Trust Fund Baby Pt. 12

Madison never called me for help, probably out of embarrassment, but feeling like she had gone behind my back and hooked up with George, I took great pleasure in turning her life upside down. I had no idea that there would be incidental benefits to me, as her financial situation worsened, and she started to reach out in desperation for a lifeline.

I called the Orange County Fire Authority first, to report an illegal dwelling above a business in Fashion Island. Madison's boss, who was gay and had nothing to gain by helping her out, had turned a blind eye to the fact that Madison was squatting above her workplace. The small room, zoned as it was for commercial office space, was not adequately ventilated for habitation, and the attending firefighters had no choice but to ask Madison to vacate the place.

Even though Madison's boss had ignored the fact that she was living at work, the discovery of her illegal dwelling spurred him into action, and he disclosed it to the corporate office of Tom Ford, disavowing any prior knowledge of it. This resulted in the immediate suspension of Madison's employment, for misappropriation of company property. The Store Manager reported her car as abandoned also, as Madison had parked it behind the store, while she tried to scrape together the cash to pay the registration fee.

Madison had nowhere to go, no money in the bank, a negative rental history having been evicted from her last apartment, few friends or family, and was really clutching at straws when she called me. She basically begged me for a place to stay, offering me anything I wanted sexually, in return.

"One night, Madison," I told her. "You can stay with me for one night, to focus and get your shit together."

Two firefighters escorted her to my place, her car having been towed for expired license tags. They helped her carry her stuff in through my garage, both of them laden with arms full of lingerie. It seemed that all Madison owned was La Perla underwear, and a few dozen pairs of designer shoes.

"Toss it all on the bed," I instructed the young guy, as he struggled to assess our relationship.

"Your mom seems very upset," he began, taking an errant guess that I was Madison's son.

"Thanks man, I will keep an eye on her," I assured him, not bothering to correct his assessment of our relationship.

In truth, I was more interested in what his partner was doing with Madison, as he tried to put the moves on her. Out of the corner of my eye, I saw him give her his business card, and whisper something to her. She smiled sweetly at him, but as soon as she came into my kitchen, I noticed that she tossed his card right into the trash. I had to smile at the naivety of the young firefighter, and admire his self-confidence. Despite being a good-looking, in-shape guy, he had no hope of getting with Madison, on his eight grand a month salary.

Once the young guys left, I gave Madison the once over. She had definitely aged since I first met her nearly a year ago, but it was a bit of a stretch to assume that she was my mother. I still found her extremely desirable, although I tried to suppress my feelings for her, because I knew that she would use them to manipulate me.

Manipulating men was all that Madison knew, and she was an expert at it. Not only was she a Newport Beach ten (on her best day), but she was also my first true sexual experience, which made for a pretty irresistible combination.

As she stood before me in a silk camisole, a pleated silk skirt, and some matching stockings, I felt a wave of jealousy wash over me. Had she stood before George in such an alluring and coquettish manner, inviting him to enjoy her sexual talents? Was she planning on telling me about the three day encounter, in which she drained his nuts so thoroughly that he didn't ejaculate for a week after she left?

My cock stiffened in my pants as I visualized them fucking in the shower, and I felt my resolve weakening, my erection stepping forward with a willingness to make all of my decisions. I wanted to know if she was wearing any panties, and if so, were they the expensive LaPerla brand that she favored? I also wanted to know how her stockings were staying up. Were they thigh-highs, or was she wearing a garter-belt? Had she self-lubricated after the firefighters had brought her home, especially as one of them had asked her out?

"Pete," Madison said, breaking me out of my trance. "Thanks for letting me crash here tonight."

Madison approached me slowly, her blue eyes twinkling devilishly, as she tried to forge a connection between us.

Her timing wasn't the greatest. I hadn't had sex for three days, which for me was an eternity. Madison had spritzed herself with the perfume that I loved, reminding me of all the times I had jerked off with her scented panties, after the last time that she left me.

