Trust Fund Baby

The following day Madison insisted that I get tested for STIs, even though I knew that my encounter with Samantha hadn't exposed me to anything. She was an eighteen year old runaway, a recent Catholic High School graduate, who had allowed me to fuck her for five hundred dollars out of desperation. I couldn't tell Madison that, of course, as the financial component and the fact that Samantha was eighteen, would have infuriated her.

Madison accompanied me to the clinic, which made the experience much worse for me. When I had my vasectomy, I had undergone a complete STI panel, a simple non-invasive, completely painless event that consisted of a blood and urine sample, and a mouth swab to check for HIV. Madison flirted incessantly with the Doctor, identified herself as my next of kin and got directly involved in the process, which didn't bode well for me. When they disappeared for a few minutes, he returned looking flushed and disoriented. I don't know if she blew the Doctor or bribed him, but suddenly my test involved a swab of my urethra, instead of a urine sample.

I couldn't object to his methodology without tipping Madison off that I had been through this before, so I suffered through it. It wasn't excruciatingly painful but it was definitely unnecessarily invasive, and seemingly orchestrated by Madison to punish me for my perceived infidelity. As expected, my results were all negative, which made the whole ordeal seem like a total waste of time.

After my appointment was finished, Madison engaged the Doctor in conversation about the necessity of using protection during sex. As an escort, I figured that she knew the importance of this, but she had one very specific question, and giggled when the Doctor asked her if she needed privacy.

"He's going to want to hear this," she said dismissively, looking in my general direction. "What is the likelihood of catching an STI from performing oral sex on a man?" she asked the Doctor.

"While I would recommend using a condom for all sexual encounters," he began, "in order of importance it would be anal sex, vaginal sex and lastly oral sex. There is a very low statistical probability of a woman catching an STI from a man solely from performing oral sex. If a man had something transmissible, it is highly likely he would know about it within hours or a couple of days. The chance is reduced even more if the man is not promiscuous."

"So," Madison intoned slowly, looking at me as I squirmed uncomfortably under this intolerable line of questioning. "If I understand you correctly, Doctor, I can safely assume that I pose myself no significant health risks by sucking off an older businessman friend of mine, once a month. He is married, not engaged in sexual activity with anyone else, other than his wife, and has a strong preference to getting blown bareback. Do you approve?"

If he had seemed bemused before, Madison's attempt to get his approval for her monthly bareback blowjob session with the older businessman, caused him to shuffle awkwardly and blurt out a totally unprofessional response, which elicited an excited giggle from Madison.

"I approve," he said with a big smile on his face. "Of blowjobs in general, and of your periodic tryst with your older friend," he added inexplicably.

Just when I thought that there was no possible way that this could get any more uncomfortable, Madison told me to go and wait in the car. Issued in a dismissive tone, her directive left no room for discussion.

"You can go, Pete," she said authoritatively. "I need five minutes alone with the Doctor. I promise I won't be long."

I felt my face redden as I shuffled towards the exit, but Madison had moved on. As she placed her beautifully manicured hand on his arm, she spoke softly.

"Do you make house calls, Doctor?"

I wasn't sure what the fuck she was up to, but as I left the examination room, I heard the door close behind me, and the unmistakable sound of it being locked. I knew that she was fucking with me, extracting her pound of flesh as punishment for my indiscretions with Samantha. Even worse, as I exited through the crowded waiting room, I felt as if all the eyes in the room were upon me, questioning the whereabouts of the fantasy blonde I had entered the facility with.

I kept looking at my watch as I sat in my Ford truck like a total fucking pussy, waiting for my girlfriend to emerge from the medical facility. What the hell was she doing in there? And why was it taking so long?

At times like this I loved and hated Madison, in equal measures. I detested her for constantly stoking my jealousy, in an attempt to gauge her worth to me. It was infuriating to sit there counting away the minutes, trying to guess the extent of her flirtatious behavior behind that locked door.

At the same time, I loved her. As my cock throbbed in my underwear, and an ever-increasing wet spot dampened the inside of my jeans, I couldn't help thinking that I loved the effect that her constant flirting, and the associated threat of infidelity had on me. I felt a tingling in my nuts as I imagined what she was doing with the Doctor.

