Trust Fund Baby Pt. 05

"You know Madison," Olivia responded, giving as good as she got, "the last time I exchanged money for sex, was when I purchased Samantha's eighteen year old pussy for Pete to bust a nut into."

I recoiled when I heard that brutally honest revelation. Although there was no way I could take it back, I knew immediately that it was going to cost me.

Madison tried to maintain her composure, but she had two questions and she couldn't contain her curiosity.

"That bitch was only eighteen?" she blurted out, followed immediately by, "You bought that slut for Pete?"

Olivia was enjoying having the upper hand for once, and couldn't resist twisting the knife.

"I procured the beautiful young girl, dressed her up in a nice suit complete with a garter belt and stockings, spritzed her with your favorite perfume, and left her bent over the counter for Pete to discover," she added, slightly embellishing the truth, but accurately encapsulating the main elements of my brief encounter with the young runaway.

"You fucking bitch, Olivia," Madison spat at her.

"Pete said he imagined that was how you looked when you were younger," Olivia added, completely fabricating my remarks.

"You're a dirty skank, Olivia," Madison said venomously, lost for a better comeback.

"That little princess even ate his asshole in the shower once we got home," Olivia said with a huge smile on her face. "Pete was whimpering like a little girl when he finally came. He kept looking at Samantha and telling her how beautiful she was, but I know he was imagining you as a younger woman, Madison."

I really liked Olivia, and while I recognized that Madison had been unjustly cruel to her in the past, this outburst was going to get me in hot water. I could see the fire in Madison's eyes as Olivia continued to taunt her. However, it appeared to be a desire for revenge rather than any malice towards the bearer of bad news, and I knew that I was going to pay for my indiscretions with Samantha.

I thought their confrontation might get physical, but as the shower turned off, a remarkable thing happened between them. Recognizing that there was still twenty five thousand dollars to be won in the football pool, the two women extended the olive branch to each other, the prospect of relieving the lucky winners of the cash, evidently more important than their grudge.

"This can wait," Madison offered, as Olivia nodded in agreement.

Moments later, George emerged from the shower, with just a towel around his waist. I had only seen him in shorts and a polo-shirt before, so I knew he was athletic, but I had no clue how well-defined he was. The girls seemed pleasantly surprised too, as the twelve millionaires waiting behind the other side of my bedroom door, were anything but athletic.

"Why don't you two get changed back into your Cheerleader Uniforms?" Madison said sweetly, any evidence of her ill-will towards Olivia having evaporated.

As Olivia and Jody entered my bathroom to freshen-up and get changed, Madison invited George to lie down on the bed. He seemed confused at first, reiterating that he couldn't justify parting with his winnings, no matter what sexual delights were on offer.

"Don't worry about the money, George," Madison assured him. "I am going to give you a little release, to take the edge off. It is going to be a long evening, and I don't want you to be walking around with a perpetual hard-on, and have to watch all these rich pricks bust a nut."

As George laid down on the bed, Madison positioned a couple of pillows under his head, and after ensuring that he was comfortable, she beckoned Jody and Olivia back into the room. Under Madison's watchful eye and strict tutelage, the three Cheerleaders slowly divested the young bartender of his towel, and once he was naked they caressed him tenderly, using just their hands.

Under those circumstances, if I wasn't a trust-fund millionaire with lots of options, I would have folded. As the three of them worked on him, with the loving tenderness that only a true girlfriend could provide, I could feel his resolve weakening. I considered the possibility that this was an elaborate scheme to relieve him not of just his pent-up sexual frustration, but also his twelve grand, but knowing Madison's history with him, this seemed unlikely.

Once George was rock-hard, Madison gave the other two girls a barely perceptible signal, and they arose from the bed and returned to the bathroom that was adjacent to my master bedroom. They closed the door behind them, leaving George alone with his long-time crush. I wondered how often he had jerked off thinking about her in the past, and how much he had fantasized about this moment. Well, not this exact moment, one in which he was about to get some pity play, a quick release offered out of commiseration for the fact that he could not afford any of what was on offer. No, George would have imagined an intimate, extended love-making session with Madison, a one on one, unrushed, sensual affair, the primary focus being his release.

