Trust Fund Baby Pt. 05

"What do you have in mind, Steve?" Madison said seductively, as she moved towards him. "We would be happy to give you a token of our appreciation as the host of today's party."

I knew exactly what Madison was up to, and I really didn't want to watch it, but I just couldn't turn away. With another barely perceptible signal she beckoned Jody and Olivia over, and the three of them began to caress and stroke his cock through his pants.

"I am not looking for a freebie," he said dismissively. "Madison, you of all people should know that."

"What then, Steve?" she countered. "Whatever you want is yours."

"I want to auction Jody's ass to the highest bidder," he said with a smirk. "I will start the bidding at two thousand dollars."

"Three thousand," the divorced Performing Arts Center benefactor responded immediately, evidently having tired of watching from the sidelines.

If the attentions of the three girls had awakened Baldwin's cock, the prospect of selling Jody's asshole made him get fully erect, particularly now he had a new bidder. As Baldwin got hard, I understood immediately why Madison had told me that Jody had "squealed like a pig" when he took her anal-cherry. He had a very impressive looking member, and as it struggled against the confines of his underwear, and she eyed it nervously, I felt sorry for the young runaway.

Anal-sex is not without some discomfort for women on the best of days, but I imagine that there are other factors in play, when you engage in it for the first time. Jody had taken that monster cock between her tight little teenage buttocks in exchange for a place to stay, and her violation had been witnessed by two other young women, one of whom will one day be my wife. It was clear from the look on her face, that she was dreading a repeat performance, particularly as it would likely be witnessed by the entire party.

"Thirty-five hundred," Baldwin bid, his erection clearly visible in his pants.

"Four thousand," a voice from the back of the room offered, which I recognized as belonging to Clarkson.

I saw a cruel smile appear on Madison's face, and it took me a split-second to realize quite what she found so amusing. As I observed the two guys bidding against each other, it occurred to me that Jody was in for a rough ride if either of them won. Baldwin had already made her squeal like a pig, and I had handled enough of Clarkson's used condoms to know that he was hung like a horse, too.

Madison seemed to view the entrance of a third bidder as a financial opportunity, and in an attempt to increase the value of Jody's asshole, slowly lowered her petticoat to the ground, before the young blonde stepped out of it. The short Cheerleader skirt barely covered her tight buttocks and as Jody wiggled her ass seductively, another bid came in.

"Forty-five hundred," the recently divorced benefactor offered, lust evident in his eyes.

Jody really did possess the perfect ass, and I found myself fantasizing about being at that party, without Madison, and bidding on her. There was a short break in the action, time which Madison used to remove Jody's skirt, and give her a firm slap on her tight little butt-cheeks, which when uplifted by the high heels she was wearing, seemed to defy gravity. As the slap reverberated around my living area, there was renewed interest in the young blonde's asshole.

"Forty-seven fifty," Baldwin said with conviction.

Jody would have had no clue that Clarkson was well-endowed, but she seemed to genuinely fear a repeat performance with Baldwin, and as he currently was the highest bidder, she decided to strut her stuff and try and engage a few more contenders. As Jody circulated the room, practically begging guys to get involved in the auction, she was rewarded with the participation of two more men. The bidding quickly surpassed six grand, before Madison proposed a five minute break.

"Let us refresh your drinks," she said sweetly. "Then you guys can assess the value of Jody's not-quite virgin ass."

As the girls left the room, the remaining bidders gravitated towards Baldwin, peppering him with questions as to the validity of her claim that she was "an anal-virgin, once removed."

"I have no reason to doubt that," he said with a smirk, and the cocky assurance of a man that took her anal-cherry. "She was tight as fuck."

"With a cock like yours, all bitches feel tight," one of the guys opined.

You could feel the camaraderie in the room as the guys shared a laugh, but right as Jody walked into the room, holding a tray full of ice-cold beers, someone else spoke up.

"If Baldwin or Clarkson win the bidding, that young girl is in for a rough ride," the guy said to a raucous response from the group. "They are both hung like donkeys."

Jody placed the tray of beers on top of my piano, and after handing them out to the guys, grabbed Madison, and pulled her into my kitchen. They were out of sight and earshot of the guys, but I was able to change camera footage and watch their exchange.

