Trust Fund Baby Pt. 05

Madison got me off four or five times a day, but we rarely coupled in the missionary position. Prior to meeting her, I viewed it as the most boring of the three sexual positions that I knew. Madison taught me at least a dozen new positions, which further relegated the appeal of the missionary to me. Furthermore, in an attempt to keep me obsessed with her, she offered me blow-jobs several times a day, and most nights she allowed me to tit-fuck her before bed. Given the amount of variety that I was exposed to, I guess it wasn't surprising that we didn't engage in the most vanilla of positions that often.

However, as I watched her writhe around under George, his tender thrusting motions elevating her arousal with each passing moment, I wondered if it was perhaps her favorite position. A few minutes later, I got my answer as she intertwined her legs around his, and had a very vocal orgasm. Although on the surface it appeared similar in intensity and duration to the ones that she experienced with me, when we first got together, the principal difference was that this one wasn't faked.

I saw her stomach tighten right before she climaxed, and she stopped kissing George to stare into his eyes as she came all over his cock. Madison seemed lost in the moment as they maintained eye-contact, and a few moments later she had a second, equally powerful release. Remarkably, over the next ten minutes or so, as George demonstrated the control that I had lacked since the day I met Madison, he brought her to three more stupendous orgasms. Finally, she relaxed her grip on his legs, and let her arms fall limply to her side.

"Oh my God," she said with a giggle, "well I never. Holy shit."

Without actually saying anything, she managed to say everything, and she let out another satisfied giggle, as George remained buried inside her.

"I want you to come, baby," she whispered softly. "I am so wet. Too wet, actually. There is one hole you haven't enjoyed yet," she said suggestively.

George didn't need to be asked twice, and as he slowly withdrew from Madison's pussy, she called out for Jody. The young blonde opened the bathroom door, and emerged expectantly as if it was finally her turn. George showed zero interest in the beautiful teenager, and as Madison spoke her breathing was still ragged.

"Can you get me a condom, honey?" Madison said sweetly. "And some wet-wipes."

A few seconds later, Jody entered my master bedroom with Olivia in tow. They took one look at George's erection, covered as it was with Madison's milky-white vaginal secretions, and both broke into an admiring smile.

"Is it our turn, George?" Olivia asked the bartender. "We couldn't help overhearing what a great job you did."

"I need to pee," Madison informed the two younger women. "Can you clean George up and put a condom on him? I am going to let him fuck my ass."

As Madison entered my bathroom, Jody and Olivia descended on George with the wet wipes. As he knelt passively on the bed, they wiped his cock and balls clean, their feminine hands teasing him incessantly in the process. They were flirting with him too, and when Madison returned to the bedroom, Olivia was massaging his frenulum with the softest of touches, while Jody fondled his nuts.

"Ok, guys," Madison said in mock exasperation, "thank you for getting him hard. Put the condom on him so that he can finish up."

I am not sure how George resisted the wiles of the two younger women, but he seemed focused solely on Madison, even as Jody showed him her new party trick.

"Rachel taught me this," she said proudly, as she lowered her lips onto the tip of George's cock.

George sucked in air reflexively, as Jody bobbed up and down on his cock-head, before deep-throating him, and then emerging with a huge smile on her cherubic face. George was sporting a hard-on and it was now covered with a condom.

"Cool trick, huh?" Jody said proudly.

"Yeah great, Jody," Madison said dispassionately, "that will serve you well in a couple of years when you are working in a massage parlor."

Jody didn't take kindly to Madison's disrespect but instead of standing up to her, decided to turn her attention to George.

"Guys tell me I am way too pretty to give rim-jobs," she said with her practiced innocence. "However, I would be happy to help you over the finish line," she added suggestively.

I don't know how the hell he turned down that offer, but at that moment I considered him a better man than I. Under the same circumstances, with the offer of Jody's tongue in my asshole, I would have folded like a pack of cards. George, it seemed, only had eyes for Madison, and watched her intently as she climbed up on to my King Size bed, and adopted her usual stance for anal sex, the doggy-style position. She looked very inviting as she waited passively for George to enter her anal-cavity, which bore the signs of having been thoroughly lubricated. Jody laid on her back with an agreeable smile on her face, the inference being that she would scoot under him and eat his ass while he fucked Madison's.

