Trust Fund Baby Pt. 02

"Clarkson has a massive cock," she said, as she looked over her shoulder at me with a huge smile, her baby blue eyes twinkling as she taunted me. "Much bigger than yours."

I moaned reflexively at her response, and we both knew exactly where this was heading.

"He has incredible stamina too, for an older man," she continued, as she wiggled her ass and flexed her vaginal muscles.

That felt otherworldly, and combined with her verbal teasing was going to get me off very quickly.

"How often do you guys fuck?" I continued, my voice shaking with desire.

"Hardly ever," she said wistfully. "He stops by the store once a month and spends a few thousand dollars on clothes for himself and gifts for his family. I walk him to his car and normally give him a blowjob, as a token of my appreciation for his custom. We fucked a couple of times when we first met, but I was sore for the rest of the day, which made for a long day at work."

"Jesus," I whispered through my ragged breath, as she continued to taunt me.

"Is he married?" I enquired, trying to establish if there was any chance of a future between Madison and Clarkson.

"Unfortunately, for me, yes," she said with an exaggerated pout. "Another reason why I always require him to wear protection. It is a real shame really. He would be the perfect husband for me."

As she continued to extol his virtues, I felt my balls tighten and Madison turned her head back to face forward, threw her head back so that her long blonde hair cascaded down her back and taunted me to release.

"The lingerie I am wearing was a gift from Clarkson," she added with a flourish. "He gave it to me the last time I sucked him off. The panties you are holding too."

That was all I needed to hear and just before I ejaculated, I leaned over her back, raised the wet panties to my nose and inhaled her scent. Seconds later I cried out her name and erupted inside of her. It was a very powerful orgasm, as it always is when I am with Madison.

I know she got her jollies thinking about whether or not this would be the occasion that I impregnated her. Once again, as our agendas converged, she was blissfully unaware of my vasectomy. Madison stayed bent over the stack of boxes for several minutes, presumably to encourage my sperm to swim deeper inside her. I was very content to remain conjoined, trying to milk every last second out of my sexual encounter with Madison.

For her part, Madison continued to try and get inside my head, presumably hoping to elevate my pleasure in future encounters.

"It seems like you enjoyed hearing all about the blowjob I gave Clarkson," she whispered seductively. "Does it turn you on when I tell you about my exploits with other men?" she continued.

My inexperience prevented me from realizing that there was a time and place for this kind of sexual talk. After I had ejaculated, I didn't want to discuss Clarkson, or his oversized cock any more, and Madison picked up on this. As we remained coupled, she changed the subject and we talked about the upcoming events that we had scheduled. We chatted amiably for several minutes, and I agreed to meet her in two days to return her freshly dry-cleaned panties.

I felt my cock twitch slightly and as my refractory period began to end, I wanted to hear more about her older lover.

"Does he pay you, Madison?" I asked, inhaling her scent as my cock started to stiffen again.

"He is a very generous man," she said coyly, avoiding the question. "I have a charge account at LaPerla that he settles up each month, in addition to the gifts he brings me each time I see him."

I couldn't stop thinking about Clarkson getting into his brand new Porsche and driving down to the Tom Ford store for a blowjob. Yes, they engaged in a choreographed routine that made it appear less like sex for money, but at the end of the day, that is what it was. Madison would kneel before the older man, adjusting the length of his hem and telegraphing her submission to him. She would flatter and cajole him into purchasing thousands of dollars of clothing, smiling up at him broadly from her knees. Once he was erect, he would pay for his purchases, and she would help him carry his bags to his car, and suck him off as part of the deal. The lingerie was just the icing on the cake, and they both seemed happy with the arrangement, although by her own admission, Madison would have been delighted to have married him, even though he was old enough to be her father.

I was rock-hard again now, and began to rock slowly inside her. I just couldn't get enough of this woman.

"I have to get back to work," she said quietly, shattering my dreams of staying inside her for round two. "Be a sweetheart and pass me my handbag."

Madison looked in the general direction of the table, and just beyond it was a

Louis Vuitton bag. I slowly withdrew from her tight vaginal cave, regretting my departure the second my cock left the warm environs of Madison's pussy. Reaching for her bag, she opened it and withdrew a spare pair of panties. Seemingly for my benefit, she grabbed her perfume and sprayed a liberal dose of her intoxicating scent all over the silky garment.

