Trust Fund Baby Pt. 04

I was an eighteen year old boy, and was no match for the manipulative blonde. She used her sexual allure to completely engross me, and as hard as I tried to terminate the relationship, I could not have imagined life without her. The sex with Madison was all-encompassing, utterly fulfilling and she kept my nuts completely drained at all times. It was all I could think about. In fact thoughts of Madison occupied my dreams most nights, and in the morning I would always wake up with a raging boner. I slowly came to the maddening realization that I was never going to be able to leave her. I was destined to put up with all of her torturous actions, as no matter how much I provided for her, unless I was willing to marry her, she had decided she was going to have other lovers. Of course, I was expected to be a one-woman man by this point, and Madison was punishing me for my indiscretions with Samantha, by forcing me to endure three days of celibacy, while she teased me incessantly.

After Madison had removed her bikini top, she invited me to rub sunscreen all over her perfect breasts. I was naked at this point, having been instructed to remain so during my three day period of forced abstinence. Once her surgically-enhanced tits were sufficiently lubricated, she sat up in her sun lounger, and told me to kneel next to her. As I struggled to get comfortable on the granite tiles of my balcony, she leaned in towards me and began to fuck with me.

As my erection danced around right under her chin, she lowered her head slightly, to hold it in place. As the tip of my cock touched her neck, some of my pre-cum was transferred to her skin, and she let out a giggle.

"Someone is horny," she said stating the obvious.

As I knelt before her, breathing heavily and leaking seminal fluids, she thrust her breasts skyward, thus enveloping my cock between the recently oiled mounds. Once my cock was wedged between her tits, she slowly lowered her head and began to barely graze the head of my penis with the tip of her outstretched tongue. This was absolute torture, as she had made it abundantly clear that I was not going to get any release until the following day.

Madison maintained eye-contact with me as she kissed and licked the tip of my cock, and I began to thrust between her oiled breasts as she held them together.

"This was Barry's favorite way to come," she taunted me. "Back when I had 38Ds."

Madison knew that I responded favorably to hearing about her exploits with other men, and I let out a whimper of frustration as she parted her lips slightly to facilitate my entry into her warm mouth. She allowed me a couple of deeper thrusts, and then removed her lips from my cock.

"Don't torture yourself, baby," she said seductively. "You don't want to have an accident and blow your load all over my tits."

With that sage advice dispensed, she allowed my cock to slip from between her oiled tits, and moved away from me.

"Madison, please," I begged through my ragged breathing, "I am so horny."

"I am horny too, Pete," she said with a twinkle in her eye. "I am going to fetch my vibrator. I want you to go down on me, while I masturbate. Wait here on your knees."

Madison got up from the sun-lounger, and as I shuffled around uncomfortably on my knees on the hard granite tiles, she walked gracefully into my condominium. When she returned a few moments later, she had her vibrator in one hand, and a glass of chilled wine in the other. After she got comfortable, she removed a large ice cube from her wine glass, and handed it to me.

"I am hot," she informed me, "use this to cool me down."

We had played with ice cubes numerous times before, and Madison enjoyed it when I ran one all over her breasts to chill and stimulate her nipples, before warming them up with my mouth.

"Good boy," she said condescendingly, as I took the ice cube from her, and began to trace it across her breasts and around her nipples, until they hardened under the stimulation.

Under Madison's tutelage, I teased her with the ice cube, running it across her taut stomach, and eventually gently grazing it across her clitoris which elicited a great response. As the ice cube finally began to melt, leaving the first drops of liquid on the folds of her labia, she took it from me, and inserted it inside her. She let out an audible gasp, presumably from the cold sensations that were now inside her body. Then she picked up her vibrator, and as she touched the rounded end onto her clitoris, she grabbed me by one ear and lowered my face between her legs.

Between her cordless sex-toy and my eager tongue, we brought her to climax several times, as the ice cube started to melt inside her. I did notice that her pussy was unusually salty, but she had just used the restroom so I thought it was maybe traces of urine.

