Trust Fund Baby Pt. 05

"We want to see Madison fuck Olivia's ass, the way that the Patriots are fucking the Packers," he directed.

This seemed like a desirable scenario for the rest of the guys, and as they cheered their approval, I had to agree that it made sense. Madison was wearing the colors of the presumably victorious Patriots, while Olivia was decked out in the Packers uniform. Of course the losing team should be on the receiving end of it. Olivia tried to remain cheerful, but I could tell she was pissed at the turn of events. Rightly so, as she and Madison had already exchanged words earlier that evening.

Madison, ever the courtesan, got into character immediately, and seemingly willing to postpone any discussion of their compensation, turned her attention to Olivia.

"Kneel bitch," she commanded with way too much vitriol.

Olivia flashed her a defiant stare, and then recognizing that today was all about the money, lowered her gaze in submission, and sank slowly to her knees. Madison placed her hand on top of Olivia's head in an overt display of ownership, and then in one fluid motion, grabbed a fistful of Olivia's hair and dragged her over to my Steinway grand piano. You could feel the renewed energy in the room as Madison manhandled the younger girl, and every one of the men was watching their interaction with interest, except the Doctor, who had locked eyes with the teenage beauty Jody, as she bobbed up and down on his cock.

Madison retrieved Olivia's studded dog collar, and one of the black leather leashes, and forced the seemingly frightened young girl to rest her upper body across the top of my black leather piano stool, thus adopting the doggy-style position. After collaring her and tying her off to one of the legs of my grand piano, Madison removed Olivia's petticoat and panties, before kicking her legs wide apart, and issuing her a one-word command.

"Stay," she said authoritatively, as Olivia remained in her supremely vulnerable position.

From the security footage, it was tough to tell if Olivia was acting scared for the benefit of the men, who would have undoubtedly found her fear titillating, or if she was genuinely frightened. However, as she laid over the padded piano stool, she appeared to be trembling, and looked anxiously over her shoulder every few seconds.

Olivia was sneaking a peek when Madison finally returned to the room, although she immediately averted her gaze upon hearing the barked command.

"Eyes front," Madison growled.

All eyes turned towards Madison as she strode into the room as if she owned it. She was still dressed in her sexy Cheerleader Uniform, as the whole intent of the exercise was for the Packers to get fucked by the Patriots, as they were in the game. However, she had a black leather harness buckled around her waist, and affixed to the center of it was a large, intimidating looking, black dildo. She had a small black bag in one hand, which she put on top of my piano, before she did a lap of the room to showcase her strap-on.

A few of the guys involuntarily raised their hands to their mouths, evidently in shock that Madison was going to use such an enormous phallus to violate her young friend. This was supposed to be just an entertaining sideshow, a depiction of how badly the Packers were getting fucked. To my surprise, it was Jody who intervened. Removing her lips from the Doctor's cock, she arose from her knees and walked over to the piano stool.

"Let me lube you up, Olivia," Jody offered, "before you get your well deserved ass-fucking."

I wasn't sure of Jody's motives, as she opened the small black bag and retrieved a bottle of Anal-Ease lubricating jelly. I don't know if she had genuine concerns for Olivia's well-being under the threat of assault from that black monster, or if she feared that she was next, but she took her time to thoroughly prepare Olivia's anal cavity. It was an erotic sight watching Jody on her knees behind Olivia, as she was sprawled over the piano stool. Once Jody deemed Olivia sufficiently lubed, she turned her attentions to Madison, who had been stood over the younger girls, eagerly awaiting her turn to violate Olivia's ass.

As the guys looked on intently, Jody extended her dainty hand to Madison's phallus, and with a counter-clockwise half-turn, released the black monster from its harness. As she slowly stood up and moved towards the black bag on the piano, she spoke.

"Let's open her up slowly, Madison," the beautiful blonde suggested. "That way she won't be too sore if one of the guys wants a crack at her asshole when you are done."

Offered that way, Jody's suggestion was tough to ignore, and Madison stood there quietly as the young blonde selected a much smaller strap-on attachment, before falling to her knees in a show of submission that drew murmurs of approval from the guys. Jody attached the thinner phallus into the harness, an ominous click signaling that it was securely fastened, and remained on her knees looking up at Madison for permission to rise.