"Be right back," she said, waving the aromatic panties under my nose.

As she disappeared into the restroom, my curiosity got the better of me, and I peered inside her designer bag. I am not even sure what I was looking for, but the first thing that caught my attention was her paycheck, or rather proof of automatic deposit of her paycheck. I wish I hadn't looked, the second I opened it. Even though I was aware of the financial component of our relationship, learning the true extent of the gulf between us, was a reality check.

I had never seen an actual paycheck. For reasons that I had little control over, I never worked a day in my life, being pampered in luxury until the accidental death of my parents, just before I turned seventeen. My trust, released to me in stages, beginning on my eighteenth birthday, currently paid me one hundred and sixty thousand dollars per month, deposited electronically on the first of each month.

Madison appeared to earn twenty-two hundred dollars her last pay period, which presumably was one week. There were other numbers on the paystub that I didn't understand the significance of, so I took a quick photo of the check, as it rested within her Louis Vuitton bag. Moments later, as I backed away from her handbag, Madison emerged from the restroom, having put her underwear on and freshened her lipgloss from sucking me off.

She looked impeccable again, every bit the purveyor of high priced men's wear. She had spritzed herself with my favorite perfume, and smelled intoxicating.

Madison leaned into me, gave me a cheek to cheek air-kiss, and reached for her designer bag. My heart was pounding in my chest as she opened the clasp and peered inside. Apparently she had no clue that I had snooped around inside her bag, although she looked me directly in the eyes as she spoke, which was disconcerting, to say the least.

"Do me a favor, sweetheart," she said with a twinkle in her eyes. "Toss this in the trash once you get outside the store."

It seemed like such an innocuous request that I gave no thought to what it was she wanted me to discard. It wasn't until her dainty hand emerged from her Louis Vuitton bag holding a used condom between her thumb and forefinger, as if it were toxic, that I realized exactly what she was asking of me.

If I had been ten years older I would have reacted with much more pushback, but Madison had controlled virtually all of our interactions, and as she held the Magnum condom aloft in the space between us, I obeyed her directive, and extended my upturned palm. The semen-filled prophylactic felt heavy as it landed on my hand, but I had very little time to process what was happening, as Madison started to leave the lunch room. I closed my fist around the luke-warm rubber, and was grateful to learn that the open end had been tied off into a knot.

I felt my cock stiffen at the indignity of being asked to dispose of her lover's used condom, and I think Madison knew exactly what she was doing because she stopped abruptly as we got to the top of the stairs. Reaching back she grabbed my erection through my jeans, gave it a playful squeeze and taunted me one last time.

"That belongs to Clarkson in case you are wondering," she said, seemingly stating the obvious. "As you can see from the lipgloss stains all over it, I made him wear protection when I sucked him off in his new Porsche."

I let out another whimper and Madison looked very pleased with herself.

"Duty calls," she said cheerfully. "Back to work for me."

As we walked down the stairs to the Tom Ford showroom, I was about to ask Madison when I could see her again.

"I get off at six tonight. Meet me here then," she said as we reached her work station.

"Can I get your number, Madison?" I asked nervously.

"I will give it to you the next time I see you," she said, leaving no room for further discussion.

As I stood there feeling like a total loser, Madison walked away from me, her ass swaying seductively in her designer suit, as she approached another wealthy looking guy.

"Bronson," she exclaimed excitedly, as if she was happy to see him, "have you been waiting long?"

"Five minutes, baby," he said in a deep, masculine voice. "Your boss said you were coming back from lunch. You are well worth the wait."

Madison walked towards him and gave him a peck on the lips, showing less concern for the appearance of her lipgloss, than she had when she gave me the air-kiss.

"Why didn't you text me?" she asked, "I wasn't doing anything important. Just having lunch with a friend upstairs."

Her words stung, dismissive as they were of our relationship, if you could even call it that. Plus, he had her phone number, so why didn't I?