Madison had prior history with medical professionals, having dated numerous Doctors in the past, most notably the Chief of Staff of a mental health facility, and a couple of surgeons. However, these guys were making over a million dollars per year, and could afford Madison's expensive tastes. In contrast, the Doctor at this Sexual Health Clinic was not in her preferred financial demographic, and almost certainly didn't meet her minimum fiscal requirements.

After what felt like an eternity, I glanced again at my watch, only to notice that two minutes total had elapsed since I sat in my car. I closed my eyes again, trying to imagine what a more assertive version of myself would have done.

In what I can only describe as an out of body experience, I threw my truck door open and strode confidently into his medical suite. All eyes were upon me as I entered the crowded waiting room, although the looks of commiseration were gone, replaced with admiration as I ignored the receptionist's pleas that the Doctor was busy, and burst through the second set of doors.

When I got to his medical examination room, the "room occupied" sign was displayed, although under the circumstances, with the Doctor likely balls-deep inside my girlfriend, maybe a "Madison occupied" sign might have been more appropriate. Even better, why not just hang a pair of her LaPerla undies from the door handle, so that the entire medical office knew what was happening behind the door. I tried the door handle, which unsurprisingly was locked.

In my escalating rage, I instinctively raised my right foot, and planted it squarely in the middle of the door. Unlike in most police drama television shows, in which a burly police officer pounds incessantly against an unyielding door, before summoning the battering ram to open it, this door flew open on the first kick, the frame splintering upon impact, causing the door to hang precariously from one hinge.

I went barreling into the room and to my horror, the bespectacled Doctor was sat at his desk, up to his elbows in paperwork, with a fresh cup of coffee by his side. He looked up through his glasses, in equal parts shock and astonishment at my violent intrusion.

"Oh my God," I said weakly, stammering out my apologies. "I will pay for the door."

I was so embarrassed as I turned my back on him and headed for the exit. When I got to the demolished door frame, I turned back towards him to convey my regrets one last time, and that is when I noticed the unmistakable red soles of Madison's high-heeled Louboutins visible under the front of his desk. As I processed the inevitability of what was occurring in that medical examination room, I found myself rooted to the spot. The silence was deafening, ringing in my ears, until after several seconds, it dissipated and was replaced by lewd slurping sounds from under the table.

The Doctor, any shock that he had exhibited having now been replaced with a self-congratulatory smirk, smugly rolled his chair away from his desk as Madison followed him, crawling on her knees with his cock in her mouth. I slowly approached the desk, and as she bobbed her head rhythmically in his lap, I noticed that he had eschewed wearing a condom, and was thoroughly enjoying an unprotected blowjob. In typical Madison style, she had managed to get lipgloss all over him, traces of the bright red lipstick that she was wearing evident on his glans, his shaft, his nut-sack and the waistband of his scrubs, which she had presumably lowered using just her mouth.

It was a much more rushed affair than Clarkson enjoyed once a month, and as I looked again at my watch, I was aware that less than five minutes had elapsed since Madison instructed me to wait in the car. My presence didn't seem to deter the Doctor, in fact quite the opposite, it appeared to embolden him. He placed both hands behind Madison's head, thrust his hips forward aggressively, tensed up and ejaculated into her mouth with a guttural roar.

"Swallow my load, you fucking slut," he said disparagingly, as he blew his load into my girlfriend's mouth.

I couldn't watch any more, and closed my eyes reflexively to blot out the image of him using my girlfriend as a cum-receptacle. The sights and sounds of their impromptu hook-up faded, immediately replaced with a loud rapping on my truck window.

"Pete, for fuck's sake," Madison said in an aggravated voice, "wake the fuck up."

When I opened my eyes, I was sat in the driver's seat of my Ford Raptor, and Madison was trying to get inside. Her appearance was unruffled, makeup flawless, and she showed no sign of having been violated, as she entered the passenger side of my truck. She leaned over to give me a peck on the lips, but my jealousy flared up and I had to know the truth. As our lips grazed together, I extended my tongue and aggressively forced it between her slightly parted lips. My tongue darted around inside her mouth in pursuit of any evidence of semen remnants, but all I could taste was the spearmint gum that she was chewing.