She was in a poor physical condition having endured some fairly rough sex for a month, but her mental state was of greater concern. On the verge of a breakdown, she needed some tender loving attention, but she had come to the wrong place. I was still very mad at her for the way she constantly tried to upgrade her position in life, by attempting to manipulate a new man. Living with Baldwin, and then allowing him to discard her and gift her to his son, had gone horribly wrong for Madison and now she needed a soft place to land, to pick up the pieces.

My apartment has four large ocean-view, en-suite bedrooms, but I wasn't going to allow that cheating bitch the luxury of sleeping in one of them. I made my conditions very clear to Madison.

"One night, and you may sleep on the floor at the foot of my bed, like the dog you are."

"Thanks Pete," she said humbly. "I really appreciate it. I owe you big-time."

Even though I agreed with her assessment that she owed me big-time, I knew her choice of words was designed to offer me sexual favors in exchange for a roof over her head. I wasn't opposed to such an arrangement, but my sexual proclivities had changed since I first met, and fell in love with Madison. Heavy-petting and an over the jeans handjob wasn't going to cut it anymore. I had matured, and so had my sexual desires.

I was in the mood for a blowjob though, and I told Madison. She smiled agreeably and started to head in my direction.

"Crawl to me, Madison," I said, reveling in the new power dynamic between us.

Madison flashed me an icy stare as if to ask, so this is how it's going to be? It seemed like she quickly remembered her situation, and in an instant broke into a very accommodating and agreeable smile. She sank to her knees, put her hands down to adopt the doggy-style position, and crawled over to me, like an obedient little puppy. As she put one leg before the other, her pleated skirt rose up over her slender thighs, and my question about her stockings was answered, as I saw the straps of her garter-belt peeking under her skirt. Once she got between my legs I spread them apart to allow her to get comfortable, as I anticipated her being on her knees for an extended period of time.

As I admired my million dollar view, my ex-girlfriend knelt before me with her back to the ocean, and a view of my belly button. I thought I was over Madison, but as she unzipped my jeans with her perfectly manicured hands, she took me right back to the first day I met her. No matter how many chicks I brought home, or how much sex I had, I just couldn't resist this woman. Her scent, her blue eyes, her pheromones, were irresistible to me, and she knew it.

I took in a sharp breath as her glossed lips enveloped my stiff cock. She looked up at me, as if to seek my approval, her eyes mocking me as we both knew she was going to break me. The thing that separated Madison from all the other girls I dated, was that I thought about her when she wasn't around. The other women had my attention when I was with them, but the second they disappeared from my sight, they were out of my mind.

Madison knew all of my hot buttons, physical and mental, and as I approached my orgasm, she started to talk dirty to me, just the way I liked it.

"I like sucking you off, baby," she confessed. "I like the noises you make just before you come, all excited like a little boy. Do you want to know who else whimpers before he comes?" she teased.

"Oh fuck, Madison," I cried out, "you are killing me, baby. Who?"

"Baldwin," she taunted me, "cries like a little girl just before he blows his wad."

Even though I knew she was making it up, it still turned me on immensely to hear about her exploits with other men, particularly guys that I had met, and could visualize fucking her.

"That guy is hung like a horse," she continued, "and he loves anal."

It was the thought of Baldwin kneeling behind my girl, balls-deep in her anal passage, that pushed me over the edge. I came so hard I saw stars, and I instantly realized that I really missed Madison, and her ability to rock my world. Madison, presumably in an attempt to secure a place to live, continued to suckle my cock until long after I came in her mouth. Predictably, I started to harden, my already short refractory period decreased by Madison's ministrations.

Madison got up off her knees, reached under her pleated skirt and removed her panties.

"You still make me wet, baby," she teased, showing me the liner of her silk undies, that was soaked with her vaginal secretions.

The old me would have been very flattered by her assertion that I made her weak at the knees, however, after all the bullshit Madison had put me through, I was a little more skeptical.

"I bet it was the firefighters that made you cream your panties," I said, referring to the two young athletes that brought her to my home.

"Maybe," she countered, as she straddled my legs and draped her panties around my neck. "But you are the one about to get balls-deep in me."

