Trust Fund Baby Pt. 03

Years later, as my success rate reinforced my belief in the process, I started to verbalize my desires. This added the additional visual component, as I got to see the woman's reaction as she processed my request. I use the word request to accurately characterize my early experiences of asking my dates to eat my ass, although emboldened by the lack of pushback, I began to demand, rather than request, the rim-job, in my late-twenties.

I loved watching a breathtakingly beautiful woman recoil in shock as they processed my directive, especially when they asked for clarification, and I got to describe the act in more graphic detail. I could see the bewilderment in their eyes as they realized what they needed to do, if they wanted to see me again. Sometimes, particularly if we had just emerged from the shower, I would let my towel fall to the bathroom floor, and resting my hands on her shoulders would apply downward pressure. I imagine nearly every woman has been in this situation, and most responded by lowering themselves into a kneeling position, for the inevitable blowjob. Once my date was on her knees, I would turn my back on her, and incline slightly over the marble countertop.

Most of the time, after a few seconds in which they made the fateful decision to accommodate me, I would feel the otherworldly sensation of a moist tongue lapping away at my asshole. Occasionally, I needed to make eye-contact with them in the mirror, to snap them out of their trance with a calm, but assertive direction to eat my ass.

As Madison knelt between my thighs, her soft tongue alternating between my nutsack and my taint, I struggled to find a way to transition her into a rim-job. I was an eighteen year old boy, with a sexual history of five partners, three of which I had exchanged money for companionship with. I knew I was going to break up with Madison after tonight, and I didn't want to part company with her until I had experienced her tongue between my butt-cheeks, even if she had never done such a degrading act before.

I decided to take the subtle approach, and scooted slightly forward on the sofa, so that my balls and asshole were exposed, and thus accessible. Madison looked up at me with a confused look on her face, and for a second I thought she was going to refuse me.

To my surprise, she smiled agreeably, and knowing that hearing about her supposed exploits with other men made me come hard, she started to taunt me.

"What is it with men and rim-jobs these days?" she goaded, as if to suggest that all men took this liberty with her.

Emboldened by my response, which was a whimper of pleasure accompanied by some expulsion of pre-cum, she continued her verbal assault.

"Steve Baldwin was into rim-jobs," she said seductively. "Although he came hardest from the prostate massage."

My cock throbbed at this revelation, and more pre-cum was expelled from the tip. Madison began to slowly jerk me off, using my seminal fluid as a makeshift lube. Then as I looked into her beautiful blue eyes, she nodded her consent, and slowly dragged the tip of her tongue towards my asshole.

I had clearly under-estimated Madison's experience and talents in the rimming department. As she utilized her tongue, lips and right hand in perfectly co-ordinated and intensely pleasurable foreplay, I felt myself on the road to orgasm.

As my release got closer, I wanted to hear all about her night with Steve Baldwin.

"Is this what you treated Steve to?" I asked, my voice trembling with excitement.

"We treated Steve to a little bit of everything," she responded, looking up at me from under my nutsack. "A guy like that gets exactly what he wants," she added.

"We?" I moaned, as Madison disappeared under my nuts. "Who is we?"

I stiffened involuntarily as Madison traced her tongue slowly around the rim of my anus, before she began to probe and eventually penetrate my sphincter. Once her tongue was inside my anal-passage, she began to wiggle it around, as she continued her slow edging hand-job.

I was fixated on her as she ate my ass, the contrast between her refined beauty and the lewd act that she was committing, turning me on immensely. Occasionally, she would look up at me from under my swollen nutsack, her piercing blue eyes twinkling as she brought me closer to orgasm.

I let out another whimper as I looked into her eyes, captivated by her breathtaking beauty. I wanted to hear more about Steve.

I whispered hoarsely, "Jesus, Madison, I am close. Is this how Baldwin came?"

Madison, recognizing that my orgasm would be enhanced by her verbal taunts, removed her tongue from my asshole, and immediately replaced it with the index and middle fingers of her left hand. She had lubricated the entrance to my ass with her saliva, and they slid right inside me, up to the third knuckle. Once she was buried inside my ass, she bent the fingers towards herself, quickly finding my prostate, and began to gently caress it.

