Trust Fund Baby Pt. 06

"Condoms are on the bathroom counter," one of the lower profile guys said, trying to be helpful.

"I need my own rubber, buddy," Clarkson answered dismissively, "the Magnum ones."

I could detect a hint of concern in Madison's voice as she answered, trying presumably to discern what plans he had that would require a prophylactic.

"Your Magnums are under my pillow," Madison said quietly, "I wasn't sure if you were planning to stay the night, again."

"I can't stay tonight, honey," he said, the regret palpable in his voice. "Next time Pete is away, perhaps?"

"I can't wait," she said, without any shame, even though their interaction was in front of several men.

Even though it made my blood boil to learn that Clarkson had spent the night in my bed with my girlfriend, it was more infuriating that he had made this admission in front of the guys. This news was sure to spread like wildfire around the wealthy Newport Beach social circles, and it could only serve to lower my status among my peers. I felt like I was having a panic attack as I watched them flirt with each other, and I ended up pausing the footage, and getting a glass of water.

I was racking my brains trying to remember when I had gone out of town recently, and then it dawned on me. I had gone to an out of state funeral in New York, about two months prior and had decided not to bring Madison. We had argued about it, with her being adamant that the first step in our road to matrimony, was her inclusion in my personal obligations, such as weddings and funerals. The last thing she said to me as I left for the airport was something along the lines of, "you are going to regret this decision."

At the time, I laughed at her seemingly idle threat, but by the time I got to my destination, I could see where she was coming from, and called her to apologize. My call went straight to her voicemail, and when she never called me back, I realized that she was still pissed at me. I was staying at the Peninsula in New York, and went down to the bar for a nightcap. To my surprise, a young Asian woman propositioned me, offering to spend the night with me.

I knew immediately that Koko was a working girl, even before the subject of compensation reared its ugly head. My experience with Olivia had taught me not to be shy, and I asked her what was on the menu for my money. To my astonishment, not only was the pricing structure comparable to the Newport Beach pay for play scene, at eight hundred dollars for the night, but apparently nothing was off-limits.

We shared a couple of cocktails at the bar, and I noticed an older, obviously wealthy man checking her out. As we walked over to a more private booth, I placed my hand possessively on her ass, and gave the guy a smirk. At this point it was just drinks, but he didn't have to know that.

As Koko got progressively more touchy-feely, rubbing my cock through my pants under the mahogany table, I felt my resolve weakening. As she catalogued the delights that she was prepared to offer me, she peppered me with questions, trying to learn my sexual proclivities.

"Do you like dirty talk?" she asked me, landing on one of my hot buttons almost immediately.

When I responded that I loved women to talk dirty, she pressed me for the details. I was reluctant to share that I came really hard when my girlfriend taunted me about her other lovers, but Koko was relentless in her pursuit of my specific kinks.

"The more honest you are with me, the better our session will be," she assured me. "Do you have a favorite type of lingerie? A special scent that arouses you?"

"Why, do you have them all in your travel bag?" I asked incredulously.

"No, of course not," she said playfully. "But we are within walking distance of the Rockefeller Center and they have just about any perfume you can buy. If you know what you like, I will scent myself for you. I have several wigs too, if you would rather enjoy me as a red-head or a blonde."

I remembered my bathroom encounter with Samantha, as she bent over the marble countertop, having been sprayed with the intoxicating scent that Madison always wore. It had been a close second to the real deal, and I was very tempted to enjoy Koko for the night.

"Rimming?" I asked, trying to suppress my shyness.

"I love giving rim-jobs," she said enthusiastically. "We just need to shower first."

As she continued to check off all of my hot buttons, I decided to go for it.

"I like expensive silky intimates, garter-belts, and Chanel No 5," I informed her, referring to Madison's fragrance of choice, and trying to customize my session for maximum enjoyment.

"You got it, Pete," she said agreeably. "I definitely have some cute lingerie in my room. Let's finish up our drinks and get out of here."

It was the picture that I have of Madison on my iPhone home screen, that made me change my mind at the last minute. I glanced at my phone to see what time it was, and was jarred back into reality by a head-shot of my girlfriend just after she had enjoyed a professional makeup session, and looking her very best.