Even though it was clearly not choreographed, their interaction was sexually charged and all of the men looked on appreciatively. The Doctor, whose pants were still around his ankles, having been interrupted mid-blowjob, was still sporting an impressive erection, and I wondered if he had employed a little pharmaceutical assistance, given his easy access to drugs.

"Suck my cock, Jody," Madison ordered, as the men continued to voice their approval.

This impromptu blowjob, which was an unexpected bonus for the guys, also crystallized my desire for the teenage runaway. Ever since I first laid eyes on her, as I watched the footage of her and Olivia blow Bob Matthews, she had elicited a strong response from me, that of fascination, merged with lust. As she lowered her young lips onto Madison's strap-on, my cock stiffened in my jeans, and I decided that I was going to fuck this young goddess, regardless of the wrath that I might incur from Madison.

I could barely avert my gaze from the visual of Jody sucking Madison's strap-on, particularly as I switched to a different camera, that provided a straight-on view of the action. She looked so innocent, so submissive as she worshipped the smaller black phallus, maintaining eye-contact with Madison the entire time. On the rare occasion when I stole a glance at the assembled men, it was evident that they were in the same state of enrapture that I was, completely and utterly captivated by this cherubic teenager.

After several moments of the oral-worship, Jody incorporated the motions of a hand-job, and while it was done in conjunction with the blow-job, it soon became apparent that its purpose was to coat the strap-on with the lubricant that remained on her hands. Jody coated the fake cock with a generous application of lube, which when mixed with her saliva, was going to provide some much needed emollient for when Madison entered Olivia's asshole. I think Jody also recognized that she might be next in line to get sodomized, and was setting a precedent for a thorough application of lubricant.

Once the strap-on was sufficiently lubricated, Jody moved aside although she remained on her knees. Madison knelt behind Olivia, and lined up the tip of her dildo with the entrance to Olivia's asshole, which was glistening from the generous coating of lube. There was no love lost between these two women, and Madison seemed intent on punishing the younger girl for her recent revelation that she had purchased Samantha's teenage pussy for my enjoyment.

What ensued was a protracted, aggressive, ass-fucking as Madison relieved some of her pent-up aggression on Olivia, and the younger girl took it like a champ. She seemed determined not to let Madison get the better of her, and managed to remain fairly composed throughout the ordeal. At one point the Doctor intervened, presumably because he was hoping to be next. After requesting a brief pause in the action, he assessed Olivia's well-being.

"I am almost finished, Doctor," Madison said sweetly, using her dulcet tone to reduce the appearance of her brutality. "Then it will be your turn to fuck her ass. You still haven't busted a nut yet."

I had to smile at her continued manipulation of the man. He had felt some obligation to intervene, but upon learning that he was next, he opted to give Olivia some amyl nitrate, which would have relaxed her sphincter almost immediately, and mitigated some of the discomfort. After Olivia inhaled the poppers, Madison resumed the protracted ass-fucking, and both girls were visibly sweating by the time Madison withdrew from the younger girl's anal-cavity.

It was evident that Olivia's asshole had been sufficiently opened up for enjoyment by the other men, but as Madison got back on her feet, I noticed vaginal secretions on the inside of Olivia's thighs, incontrovertible evidence that she had enjoyed her public violation.

Even before she approached Jody, I knew that ass to mouth was next on the menu. As the realization dawned on the young blonde, she wrinkled her cute little button nose in disgust, before remembering that they were putting on a show for the men, and affecting a broad smile for their benefit. With a certain amount of theatricality, Madison bypassed Jody and walked around to the other side of the piano stool, where Olivia's head was positioned.

"Suck me clean, you fucking bitch," she said venomously.

I knew enough about high-class working girls to understand that they always prepare themselves for every eventuality. Olivia had given herself a thorough anal-cleanse prior to appearing at the party, so the only fluids that she sucked from the phallus, were lube, saliva and traces of blood. However, it was an unnecessarily humiliating situation to be put in, and deepened the rift between the two women.

Even though the Doctor had paid two grand for the privilege of a blowjob from Jody, she had thus far been unable to get him off, which was surprising to me. In the same circumstances I would have been a very easy come for the young blonde. Recognizing his unworldly stamina, Jody suggested that he finish in Olivia's ass, hoping that perhaps the change in stimulation would get him to the finish line.