By the time I realized that Madison had semen leaking from her pussy, I was too horny to care. I knew that it wasn't mine, and I began to wonder who the hell had deposited a load inside my girl, and when? We had been together for most of the last two days, so things weren't adding up. Madison enjoyed another very vocal release on my tongue, as I continued to ingest the semen leaking from her. At some point I made eye-contact with her, and I must have had a confused look on my face, because she clarified the situation for me.

"Clarkson's," she said with a giggle. "From the used condom that you guys shared a while back. Make sure you eat every last drop, and then I will let you fuck me."

While I wasn't enthralled with the idea of eating another man's semen from my girlfriend's pussy, the promise of sex was all I could think about. I did my best to clean the last remnants of his load from her as the ice cube continued to melt. Madison was enjoying my submission to her and came twice more on my face. I heard her vibrator drop to the ground, which signaled that she was satisfied. She put one hand behind my head and pulled my face deeper into her sex.

"Open wide," she said cheerfully, and as I obeyed she squeezed her Kegel muscles and expelled the small remains of the ice cube into my mouth.

"Mount me," she instructed.

I wasn't going to need a second invitation, and within seconds I was in position on top of her. My oral attention had caused her to self-lubricate, and in my state of readiness, I was able to slip right inside her.

Once I was buried balls-deep inside her, I lay motionless awaiting her permission to fuck. This was our routine, established by her preference to be in charge of my every movement. Her pussy felt unnaturally cold and less inviting than usual, which was probably by design, a punishment for my encounter with Samantha that started my whole enforced celibacy.

"Ok, baby," she whispered gently into my ear, as she patted me on the ass. "Eat the ice cube containing Clarkson's load while you make love to me. Nice and slow."

I began to rock slowly inside of her, and felt my orgasm building almost immediately. It had been two full days since my last orgasm, during which time Madison had kept me naked and teased me relentlessly. As I sucked on the ice cube containing the remains of Clarkson's ejaculate, and slid in and out of her cold pussy, Madison started to taunt me.

"I can't wait to tell Clarkson that you got sloppy seconds again," she whispered as she nibbled my earlobe. "He will love that we used his semen as lubrication."

A few moments later I ejaculated deep inside Madison's vaginal cavity, which had warmed to almost body temperature by this time. I came so hard that I almost passed out, a combination of the almost three day enforced celibacy, and the humiliation of another man's semen acting as both my lubricant and my protein snack. Madison let me rest on top of her after I came this time, her unspoken gesture acting as an acceptance of my apology for my screw-up with Samantha.

For me, it was a turning point in our relationship. Even as she confused me by vacillating between submission and dominance, the sex was so good that it set me right back to square one, the day I met her. I knew at that moment that I would never be able to leave her, no matter what she put me through.

Despite Madison having quantified the amount of financial support that she would need from me, in order to be monogamous, I never really came through for her money-wise. At least not in the sense that I handed her a regular monthly stipend. I had made peace with the idea of giving her six thousand dollars a month in exchange for monogamy and "unrestricted access to all three of her holes," as she so eloquently put it. However, even though I got virtually unlimited sex, the monogamy was now contingent upon us getting married.

I needed some impartial advice, so I ran it by my uncle one day, when my nuts were completely drained and I wasn't thinking with the little head.

"Personally, I think you are crazy to settle with one woman with the amount of options available to you," he started, before softening his approach slightly. "However, if you feel that you must compensate Madison for her time, treat her to some sexy lingerie or give her the occasional bonus in cash. Whatever, you do, don't obligate yourself contractually to anything, don't even establish any discernible patterns of financial assistance. Promise me you will require her to keep working at least, so that she can be shown to be capable of self-sufficiency."

This made sense as soon as he verbalized it. In the event that we split up, if Madison sued me for breach of contract, the court would have a far more favorable view of her claim for continued support, if I had paid her rent, or her car insurance every month. Probably even more so if I agreed to her request for a monthly stipend of six thousand dollars per month. However, if I gave her the occasional piece of lingerie, or gifted her cash once in a while, it would be far less obvious that I had agreed to support her. Particularly if she still had a full-time job.