Olivia wanted to be part of the action too, and waited eagerly on the sidelines for direction. When none was forthcoming, she posed the question directly.

"Where do you want me, George?" she asked seductively. "Do you want me to suck your nuts?"

Again, under that kind of sexual provocation I would have been unable to resist the two younger women, but George looked admiringly at Madison and verbalized his desires.

"I want you two in the bathroom," he began assertively, as if to remind them that he was calling the shots. "Madison," he continued, "can I finish in the missionary position, the lovers' position?"

Jody came back with one more suggestion, one which I would have instantly agreed to.

"Can we at least watch you put the wood to Madison?" she asked in a flirtatious manner.

"Bathroom. Now," he repeated, as the two of them arose from the bed, and left the room holding hands.

As I watched the two of them enter the bathroom and stand within the threshold, signaling their complete availability, I thought George was going to change his mind. However, demonstrating his desire for Madison, he climbed on top of her as she lay on her back, in his requested position. As he lowered his lips to meet Madison's, he told Jody to close the door.

Over the ensuing years, whenever I engaged in anal sex, intimate was just about the last descriptive I would have used to illustrate the sex-act. I used sodomy as a way to dominate and subjugate young women, relishing in their discomfort, particularly if I was taking someone's anal-cherry. After rim-jobs, subjecting women to a protracted fucking of their anus, was my favorite sexual activity.

By Jody's admission, and in her own words, Baldwin had made her "squeal like a pig" when he sodomized her. Her characterization resonated with me, and became my goal during this activity. I loved to hear a girl pretending to enjoy it, trying to suppress her urge to cry out from the discomfort. After I came, I loved to withdraw my cock from a virginal anus, and make the bewildered young woman suck my cock clean.

Before you judge me, remember that I was operating within a vacuum. I had no parental influence, and my only guidance was from my morally bankrupt uncle, who persuaded me to use and abuse as many women as possible. In addition to this, I was so fabulously wealthy at such a tender age, that most women gave me little to no pushback, agreeing to the most depraved and uncomfortable sex acts, in the hope that they would be the one. I submit to you, that most young men in my position would have acted in the same morally reprehensible way.

For this reason, and because sodomy is rarely depicted as an intimate act in pornography, I had no clue what the hell George was doing as he lay on top of my girlfriend, and asked her to line the tip of his cock up with the entrance to her asshole. As she guided him, he eased slowly inside her anus. Once he was balls-deep, he resumed his gentle, rhythmic rocking motion, and somehow turned the lewd act of sodomy, into an intimate one.

They kissed tenderly as he rocked slowly inside her, and even though she never experienced another orgasm, I could tell that she was thoroughly enjoying getting ass-fucked.

"Are you completely satisfied, Madison?" he asked as he approached his orgasm.

"Completely and utterly, George," she responded, as she kissed the end of his nose and smiled up at him. "Come in my ass, baby."

I watched as he tensed up, his broad muscular back flexing as he emptied his nuts inside my girlfriend's ass. He let out a quiet moan, and continued to rock inside her for several moments, as they kissed and whispered sweet nothings to each other. Madison made no attempt to rush him either, despite the men waiting in the living area, and they remained coupled long after he had ejaculated. It was as if he had single-handedly lowered her defenses, touched her soul and given her the defining sexual moment of her life.

Finally he withdrew, his softening cock drooping between his muscular thighs, and as he climbed off the bed, Madison knelt before him and lovingly removed his condom. She kissed the tip of his cock, and then licked it clean, before making a big show of glossing her lips with his seminal fluids.

"I can't wait to do that again," she informed him. "That was incredible. You are fucking incredible, George."

He helped her to her feet, and they kissed tenderly for a few more moments. I thought that they were going to go for round two but my bathroom door opened and Jody emerged butt-naked.

"Do you need any help with the clean-up?" she asked sweetly, licking her lips.

"You bitches are welcome to what's left," Madison said dismissively, handing Jody the semen-filled prophylactic. "I need to take a shower."