"Steve came several times," she informed me with a smirk on her face. "We fucked all night. That guy is an Alpha male."

As Madison stimulated my prostate and slowly jerked me off, she taunted me about her evening with Steve Baldwin. A few seconds later, as she told me that she had sucked him off in his multi-million dollar LaFerrari as they drove up Pacific Coast Highway, I exploded all over my stomach, an incredibly powerful and satisfying eruption, that completely drained my nuts.

At the time, at eighteen years of age, with five lovers to my name, it was the highlight of my sexual life. Undoubtedly, the single most powerful orgasm I had ever experienced, and I realized at that moment that I loved Madison, and I wanted her in my life, whatever the cost.

In what would be the first of many changes of heart on my part, I began to consider the pros and cons of dating Madison. At my age sex was the most important thing in my life, and Madison rocked my world between the sheets. Without actually issuing me an ultimatum, she had managed to convey clearly to me that she expected more from me in exchange for a monogamous relationship. Whether that meant co-habitation, marriage, or an agreed upon monthly stipend hadn't been established. However, it was obvious to me that my other options were to either break up with her, or to continue our current arrangement, in which she could fuck other guys and get her kicks by rubbing my nose in it. I was in a horrible predicament, handcuffed to her by virtue of the otherworldly sex that she constantly provided me.

I think Madison knew that she had me too, my youthful inexperience making me an easy mark for a talented and manipulative older woman. She didn't leave it there though. As I struggled to compose myself, she continued the three-pronged teasing session. In a co-ordinated effort to get me hard again, she was massaging my prostate, extolling Steve Baldwin's sexual prowess and overall superiority to me, and gently sucking and nibbling my deflated nuts.

To my complete surprise, my cock began to twitch and we both knew that she had me exactly where she wanted me.

"Steve has a remarkable refractory period, for a fifty-year old man," she taunted. "Although there were three of us working to get him ready to go again," she added with a flourish.

"Three girls?" I grunted, as I got hard again. "Baldwin had three women at once?"

"Well, two girls and a woman," Madison teased. "Jody was only nineteen years old and the other girl had just turned twenty. Believe me, I was the only woman in his bed that night."

Madison had moved her lips to my taint now, and had locked her baby blue eyes onto mine as she teased me. Finally, I reached under my nuts and grabbed one of her ears. I slowly extracted her from my taint, allowing her extended tongue to drag across my nuts and the base of my cock.

"Suck my cock, Madison," I whispered. "I am ready to come again."

Madison hesitated for a split-second, as if to decide if she really wanted to allow me to dominate her, and then, presumably focusing on her path to an easy life, she parted her glossed lips and allowed me to enter her warm mouth. Madison had sucked my cock once before, in her living space above her work. However, it was a rushed affair, borderline mechanical, and I had come very quickly. I wanted a loving, protracted cock-worship session, and I found the courage to tell her.

At first she seemed a little disjointed that an eighteen year old boy was being so demanding, but her financial circumstances were such that she needed to earn this seven hundred and fifty dollars, so she began to lovingly tease me. She licked and nibbled every square inch of my cock, and brought me close to orgasm several times. Each time I got close, I slowed her down by placing my hand under her chin and removing her lips from my cock. I whispered increasingly demeaning commands to her each time I slowed her progress.

"Not yet baby. You haven't earned my load yet," was the last thing I said, met with zero pushback from Madison.

If I was getting under Madison's skin she wasn't showing it. I imagine she was focusing on getting out of there with her seven hundred and fifty dollars, and trying to get a little relief from her bills. It made sense now that she was broke. George told me that she hung out in the bar drinking water until someone bought her a drink. She had been evicted from her scummy apartment, the rent of which couldn't have been much more than twelve hundred per month, which is nothing in Orange County. She had latched on to me, an inexperienced eighteen year old boy with nothing to offer her except a way out of poverty. She was at the end of her rope, and I was her lifeline. For this reason, the beautiful woman continued to try and "earn my load."