"Is it true what they are saying about Clarkson?" she asked, her face sick with worry. "You should know, Madison, you guys get together once a month."

While I wasn't ecstatic that Jody knew about Madison's monthly encounter with Clarkson, I was glad that the young blonde was about to get some fair warning about the challenges she would face if Clarkson ended up sodomizing her.

"I wouldn't wish that on my worst enemy," Madison said. "I haven't had sex with him in years because he is too well-endowed. I limit my encounters with him to blow-jobs and titty-fucking."

Well, that was a kick in the nuts for me to hear. It was bad enough knowing that my girlfriend gave him a loving, edging, monthly blow-job, particularly as of late he had eschewed wearing a condom. However, to know that he also fucked her tits was distressing to me, although it did offer a reasonable explanation for the semen that was matted in the lace bodice portion of her new mint-green chemise.

"Really?" Jody said dejectedly. "He is that big?"

"I think he is bigger than Steve," Madison added. "He uses Magnums."

"Magnums?" Jody responded, her innocence suddenly on display. "I don't understand."

"Did Baldwin wear a rubber the night you, Rachel and I spent with him?" Madison asked the younger girl?

I had no clue who Rachel was, but putting a name to the third girl that spent the night with Baldwin, made it all the more real, and pissed me off.

"Not when we had vaginal sex," Jody, said shyly, "or when I sucked him off."

"How about for anal?" my girlfriend asked, as I was still processing Jody's comments and trying to figure out how many times Baldwin came that night.

"Yes," she said quietly. "He did use a condom when he ass-fucked me."

"Ok," Madison said. "What kind of rubber did he use? Did you put it on for him?"

"No," Jody admitted. "He made the decision at the last minute. He was fucking me bareback, doggy-style. Rachel was sucking his nuts while we fucked and I think you might have been in the shower. At one point his cock slipped out of me, and as he went to put it back inside me he asked me if I had ever had anal sex. When I admitted that I hadn't, he told me that he was going to take my anal-cherry from me."

"He told you, Jody, or asked you?" Madison said quietly.

"He certainly never asked for my permission," Jody responded. "Guys like Steve don't really ask, do they?"

There was a moment of silence between them and they exchanged a knowing glance, before Jody spoke up again.

"After Steve told me he was going to sodomize me, he told Rachel to fetch a condom and she put it on his cock for him. I never saw what type he used."

"Did you take the condom off after he ejaculated?" Madison continued. "Or see it on the bed or floor?"

"No," Jody admitted. "Right after he came he withdrew and told Rachel to suck him clean. She took one look at the soiled condom and removed it before she blew him. I never saw it after that."

"Did you see the packaging?" my girlfriend asked.

"Yes," Jody admitted, "I did see an empty condom wrapper on the bathroom countertop when I went to clean up."

"Magnums have a very distinctive packaging with a black circle in the middle," Madison informed her. "Did you see that?"

"No," Jody admitted, "no black circle."

"Baldwin ass-fucked me that night too," my girlfriend confessed, which was hard for me to hear. "I was in the shower and he came in behind me and entered my back-door. He was already wearing a condom so I didn't see the brand either. However, having had intimate experiences with both of them, I think Clarkson is bigger, and poses you a greater threat of discomfort if he ends up being the highest bidder, and winning your asshole."

"Oh fuck," Jody said dejectedly, "neither of those guys can win. Baldwin almost made me cry, and I was squealing like a pig just before he came."

With that proclamation issued, Jody returned to my living area, and in an attempt to avoid being violated anally by Baldwin or Clarkson, circulated the room practically begging guys to enter the bidding war. Even as she pulled guys aside to talk privately, I had enough security cameras in my place to eliminate any blind spots, and witnessed all of her attempts to influence the outcome of the auction.

Her initial course of action was to offer extras to each potential bidder, both in the form of the promise of future hookups, and the prospect of involving one, or both, of the other two girls. She managed to engage two other bidders, but once the price broke the nine grand threshold, they withdrew, demonstrating how much easier it was to blow football pool winnings on sex, rather than to spend your own cash.

