Trust Fund Baby Pt. 03

"Don't worry about my needs, Pete," she cooed. "Right now is all about you. I want you to bust a nut inside my tight teenage pussy."

"Oh fuck," I whimpered, "I am not going to last long."

Upon hearing this, Olivia tapped the inside of my knees and I reflexively spread my legs further apart. Lowering herself to her knees behind me, she dragged the tip of her tongue lazily up the length of my inner-thigh, from my knee to just under my nutsack. She gave my scrotum a gentle nibble, and then placing one hand on each of my butt-cheeks, she slowly spread them apart, and her moist tongue disappeared between my ass-cheeks.

This would end up being a life-changing moment for me, as I enjoyed my first rim-job. It was an otherworldly experience being balls-deep in a teenager I had just met, while simultaneously having my ass eaten by Olivia. Most men remember the day that they lost their virginity, and I suspect a few can recall their first blowjob, but for me this was the seminal moment in my ongoing path to sexual self-awareness. From that day forward, analingus became my favorite sexual activity, and the more I shared my proclivities with other men, the more apparent it became what a lucky bastard I was.

Nearly all of my friends were sexually active with their wives or girlfriends, most of them enjoyed the occasional blowjob as a treat, and a few of them even enjoyed anal-sex once in a while. However, once the subject of rim-jobs reared its ugly head, most of them admitted that it was an unrealized fantasy, one in fact which most of them would be reluctant to even broach with their significant others. Learning that the act was taboo made it even more appealing to me, and from that day forward, it was a deal-breaker for me if I encountered a woman that wasn't willing to eat my ass.

Of course, as an eighteen year old trust-fund baby I recognize that I had more options than most men, other than maybe rockstars or professional athletes. Every woman I ever met took one look at my Lamborghini Aventador and determined that I was marriage-material. Normally, their next realization was that they had a lot of competition, and shortly thereafter they would recognize that they needed to stand out from the crowd to have any chance of an easy life on my dime. The average eighteen year old man has a fairly simple hierarchy of needs, and sex sits right on top of that pyramid. So, it stood to reason that the serious contenders worked very hard to keep me sexually satiated.

The younger women, eighteen to twenty-five, were far more malleable and accommodating when it came to sex. Rimming has emerged as a much more mainstream sexual activity among young people, and, in general, young girls were much less resistant to my requests. It was the older generation that found it more repugnant, and I really got a kick out of taking a thirty-something year old woman completely out of her comfort zone.

The more direct my approach, the more successful I was, although I did occasionally get slapped for my candor. However, with the overwhelming odds being in my favor, I learned to be brutally honest, with every woman that I dated. It really turned me on to watch a thirty-year old, college-educated woman, invariably reared on the notion that they didn't need a man, grapple with the fact that I was willing to help them out with their rent, if they were amenable to the idea of sticking their snooty little nose deep between my butt-cheeks.

Olivia was cut from a different cloth and didn't need much coercion to eat my ass. She was a working girl and we already had some history, the most recent being a true connection and undeniable chemistry in my bathroom that night.

She got paid to facilitate men's fetishes. Rimming was on her menu of options, though she took great pains to ensure that I was always clean in my nether regions, before she stuck her tongue in my asshole.

Evidently my wet hair provided sufficient evidence that I had just showered, because as I got balls-deep inside Samantha's tight, teenage pussy, I felt Olivia's tongue brushing gently across my taint. She was barely grazing it, the moist tip of her outstretched tongue, stimulating this very sensitive area, as I rocked slowly in and out of Samantha. I locked eyes with the young blonde, taking in her cherubic young face and appreciating quite how beautiful she was. Judging by her accommodating nature, and her agreeable demeanor, she was not a virgin, but she had a look of innocence plastered across her youthful face.

She smiled sweetly at me, her blue eyes twinkling, even in the half-light of the bathroom. I felt my nuts constrict, a sure sign that I was on the road to orgasm, and Olivia immediately recognized my involuntary reaction to their joint efforts.

"Pete's getting close," she informed the young blonde. "He's going to blow his load soon."

"Yeah," Samantha exclaimed excitedly. "Come deep inside my tight pussy, Pete."