To Madison's credit, that is exactly what she provided the young bartender. As Olivia and Jody prettied themselves up for the second half of the Super Bowl, and the dozen guys in the other room watched the half-time extravaganza on the huge television screen, Madison grabbed a bottle of KY lubricant, and lay down on the bed next to George. He was already erect, visibly excited, and ready to go, some pre-cum having dribbled onto his stomach.

However, despite his apparent readiness to get on with it, she took the time to position him in such a way that the CCTV camera had a straight-on view. As I watched the security footage, I knew immediately that this was payback for Olivia's revelations about my indiscretions with Samantha. Using the blinking red camera light as a marker, Madison maneuvered herself so that she was also in the center of the frame. Then, after blowing a kiss at the fish-eye lens, thereby assuring anyone who was watching that her actions were consensual, and meant to be shared, she lowered her lips to his ear.

Recognizing that the verbal stimulation was as powerful as the physical, she began to whisper sweet nothings to him as she drizzled a copious amount of lube all across his cock, balls and inner-thighs. Once she had him covered in the slippery liquid, she let the KY bottle drop to the floor, and ran her manicured fingertips across his ever-tightening stomach.

As I watched her trace her nails across his lower torso, raking around the rim of his belly button before slipping under his swollen nuts, I remembered that she was my girlfriend, not his. She was creating such an illusion of intimacy between a loving, committed couple, that for a brief moment I forgot that Madison belonged to me. She had, thus far, managed to avoid any sexual contact with the partygoers, other than sucking and licking Bob's earlobes as the two younger women blew him. Now, in the comfort and privacy of my bedroom, and with no apparent financial motive or reward, my girlfriend was pleasuring another man.

As I watched her slowly envelop his cock and started to jerk him off, I wasn't sure what pissed me off the most, the intimacy with which she was performing the act, the way in which she appeared to pose for the camera, or her fucking fingernails, which painted in the colors of the New England Patriots, only served to enforce the fact that she was playing for the other team.

As I would learn in later life, one of the principle differences between a girlfriend and a courtesan, is the efficiency with which they coax an orgasm from your nuts. I had numerous girlfriends over the years, and it never ceased to amaze me how often a woman would quickly undress me, stick my cock between their lips, and work tirelessly for fifteen or twenty minutes to get me to release. Madison, on the other hand, would playfully remove my clothes, using this time to build my anticipation of what lay in store for me. Using the softest of touches, she would wait until my underwear was sticky with pre-cum, before removing them. Once I was naked, her dainty hands would roam freely across my body, caressing my erogenous zones, tenderly stroking my butt-cheeks and the sensitive areas between them, probing my taint and anal-cavity with the tips of her manicured fingertips.

Once I was leaking profusely, and whimpering under her ministrations, she would apply the appropriate lubricants depending on the form of release she had decided to offer me. A few moments of barely perceptible grazes on my shaft, frenulum and glans, would be all it took before I would be approaching orgasm. More often than not, she would slip her moist lips over my cock-head right before I exploded, thereby reducing the actual act of oral-sex to a few seconds of work for her.

Even though I knew, and accepted, that Madison was a courtesan, I took solace in the fact that there always appeared to be some distinction between the mechanical sex acts with a paying customer, and the loving, intimate way in which she skillfully brought me to climax. Even when she incorporated her vaunted GFE, for which men paid considerably more money, there was still a noticeable difference between her encounters with her clients, and her encounters with me.

However, as Madison appeared to still be processing the recent revelation that Olivia had procured Samantha's teenage ass for my enjoyment, she seemed hell-bent on payback. As she maintained eye-contact with my security camera, her blue eyes twinkled with delight, and as she worshipped the young bartender, it seemed as if she wanted nothing more than to rub my nose in it.