"How much extra is that going to cost me?" he asked, highlighting the fact that he wasn't in the same financial league as most of the other men.

"It's not worth much," Madison said coldly. "Let's call it an extra hundred bucks."

"No way," Olivia interjected, the fear palpable in her voice, as she contemplated her continued violation, for a measly hundred dollars, which would be split three ways.

Even watching the security footage, I could tell that she was uncomfortable, if not actually injured. After a cursory medical examination of her rear end, the objectivity of which I had to question, seeing as the examiner was next in line to sodomize her, she was deemed healthy to continue.

Madison noticed the slick juices coating Olivia's inner-thighs, and immediately remarked on it.

"That bitch is fine," she said coldly. "She leaked all over herself. She actually enjoyed it. Go for it, Doctor."

"I will need a condom," the Doctor said matter of factly, well aware that anal sex increases the risk of transmission.

As Jody retrieved a prophylactic from the small black bag, and began to roll it over the tip of the Doctor's cock, Olivia looked fearfully over her shoulder, trying to assess the physical dimensions of her next assailant. Luckily for her, the Doctor possessed an average size cock, although judging by the fact that he had been rock-hard for the last thirty minutes, it was evident that he had ingested some kind of performance enhancing drug.

Jody took the time to ensure that the exterior of the condom was thoroughly lubricated with Anal-Ease, before she helped the good Doctor slip inside Olivia's asshole.

I could see Olivia relax as it became apparent that the Doctor's cock was significantly smaller than the strap-on that she had just been violated with. In addition, because he was making love to her for his pleasure and eventual release, rather than trying to punish Olivia and release pent-up anger the way Madison had, it was a much less brutal encounter. Jody knelt next to the Doctor and kissed him tenderly on the lips.

"Do you want me to lick your ass?" she asked, with her practiced innocence.

I felt my cock throb at this prospect, and vowed that one day Jody's tongue would be between my butt-cheeks. The Doctor let out a whimper at her offer, and appeared to edge closer to his release.

"You are way too beautiful to be eating a guy's ass, Jody," he responded, as he kissed her on the forehead.

She seemed to respond favorably to his compliment and the paternal way that he had shown his affection. However, tonight was all about business opportunities, and I knew she was playing him the second she responded.

"Wouldn't that turn you on to have such a pretty young girl stick her tongue in your ass?" she countered, trying to break him down. "It would be my first time," she added seductively.

My heart sank at the thought of that lost opportunity. I had no clue that Jody had never rimmed a guy before, and would have loved to have taken that from her. Baldwin flashed her a knowing look, as if to call bullshit on her claims of innocence, and it became apparent to me that she had rimmed him the night that he took Madison and the two teenagers to bed. Either way, for whatever reason, Baldwin didn't feel compelled to burst the Doctor's bubble, and Jody continued to manipulate him.

"I am going to get behind you, Doctor," she informed him. "If you don't like it, just tell me to stop."

He lowered his head, and let out another whimper of anticipation, as she gave him one more peck on the lips, allowed him to digest how stunningly beautiful she was, and then disappeared behind him.

I saw his eyes widen with pleasure, and he shuddered with delight as her soft hands parted his ass-cheeks. She lowered her head towards his buttocks, and extending her moist tongue, gave his taint a couple of tentative licks.

"Does that feel good, Doctor?" she asked, as he shivered with excitement.

Madison sensing a fresh business opportunity, moved towards the medical practitioner and began to suck on his earlobe. As he fucked Olivia's ass, and Jody teased his taint with the tip of her tongue, Madison went to work on him, utilizing her expertise in verbal stimulation.

"What are you doing to Olivia?" she asked him, as she sucked and nibbled his ear. "She seems to be loving it."

"Ass-fucking her," the Doctor said shakily, seemingly in disbelief that he had three girls working on him simultaneously.

"Yeah, buddy," Madison said enthusiastically. "You paid good money for that ass. Fuck the crap out of it. You own it."

"Oh fuck, I am getting close Madison," the Doctor whimpered. "Talk dirty to me, baby."

"What the hell are you making Jody do?" Madison asked in mock horror, as if the indignity was too much to believe.