I let out a whimper of pleasure and increased the speed of my thrusts slightly, my upcoming orgasm becoming the most important thing in the world to me at that exact moment. Olivia, being totally in tune with my body, dragged her tongue across my taint and raising her head slightly, adjusted its position so that the tip of it encircled the entrance to my asshole. I stiffened reflexively, and let out a low guttural moan.

Olivia's tongue flicked rapidly across my anus, eliciting an otherworldly response from the myriad of nerve endings concentrated in that highly sensitive area. I felt goosebumps on my ass and lower back as I steadily approached my orgasm. My hands were resting on Samantha's hips, both to facilitate my balance and to control the pace of my thrusts as we fucked. I could feel her garter-belt through the material of her suit, and as I got close I slid one hand under the tailored skirt and hooked my thumb in the strap.

"You can pull my hair if you want," Samantha invited me, as she looked at me adoringly in the mirror.

The contrast between Samantha's beautiful innocent face and her lewd actions made me let out another whimper, and recognizing that I was close, Olivia forced her tongue through my sphincter and deep into my anal-passage. As Olivia wiggled her tongue inside my asshole, I grabbed a fistful of Samantha's hair and pulled her head back sharply. As she egged me on with her angelic smile, I unloaded my nuts deep inside her tight pussy.

It was a profoundly pleasurable experience, made even better by the fact that neither of the young women seemed in any rush to disengage. Samantha remained bent over the bathroom countertop, panties on the floor, her head tilted backwards as I kept my fist embedded in her blonde locks. Olivia continued the ministrations of her tongue, extended fully as it was and buried deep inside my anal-passage. I continued to rock slowly inside Samantha, ensuring that every last drop of my seed was drained from my nuts.

Once I was completely satisfied, I released my vice-like grip on Samantha's hair and slumped forward over the young blonde. She turned her head to the side and we began to kiss tenderly. She was very receptive to my advances and I felt an immediate connection between us. I am not sure if Olivia felt we were ignoring her, or if she was jealous of the tenderness between Samantha and I, but she removed her tongue from my asshole and rose to her feet.

Olivia moved in to kiss Samantha, but in a clear indication that Samantha viewed rim-jobs as repulsive, she wrinkled up her cute little button nose, and turned away from Olivia. This clue that Samantha was not on board with eating ass made me more determined to take that from her, and while I allowed the young blonde to exercise her right of refusal in that gender-neutral restroom, my plan was to get her snooty little nose between my butt-cheeks as soon as possible.

At this point in my life I was still keeping score of my sexual partners, and Samantha was the fifth girl that I had made love to. As my self-confidence and sense of entitlement increased with every passing conquest, I was determined not to let her slip from my sphere of influence without enjoying her tongue in my ass. I would eventually stop counting my lovers at the age of twenty-three, the drug and alcohol fueled orgies that I frequently attended, rendering an accurate count all but impossible. It was about this time of my life that I started going to frat-house parties, and some of the glory-hole games, that involved oral, vaginal and anal sex with anonymous partners, made it difficult to know exactly who I was busting a nut into.

I was frequently the guest of honor at these crazy events, mainly because I would procure the alcohol. Being one of the few guys over twenty-one, and thus legally allowed to purchase alcohol, I would drive my Ford truck to the local liquor store and load up on kegs of Budweiser or Coors light. At around ninety dollars per keg, and with each barrel containing fifteen and a half gallons, I could get a decent size frat-party wasted for less than three hundred dollars.

For my investment of three hundred bucks, I got to go first on the glory-holes. Better yet, once the fraternity got to know my sexual preferences, it was my ass rather than my cock that I inserted through the hole cut in the sheet, or drilled in the plywood, which ever method they were using that night to provide the drunk sorority girls with anonymity. There were no shortage of volunteers too, the alcohol dimming their inhibitions, and rim-jobs having emerged as a fairly mainstream sexual practice among college kids.

I literally lost count of my sexual partners and focused more on ensuring that every single young lady I hooked up with, got a taste of my bunghole. As I previously mentioned, my direct approach got me slapped occasionally, but nonetheless provided me a very high closure ratio when it came to my preferred sexual activity.