I am a naturally jealous person, but as I watched Madison treat George to all of the intimate touches that she typically reserved for me, and that I assumed to be our secret, I felt my jealousy raging through me. I have no fucking clue what she was whispering in his ear, the entire time that she was giving him such an exquisitely intimate and gentle hand-job. However, whatever the fuck it was that she was promising him, was driving him rapidly towards the edge of release.

As his breathing quickened, and his stomach muscles tensed, she removed her glossed lips from his earlobe, placed one feminine hand on the side of his face, and began to kiss him. Much to my chagrin, even their intimate, sensual kissing was almost identical to the way she made out with me. She was licking and nibbling his lips, the tip of her tongue darting in and out of his slightly opened mouth, as she grazed her fingertips across his temple.

The whole time that she was attending to his needs, her face conveyed a look of utter delight. It was as if she was simultaneously grateful for being allowed to pleasure this man, and also in awe of the experience, as if it were her life-long dream. I know that she was playing it up for the camera, but the vision of her seemingly deriving so much joy from servicing another man, was really pissing me off.

"Oh fuck, Madison, I am getting close," George whimpered.

"I know, baby," she cooed, "blow your load whenever you are ready."

When it was evident that George was about to come, Madison lowered her head slowly towards the tip of his cock. She parted her glossed lips, took his glans between them, and with a quick wink at the camera, to keep my jealousy elevated, began to suckle his cock-head as she lay motionless on his abdomen.

George, fast approaching his orgasm, and under the relentless and sustained provocation of her teasing, began to slowly thrust his hips. Despite the disrespectful move, Madison offered him zero pushback which apparently emboldened him to begin to fuck her mouth in earnest. I have never viewed Madison as a passive lover, but she laid quite still as George used her mouth, a large smile still evident across her face as she mocked me through the lens of the camera.

As he increased the speed and depth of his thrusts, he placed one hand on the top of her head to hold her in position. Madison flashed a look of mock surprise at the camera, and once again her blue eyes twinkled. As he held her in place, I realized that by doing so, he had reduced her options when he finally ejaculated in her mouth to one, that of swallowing. She seemed fine with it, remaining surprisingly compliant, not only offering him zero resistance, but also maintaining eye-contact with the camera, as he fucked her mouth.

George came in my girlfriend's mouth moments later, a copious load it appeared, judging by her harried attempts to swallow it. I can't imagine how good it felt for him to enjoy his fantasy girl, particularly as he had been quite candid about jerking off to the thought of her, when I pressed him for the details of their sexual history.

George had rolled slightly onto one side to provide himself more leverage as he face-fucked her, and after he was finished ejaculating, Madison rested one of her beautifully manicured hands on his ass, to prevent him from pulling out. She continued to suckle him for several moments, before she rolled him onto his back, and then gazing directly into the camera, she parted her lips slightly to allow his softening cock to slip from her mouth. As she did so, the combination of her saliva and his semen rolled out over her lips, across her chin and down her neck, drying as it coated her.

She gave her lips an exaggerated lick, blew an air-kiss at the camera, and then moved her head slowly up his body until their mouths touched, and she began to kiss him tenderly as if she truly loved him, and was honored to have been allowed the privilege of satisfying him orally. As they French-kissed, it felt like a kick in the nuts, and I knew that Madison felt like she had extracted sufficient payback for my encounter with Samantha. She didn't exactly rush from his arms either, and it was several moments later before she arose from the bed, kissed him tenderly on his forehead and entered my bathroom, the door of which was still closed to give them privacy.

Olivia and Jody emerged from my bathroom, attired in their matching Green Bay Packers Cheerleader Uniforms, and made their way back to the party. The guys greeted them with a raucous cheer, and I switched back the security camera feeds, just in time to hear the girls fend off any questions about what the hell the four of them were doing in there. Satisfied that the women had earned their twelve thousand five hundred dollars, the men stopped their interrogation and got back to the game, right at the start of the third quarter. Jody and Olivia resumed their game positions, kneeling submissively in the center of the room, waiting for drink requests.

