Trust Fund Baby Pt. 04

"Doggy-style," I said, through gritted teeth, wishing that I had the intestinal fortitude to decline her offer, and tell her to go fuck herself.

Truly sensual women have a lightness about the way that they move, and as Madison seductively positioned herself on all fours, there was nothing more in the world that I wanted at that exact moment. Once she was in my desired position, she shook her head from side to side, and then threw it back so that her blonde platinum locks cascaded down her back.

I was absolutely powerless to resist her, and I climbed up onto the bed on my knees behind her. She gave me a quick wiggle of her hips, a sign of her willingness to accommodate me, and I lined the tip of my cock up against the entrance of her vagina. I couldn't feel any heat emanating from it, as the ice cube continued to chill it, and this somewhat diminished the anticipation that I normally felt, right before easing into the usually warm, and tight environs.

Madison looked phenomenal in that mint-green ensemble, and even though I was the second man that day to enjoy her wearing it, I was still extremely excited as I started to fuck her in a slow, rhythmic cadence. Within moments I began to increase my pace, recognizing the signs of my imminent orgasm as it built within me. I was addicted to Madison, the way I imagined a crack-head forgoing everything else in exchange for drugs. Sex with her was all I could think about, and as soon as I was balls-deep inside her, nothing else mattered.

I was fucking her furiously now, with little regard for her needs, focusing solely on blowing my load deep inside her. She continued to wiggle her ass seductively, occasionally looking over her shoulder at me, her blue eyes twinkling as she saw my face contorted with pleasure. I had my hands resting on her hips, both for support, and to give me some control as I pounded into her. As I approached my orgasm I was admiring the back of her long platinum locks, and as my eyes drifted across the beautiful mint-green ribbon that was affixed to her hair, I noticed that it also had remnants of Clarkson's semen splattered across its silky surface.

I averted my eyes in disgust, and as I looked down at the bed, four crisp one hundred dollar bills assaulted my vision, Clarkson's reimbursement for the lingerie that my girl had worn to pleasure him earlier that day.

"Did he take long to come?" I whispered hoarsely, as I felt my nuts constrict.

"Who?" Madison answered, without any hint of sarcasm, as if she had serviced multiple men that day.

"Clarkson," I said with exasperation, "did Clarkson take long to come?"

My release was imminent now, and my desire to hear some of the lewd details of their coupling in order to improve my release, was significantly elevated.

"Which time?" Madison asked, torturing me, right as I got to the edge.

Predictably, that was all it took. One perfectly timed, exquisitely worded, suggestive remark from Madison, and I let out a low guttural moan, and unloaded my nuts deep inside her tight, wet pussy. Madison taunted me the entire time that I was ejaculating, and I ended up having a fantastically satisfying orgasm, after which I slumped forward onto her back. Madison let me rest on her until I had gathered my composure, after which we rolled over and she announced that she was going to take a shower before bed. Alighting from the bed, she grabbed the four crisp hundred dollar bills, and in a move reminiscent of her days as a stripper, stuck them down the front of her chemise, where they protruded from between her ample breasts.

That night, after Madison fell asleep, I googled Clarkson's Hazmat and Environmental Clean-up, trying to get an assessment of how he stacked up against me financially. Based on our mode of transportation, my Lamborghini clearly trumped his Porsche SUV. However, as I would learn repeatedly over the next few years, some older guys grew out of the display of material possessions game, preferring to use their wealth to work for them, or for philanthropic endeavors. Clarkson was the sole proprietor of his company, and they had a gross annual income in excess of three hundred million dollars per year.

After I went to bed I ruminated on the numbers, and the fact that he was so wealthy, yet felt no pressure or desire to showcase it, made me even more jealous of him.

As luck would have it the Green Bay Packers did make the playoffs that year. Madison followed through with her promise, and every Sunday during the playoff season, she dressed up in her three hundred and fifty dollar Trashy Lingerie Cheerleader Costume, and sucked me off at half-time. It was a fantastic time in our lives, and in addition to giving me something to look forward to all week, I felt very connected to Madison.

Incredibly, we actually got to the Super Bowl, and my best friend scored me fantastic tickets for the game in Miami. Madison was not happy when I told her that I was going out of town for a couple of days, but didn't overreact, which I was grateful for. We were playing the Patriots who were overwhelming favorites, and the team everyone loved to hate. A few days before the game, I noticed that Madison had increased her tanning regimen and was looking particularly brown, which really suited her lithe, taut frame, and made her platinum blonde hair look even lighter, almost white.

I complimented her hair color, and she responded with gratitude and informed me that she had just had it lightened again. I didn't think much more of it until the morning of my flight to Miami, when a mobile cosmetologist arrived at my condo, and proceeded to give Madison a full Brazilian wax treatment. An hour later a nail technician arrived to do her nails and when I went into her dressing area to put her running shoes away, I noticed that her Trashy Lingerie Cheerleader Uniform was hanging on the outside of her closet, in an opaque dry-cleaning bag.