Madison began to stay at my place with increasing regularity, and she began to bring more of her clothes over. At first it seemed like it was done out of convenience, particularly as she was there three or four nights a week. However, once the walk-in closets in the master suite were completely full of her belongings, and she started to commandeer the storage space in the second bedroom, I realized that she was staking her claim to what she considered her territory. I never really snooped through her closets, but a couple of times I went in there to bring her some additional hangers, and immediately noticed two disturbing trends.

Firstly, her wardrobe was comprised predominantly of lingerie, designer shoes and handbags, with a few expensive tailored women's suits, the latter of which I assume she wore to work.

Secondly, as I looked more closely through the packed drawers of LaPerla lingerie, I noticed that she had numerous duplicates of the same item. She had arranged the intimates in such a way that the identical items were buried at the bottom of the cedar lined drawers. Interestingly enough, many of the tremendously expensive items still had the price tags affixed to them. It appeared that Madison had positioned herself in such a way that she could return the items if she needed the cash. I am sure that outside of the LaPerla store, this might have been the largest collection of these pricy intimates in Southern California.

In addition to filling the closets in two of my bedrooms, Madison also had her makeup and beauty products clearly visible in the master bathroom, again staking her claim to her territory.

She didn't need to do that as I never had other women over. After my fuck-up with Samantha, I was subjected to a very invasive and uncomfortable urethra swab, after Madison got involved and dictated this unorthodox approach to my STI testing. Once I got home, I was also given a three day forced sobriety, a period of time to reflect on my misdeeds. This one-two punch was enough for me, and from that day forward I eschewed other women, declaring my commitment to Madison by being totally monogamous with her.

It would have been really nice if she had opted to treat me with the same respect, but Madison wanted more than a couple of closets and my unwavering gesture of faithfulness. I had to respect her candor, even though her words cut me to the bone.

"Until such time that you decide that this relationship is the one, I intend to exercise my right to fuck other guys," she informed me matter of factly. "As a courtesy to you, I will use protection for vaginal and anal penetration," she added coldly, as my cock stiffened at her provocative words. "Although not for blowjobs," she added as a final kick in the nuts.

"You are my soul-mate, Madison," I said, completely believing this to be true. "Please have a monogamous relationship with me."

"Being your soulmate doesn't pay my bills," she said on more than one occasion. "If you truly cherish me enough to want me as your own, step up to the plate and do the right thing."

Even though she never specifically mentioned marriage, it was evident that it would be matrimony, or at least the promise of it through a widely announced, and very brief period of engagement, that would stop her fucking and sucking other men.

I could never be quite sure what bills she kept referring to, as she was paying no rent splitting her time between my place, and the small space that she called home above the Tom Ford store. She had no car payment, or any other transportation related costs, as she had parked her beat up Honda behind her work after her registration tags expired. I offered to pay for her car registration, but she rebuffed me, because as I discovered later on, she had numerous unpaid parking citations. However, I ended up adding her to my insurance and letting her use my Ford Raptor as her daily driver.

I think Madison felt like unlimited sex with me was a fair trade for her greatly upgraded living accommodations, and life-style improvements, and we settled in to a routine. Madison was available sexually to me twenty four hours a day, and to her credit never refused my advances. However, about once a month, but not on a strict enough schedule that I would ever know the exact date, she would flatter and cajole Clarkson into a large purchase at Tom Ford, and then suck him off in his car as a way of showing appreciation for his custom.

Initially she kept the timing of the event secret from me, but this created a significant amount of stress in our relationship, particularly as the date approached on our calendar. I guess I asked too many questions one day, and Madison, feeling that our current status afforded her the right to service Clarkson as she pleased, reacted in a particularly assertive fashion.

"From now on," she told me forcefully, "not only will you know when my date with Clarkson is, but you will be on restriction for the day that I suck him off."