Bronson, seemingly encouraged by Madison's indifference to me, began to size me up. I could see the disdain on his face the second we made eye-contact, which was surprising to me. At that moment in time, with my recent sexual encounters fresh in my mind, and my four hundred thousand dollar car parked just outside the showroom, I saw myself as a total stud.

Through Bronson's eyes I was a boy, not yet fully developed, standing there awkwardly with my erection visible in my jeans and my right arm hanging limply at my side, which became more noticeable as he stepped forward and extended his right hand to greet me. Immediately after I raised my right hand I remembered that I was clutching a used condom. I probably could have transferred it to my other hand without Bronson even being aware of it, but Madison cleverly interceded to save me the embarrassment.

"Pete has just recovered from the flu," she said without missing a beat. "I think fist bumps are in order."

Bronson extended his fist to mine and we touched knuckles as way of introduction.

"I'm Pete," I said, with as much confidence as I could muster. "Nice to meet you..." I added, my words trailing off as I waited expectedly for one of them to tell me his first name.

"Pete, this is Mr. Bronson," she added cheerfully, adding nothing to what very little I knew about this imposing individual.

"I stopped by earlier," Bronson continued, ignoring me completely. "You were busy entertaining Clarkson," he said without a hint of jealousy. "Looks like he got another new Porsche."

"Which is exactly why you should come at the appointed time, Bronson," Madison teased without any shame. "Not showing up an hour early and stalking me in the parking lot."

"You got me!" Bronson said good naturedly, throwing his hands up in the universal surrender gesture. "Guilty as charged."

I faded into the background as Bronson and Madison flirted incessantly, their body language leaving no doubt that they had been lovers at one point. I moved slowly towards the exit door, hoping that Madison would acknowledge my departure and say goodbye. However, when I looked back over my shoulder as I exited the showroom, I was shocked to see the two of them ascending the staircase to the stockroom. They were still laughing and carrying on, and the straps of Madison's garter-belt were peeking from beneath the hem of her exquisitely tailored skirt, as she climbed the stairs.

When I got into the sanctity of my car, I tried to gather my composure. I was breathing heavily which I initially attributed to rage at Bronson's dismissive attitude towards me. However, as I took stock of my body's other reactions, I noticed that my face was flushed and I had a massive erection. Madison had a profound effect on me sexually, but I doubted that the sight of her garter-belt straps would have aroused me so intently. My heart sank as I realized that it was her interaction with Bronson that had excited me. I had yet to learn the word "cuckold" but it was a fitting description for my new found sexual identity.

I raised my clenched fist and opened it to allow the used condom to hang freely from my thumb and forefinger. The weight of the copious load within it stretched it, and as it hung before me I questioned whether or not Clarkson only orgasmed once a month, during his regular visit with Madison. The volume of semen contained within the condom would certainly have supported this theory.

It was huge, too. I had only used a condom twice before and they had looked nothing like this after I had completed my business. Granted, my used prophylactic went straight into the trash as soon as I removed it from my softening cock, so I never really got to examine it, the way I was checking out this Magnum rubber. Clarkson's thirty-day load, as I referred to it, in order to make myself feel less inadequate, filled the bulbous tip of the condom.

As it hung from my fingertips, I also noticed that it was covered with traces of peach lipgloss, identical to that which Madison had worn when she exited the brand-new Porsche. One would expect to see lipgloss at the tip of a condom that had been worn during fellatio, I mused, but she had transferred her preferred color of lipstick to the entire length of the rubber. At the time, this didn't make much sense to me, but a quick question posted to a Reddit thread devoted to oral-sex, opened my eyes to such previously unknown sex acts as frenulum teasing, ball worship and deep-throating, all of which Clarkson had apparently been treated to in the front seat of his Porsche.

Disturbingly, I couldn't deny my reaction to the visual of the used condom as I held it skyward, jealously eyeing it. My cock throbbed as I contrasted the loving cock-worship session that Clarkson had enjoyed, to the abbreviated vanilla blowjob that I had been treated to. I wanted to jerk off in my Lamborghini and had to remind myself that I was a man with options. I almost called Olivia to take the edge off, but ended up firing up the obnoxiously loud V12 engine and without considering the ramifications, tossed the used condom into the minuscule glove compartment, and sped out of the parking lot.