I just couldn't resist her. She was beautiful, possessed the body of a swimsuit model, was wearing a heavenly scent, and even in her beat-down state, was the most desirable woman I had ever laid my eyes on. As she lowered her warm pussy onto my stiff cock, I grunted, still in awe of how tight she was. I knew that she had undergone vaginal rejuvenation surgery, paid for by at least one of her lovers, but I focused on the positives. Whoever had paid for whatever surgery she had undergone, was immaterial. All that mattered right now, was that I was balls-deep in this tight, little, surgically enhanced fuck-hole.

Madison bounced slowly up and down on my cock, in a perfect rhythm, determined to induce another orgasm from me, as she tried to soften me up to the idea of her staying with me. She moved her glossed lips to my ear, nibbling my earlobe as she whispered to me.

"Do you want to fuck my ass, baby?" she offered.

In truth, when Madison slinked back into my life in her broken state, her anus torn up from being ravaged by those Baldwin pricks, and their insatiable desire for anal-sex, I wanted to punish her. I wanted to collar her like the dog she is, tie her off on a short leash to the jet-ski trailer in my garage, and ass-fuck her every time I got hard. Which, at my age, with my diminished refractory period, was about every half an hour.

I wanted to tear her ass up, hear her cry out in pain, as I sodomized her. I wanted to invite my friends over to play poker, the winner of each hand getting a crack at Madison's asshole.

However, as we made love on my sofa, overlooking the Pacific Ocean, my heart softened towards her, and I felt a strong urge to protect her. For this reason, I declined her offer of anal, deeming it wiser to get medical consent before I ass-fucked her again.

"No baby, I am close," I exclaimed, as I felt my nuts constrict.

"I am just fucking with you," she taunted. "My ass belongs to Baldwin."

That was all I needed to hear to push me over the edge. I let out a guttural roar, and exploded inside Madison's impossibly tight pussy. She kept whispering in my ear, a combination of encouragement, and taunts of her encounters with other men. It took me a while to compose myself after my tremendous orgasm, and during this time, Madison and I kissed tenderly.

"I will make you something to eat, baby," Madison said cheerfully, hopping off my lap and heading towards my kitchen.

I watched her tight little ass wiggle seductively as she moved away from me, and even though I had just ejaculated inside her, I wanted more. I kicked my jeans off from where they lay around my ankles, and tucked my softening cock inside my briefs. My thoughts turned to George and his all-encompassing three-day encounter with Madison. They had eaten lunch together too, right before she crawled towards him and sucked his cock. I knew I needed to keep my knowledge of their encounter to myself, but it was eating me alive, and before I could stop myself, I involuntarily blurted it out.

"I know about you and George," I said, through my gritted teeth.

Madison barely reacted to my outburst, continuing to make my tuna sandwich as if we were discussing the weather. In retrospect, she knew me well enough to know that her extra-curricular activities aroused me, and had I been truly perturbed about her three day tryst with the bartender, I wouldn't have allowed her to stay with me. For this reason, she made no attempt to apologize for her actions, but began to rub them in my face.

"What do you know about me and George, baby?" she cooed seductively. "That I fucked him at the Super Bowl party? In our bed! That I just spent three days holed up in his dirty little studio apartment, accommodating each and every one of his depraved sexual desires? That he didn't ejaculate for a week after I was done draining his nut-sack? That he is the only white guy who has ever made me orgasm?"

I was on auto-pilot as I closed the distance between us, arriving in the kitchen as she continued to cut the onions for my sandwich. I could feel the rage of unbridled jealousy surging through my body as I stood right behind her. As I inhaled her scent, her taunts reverberated around inside my brain, and I felt my cock twitch. Madison knew the effect she had on me, and bent over slightly at the waist, which caused her tight little ass to brush against my crotch.

Once she had made contact with me, she wiggled her ass slowly from side to side, the silky material of her pleated skirt, teasing me through the fabric of my briefs.

"George was just what I needed after the shit-show at Baldwin's," she taunted. "A trusted friend without any of the complications of a long-term relationship. George can't afford me, and we both know it. However, that man can make my toes curl like no other, and I am happy to reciprocate. I came so many times, I was seeing stars."

As she continued to mock me, I felt myself get hard, and my reaction didn't go unnoticed by Madison.