"I love you too, baby," she said, laughing at my spontaneous open-mouthed kiss. "Are you okay? I was just renewing my birth-control pills."

The realization that I had imagined this entire scenario, forced me to face some harsh realities about my own mental health. Madison had burrowed deep inside my psyche, threatening to undermine my sense of self-worth, while simultaneously forcing me to fantasize constantly about her involvement with other men. I knew deep-inside that this poorly compensated medical professional couldn't afford a woman like Madison, a fact that was quickly confirmed when we passed a late model Honda Civic parked in the space marked "Reserved for Doctor." However, part of me wanted some kind of sexual interlude to happen between them. I wanted to taste his ejaculate when I French-kissed her, knowing that she had taken his advice about bareback blowjobs to heart, and thanked him for his medical advice by giving him some unprotected oral action.

"Good news about my negative test results," I said cheerfully, "and about the relatively low risk associated with bareback blowjobs," I added, grabbing her hand and placing it on my erection.

"Hopefully you have learned your lesson, to keep your dick in your pants," she responded with a dry smile, as she stroked my cock through my jeans. "I am cutting you off for three days," she added dispassionately.

"Madison, I am clean," I started to say in my defense. "I am no threat to your health."

"Your three day celibacy is a punitive measure not a preventative one," she told me with a straight face.

Madison would use the threat of enforced celibacy repeatedly during our relationship, cutting me off from sexual release for the slightest infraction or perceived slight on my behalf.

"Of course," she would inform me, "I still have needs and intend to get them met."

During these times of celibacy, Madison would fuck whoever she wanted to, although she never deviated from her commitment to engage in protected penetrative sex. However, now that she was armed with the knowledge that it was extremely unlikely to catch an STI from oral sex, she would frequently suck guys off without requiring them to use a rubber. I would be forced to wait in the car as she visited Steve Baldwin's office to offer him some oral release, or I would watch the Tom Ford showroom as she went upstairs and took care of Clarkson's needs. My period of celibacy was punishment enough for whatever minor fuckup I had made, but knowing that she would be pleasing other men was torture, and I tried extremely hard to comply with her every wish.

Unsurprisingly, my efforts were never enough, and I found myself being cut off from all sexual release at least once a month. The first time was probably the hardest, as it was completely new to me. As we drove home from the Sexual Health Clinic, Madison teased me incessantly, keeping me erect until we got to Newport Beach. I was leaking profusely by the time we got back to my place, and was in desperate need of some release.

Madison was resolute in her desire to keep me hanging for three days, during which time she managed to keep me constantly hard. Through a combination of skilled touches, a continuous verbal assault of taunts, and an ever-changing parade of sexy outfits, she finally broke me on the third day. I was eighteen years old, in an elevated state of arousal, and accustomed to getting my rocks off several times a day. Madison was sunbathing on one of my ocean-front balconies, wearing a tiny thong bathing suit that did little to protect her modesty.

She kept me naked for the entirety of my periods of forced celibacy, both so that she could continually observe my state of arousal, and to enforce the hierarchy of our relationship. I was trying to busy myself around the house, but couldn't stop admiring her tanned, lean form as she lay almost naked in the sun. Madison beckoned me to bring her a glass of wine and as she relaxed on her sun-lounger, she asked me to apply some sunscreen to her back.

Predictably, one thing led to another, and as I lovingly applied the protective oil to her back, she ended up taking off her bathing suit top, and turning over onto her back. Madison had fantastic breasts, having had breast augmentation surgery on at least two separate occasions, that I was aware of.

Prior to becoming an escort, Madison had paid her bills by stripping in a local Gentleman's club, and one of her regular clients, Barry, had allowed her to live at his Newport Coast mansion, rent free.

Of course the term "rent-free" is a bit of a misnomer, as the concept of a totally free ride does not really exist for beautiful young women. Madison paid her rent on her knees most mornings in the shower, as her older boyfriend prepared for his busy day as a prominent defense attorney. She ended up living with him for two years, during which time he paid for her first breast enhancement, a pair of obnoxiously in your face 38Ds, which must have looked comical on her lithe 115 pound frame.