I knew I had pushed Madison into a corner with my incessant grumbling about her continued encounters with Clarkson, and no matter how much I begged her to reconsider, she had made her mind up. For his part, Clarkson loved the idea of my forced celibacy on his big day, and would let Madison know two or three days prior to his visit. She would take great pleasure in marking the date on the calendar hanging on our refrigerator, initially with a large red X, but later on by kissing the calendar while wearing the exact shade of lipgloss that she intended to use to fellate him. I struggled with jealousy when it came to Madison, and she got her jollies from stoking it whenever she could.

After her conversation with the Doctor at the Sexual Health Clinic, she relaxed her requirement that Clarkson wear a condom for his monthly blowjob, which undoubtedly increased his enjoyment of her edging, teasing suckfest. Occasionally, because he is an asshole and an Alpha, he would ask her to slip one of his Magnum condoms over his blood-engorged cock, just before he ejaculated. I know he did this to fuck with me, as the used prophylactic, would usually end up in the glove compartment of my Lamborghini for me to discover. This never took long, as the lack of interior space within the exotic car, meant that I had to store the key within this tiny compartment whenever I drove it.

I was pissed the first time I discovered his semen-filled rubber in my four hundred thousand dollar car. I came flying out of my garage holding the Magnum rubber between my thumb and forefinger, livid at the indignity of finding it and yet in awe of the weight of the load held within it. Madison reacted to my jealous outburst by taking it from me and hanging the lipgloss covered prophylactic on our fridge, using a large magnetic business card. Not any business card either, but one emblazoned with the name, Clarkson's Hazmat and Environmental Clean-up. Displayed in such a way that one could compare the lipstick kiss on the calendar, to the traces of lipgloss all over the used rubber, this was even more of an indication that she had sucked off another man, presumably Clarkson.

I immediately asked her to move it back to my car, figuring at least this kept her infidelity between us. However, she waited one whole day, until both the personal trainer and our cleaning lady had a chance to digest her indiscretion, and figure out by the mark on the calendar that it was premeditated.

Had I been a few years older, I would have kicked her to the curb. However, at the tender age of eighteen, and having unlimited access to phenomenal sex, I was willing to put up with a lot of crap from her, in order to preserve the status quo.

Madison was playing us both, pleasuring Clarkson in exchange for his generous financial support, and keeping me in a perpetual state of turmoil, by alternating between the best sex of my life and the insanity of my unbridled jealousy. I knew the way out involved agreeing to marry her, but I continued to fight the inevitable.

I tried to keep my jealousy in check, but would routinely make discoveries that inflamed it. Once, when Madison was soaking in my Japanese bathtub, I snooped through her purse, only to discover the depth of Clarkson's financial assistance. When coupled with mine, Madison was living a very nice lifestyle.

She lived rent-free in my opulent oceanfront condominium, and had my brand new Ford Raptor as her daily driver. In her wallet were two LaPerla charge cards, one bearing my name and one in the name of Clarkson. She was also listed as an authorized user on his Black American Express Card, which was a very trusting move on his part, in the absence of any credit-limits. I had also given her a credit card which was intended for day to day incidentals, like gas or the occasional lunch with friends. Of course, Madison being Madison, and her definition of incidentals being considerably different from the rest of the Western Hemisphere, she spent an inordinate amount of money on manicures, hair extensions, massages, Botox and tanning salons.

I never gave her any pushback, especially as most of the stuff she spent money on, contributed to a more enjoyable sexual experience for me. I loved her tanned, lithe frame, and as she knelt before me with her long platinum hair extensions cascading down her back, and her freshly manicured nails grazing across my stomach, my money seemed well spent. You would think I knew exactly how much Madison was costing me a month, but my finances were fairly convoluted, with the automatic deposit of one hundred and sixty thousand dollars per month, dwarfing my expenditures. My bills were on auto-pay, and I had more important things to worry about than Madison buying a few extra garter-belts. I never really even totaled up how much she was spending, assuming it was far less than the six thousand dollars she had asked for in exchange for our exclusive three-hole arrangement.