As I kissed Samantha, I felt my cock start to soften inside her. I slowly withdrew from her warm love-canal, and impulsively wiped our combined juices from my cock, onto the back of her skirt. Samantha was still bent over the bathroom countertop and was none the wiser, but Olivia looked surprised at the liberties I was taking with the young blonde. I shrugged at Olivia and she nodded her consent as she recognized my indifference.

I wasn't trying to be a dick, but Olivia had paid good money for Samantha and her designer label suit, and I needed a place to wipe my cock. If I was being an asshole I would have cleaned myself off using her hair, something that I did many times in my twenties, just because I could. It did occur to me that I would never have even considered such a disrespectful act with Madison. She would have clipped my nuts if I had compromised her impeccable appearance in any way.

After I put my cock back in my pants, I started working on a plan to ensure that Samantha gave me a rim-job before the night was through. My thought process was a little disjointed thanks to the vodkas I had consumed, but I mentioned a night cap at my place, and dangled the prospect of five hundred dollars in front of Olivia if she made it happen. A few moments later, after we made ourselves presentable, the three of us were heading out to the parking lot, arm in arm, feeling no pain.

That is until we literally bumped right into Madison. As soon as I saw her, I fell right back under her spell, my universe realigned, and any thoughts of a connection with Olivia seemed laughable. Madison was looking exceptionally well put together tonight, and I felt my cock stiffen in my jeans, even though I had just busted a nut.

Samantha and Olivia were hanging all over me, and I had Samantha's lipgloss on my face from our extended make-out session. Madison glared at me as I struggled to form my words. I stood upright and began to apologize to her for my inebriated state, but she wasn't interested in my excuses, and looked at me with contempt in her eyes.

Olivia had come to the realization that she was too intoxicated to drive, and went with Samantha to the valet-parking area to ask them to call us a cab. I made small-talk with an increasingly hostile Madison, and despite my apologetic nature I was getting absolutely nowhere. In fact, as I watched Olivia and her young friend making a complete ass of themselves, Madison appeared even more classy and mature, and it highlighted the gulf between a true woman, and a couple of drunk girls.

Madison was not going to allow me to disrespect her, and in a move that would forever change the dynamic between us, she approached the valet-parking area, her Louboutins clicking on the cement, as she eyed up her options. There were two or three Porsches, a Dodge Viper and a Ferrari 488 Spider parked up front, on display for the bar patrons on the patio. While this would be an unusually exotic assembly of sports cars in many parts of the world, this was a regular Monday night in a Newport Beach cocktail bar. Madison knew enough about cars to recognize that the Ferrari was the true exotic of the group, but in a fateful twist, a brand new Ferrari LaFerrari Aperta pulled into the parking lot, its middle-aged owner presumably trolling for young pussy.

Madison flashed me an icy stare, and seeing that the Rosso Corsa hyper-car had a single male occupant, flagged it down before it even made it to the valet-parking area. An older grey-haired gentleman emerged from the driver's seat in a beautiful bespoke suit, smiling like he had won the lottery.

I recognized him immediately, Steve Baldwin, a retired casino executive, who had recently relocated to Newport Beach from Las Vegas. He was known around town as a cock-hound, and I had seen him at a few local car meets, always with a different young blonde. As wealthy as I was, he was in a different stratosphere, and this compounded my jealousy as he strode confidently towards my girl.

After a very brief conversation with Madison, during which she pointed my way several times, the older man escorted her around to the passenger seat, lifted the butterfly door and helped Madison over the raised sill and into the deep bucket-seat.

She made a big fucking exhibition of it too, hiking her short skirt up several inches to flash me a glimpse of her garter-belt, just so that I knew exactly what I was missing out on. In the brightly-illuminated valet-parking area, I could see that her silk stockings and the garter-belt that held them up, were a matching shade of turquoise, a delightfully feminine and undoubtedly expensive ensemble, probably paid for by one of her lovers, maybe even Clarkson. Her Louboutins were turquoise too, the long slender heel extended seductively as she pulled her toned legs into the car.

Steve closed her door remotely and returned to his side of the car. As he passed the incredibly bright LED headlights, I could see he was sporting an erection, which he was making little attempt to hide. As he settled into the driver's seat of his exotic, Madison was shuffling around in her seat, and I wasn't sure if she was struggling with the five-point safety harness that the owner had optioned on the vehicle, or if she was trying to pull down the hem of her skirt, to retain some modesty.