To hear Madison tell it, Barry never had penetrative vaginal sex with her, preferring blowjobs during their initial period of cohabitation, and switching to titty-fucking her once her post-surgery breast swelling subsided. His preferred way to come was on her face, although he later paid for her to have lip augmentation, so that he could fuck her mouth, using it as one would use a vagina. Barry was very controlling, and became borderline abusive as he tired of her. Madison didn't have anywhere else to go so she put up with his games, even as they got continually more degrading. It was at this point that she identified as a submissive, and this emboldened Barry to take more liberties with her.

He made her change her hours at work from the more lucrative night shift, to the more lunch-focused day shift. This had the effect of significantly decreasing her income, as the horny, alcohol-infused night crowd were much better tippers. Becoming increasingly dependent on Barry, he offered her a lifeline by bringing his fellow lawyers to her place of employment for lunch. As Madison hustled for tips, Barry would turn a blind eye as she gave his co-workers lap dances, and the occasional hand-job in the VIP room.

Shortly after Barry made partner at the law firm, he started to allow his subordinates protected vaginal sex with his live-in girlfriend as a perk of the job, and she was passed around the upper management team as a bonus. Madison has always struggled with her mental health, and after one particularly demeaning incident, in which Barry allowed one of his junior law clerks to fuck Madison for his birthday present, she ended up getting hospitalized for depression.

Even though Doctor/patient fraternization was strictly frowned upon, Madison used her looks and sex appeal to tempt the Chief of Staff, John Thompson, to cross the line. Over a period of a few weeks, as she recovered in a mental health facility and he treated her through regular counseling sessions, she enticed him into a sexual relationship. Initially, it was a twice-weekly blowjob, but as the medical practitioner became more enamored with her, she moved in with him, once she was discharged.

Seeking to keep his relationship with her clandestine, due to the potential blowback on his career, the good Doctor kept her as a virtual recluse in his Laguna Beach compound, where she often wouldn't leave the house for weeks at a time. John was obsessed with her sexual history, and ended up paying for her vaginal rejuvenation, even though she was only twenty-three years old at this point. He ass-fucked her regularly during her recovery from surgery, and ended up making a few other cosmetic adjustments to her, even as she was too emotionally fragile to really object.

John wanted to make her look less like a stripper, so he returned her cartoonish blow-job lips to their natural state, and had her undergo a breast reduction, returning her to a 36C cup, that matched her taut, lithe frame perfectly. He also made Madison cut her hair into a bob, and color it a mousy shade of brown, a huge departure from her long platinum locks. She was kept in a gilded cage like a bird for the two years that she lived in his private enclave, and then one day John came home with a young college girl, and unceremoniously kicked Madison out.

He only gave her an hour to pack, as his new girlfriend waited by the swimming pool to be shown to her new accommodation. Madison didn't have much to her name at this point, but had the foresight to steal two of the Doctor's brand new Tom Ford suits, that still had the tags attached to them. She entered the Tom Ford Store in Newport Beach later that day, with the intent of returning them. Posing as the Doctor's girlfriend, she was convincing enough that the Store Manager agreed to give her a cash refund, after first clearing it with the Corporate office.

In a stroke of luck, as the Store Manager was on hold with corporate, an older male entered the store, and assuming that she worked there, made a beeline for Madison. Even though her appearance had been somewhat toned down by John, she still exuded sexuality, and as the Store Manager waited on hold to garner approval for her refund, she engaged the older businessman, and ended up selling him five suits and a plethora of accessories. The Store Manager had to terminate his call with the corporate office to ring up the multiple items of clothing, and after the customer left, he made the unilateral decision to refund Madison in cash, and he offered her a job.

That is how she began to work at the upscale men's clothiers, and with a renewed sense of purpose, and the constant positive affirmations that the predominantly male clients constantly heaped upon her, she nursed herself back to a healthy place mentally. She used the cash refund from the suits to secure herself a cheap apartment, and to purchase long, platinum blonde hair extensions. It took less than two days for her to get propositioned, and she fell right back into paid sexual encounters, as an escort. It would be about five years later, that she would identify me as an easy mark, as I entered her preferred bar in my four hundred thousand dollar Lamborghini.