"Jody is eating my ass," he replied, his voice growing increasingly shaky as he got closer to ejaculating.

"That dirty slut," Madison added, pretending to be shocked. "You know she is only eighteen, right?"

"Oh fuck," the Doctor moaned, "I can't believe that beautiful teenager is licking my ass."

It was a testament to Madison's skill at pushing men to their limit, before finally breaking them. It was both incredibly sexy, and extremely difficult to watch, because I knew from personal experience that the other shoe was about to drop. Madison had taken me to the brink of orgasm so many times, before abruptly halting the proceedings to ask me for something in return. She was an absolute master at this game, and the good Doctor was her latest victim.

"How much did you pay Jody to lick your taint?" Madison asked, a few moments before the Doctor climaxed.

"I gave her two grand," he said, through ragged breaths.

"No," Madison corrected him. "The two grand was for the blowjob that she gave you. And you paid an extra hundred dollars to fuck Olivia's not so virgin ass," she added, continuing to diminish Olivia's worth. "My question is, how much are you wiling to pay this stunning teenager to rim you until you ejaculate?"

The Doctor had already parted with two thousand one hundred dollars of his football pool winnings, and had apparently decided that this was more than ample compensation for his upcoming orgasm. Not only did he completely evade the question, but he began to accelerate his thrusting motions, trying to get release before they got deeper into his wallet.

As a man, and a perpetual victim of Madison's skillful manipulation, I knew exactly the sexual torment that he was about to experience. Madison placed one hand on his abdomen thus preventing any further forward motions on his part. This effectively halted his impending release, and put the girls in a powerful negotiating position. I had been in this position many times before, with my nuts churning and ejaculation the only thing on my mind. Even though I had often regretted it shortly after I blew my load, I had made countless concessions when I was in the throes of sexual delight.

Jody emerged from between his buttocks, and knelt on one side of him.

"Did that feel good, Doctor?" she asked him in a girlish voice. "Are you ready to feel my tongue inside your ass?"

"Tell us how you want to finish," Madison said seductively. "Whatever you want is yours. Don't be shy!"

"Why don't you fuck my ass?" Jody offered, her vulgarity seemingly in contrast with her angelic looks. "You can do me bareback."

As they offered him numerous different scenarios, you could see his resistance being worn down, and he verbalized part of his fantasy, in a trembling voice.

"I want Jody to keep rimming me," he informed them. "And I would like to take off the condom."

"Whatever you want, baby," Madison whispered, as she eased his cock out of Olivia's asshole, and deftly removed the sheath.

I empathized with the Doctor at that moment, as he had lost sight of the battle, choosing instead to focus on the exact fantasy scenario that he wanted for his impending orgasm. They had him right where they wanted him, and every single person in that room knew it, except the hapless Doctor. He had been right on the brink of orgasm when Madison pulled the rug out from underneath him. The head of his cock was swollen and throbbed involuntarily as he verbalized his desires to them. There was a large glob of pre-cum pooling at the tip of his erection, and several blood-engorged veins visible on the shaft. His cock looked warm to the touch, and his nuts were drawn tight against the base of his penis, which occurs just before the male release.

Madison's beautifully manicured hand rested on his stomach, moving in and out in concert with his abdomen under his labored breathing. They had brought him tantalizingly close to orgasm, before terminating any stimulation and turning their collective focus to how much he was willing to pay to finish. Jody extended her dainty hand, dipped one fingertip into the pre-cum that was gathered at the tip of his cock, and scooped it up. Looking every bit the teenage angel, she licked the seminal fluids from her finger, before offering Madison a taste. The girls devoured his pre-cum as if it was the nectar of the Gods, prompting another moan from the Doctor.

"I want to fuck Olivia bareback, while Jody worships my asshole," he admitted. "Madison, I want you to kiss me and talk dirty to me until I am right on the brink, and then I want to come in your mouth."

"Wow that sounds amazing," Madison squealed. "We would be honored to do that for you."

Even though I was watching this on a large screen television, Madison was getting me hot and bothered. I had been erect for most of the time that I had spent reviewing the security footage, and as they tormented the Doctor, I wanted to jerk off. The way they were manipulating him was impressive enough, but the dialogue, the way they chose their words so carefully was exquisitely erotic.