I am a naturally jealous person, and Madison derives intense pleasure from stoking it, and while I didn't want to get into a fight just before I boarded my plane, her actions did invite some questions. Predictably, I couldn't contain my curiosity and I asked her about the Cheerleader costume.

"I have Super Bowl plans too," she said cheerfully, without much elaboration.

"What kind of plans, Madison," I said, trying unsuccessfully to suppress my jealousy.

"I have been invited to a party," she said smiling broadly, but still not offering me any illumination.

"What kind of fucking party, Madison?" I snapped, finally losing my cool.

I only had about thirty minutes before my Town Car was due to arrive to take me to the airport. I didn't have time for this bullshit.

"Well," I said expectantly, "What kind of party?"

"Steve Baldwin has invited me to his house to cheer on his team," she taunted, her blue eyes twinkling with delight at the reaction she was getting from me. "Go Patriots!"

As she stuck her hands in the air, in an exaggerated girlish cheer, I noticed that her freshly manicured nails were painted in the colors of the New England Patriots. In a split second everything fell into place, and I realized that the almost white hair, complete with color matched extensions, her Brazilian Wax treatment, and her bronzed skin were all for Baldwin's visual delight. Madison was a very skilled courtesan, and always made sure every single detail was perfect, so it was highly unlikely that she planned to cheer Steve's Patriots on, wearing the Blue and Gold Packers Cheerleader Uniform.

I could feel my jealousy rising uncontrollably as I walked briskly into her dressing room. Madison followed me in there, a smug look of satisfaction on her face as I ripped open the opaque dry cleaning bag.

"What the fuck, Madison?" I exclaimed as her New England Patriots Cheerleader Costume hung from the exterior of her closet. "How much did this cost me?"

"Steve paid for it," she said way too cheerfully for my liking. "Steve paid for everything."

"Including you?" I asked incredulously.

"Baby, you know I am not for sale," she cooed, as she stepped closer to me and tried to cool my rage with her seductive ways. "Although he is paying us thirty grand for our company."

"Us?" I responded angrily. "Us? Who the fuck is us?"

"Don't you have a flight to catch, baby?" Madison teased.

"Madison, please," I begged, "who else is going to be at Steve's Super Bowl party?"

As time ticked away before my car arrived, Madison released the details of her invite piece by piece, and by the time my car arrived, and was honking in my driveway, I was not at all comfortable with this arrangement.

Steve Baldwin was paying Madison and Olivia thirty grand to entertain him and twelve of his friends, at his annual Super Bowl party. I had one last look at my watch and knew it was decision time. For me and Madison.

"Madison, don't do it please," I begged her. "I don't trust that fucker."

In truth, there wasn't much to worry about as far as Steve was concerned. He already had history with Madison, after she had offered herself to him in the parking lot of our favorite bar, during one of our fights. I never asked her the specifics of her night with him, simply because she loved to tell me the sordid details in excruciating specificity, most of which I assume were embellished to stoke my jealousy. However, I do know that Madison and two teenagers spent the night with him, so I have to assume he already had intimate carnal knowledge of my girlfriend. My overriding concern were his friends, all twelve of them.

I knew from experience that people tend to surround themselves with like-minded people. I had drifted away from my High School friends by virtue of our disparate financial situations, preferring to associate with older, more established men, who had the leisure time and disposable income to do fun things. Surely, Steve Baldwin was in the same boat, his inner social circle comprised of wealthy Alpha Males. I shuddered to imagine the liberties that would be taken with Olivia and Madison, once these self-entitled pricks were liquored up.

I heard my car honking in the driveway, and for a brief moment contemplated missing my flight.

"Call me from the car," Madison suggested, clearly enjoying my turmoil.

It wasn't the way I wanted to spend my car ride to the airport, but after much give and take, primarily give on my part, and take on Madison's, we hashed out a compromise. Madison agreed to change the location of the Super Bowl party to my condominium, which eased some of my concerns. My exclusive condo complex had strict security in place, starting with a gate-guarded enclosure. As I headed towards the airport, I informed the guard house that Madison was having a party the following afternoon, and they agreed to require a copy of each guest's driver's license. This was done under the pretense of age-verification, as alcohol was to be served, but it also ensured that each participant's identity would be noted, upon entry. I figured that this alone would discourage anti-social or aggressive treatment of the two young women, but, in addition, security agreed to check in on the women every thirty minutes.