I kept that bitch on her knees for nearly thirty minutes, an eternity for me to maintain control and prevent my orgasm. Finally, as I could delay it no longer, and without affording Madison the courtesy of any warning, I unloaded my nuts down her throat. The shock of my unexpected release caused her to choke and gag, but I held her in place by the ears, until I had emptied my nuts.

When I let her go, she pulled her head back reflexively, gasping for air. She had tears in her eyes, and some of her eye makeup was running. It felt good to blow my load in her mouth, and as always happened right after I came, I felt a renewed sense of confidence that I could escape the hooks she had in me.

As she knelt before me, breathing heavily, she had lost some of her composure, and with it some of her allure to me. However, I wanted plenty more from Madison tonight, both sexually, and in the form of answers as to what it would take to have her commit solely to me. First off though, I felt like I owed her an apology for my aggressive behavior.

"Oh baby, that was amazing," I told her. "I am so sorry I lost control. You drive me out of my mind with desire."

Madison didn't respond immediately, but as I observed her body language I could see that her nipples were fully erect, and she was visibly flushed around her neck and chest area. She was also still breathing heavily, and when she finally spoke, her voice was trembling.

"I like being used by men," she said shakily. "That was hot!

Once again her choice of words was designed to make me feel insecure. I wanted to hear that she liked being used by me, not that she was a willing fuck-toy for any dominant wealthy man. However, as I pictured her on her knees in front of Clarkson, flattering him as he decided which suits to purchase, before sucking him off in the front seat of his Porsche, I knew that she was a true submissive. She had given Steve Baldwin a blowjob within ten minutes of meeting him, as they sped up Pacific Coast Highway in his multi-million dollar hyper-car, submitting willingly to his dominant approach. Madison didn't want my apology, she wanted me to assert myself over her.

Her revelation that she liked being used, increased my desire to have a monogamous relationship with her, and I moved towards her and helped her to her feet. After she had wiped her eyes, and freshened up her makeup, I asked her to come and sit with me. Then, moving completely out of my comfort zone, I began to lay out my aspirations for our relationship.

"Baby, I really love being with you," I began. "What would it take to make you stop working and be with me exclusively?"

Madison had obviously anticipated this question, from somebody at least, if not me. She had formulated a well put-together and tempting offer, and to my surprise, it involved neither co-habitation or matrimony.

"I can make seven hundred and fifty dollars per day," she began, "a touch over twenty-two grand a month, plus tips."

She paused for effect to let the number sink on. Twenty-two thousand was a lot of money to pay for a girlfriend, although, Madison was model-quality and exuded sexiness from every pore.

"I was thinking six thousand per month," she said, "for an exclusive, monogamous, all access to every orifice, twenty-four hours a day, guaranteed to keep your nuts drained, total girlfriend experience. I will fulfill all of your fantasies."

I chuckled at her confidence in her ability to manipulate men. However, as soon as Madison identified herself as a hooker, by putting a price on her wares, I was no longer interested. I kept close to a hundred grand in my wall-safe, but Madison didn't need to know that.

On the spur of the moment I decided to play along with her cash for ass scenario, in the hope that I would get my money's worth out of tonight's encounter, before I cut her loose in the morning.

"All things considered, Madison, that sounds fair," I said. "Can I write you a check for the first month, or would you prefer I get cash on Monday?"

I knew the answer to that before I even posed the question, and Madison told me I could pay her on Monday.

"I trust you," she responded sweetly, as she slowly rose from her knees.

"Come here, baby," she said enthusiastically, "You must be ready to come again."

I couldn't wait to have sex with Madison and as she lowered herself onto the white sheepskin rug, I laid on top of her, supporting the majority of my weight on my forearms. We kissed and whispered sweet nothings to each other. Inevitably, as she sought to get me erect, the conversation turned back to her encounter with Steve Baldwin. She was very forthright, telling me all about how the three of them took care of the older man.

"Jody is stunning," she added out of nowhere. "Like a younger version of me."

I had lowered my defenses as we chatted amiably, and when the subject of my evening with Olivia and the mystery blonde came up, I answered Madison's questions honestly, and without censorship. In retrospect, this was a dumb move, but I was a naive eighteen year old boy, trying to gain brownie points by being honest. As soon as I admitted that I had fucked Samantha, without protection, Madison's vibe changed completely.

