Trust Fund Baby Pt. 03

Judging by the number of contact points of her lips on the condom, she certainly had taken her time to pleasure him. She had apparently stimulated his cock-head, frenulum and nutsack, in attempt to get him to bust a nut.

"I basically edge him the entire time," she informed me, "he is whimpering like a little girl by the time I allow him to come."

This was way more information than I needed, but as was the case every time Madison regaled me with tales of her sexual exploits with other men, my cock was rock-hard. Finally, after I waited patiently with my pre-cum leaking in a steady stream, joining Clarkson's seminal fluid inside the used rubber, she made her decision.

"I have decided to allow you the privilege of an orgasm," she said magnanimously, enjoying her total control over me. "After I wipe my lipgloss from Clarkson's condom."

As always her choice of words was exquisite, designed to elicit the whimper from me that was my only response. By referring to the prophylactic as Clarkson's condom, she had effectively delineated the hierarchy between us, and this made me want to fuck her even more. Madison extended her perfectly manicured hand and took the proffered wet-wipe from me. Then, as I knelt there, willing myself not to come prematurely, she gently wiped every trace of her peach lipgloss from the exterior of the already enjoyed condom.

Because she is a seasoned courtesan, each cleansing pass was accompanied by a descriptive explanation of what particular pleasure Clarkson would have derived from the attentions of her soft lips. That day, under her expert yet tormenting tutelage, I learned more about the art of edging, than I could have ever learned from Pornhub.

"This is the frenulum," she informed me, as she wiped numerous traces of peach lipgloss from this area. "A particularly sensitive area of a man's penis, and one from which an orgasm can be induced with the lightest of sustained stimulation. Relax your pelvic muscles, Pete," she instructed me. "That is key to the eventual release."

Even though I had anticipated having sex with Madison to achieve the privilege of an orgasm that she had just granted me, I was also game to experience a frenulum orgasm. Madison held my cock at the base, and without applying any force or pressure on the opposing side of my shaft, began to lightly caress the underside of my shaft, just under the cock-head using the pad of her thumb. Even with the condom on, this felt heavenly, and I struggled to keep my pelvic muscles relaxed, as my desired response was to start thrusting in reaction to her stimulation. Madison gently brushed her thumb across my frenulum, in a light but continuous motion, and with absolutely no other stimulation from her, I felt myself start down the path to an orgasm.

"This takes a long-time," she informed me, "at least with Clarkson. Sometimes, I edge him for thirty minutes before he blows his load. I am not willing to spend that kind of time or effort on your release," she added coldly, "although I have a feeling you would come much more quickly than he does."

With that disappointing proclamation hanging in the air, Madison abruptly stopped my frenulum massage, and continued to clean the traces of her lipgloss from Clarkson's condom that I was preparing to reuse.

"Oh, he likes this too," she added as an afterthought, as she lowered her face to my shaft and began to rub the tip of her nose gently over my frenulum.

Madison let out a giggle as I stiffened reflexively under her new stimulation. That felt fucking fantastic, and I knew I would have been a very easy come had she kept that sustained teasing up.

"Seems like you do too," she added, cheerfully.

As I looked on in frustration, she removed her cute little button nose from the underside of my cock-head, and moved her attentions to the tip of my cock. There was quite a concentration of lipgloss traces around this area, evidence that she had kissed and nibbled Clarkson's glans repeatedly as she slowly edged him to his eventual release. Madison wiped this area clean, and finally moved to the shaft of my cock. She knew exactly what she was doing as she wiped her lipgloss from my condom using a repeated up and down motion, simulating a handjob.

My breathing quickened under her gentle teasing motion and for a split second I though that I was going to have my orgasm earlier than anticipated.

"Nice and clean," she announced as she removed her hand from my shaft, and positioned herself on her back, on top of my sheepskin rug.

As soon as she was on her back, I tried to mount her but she slapped me once really hard across the ass, which got my attention.

"On my signal," she said firmly, as she grabbed the tip of my cock and lined it up with the entrance to her pussy. "Nice and slow. I don't want you to break the condom, God knows Clarkson already stretched the fuck out of it."

Unlikely as it was that Clarkson, or indeed any man, had exceeded the mechanical limits of a Magnum condom, I knew this remark wasn't literal, but was designed to emasculate me. I let out a whimper of satisfaction as I slid inside her tight, warm, vaginal cavity.

"Saving Clarkson's rubber was a real stroke of luck," she taunted, as I started to rock rhythmically inside her. "I am going to make you keep all of them in the future, in case you fuck up again and need protection."

The prospect of being handed a used condom containing Clarkson's thirty day load, for use in case of emergency was emasculating enough, but as we fucked Madison continued to taunt me.

"I can't wait to tell Clarkson," she mocked as I increased my pace under her sustained verbal assault. "That is the epitome of sloppy seconds."

Madison was a seasoned courtesan, so it wasn't surprising that she was able to get into the head of an eighteen year old boy, and rock my world with every encounter. In what would be some a sustained pattern during our torrid love affair, Madison would regale me with the sordid details, in excruciating specificity, of her numerous hookups with other men.

After I came, or in the cold light of day when she wasn't around, I hated the thought of her fucking other men. In fact, more than a few times, especially after consulting my uncle, I made the decision to get out of this toxic relationship and dump Madison. I was a young, good-looking trust-fund baby, with options galore. I didn't need Madison in my life. However, as soon as I was balls-deep inside this goddess, and on the road to orgasm, I liked nothing more than to be taunted by her, particularly as she liked to dwell on my physical and sexual shortcomings. I would come so hard as she shared how well-endowed Clarkson was, how much stamina Bronson possessed, or how completely and utterly fulfilled Madison was the night that Steve Baldwin fucked the crap out of her and the two young girls that had spent the night with him.