"Maxwell," she said quietly, as she continued to tease me through my briefs by wiggling her ass from side to side. "In case you are wondering why I said that George is the only white guy who has ever made me orgasm. As you know, Maxwell got me off good, too."

As I began to dry-hump Madison from behind, she gyrated slowly, and continued to make my sandwich. I fished my erect cock from my briefs, and breathed in deeply as the silk material of her pleated skirt caressed my frenulum, as she rocked slowly from side to side.

"I am wearing a six hundred dollar silk skirt," she said firmly. "I don't need your teenage, pre-cum stains all over the back of it. If you are going to make me take it to the dry-cleaners, act like a man, and make it worthwhile."

As I processed her words, it occurred to me that she was trying to get me to be more assertive, and I responded by bending her over the kitchen island, and rubbing my cock-head between her ass-cheeks, the expensive silk material of her skirt feeling absolutely phenomenal as I dry-humped her.

"Finally," Madison taunted. "Use me the way a real man does. Like Clarkson. Or Baldwin."

A few moments later, as Madison remained bent over the island, her provocative and sexually-charged verbal assault never ending, I felt my nuts tighten, and I ejaculated all over the back of her six hundred dollar skirt, and her matching silk camisole. I continued to grind into her even after I came, such were the tremendous sensations of the silk on my glans and frenulum. My semen stains were evident all the way from her ass-cheeks to her mid-back, and I struggled to regain my composure as Madison lay passively beneath me. Finally, as I stood up and admired my handiwork, she spoke.

"Lunch is served," she said cheerfully, as she carried two plates into the breakfast room, adjoining my kitchen.

As we ate in silence, Madison played footsie with her stockinged feet in my crotch the entire time. It took a while, but long after I had finished my sandwich, she managed to get me semi-hard again, and in an attempt to make herself completely indispensable, Madison crawled under my breakfast table and started to suck my cock.

I knew I wasn't going to come again, but as a nineteen year old man, few things feel as good as a blowjob, so I let her work on me for an extended period of time. Of course, being Madison, the stimulation was physical, visual and auditory, and once I was fully erect, she began to taunt me again.

"Look at all the cum stains on the back of my expensive silk outfit," she teased. "At least they are yours this time," she added with a giggle. "Normally Clarkson or Baldwin blow their loads on me, and send me home to you in this state."

Even though she knew exactly how to rock my world, being back in her web, was the very last place on earth that I wanted to be. Surprisingly, that manipulative bitch did manage to get me off again, albeit a feeble dribble of semen. However, as she cleaned me up with her tongue, I could feel my resolve weakening around her. For this reason, I excused myself and called my uncle.

My uncle listened to my heart-felt rationalization of why I should allow Madison to stay with me. I told him that she was homeless, and currently suspended from work pending an investigation into her use of company premises as living accommodation. In addition to that, she had less than one thousand dollars to her name, no car and no other friends or family.

Her options were limited. She could pretty herself up, hit the bar scene, and wait for men to hit on her, in hopes of scoring a place to crash for the night. Of course, she would have to lower her standards, which in addition to requiring her to have sex with working class men, and men with lower standards of personal hygiene and grooming, would open her up to physical abuse and the potential of sexual assault.

Or she could check into a women's shelter, as an indigent. There was one about two miles from my house, recently renamed The Jamie Baldwin Women's Refuge, in honor of the man who had recently made a large donation, the odd size of which had made the local news. According to the news reports, Jamie had shown up unannounced at the center, with a bank check for one hundred thousand dollars, and two hundred and eighty dollars in cash, inexplicably all in five dollar bills.

When pressed later for the details of how he decided to donate such an odd amount, he publicly thanked Madison DuPont for her fundraising efforts, which caused quite a stir in the upper echelons of Newport Beach.

Of course, if Madison decided to check into the women's refuge, one look at her personal belongings, dozens of sets of LaPerla lingerie and a few designer handbags, would open her up to ridicule and scorn within the shelter, and it was a safe bet that her stuff would be stolen from her, within hours of entry into such a facility.

"Madison is fucked," my uncle eloquently exclaimed, "and you need to be the one to point that out to her. She tried to use you when you guys first met, don't forget that."