Even though Koko had kept me hard for much of the last hour, the second I saw the picture of Madison, my arousal elevated and I knew I owed it to her to be faithful. I was apologetic and polite when I declined Koko, and I gave her three hundred dollars for her time and companionship, which eliminated any notion of time-wasting that she may have harbored.

"That distinguished looking gentleman in the expensive suit has been checking you out for the last hour," I said kindly. "Thank you for your time, Koko."

Koko arose seductively from the leather seating area, moving with the grace of a seasoned courtesan. She leaned into me, kissed me gently on the temple, and moved towards the older gentleman, who broke into a broad smile as he realized that she had unexpectedly become available. Koko and the well-dressed man chatted for less than two minutes, before he signaled the bartender and paid his tab. Moments later, it was his hand on her pert little ass, as they exited the bar together.

At the time, I was proud of myself for doing the right thing, and I sat in the booth for a few minutes to let my erection subside. I called Madison again but it went straight to voicemail, and being three hours ahead of California time, I went to bed before she could respond.

Now, as I digested the fact that Clarkson may have been in my home when I called Madison to say goodnight, my pride at doing the right thing turned into regret of a lost opportunity. Koko was a spectacular woman, and undoubtedly would have rocked my world had I invited her to spend the night with me. I had gone to bed alone in my suite with a erection that just wouldn't quit. It had taken me ages to fall asleep too, as I ruminated on the lost opportunity with Koko, and consternated over why it was taking Madison so long to call me back. Had I known that she was getting seduced by Clarkson, I would have made very different decisions that night in New York.

After I drank some water and did some breathing exercises, I felt my blood pressure return to normal. I am a naturally jealous person, although this state is elevated around Madison because of the pleasure she derives from stoking it. I am also slightly OCD, and the two character traits combined are not conducive to letting things slide. For this reason, I began to obsess about the exact time-frame of Clarkson's intrusion, and what Madison was doing that prevented her from answering her phone, twice.

I searched my outgoing phone history by logging onto the iCloud, and immediately learned the date and time of my calls to Madison. I knew I wouldn't be able to wait too long before I checked my security footage from those times, to establish whether Clarkson had been in my house at that exact moment. However, I wanted to see what happened next, so I pressed "resume" on the footage that I had been watching.

Madison had just informed Clarkson that his Magnums were under her pillow. He got up from the bed, and reached under my girlfriend's pillow, where to my astonishment she had stashed a multi-pack of the over-sized rubbers. Clarkson removed one from the distinctive looking box, and entered the bathroom.

"This you guys have got to see," Baldwin informed the group. "He is going to tear this bitch's ass up."

While I wasn't happy with Baldwin's use of the pejorative to characterize my girlfriend, I knew that this was how he viewed her. To him, a wealthy man with a multitude of options, Madison was merely a bitch. Jody, Olivia, Rachel, and Madison were interchangeable in his eyes, local Newport Beach hoes, that were available for him to use as cum-receptacles, whenever he felt like busting a nut.

After he voiced his suggestion, the other guys went from a half-hearted interest in the Clarkson show, to being fully engaged in what he was about to put Madison through. As I watched the security footage, I heard him taking a piss although judging by the splashing sounds he was the one who had the bad aim, and had urinated all over my toilet seat. A few moments later he emerged from the bathroom with a semi-erection, which answered my question about how difficult could it be to just urinate into the bowel. His massive member was sheathed by a Magnum condom, and had been coated with Anal-Ease.

Even though he wasn't fully erect, it was an impressive sight. He possessed the largest cock I had ever seen outside of interracial porn movies, and the rest of the guys watched on in awe as he approached my girlfriend. They had enough sexual history that she knew exactly what he liked, and as she rubbed his frenulum gently, he slowly stiffened until he was completely hard.

"Get on all fours," he instructed her, "on the edge of the bed."

Once she was in his desired position, he scooted over to the side of the bed, and remaining in a standing position, rested the tip of his cock against her rosebud. She was much less comfortable than before, as she waited for her impending violation. She kept looking nervously over her shoulder, and Clarkson seemed to relish her anxiety.