As an additional security measure and deterrent against unwilling advances against the girls, my condominium was equipped with a state of the art CCTV system. I hoped that the flashing red lights that were embedded in the eye of each camera, would keep each invited guest in check. I had disabled these lights in the cameras in my master bedroom and master bathroom several months ago, so that I could surreptitiously record any sexual encounters in the privacy of my suite. I left the bathroom one off, but at the last moment I activated the one in my bedroom. I figured that none of the guests would be presumptuous enough to violate the sanctity of my personal space, but in the event that they did, the flashing red light might deter them.

Surprisingly enough, Madison agreed to the conditions without a fight, and texted me right as I boarded my flight to Miami.

"Thanks for always protecting me and providing us with a safe environment for tomorrow's party," it began.

I was feeling quite magnanimous and was just about to respond, when she dropped a bombshell.

"Great news! Jody is joining us for the party! Now that we have relocated to a more controlled environment, the promise of ten grand for a few hours work was too much temptation for her to resist."

"Jody?" I asked, my curiosity having been piqued.

"Jody, one of my cute friends," she said evasively.

"Fantastic," I said, less than enthusiastically, my concern being that a new girl might be amenable to exchanging sexual favors for tips, thereby changing the dynamic of the gathering.

"Less work for you if split it three ways," I added, referring to the constant drink replenishment and cigar lighting that I envisioned would be the majority of their duties.

Even though Madison had taken the gig to get back at me for going to Miami instead of enjoying her oral delights during the Super Bowl, I knew it was going to be harmless fun. I wasn't ecstatic about the idea of Olivia being there, and the potential can of worms that she might open up. However, at least the party wouldn't get out of hand at my condo, with the additional security measures in place. Right as my plane was about to get cleared to taxi, it occurred to me who Jody was. It suddenly made sense why Madison was so evasive.

"Where do you know Jody from again?" I texted, realizing that it was too late for me to change my mind and disembark my flight.

"I told you baby," came the response, as she continued to prevaricate. "One of my cute friends."

"One of your cute friends that helped you drain Steve Baldwin's nuts the night you left with him in his LaFerrari?" I responded, unable to contain my jealousy. "The Jody that surrendered her anal-cherry to Baldwin? The one that squealed like a pig?"

As the flight attendants made the final announcement to turn off cell phones and other electronic devices, I tossed my iPhone into my travel bag, and tried to think of something else.

Try as I might, within the luxurious confines of my first-class cabin, and despite the flirtatious behavior from the young, all-female cabin crew, I could think of nothing else but that fucking Super Bowl party. Madison had engineered another evening with Steve Baldwin, although this time he had the run of my place, the services of Olivia the escort, assisted by two women he had already been intimate with, and twelve of his buddies to egg him on. How could this possibly go wrong?

The Super Bowl ended up being very exciting, although predictably the Patriots won quite easily. I texted Madison several times during the game but she responded sporadically and finally sent me a text, asking me to stop bothering her.

"I am working baby," she texted, after my first few attempts to reach her. "Earning my ten grand!"

I didn't think much more about Madison, until I was on the return flight from Miami. I called her from the car but she didn't respond, and that caused me to worry about her all the way home. I needn't have concerned myself, because when I finally let myself in my front door, Madison was fast asleep on the sofa in my living room. Olivia and Jody had apparently left already, and other than a few bags of trash outside my front door, there wasn't much evidence that a party had occurred.

At least until I stepped foot inside my master bedroom. I wouldn't characterize the place as trashed, but it was if some teenagers had decided to party in my room, and then made a half-hearted attempt to clean it up. There was an ashtray on the end table by

the side of my bed, with a half-smoked cigar in it, that I knew didn't belong to any of the girls. Apparently, one of the male guests had taken the liberty of relaxing in my King Size bed and enjoying a leisurely smoke. I could feel my rage start to surface at the cheek of it, but at this juncture I had no one to point the finger at.

My bed was disheveled, and had been used at some point during my two-day absence. I did consider that perhaps Madison and one, or both of the other girls had slept in it, but Madison knew that I was a clean-freak, and would have undoubtedly made the bed in the morning. It was when I entered my bathroom, that I realized that somebody was fucking with me, presumably one of the guys from the Super Bowl party, taking advantage of the fact that I wasn't home.

There was a pair of men's briefs hanging over the frameless glass wall of my shower enclosure, and, to my disgust, a used condom discarded on the floor. I picked it up using a paper towel, and when I discarded it in my bathroom trash can, I noticed at least two additional prophylactics were in the trash. They had also been ejaculated into, and one of them bore traces of bright red lipgloss. My toilet seat was up, and somebody with very poor aim had evidently attempted to urinate into it.

I had seen enough, and went to wake Madison up. Before she had even opened her eyes and gathered her composure, I was on her.

"What the hell happened at the party, Madison?" I said angrily. "And who the fuck was in my bed?"