As a last resort, Jody latched on to George, first of all practically begging him to buy her ass, and then as her desperation grew, offering him a full refund of his winning bid, thereby offering up her tight little asshole for free. There were still five guys actively involved in the bidding war, but the second George entered the ring, bidding an even ten grand, Baldwin bowed out.

"Out of respect for the working man willing to put up three months salary for a crack at Jody's ass", he said, as he raised his glass to toast the bartender.

Taking their lead from the Alpha of the group, the other guys folded immediately, and Jody skipped happily over to George, and gave him a huge hug.

"Thank you, thank you," she whispered repeatedly, as she led him into the master bedroom, her tiny thong the only thing between George and his prize, now that Madison had removed her skirt and petticoat. "You literally saved my ass."

While my generation was guilty of repeatedly misusing the word "literally," in this case it was the right descriptive and George knew it. The way the bidding had been heading, it was undoubtedly going to be Baldwin or Clarkson who emerged victorious, and even though they were both fabulously wealthy, neither man had got that way by being excessively charitable. Having parted with over ten grand of their cash, whoever won would have wanted to pound Jody's anus, which didn't bode well for her. George, had indeed, literally saved her ass.

He knew it too, and as she continued to offer her gratitude, he announced his intention to enjoy his brief moment as a winner.

"I am going to get balls-deep in your anal-cavity, Jody," he warned her. "I won the auction, and if you give me any push-back, I will let Baldwin know that you are scamming him."

"George, please," the young blonde begged. "I have only been butt-fucked once before and I hated it. How about I get on my knees and blow you instead? You can even come on my face if you want to."

Unfortunately for Jody, Madison entered the bedroom shortly after the two of them and put her support fully behind George. She told the young blonde in no uncertain words that she needed to fulfill her obligations to the bartender, and reached for a condom.

"Is red still your favorite color lipgloss, George?" she asked the bartender. "You often say that if we hooked up, you would like to see my red lipstick all over your cock."

As I struggled to process the context under which the two of them would have had that conversation, Madison reached into her makeup drawer and retrieved her bright red glossiest lip covering. With her practiced innocence, and George's erection visible in his shorts, Madison applied a liberal coating to her lips, and sank to her knees in front of him.

"You should probably use this time to lubricate your anal-passage, Jody," she said patronizingly to the nervous looking blonde.

As Jody removed her thong and began to apply Anal-Ease to the entrance of her butt-hole, Madison started to unzip George's shorts.

"One to make the boys jealous," she said with a giggle, as she planted a kiss right on the crotch of his shorts, leaving a perfectly formed, bright red, impression of her lips.

Once she had his shorts off, my girlfriend started to give him a loving, teasing blowjob, stopping once he was completely erect, to slip the condom on. George was certainly in no need of a Magnum condom, and Jody seemed to take some solace in this revelation.

"Do you want Olivia here too?" Madison asked him, once the condom was on securely.

"Fuck, yes," he responded excitedly, "the more the merrier."

As soon as Madison instructed Jody to go and get Olivia from the other room, I knew what she was doing. As the beautiful young blonde entered the main living area, she was a sight to behold, naked as she was from the waist down, other than her high-heeled shoes and her Bobby-Sox. Her pert butt-cheeks, delectable as they always were, seemed even more enticing, now that there was evidence of lubricating jelly all around her rosebud. I was surprised that one of the guys didn't take one look at her well-prepared asshole, and resurrect the bidding.

Olivia and Jody returned hand in hand, to a smattering of lewd comments, which ceased as soon as they shut the bedroom door behind them. Even though George was already hard, Madison blew him for a few minutes, answering my earlier questions about who had been wearing the lipstick-covered prophylactic, that I had discovered in my trash can on my return home.

As George looked down at her admiringly, she sought to involve Olivia, in her typical disparaging manner.

"Ah, the rim-job girl is here," she told him, lacking the decency to call Olivia by name, with the intent to continue to diminish her.

At this point I was not sure if Jody and Madison had informed Olivia that they were working for free, but seemingly undeterred, Olivia begin to give George an enthusiastic rim-job. As Madison sucked his cock, and Olivia ate his ass, Jody climbed up on to my King Size bed and got into the doggy-style position. She gave her ass a seductive wiggle when she was ready, and George pushed my girlfriend's face away from his cock, and sidled up behind Jody.