"Push back against me," he ordered, seemingly having decided to make her do all the work.

What happened next was excruciatingly hard for me to witness. With a look on her face that you would expect to see from a woman giving birth, Madison pushed back against the tip of his greased cock-head, and slowly impaled herself on it. It was a protracted struggle to get his entire length inside of her ass, and by the time he was balls-deep, she was sweating and in considerable discomfort.

Clarkson by contrast, had a smug smile on his face as Madison grunted and occasionally cried out in pain.

"Fuck yeah," he said, as he started to slowly withdraw, "just as I remember it."

I knew that he had sodomized her in the past, although my understanding was that it had been a limited number of times, due to his size. In fact, Madison had warned Jody about the danger she faced if Clarkson won her asshole in the auction. Now as my girlfriend was getting butt-fucked by this stallion, it was her to turn to suffer.

Clarkson used steady, rhythmic strokes to ass-fuck Madison, and after a few moments she began to bleed.

"That is why I wore a condom," he said to no-one in particular, as traces of blood appeared on the outside of the Magnum.

To her credit, even though Madison was clearly in distress, she allowed the older man to continue his assault on her anus, and a few moments later he came inside her anal passage. This was just sex for him, and he did not engage in any post-coital intimacy, but rather withdrew from her gaping butt-hole, and issued his next directive.

"Stay in that position, in case anyone else wants a crack," he instructed her.

As expected, no-one wanted to follow Clarkson, and as the remaining guys averted their eyes, he told Madison that she was excused. He watched her intently as she struggled to get up from all fours, his softening cock starting to droop between his legs. It was a different woman that alighted from the bed after his violation. Gone was the feminine allure, replaced by an awkward gait as she limped to the bathroom.

She emerged a few moments later, wearing a bath robe and forcing a half-smile as she asked them if they needed anything else.

"I think the party is over," Clarkson declared, "your cash is on the piano."

"I do need you to do one more thing for me," Baldwin said, as the smile disappeared from my girlfriend's face. "Bring me your new chemise."

Madison had apparently made the decision to obey his every directive, and sensing that her ordeal was almost over, fetched the baby blue garment.

You would have thought that complete sexual release would have been enough for Baldwin and his cronies. After all, they had totally violated my girlfriend, taken all three of her orifices, dressed her up like a little fuck-toy in the Valentine's Day gift that I had purchased for her, before Baldwin ejaculated all over the back of the four hundred dollar piece of lingerie. However, because he is a total asshole, he wanted to heap more humiliation upon me.

"Re-wrap your gift," he instructed Madison, to a round of sniggers from the men.

As the guys watched on intently, Madison folded the exquisite garment in such a way that the dried semen stains on the rear of it were not visible when she placed it back into the LaPerla box. It looked exactly the way it had when she first unpacked it, and Clarkson remarked that I would never know until Madison put it on. Truth be told, the fact that the tags were already removed would have instilled the same level of doubt in my mind, but Baldwin wanted more.

"I want him to know as soon as she opens it," Baldwin said. "Toss the condom on top of it."

As the three other guys looked on in amusement, Clarkson removed the Magnum from his flaccid dick, and laid it on top of the baby blue chemise. Some of his ejaculate spilled immediately from the used rubber onto the silky garment, turning it a darker shade of blue. Madison retied the ribbon, scented the box with her perfume and reattached the Valentine's Day card to the front of it. If I hadn't been watching it unfold on the security footage, I would have been treated to a truly disgusting surprise, and been presented with incontrovertible evidence of my girlfriend's philandering.

"Put it back where we found it," Baldwin ordered her. "And not a word until Valentine's Day."

"I don't know why the fuck Pete doesn't just marry you and put an end to this madness," Clarkson said, with a chuckle.

The five of them were having a laugh at my expense, which hurt almost as much as their sexual encounters with my girlfriend. As fellow Newport Beach millionaires, I considered these men my peers, and it was very humiliating to hear them openly mock me.