In fact, she asserted that she would no longer have unprotected sex with me until I had undergone a full battery of STI tests. I was lying of top of her, with a raging boner, the tip of my erection, right at the entrance of her vaginal cavity. I could feel the warmth emanating from her pussy, as she denied me unprotected access to it. I was an eighteen year old boy, and didn't have a bunch of condoms lying around in my condominium, and Madison claimed to be fresh out too, which seemed unlikely seeing as she was an escort.

I begged and cajoled Madison to cut me some slack, but she had evidently made up her mind to punish me to prove a point, and dug her heels in.

"You can jerk off on me if you want," she offered with a sneer, enjoying the control she had over me. "But I don't want your semen anywhere near my pussy until you have been tested."

I was beside myself with frustration, but I was not sober enough to drive and the nearest liquor store was about a ten minute walk. Madison resolutely refused to drive me to buy condoms, preferring to punish me for my indiscretions with Samantha.

I don't know at what point I remembered that I had discarded Clarkson's used rubber in the glove compartment of my Lamborghini, but in my desperate state, it seemed like an option, albeit a decidedly unappetizing one.

In what would be one of the low points of my sex life, I ended up retrieving the used prophylactic from my car, and as Madison looked in in amusement, I laid out my case for being allowed to enter her, wearing her other lover's used condom. Madison was thoroughly enjoying my abject desperation, and finally relented once I got on my knees and had begged her sufficiently.

"I will never forget this moment," she said with a laugh, "you on your knees pleading with me to allow you to re-use Clarkson's condom. I want a picture of this."

I only followed her direction because I desperately wanted to bust a nut. As Madison posed me for the camera, I felt completely humiliated. The picture would end up being worth a thousand words, and she made me convey my desperation as she snapped a few shots. I was kneeling on the sheepskin rug, fully erect in anticipation of getting balls-deep inside this goddess. She made me hold the used condom up in the air right next to my face, the bulbous end of it swelling with the contents of Clarkson's prodigious release. Traces of her peach lipgloss were all over the used prophylactic, evidence that she had lovingly coaxed this load from his nutsack. The look on my face, directed and encouraged by Madison, was one of proposition, as if a light had just gone on in my head, as I realized I could re-use Clarkson's rubber, to protect Madison.

Madison had tied a knot in one end of the Magnum, and even though I tried initially to untie it, she suggested simply cutting the end off.

"The Magnum brand will be way too big for you, baby," she mocked. "If you cut three inches from the length, it will be way more size-appropriate. It will need cleaning too."

Once the end was removed, I went to pour the congealed contents into my trash can, but Madison stopped me abruptly.

"Don't you dare waste a drop of that man's precious seed," she instructed me. "Pour it into your ice-cube tray."

I knew she was toying with me just for the sake of it, but I was about to get my rocks off, and at that point I would have eaten the contents of that fucking condom if that's what it took to get back inside of Madison. I poured the congealed mess into my ice cube tray and then inserted a wet-wipe to remove most of the remnants of Clarkson's semen from the interior of the used rubber. It was a disgusting job and if Madison hadn't been taunting me constantly about how I failed to stack up against the well-endowed Porsche owner, I would have lost my erection. As it was, fifteen minutes later, with the used condom protecting Madison from any potential STIs from my dalliance with Samantha, she gave me a quick inspection before she decided whether or not to allow me to mount her.

Even with the top three inches cut off, the Magnum condom was still too big for me, both in length and girth. The base of it extended all the way down my shaft, covering my nuts. Even though the interior was still slightly sticky from the remnants of Clarkson's semen, it was the exterior surface that revealed the most clues about the first time it was utilized.

There were traces of peach lipgloss all over the large prophylactic, and Madison took great delight in explaining to me the techniques that she employed to help Clarkson bust a nut once a month, after his Tom Ford shopping spree.

"It is cock-worship, at its finest," she teased, as I waited patiently to see if she was going to let me enter her. "The epitome of a protracted edging blowjob. I know how to rock that man's world," she boasted, as I listened on jealously.