After I ejaculated inside the used condom, adding my load to the remnants of Clarkson's, Madison made me withdraw immediately. I was accustomed to us remaining coupled long after I came, as we basked in our post-orgasmic bliss, kissed tenderly, and whispered sweet nothings to each other. However, due to my indiscretions with Samantha, Madison wanted no part of our typical post-coital intimacy, and was determined to limit her potential exposure to STIs by kicking me out of the warm environs of her pussy, the second after I came.

This overt rejection caused me to soften almost immediately, and as she mocked my lack of staying power, she told me to kneel in front of her and took a few pictures of me, with my limp dick hanging forlornly between my thighs. She adjusted my position occasionally, as she continued to take snapshots. At some point she told me to remove the condom and hold it up next to my face.

"Smile for Clarkson," baby, she told me cheerfully.

Dissatisfied with my attempts to look happy, Madison took multiple photos until she had the look she was trying to capture. I had forced a smile on my face although my primary emotion was one of abject emasculation, as she documented the stark difference between our semen production capabilities.

She sent me three of the photos, with the caption, "the difference between a man and a boy."

The pictures painted me in a horrible light, and were embarrassing enough to view, until I realized that she had created a new group to receive the text, which included Clarkson and Olivia. I frantically scanned the photos to see how damning they were, and if they gave away any additional clues that I didn't want to share, especially with Clarkson.

The first picture, taken before we modified the condom, was emasculating enough when viewed on its own. It depicted me holding Clarkson's condom up in the air, as Madison and I looked upon it with wonderment and a palpable sense of admiration. The Magnum rubber, stretched as it was from the weight of Clarkson's load, hung several inches below my thumb and forefinger, as they gripped it by the end that had been knotted. The bulbous end swelled from the impressive pool of ejaculate contained within it. Traces of peach lipgloss were visible all over the tip of the condom, making it obvious that this particular load had been coaxed from Clarkson's nuts by Madison's lips.

Anyone observing the lewd photo would have concluded that Madison had given the lucky wearer of the condom, a loving and protracted extended blowjob. Judging by the sheer number of times her peach-glossed lips made contact with the rubber, as it encased his impressive cock, she had apparently engaged in a full-on cock-worship session. There were traces of the lipgloss on the tip, all up and down either side of the shaft, and all the way down to the very end of the Magnum, which would have been nestled against his swollen nuts. Even the knot that had been tied in the end of the condom to safeguard its contents, had traces of lipgloss all over it.

Yes, one could safely conclude, this lucky bastard had been treated to a world-class blowjob, an unrushed, life-changing edging experience that every man hopes to enjoy once in their lifetime. Unbeknownst to me at that exact moment, as I held the huge load high in the sky, and Madison and I looked upon it with admiration, Clarkson actually enjoyed this once in a lifetime event, every single month, in the front seat of his car, outside Madison's place of employment.

If the first picture invoked envy from all who viewed it, the second photo only inspired one emotion, commiseration. Viewed directly after the first picture, the one that encapsulated the potential virility of an Alpha Male, this pitiful snapshot, made the viewer feel genuine compassion for the poor impotent bastard who could only muster this puny load, under the same sexual provocation. Although, upon closer inspection of the condom, which though designed as a single use contraceptive device, had been cleaned and made smaller to accommodate the second user, it became apparent that the hapless sloppy seconds guy, had not been treated to the same sexual stimulation as the first.

Firstly, some of the tactile sense surely must have been diminished by the poor fit of the modified prophylactic, the open end having been unceremoniously hacked off. Also, there was no evidence that the second user of the condom had been treated to any of the delights of the extended cock-worship session, that the first guy had enjoyed. There were no traces of lipgloss on the exterior of the condom that would suggest that Madison had teased his cock-head, frenulum and nuts the way she had the first lucky guy.

That aside, there must have been an explanation for the disparity in the size of their loads, as they were displayed side by side. The typical, and much overused justification of the Alpha Male over the Beta was an over-simplification of their incomparable semen-producing capabilities. Yes, Madison had undoubtedly put much more effort and love into coaxing the load from Clarkson's nuts, but that in itself couldn't account for the fact that he ejaculated four or five times the volume of seminal fluid into the same condom.

The last question a casual observer might have had as they digested the two photographs, was could the two cum-shots possibly belong to the same young man that was holding the condom aloft? A reasonable assumption at first glance, maybe the first load represented his first orgasm in several months, and emboldened by the impressive load, he decided to blow a second wad into the condom, presumably having vastly overestimated his recovery period.

This assumption was rendered unlikely, the moment one looked more closely at the facial expressions of Madison and I, as we observed the two offerings. The first condom, bulging at the seams with Clarkson's load, was being looked upon with admiration by Madison, and envy by me. It was as if I was viewing it, as something to aspire to.

The second puny dribble of semen barely filling the deflated tip of the Magnum, was looked upon with disdain by the gorgeous blonde, while my face was unable to hide my embarrassment, leaving no doubt that I was responsible for the second sperm deposit. My heart sank as I digested the photos, and I prayed to God that Clarkson was too busy to waste time looking at them.

A few seconds later, when Madison's phone chimed in unison with mine, I knew he had responded.

"Pathetic," his one word text read.

My first thought was that Olivia would see his disparaging comment, and this compounded my embarrassment. What I didn't expect though was a fairly rapid response on her part. Less than five minutes after Clarkson kicked me in the nuts, Olivia shared her thoughts.

"I am calling bullshit on the first picture," she said emphatically. "There is no way one man came that much. Samantha thinks it is photoshopped," she added, suggesting that my picture had already gone viral.

A few seconds later, as our phones chimed again, Clarkson added, "I can assure you the first load is all me. Sloppy seconds at its finest for Pete. Fucking cuckold!"