Madison grabbed the tip of his cock and lined it up with the entrance to Jody's asshole. George had a very smug look on his face, although I wasn't sure if it was because he was about to enjoy the attentions of three women, or if it was because Jody was offering him her ass for free, when other men had been sufficiently desirous of it to offer nine grand for the opportunity to fuck it.

Either way as he eased his way in, and Jody breathed a sigh of relief as she assessed his size, and adjusted to his invasion, it was evident that he planned to enjoy her tight little butthole.

"Spread your legs slightly, baby," Madison whispered. "Give the rim-job girl room to operate."

Olivia's facial expression was obscured by George's lower back, but I am sure she didn't react favorably to being continually referred to as the rim-job girl. However, shortly after George widened his stance, she lowered her head and her tongue disappeared between his buttocks. George's eyes widened under the ministrations of Olivia's tongue, and he let out a whimper. I saw his abs tighten, and knew immediately that he wasn't going to last long. I am not sure how much sexual experience that Jody had, but she had learned that her cherubic face made men come more quickly. Using this knowledge, as George increased the pace of his rhythmic thrusting, she looked back over her shoulder at him, and with an innocent look on her face, she bit her lip.

"I can't believe that you are butt-fucking me George," she said sweetly, "Do you want to come on my face?"

Unfortunately for George, he wasn't going to have time to take her up on that offer, because immediately after she said that, he tensed up, let out another whimper, locked eyes with my girlfriend, and exploded inside Jody's tight little ass. I could see the look of ecstasy on his face as he orgasmed, and after he had emptied his nut-sack, it was replaced by a look of desire, as he admired Madison.

"You can go again, if you can manage it," Madison offered him, recognizing that this was undoubtedly the pinnacle of his sex life.

"Kiss me, Madison," George asked my girlfriend, as he gained control of his breathing.

This was much harder to watch than any of the sex acts, and I contemplated fast forwarding through it. As George remained balls-deep inside Jody's anal passage, and Olivia continued to lick his ass, Madison leaned in towards the bartender. They were much closer in age than Madison and I, and I had to admit that they made a fantastic looking couple, but I could feel my jealousy surface as their lips touched.

I could sense a real connection between them. Madison was an expert at making men feel things that weren't real, and did a very effective job of faking intimacy, closeness, even orgasms. However, this was more than that, it was something that you couldn't fake, chemistry I guess you would call it. As they kissed tenderly, their lips barely grazing, it was reminiscent of earlier when she had given him a loving hand-job, allowing him to finish in her mouth.

The tips of their tongues danced around in each other's mouths, and I could see Madison's nipples harden. She placed one hand on his temple, which made the connection seemingly stronger. George didn't even notice when Olivia emerged from between his buttocks, and left to wash her face. Prior to Jody speaking, it was as if they were alone in the room.

"He's getting hard again," Jody announced, as George's cock swelled within her anal-cavity.

"Can I make love to you, Madison?" he whispered to her.

As Madison nodded her consent, Jody eased forward and his semi-erect cock emerged from her asshole. Jody turned to face George, and as he French-kissed Madison, the younger blonde removed the lipgloss-covered condom from his ever-growing cock, before joining Olivia in the bathroom. Left alone with his fantasy woman, George hardened completely, as Madison traced her nails across his nuts.

"What position do you want me in, George?" she asked.

I would have to think that most men would choose doggy-style in that situation, particularly as George had wanted to fuck her for years. However, based on the tenderness between them, I wasn't surprised when he said missionary.

"My favorite," Madison said seductively, although I knew she would have given that response, whichever position he chose. "The lovers' position," she added. "No condom necessary. I want to feel you inside me."

As she got comfortable on her back, George mounted her, slipping easily inside her self-lubricated pussy. Supporting his weight on his forearms, and cupping one hand under the base of her head, they began to rock slowly, in unison as they kissed. He ground his pelvis into hers as they made love, and the additional stimulation of her clitoris was having its desired effect, as she wrapped her feet around his ankles and let out a moan, muffled as it was by their open-mouthed kissing.