As I flipped back to the footage of my bedroom suite, I noticed George and Madison, still flirting, exchanging the occasional kiss as she helped him to dress. Attired as he was in his customary shorts and polo shirt, this didn't take long, although his underwear was sufficiently slick with his pre-cum that she grabbed him a pair of fresh briefs from my underwear drawer. There was a brief awkward moment as Madison handed him his cash winnings, and George seemed to contemplate giving her some of it. However, in true Madison style, she repeated her assertion that what she had treated him to, was without charge.

"Truth is George," she said, as she smiled into the bedroom camera, "I have wanted to suck you off for years. I hope that you enjoyed it as much as I did. In fact, I need to change my underwear. Blowing you made me wet."

With that disturbing proclamation issued, Madison wriggled out of her one hundred and forty dollar, black LaPerla undies, and taking great care to ensure that the crotch was visible on the camera, showed George the evidence of her arousal. True to her word, there was a large slick patch of her vaginal secretions in the liner of the panties, although I have no doubt that it was triggered by the large amounts of cash that had been exchanged so far, rather than her oral servicing of George.

"Keep them," she offered. "A little reminder of our first hookup, until next time."

George did take her pro-offered panties, and followed her directive when she offered him a place to store them temporarily.

"Stuff them in my top drawer in the bathroom along with your cash," she said. "No-one else will be in there tonight."

I switched camera feeds as George entered my bathroom, and watched him nervously wedge twelve thousand five hundred dollars, and a pair of very wet expensive panties into the top drawer. Madison followed him in there, and as he closed the drawer, he turned to thank her one more time. He leaned in for a kiss, but she immediately shut him down. Claiming that she had just freshened her lipgloss, she ignored his advances, and even I was surprised at the change in her attitude towards him. They made uncomfortable small talk as she freshened up her mascara, and wiped his dried ejaculate from her chin and neck. Then she announced that they should return to the party.

George seemed confused, a little disappointed by her mercurial attitude towards him, but this was amplified when they went to leave the bathroom, and she placed his hand on her ass and snuggled in close to him.

"Walk me back into that room, as if you own me," she instructed.

Once they rejoined the party, George returned to his seat to a round of applause, and Madison took a quick bow, and then knelt in the middle of the room awaiting further instructions. I, too, was confused by her change of heart towards him, and ended up rewinding the security footage. As I switched between the cameras in the bedroom and the bathroom, it dawned on me. Madison had no clue that I had a security camera in my bathroom, and so didn't feel it necessary to hang all over George to make me jealous, when they were in there. I had disabled the red flashing light in the bathroom fish-eye lens, so that I could record surreptitiously, and Madison hadn't noticed the presence of the recording device.

Switching back to the main living area, I fast forwarded through a relatively uneventful third quarter, at least as far as the action that I was interested in. The football game was very exciting, with the Patriots extending their lead. However, I had seen the game live the previous day, and was way more interested in the sex. At the end of the quarter the Patriots had secured an almost insurmountable lead, and the Doctor was the lucky winner of the pool. The three girls descended upon him seconds after he was handed the twelve thousand five hundred dollars in cash, determined to pry it from his hands.

While the Doctor didn't have the pressing financial concerns that George had, he wasn't interested in blowing his entire windfall on one orgasm, and he began to negotiate. I found myself shouting at the tv monitor as I watched the event unfurl a day later, willing him to back away from the young Cheerleaders and negotiate from a safe distance. However, as they surrounded him, and began to caress, grope and kiss him, I could see his resolve weakening, which was completely understandable. He had three beautiful young girls, dressed as sexy Cheerleaders, offering him every possible imaginable option for release.

In the end, as Jody dropped to her knees and began to unzip his pants, he agreed to a blowjob from the young goddess, for two grand.

"What do you want us to do while she blows you?" Madison asked seductively. "We want to be part of your pleasure, too."

I think Jody recognized the dynamic between Olivia and Madison, because right before she slipped her teenage lips over the tip of the Doctor's cock, she made a suggestion that resonated with the medical professional.

"Have them put on a sex show, while I blow you," she whispered.

The other guys let out a raucous cheer at the thought of this, and Baldwin laid out their expectations, in his typical Alpha style.