

"Bob wants to get pampered again," she announced to the room, as she beckoned Jody and Olivia over.

The three of them eagerly surrounded the guy, and as the rest of the guys listened on intently, they sent a unified message that Bob's generosity was to be well rewarded.

"What are you in the mood for this time, Bob," Jody asked him, as she snuggled up close to him and rubbed his cock through his pants.

"I still like blowjobs the best," he said, "although I hope you don't think I am being boring."

"Of course not," Jody said, "we like blowjobs too, Bob. How do you want us?"

As I watched the security tapes, I couldn't blame the guy for choosing oral sex again. Not only is it the safest bareback option, according to my recent education from the good Doctor, but it requires the least effort and participation from the man. Bob Matthews wasn't in the greatest shape, and much as he probably would have wanted a crack at Jody's tight little asshole, or Madison's twice-rejuvenated pussy, he didn't want to exert himself in front of the assembled millionaires.

"On your knees," Bob answered, with virtually zero hesitation.

I wouldn't have viewed him as a man who could get off more than once in an evening, but as the three of them sank gracefully to their knees, and he began to tent in his pants, it just goes to show that under the right sexual provocation, anyone can get it up again. As it turned out, Bob's issue was not one of getting an erection, but rather of delaying his orgasm under the visual delight of the three young girls on their knees.

Even though they took turns blowing him, it was evident that this was not going to be a protracted oral-worship session. Bob enjoyed Jody, Madison and Olivia's eager lips for less than three minutes before he signaled his intention to come. His legs had already started to shake, which was one of his pre-orgasm indicators.

"He's close," Madison informed the other two young women, "any minute now."

Even though Bob had experienced an otherworldly orgasm earlier on that evening, the volume of his seminal discharge hadn't been momentous, and knowing that his second cum-shot would undoubtedly be weaker, Madison upped the ante for the generous benefactor.

"Come on our faces, Bob," she offered enthusiastically, "we would love that."

I wasn't ecstatic about this turn of events, as I consider facials to be a particularly demeaning sexual act. However, Bob seemed delighted by that idea, and as the girls tilted their heads back and looked up at him smiling, he started to jerk off, blowing his load across their upturned faces, a few seconds later.

Bob sprayed them all too, in a move reminiscent of a Peter North cumshot. He shot his wad on Jody's innocent face first, the teenager squealing excitedly as he coated her lips and chin. With a slight turn to the right, he got Madison next, his second shot landing on her nose. Olivia parted her lips for his final rope of ejaculate, before taking Bob's softening cock into her mouth, as my girlfriend and Jody sucked and nibbled his nuts. He looked down appreciatively as the three young women cleaned their combined juices from his cock, and then to my surprise, declared his intention to leave. The game wasn't even over yet, but Bob had decided that he was done and wanted to get home to his wife.

After Bob's departure, the mood in the room got more serious. Even though I wasn't there, from the security footage I could see the guys eyeing each other up as they processed the fact that there was only one football pool winner to be determined. There were twelve hard cocks remaining for the fourth quarter, and only one of them was going to get lucky.

Of course, George and the Doctor had already enjoyed a little release, but all twelve of them were ready to go if the situation arose. The game concluded a few minutes after Bob's Uber arrived and to everyone's chagrin, particularly the three young girls, the Doctor won the final pool. Even though I had no vested interest in who won the twelve thousand five hundred dollars, the Doctor would have been my last choice. He had disrespected the girls by continuing to negotiate right up to the point of his release, and shown his lack of character by his reticence to pay up immediately after he came.

The girls had treated him to his fantasy orgasm, choreographed and presented to him exactly the way he had detailed it. He should have happily handed them the agreed upon sum of eight thousand one hundred dollars, and now he was going to regret his earlier actions. As Madison handed him the cash, the three girls adopted a united front, making it very clear that their pricing structure had just dramatically increased.

They were nice about it, offering excuses about it having been a long afternoon, and intimating that the ratio of men to women was too much for them to accommodate.

"Olivia's asshole is sore, Jody is recovering from the shock of giving her first ever rim-job," Madison began, as if to justify the increase in cost. "George put the wood to all three of us in the master bedroom," she lied, doing a fantastic job of saving face for the other participant who couldn't afford to be there. "I think we are done for the day," she added, as the two other girls nodded in agreement.

"How much for Jody's asshole?" the Doctor asked, clearly not getting the hint.

"Seventeen grand," Madison said with a straight face, as the rest of the room began to laugh nervously.

"Seventeen thousand dollars?" he repeated incredulously, "are you joking? She offered it to me bareback for free, less than an hour ago."

As I did the math in my head, I realized that Madison had arrived at a number that would have relieved the Doctor of every last cent of his remaining winnings, and required him to fork over an extra hundred bucks of his hard-earned cash. I knew that she was a mercenary bitch, but I was left in awe of her mathematical acumen. A few seconds later, as the rest of the room did the calculations on their iPhones and Apple Watches, everyone was up to speed and was in on the joke.

"How much to fuck Olivia's ass?" he enquired, having purchased it for one hundred bucks at the last break.

"Seventeen thousand dollars," Olivia said firmly, just to demonstrate that the three of them were on the same page.

I had to smile at the way they stonewalled him. I have a feeling that had he asked for a hand-job, he would have been quoted the same fixed price, seventeen grand.

Recognizing that his day was done, the Doctor announced his intention to leave.

"Can your driver run me home, Madison?" he asked her, under the impression that the limousine was still at his disposal.

"Only if you stay until George leaves," she said with a smile on her face, enjoying messing with the cheapskate.

The Doctor got the message that he was persona non grata at the gathering, and called an Uber shortly after his exchange with Madison. As he said his goodbyes, Baldwin couldn't resist kicking him in the nuts.

"By the way Doc," Baldwin said with a condescending smirk, "today wasn't Jody's first time eating a guy's ass. I had the pleasure of her young tongue between my buttocks a few weeks ago."

The Doctor glared at Jody, and she made no attempt to deny it.

"Madison and I both rimmed you that night, Steve," she said with a broad smile, engaging Baldwin.

After the Doctor left, Baldwin was quite vocal about the inclusion of guys that couldn't afford it.

"No more poor guys allowed," he said authoritatively. "They upset the dynamic with their reluctance to part with the cash."

Recognizing that there was a bartender in the room, who had emerged from the master bedroom with his hand all over Madison's ass, and having been relieved of his football pool winnings, he qualified his statement.

"Not you, George," he said apologetically, "You had no problem paying for your orgasm."

"No offense taken, Steve," George said in a friendly tone, presumably thankful that only the girls knew that his cash was nestled safely in the top drawer of my bathroom, along with Madison's wet panties.

With the game over, Baldwin took over the room, electing to steer the conversation back to Jody's ass, or rather how much it would cost for him to fuck it.

"The Doctor left with sixteen thousand, nine hundred dollars that should have gone to these lovely ladies," he began. "Let's give them an opportunity to earn some extra cash."