There was no way I could have known what the hell my girl was doing fidgeting around in the front seat of that hyper-car. In fact, it wasn't until the LaFerrari stopped right next to me, and the passenger window slowly lowered, that I realized that Madison had removed her matching turquoise panties.

"I won't be needing these," she said coldly, as she extended her perfectly manicured fingernails, the tiny silk undergarment held aloft between her thumb and forefinger, which I noticed were painted the exact same shade of turquoise. "See you around Pete."

Reflexively I took her panties, eliciting a laugh from Baldwin, piloting the multi-million dollar car.

"What time do you want me to bring your girlfriend home in the morning, Pete?" he asked with a huge smirk on his face.

Olivia and Samantha showed up right at that moment, their youthful wasted exuberance contrasting with Madison's poise and desirability, and for me at that moment, complete unattainability.

Madison gave Samantha a look of contempt, and as the two of them came into my view, I realized what a second rate stand-in the young blonde had made. Madison's bespoke tailored suit fit her like a glove, highlighting and flattering every curve of her toned body. The skirt, hiked up though it was to facilitate the removal of her LaPerla panties, was pressed to perfection, and looked brand new. By contrast, Samantha's off the rack knock-off suit, wrinkled as it was from her extended session bent over the bathroom countertop, also had a large semen-stain on the rear of it. Even though the splatter had partially dried, and was now presenting itself as a flaky residue, I hoped that Madison didn't notice it.

Of course, as perceptive as Madison is, she was unlikely to miss this obvious fashion faux pas, and she crooked the index finger of her left hand and beckoned me forward to her. I moved towards her instinctively, unable to resist her. As I got close, I smelled her intoxicating scent. Even though Olivia had heavily spritzed Samantha using the same perfume, it had a much more appealing fragrance when worn by Madison. It was as if it had interacted chemically with her pheromones, creating the perfect aroma.

"I think your bitch sat in some ice-cream," she said quietly, causing Baldwin to laugh out loud again.

It was such a spiteful put-down that I had no comeback for it. I inhaled Madison's scent and looked down at her slender toned legs, checking out her garter-belt straps as they peeked from beneath the hem of her short skirt. This inappropriate glance didn't go unnoticed by Steve Baldwin. Sensing my obvious desire for Madison, he extended his hand and placed it on her exposed upper-thigh, which served to delineate what he now considered his territory,

I backed up slightly, still clutching Madison's LaPerla panties in my hand as if they were to be my final memory of her. Baldwin revved the Ferrari aggressively, invoking an incredibly loud response from the V12 engine, which brought a few more admiring bystanders over. Madison was reveling in the attention, but it was Samantha that induced a chuckle from the crowd of mostly young males.

"Wow, two Ferraris in the same parking lot," she said with way too much enthusiasm, highlighting the fact that she was from a small Mid-Western suburb. "Our cab just arrived."

I felt compelled to point out to her that one was a mass-produced, albeit still desirable car with a production run of over ten thousand units, whereas the other was a multi-million dollar hyper-car, of which only 210 units were ever made. Costing two million dollars new, the Aperta traded for much more than that on the pre-owned exotic car market. However, I didn't want to stroke Baldwin's already out of control ego, so I kept that knowledge to myself.

I felt like a total pussy standing there with Madison's panties in my hand, as Baldwin continued to assert his financial superiority over me, by flashing his Patek Philippe Nautilus watch in my face. The stainless steel blue-faced timepiece cost more than Madison made annually, and I knew that the display of wealth was not lost on her. She got off on this kind of thing, and now that she had willingly removed her panties, and was probably self-lubricating at my humiliation, there was very little to prevent Baldwin from getting balls-deep in my girl tonight.

I heard the repeated honking of my taxi, and to my despair a white Toyota Prius pulled up alongside the red Ferrari. Baldwin had seen enough, and having moved his hand further up Madison's perfectly sculpted thigh, in an overt sign of ownership, roared away in his hyper-car, garnering the approval of most of the patrons of the patio, who were documenting his departure on their cell phones.