After I left the Tom Ford showroom, I called my uncle. It had been a few days, and I needed a debrief, and a pep talk.

A few minutes later, as I debriefed with my uncle, my education began. As we dissected my performance, from the evening that I met Madison at the bar, I went from feeling like a porn-star to realizing Madison had played me. Coached, and encouraged by my uncle to remember the specifics, I recalled that there were some noticeable physical differences between the orgasms Madison had experienced when she was writhing in ecstasy on my teenage cock, and the ones I had witnessed her rub out.

My uncle was very patient as he guided me through her deception, and as the truth unfolded I felt like a chump. Madison had faked the orgasms that had occurred when we were coupled. As I replayed the moment in my head, I realized that there had been no flexing or tensing of her abdomen, no perceptible change in her breathing, no noticeable increases in wetness caused by self-lubrication.

"Madison faked her orgasms, at least during sex," my uncle informed me. "Don't feel bad. A lot of women fake climaxes, particularly if they want something from you. It is a form of flattery, as every man likes to think that they are a great lover."

"Fuck," I exclaimed dejectedly. "Madison was the best sexual experience of my life, and I thought there was some reciprocation on her part."

"Best sexual experience of your young life," my uncle corrected me. "Are you up to three partners now, stud?" he teased.

"Four," I said proudly, "I fucked this chick Olivia, although she is a hooker."

"In your financial situation, working girls are one of your better options," he said without judgement. "Look I know you really like this chick, Madison, but at her age she is only with you, because she wants something from you. Sorry to be so blunt. Have you given her any money?"

"She hasn't asked for any," I said, jumping to her defense.

"The good ones won't," he assured me. "But that wasn't my question. Have you given Madison any cash?"

"One hundred dollars," I admitted, "the first night, for cab fare."

"Maybe, she doesn't need your money," my uncle mused, "maybe she is independently wealthy."

I went on to explain that Madison was a salesperson at the Tom Ford store, and that I had seen her paycheck. I tried to describe the numbers on the paystub, but there were a lot of different figures on there, and as I had never seen a paycheck before, it didn't make sense to me. I ended up sending my uncle the photo I had taken of it.

"First of all," he said with a chuckle, "the twenty-two hundred is her gross pay. She actually deposited a touch over eighteen hundred dollars. Secondly, that amount was for two weeks, not one. She definitely needs a little financial assistance, and if you don't give it to her, some other Newport Beach schmuck will. It's okay to spend a little money on her," he advised," just remember to spend it on something you will enjoy, like lingerie or a manicure. And always get something in return."

I felt much better after my debrief with my uncle, and at the end of Madison's shift, I showed up to take her for a drink. The store Manager had already left for the day, leaving Madison to lock up. After, she secured the front doors, she invited me back upstairs.

"To the lunchroom?" I enquired naively.

Madison gave me a smile, her blue eyes sparkling as she processed my innocence.

"I have a little closet up there," she admitted. "I want to get changed before we head out."

Madison led me upstairs and we went past the store room and into another smaller room, that had a small daybed and a beautiful cedar closet. Madison started to remove her custom-fitted suit, and when she was down to her lingerie and heels, she turned to face me.

We made eye-contact for a few seconds, which was long enough for my cock to stiffen in my pants. Madison moved closer to me, and we began to kiss. I was respectful in the way I touched her, lightly caressing her shoulders and neck as we made out. She was anything but, groping and squeezing my nuts, cock and ass, unzipping me as we kissed.

Once my cock was freed from my jeans, she turned away from me, slid her silky panties to one side, and grabbed the tip of my cock. She looked over her shoulder as she lined my cock-head up with the entrance to her pussy.

"Don't worry, baby, I am on the pill," she assured me, as if she had forgotten that she had already told me that.

As I entered her impossibly tight vaginal-cavity, I wondered how many guys she was fucking, for her to forget our birth-control discussion. However, as her warm, wet pussy enveloped my cock, it felt so good, that who else she was fucking ceased to matter.

"Fuck, yeah, baby," Madison exclaimed with pure delight, "that feels so good."