With that proclamation issued, Madison entered my bathroom, and Jody and Olivia approached the bartender. I heard the shower running, and as George looked on in bewilderment, Olivia shed her remaining clothes, and then the two of them sank to their knees and began to lick his juices from his now flaccid cock. He never got hard again, but enjoyed their tender ministrations for several minutes until Jody held up the used rubber containing the rest of his load. With a devilish smile, and the confidence that she was absolutely fucking irresistible, Jody raise her hand to her lips, and as George watched on in admiration, poured the contents of the condom into the palm of it.

"Let's eat," she said seductively, inviting Olivia to join her.

It was at that moment that I decided I wanted to fuck Jody. She was incredibly beautiful, insanely sexy and was a master at manipulating men.

That little vixen knew exactly what she was doing, as she lowered her face into her palm, simultaneously managing to coat her lips and the tip of her nose with George's semen. She lewdly slurped up a glob of his ejaculate, and with a look of mock horror on her face, raised her head slowly to look at Olivia. Her cute button nose was slick with George's seminal fluids, and her big blue eyes twinkled devilishly as she turned to kiss Olivia. I saw George's cock twitch to life as he watched on in awe, as Jody extended her tongue between Olivia's slightly parted lips, and spat the jism into her mouth.

There was a playful sexiness between them as they spit-balled his load, as if it was the most incredible delicacy that they had ever tasted. They were getting to George too, as evidenced by a noticeable increase in his rate of breathing, and his ever-swelling cock, which was impressive as he had already had multiple orgasms.

I couldn't tear my eyes away from the footage of Jody as she cavorted on her knees in front of the bartender, playing with his semen until Olivia and her had ingested it all. George had a semi-erection by now, the image of the two girls causing blood to flow to his crotch.

Shortly after the two-girl show, Madison emerged from the shower, also naked. As Olivia and Jody remained on their knees, Madison kissed George tenderly on the lips. In a testament to the chemistry they shared, his cock grew to its fullest, surprising the hell out of the two younger women, who had been trying to get him hard for the last twenty minutes.

In a scene reminiscent of a Bangkok soapy massage parlor, the three attentive young women fawned over him, caressing him all over with their fingertips, lips and tongues as they helped him to get dressed. When they finally managed to get his shorts zipped up, he was rock-hard again and it was Jody that sought to take advantage of his new-found sexual tension. Looking up at him from her knees, where she had remained in order to tie his shoelaces for him, her nose still coated with his ejaculate, she hit on him one last time.

"Do you want me to walk you to the limo, George?" she asked, as she caressed his erection through his shorts.

Just watching her offer herself up to him on a platter made me erect, and I have no clue how he managed to resist her.

"Thank you Jody," he said appreciatively. "I am going to make a move, but I can see myself out."

Turning to Madison, he added, "Thank you for tonight, that was the time of my life."

"Don't forget your stuff," she said cheerfully, as she retrieved his cash and her wet panties from the bathroom drawer.

As I watched on in disbelief, and the three girls steadfastly refused any of his attempts to pay them for their time, the most unlikely of scenarios had unfolded. The poorest man in that room full of millionaires, left that Super Bowl party in a limousine with twelve thousand five hundred dollars in cash, Madison's soiled panties, a completely drained set of nuts and the memories of a lifetime. He had been treated to a three girl hand-job in which he finished in Madison's mouth, entry into the hardly explored environs of Jody's ass, a loving rim-job from Olivia, and finally vaginal and anal sex with my beautiful girlfriend, all completely free of charge. Well, unless you count his initial investment of five hundred dollars, with which he parted reluctantly to buy one square of the football pool.

George stuck his cash in one pocket of his shorts, Madison's panties in the other, and with a satisfied smile on his face, and the three naked girls in tow, entered the main living area. As I switched camera angles, the first thing I noticed was the perfectly-formed red lipgloss mark on the front of his shorts, strategically placed there by Madison to evoke a response from the other men.

"You lucky bastard, George," Baldwin yelled enthusiastically, as he noticed the bartender with three seemingly compliant bitches in his wake. "I hope that was worth ten grand."

None of the other guys would have known that all of George's play was complimentary, and knowing his depleted finances, they probably wouldn't have cared. However, I knew, and as Madison and George exchanged one more longing glance, I realized that I had to do something to prevent them from hooking up in the future.