When it became evident that they were about to leave, Madison excused herself to freshen up, and Baldwin lit a cigar and laid on my bed. That prick acted like he owned my place, casually flicking his ash on my bedside table, before Madison emerged from the bathroom in a panic after smelling the cigar smoke in my bedroom.

"You can't smoke in this room," she said animatedly.

"I can smoke wherever the fuck I want, Madison," Baldwin responded arrogantly, prompting her to grab an ashtray.

As she placed the glass receptacle on the side table, she turned to Clarkson who was also lighting up a cigar.

"You pissed all over the toilet seat you dirty bastard," she admonished him. "I told you guys not to trash the place."

"I did that on purpose," Clarkson responded, as Baldwin started to chuckle. "I want you to leave it that way for Pete to find. As a man, he will understand the significance of it."

As a man I did understand the underlying meaning behind his disrespectful act. What I didn't understand was why the fuck Madison hadn't cleaned it up, after they left. Even though the security footage had been incredibly difficult to watch, I had the answers that I needed, and for the first time in months, I felt strong enough to kick Madison to the curb. Part of me was experiencing intense arousal, as the thought of all those other guys enjoying my girlfriend was titillating, but now that I knew that I was the laughing stock of Newport Beach, I realized that I had to end it with Madison.

I heard her stirring in the living area, and went in there with a renewed resolve to terminate our relationship. As soon as I saw her on the couch, I had the first tinge of doubt. She looked up at me with her baby blue eyes, and I felt my cock twitch in my pants. As she rolled onto the carpet, and began to crawl towards me, I could tell that she was still out of it.

"Did you have a lot to drink, Madison?" I asked, suspecting that she was still intoxicated.

"I hardly drank anything at the Super Bowl party," she said, as she struggled up onto her knees and reached for my zipper. "Unless you count George's semen," she added with a giggle. "I have lots to tell you, baby," she continued, as she freed my erection from my shorts.

In typical Madison style, unaware that I had already viewed the entirety of her misdeeds, she began to recount the events of the party, in excruciating detail, as she intermittently sucked my cock. I was powerless to stop her, infatuated by the combination of her world class blow-job skills, and her ability to get into my head with her lurid tales of infidelity. You would think I would have blown my load and then, freed temporarily from her web by virtue of my empty nut-sack, could have found the courage to dump her.

In fact, the exact opposite occurred. As I approached my orgasm, she invited me to come on her face, and I had a stupendous orgasm and pretty much collapsed onto my knees. She helped me over to the sofa, and told me to relax, before leaving the main living area. As I watched her limp gingerly from the room, making no attempt to hide the fact that she had been brutally ass-fucked by Clarkson, I felt my cock stir, and I knew that she had her hooks back in me.

Thoughts of banishing her disappeared, replaced by the contemplation of matrimony, to "end this madness" as Clarkson had so eloquently phrased it. A few moments later she returned with her makeup freshened up, and her platinum hair arranged neatly into pigtails. She wearing her new baby blue chemise, the Valentine's Day gift that the men had discovered and enjoyed her in.

"The guys found my Valentine's Day gift in the closet," Madison began, unaware that I had seen her get completely defiled in it, yet seemingly with nothing to hide. "They made me wear it to service them. I hope you don't mind. I know you were probably hoping that I would wear it for you first."

As I took her in I was fighting an internal battle, and my lust had the upper hand against my rational side. Madison made no attempt to hide the large semen stain in the chest area, and even offered an explanation for how it got there.

"Clarkson tossed his used rubber into the LaPerla box for you to discover," she said without a trace of regret. "His seed leaked all over it."

With that opening salvo fired, she twirled slowly in the exquisite garment, and my eyes took in the copious stains on the rear of the lingerie.

"Those are Baldwin's," she added, matter of factly, as if it was the most natural thing in the world. "That asshole came all over my back."

My rational mind was screaming at me, telling me that this was fucked up, that I deserved better, that I should dump Madison and find myself a new partner. However, she had fully engaged my physical side, and as she continued to allude to the fact that the guys had given her a thorough seeing-to, I couldn't resist her. I moved towards her, as if on auto-pilot, until she was in my arms, and our lips touched with the gentlest caress.