Trust Fund Baby Pt. 03

My libido, as an eighteen year old boy, was off the charts. I don't know why I kept Madison's panties, but in her absence they were the next best thing. To be honest, just the sight of them got me hard.

I hit the bar with the patio several nights in a row after our dinner date, but there was no sign of Madison. I kept imagining her on the floor of a limousine, or on a King Size bed in a First Class hotel getting jerked off on, for cash.

Not knowing what she was up to was driving me out of my mind with jealousy, but it was also stoking my desire for her, and I had a permanent erection as I fantasized about her with other men. Each time I entered the patio bar I was hopeful that I would encounter Madison. I would park my Lamborghini in the valet-parking area, clearly visible to all of the patio patrons, enter the bar and approach George for any intel on Madison.

I think he could tell just how worked up I was because he was very sympathetic as he informed me that he hadn't seen her. I was starting to wonder how long it might be before I bumped into her again, and I cursed my lack of assertiveness in asking for her phone number. As I circulated the bar and the outdoor patio area, I was approached by several young women, with various degrees of aggressiveness.

A few of them were stunning, Newport Beach "tens" in their own right, but chemistry is a very difficult thing to quantify, and I wasn't feeling it with any of these young hotties. I had to marvel at the approach some of them took, and wondered if I would have had the same level of celebrity, had I driven my Ford truck to the bar. A few of the young girls blocked my path to initiate conversation, some of them asked me to join them for a drink, a couple even asked me to take them for a spin in my car. Occasionally, I did invite one of the beautiful women to join me for a drink, but as we spent time together it only highlighted how much I liked Madison.

Madison was classy, educated, articulate, opinionated and knew how to hold my attention. In contrast, even though some of the young Newport Beach hotties were model-quality, I felt no chemistry towards them. A couple of times I was tempted to take one of the babes home, the relaxed attitude towards random hookups that pervades today's young people, making sex a sure thing. However, on each occasion I left the bar alone, and ended up masturbating furiously into Madison's silky scented panties.

I came close to taking Olivia up on her offer of a repeat encounter twice, but fortunately for me my big head took control of my little head on both occasions. To my surprise, my body reacted favorably to Olivia, which gave me hope that I would find sexual interest in somebody other than Madison, in the future.

The first time Olivia propositioned me for a repeat visit, she was wearing her black leather pants and her dog collar, the visual bringing back vivid memories of the way she had allowed me to dominate her. We enjoyed a couple of drinks together and she offered to come home with me, at the reduced fee of five hundred dollars, with everything included. I took this to mean that I could urinate on her again and was tempted to take her up on her invitation. However, at the last minute I had a change of heart, preferring to stay faithful to Madison, even though I had no clue whether or not Madison was being a good girl.

Olivia made it very clear to me that anything I desired was available, but she could tell I was hung up on Madison. So, being a resourceful and enterprising courtesan, she engineered a scenario that I just couldn't refuse. I don't know how she was able to pull it off, but a few nights later, as I sat home alone enjoying a cocktail, I got a text from Olivia.

"Madison is here," the text began. "And she is looking good!"

The text was accompanied by a photo of my girl and she was definitely looking good. I don't know who had taken the picture, but it was taken from above and behind, as Madison was playing pool in the games area below the main bar. She was bent over the table, wearing one of her trademarked tailored suits, the hem of the skirt rising up her shapely legs exposing the straps of her ever-present garter-belt. As she leaned over the rails of the pool table, she had raised her right leg from the floor to maintain her balance, the red sole of her color-coordinated Louboutin shoe, confirming her identity, even as her face was hidden from view.

Seconds later, as my cock stiffened in my pants, my phone rang.

"Get your ass down here Pete," Olivia said cheerfully. "Grab your girl before someone else does."

I had imbibed a couple of vodkas already and decided I need to get a cab to the bar. Having an Orange Lamborghini was a great way to meet girls, but it also garnered a ridiculous amount of attention from law enforcement. I had been pulled over multiple times by the Newport Beach Police Department because I am eighteen years old, and am an unlikely owner of such an exotic car. For this reason, I told Olivia I was going to call a taxi, but she offered to come and get me instead.

The bar was only about one mile from my house, but most of the taxis in my area are dispatched from the Santa Ana Airport, so I figured it would be much quicker if Olivia came and got me. She arrived less than ten minutes later, during which time I took a quick shower, and pounded another vodka.

I was very excited at the prospect of seeing Madison again, and the alcohol had lowered my inhibitions. When Olivia got to my front door, she waited just outside the threshold, presumably for an invitation to enter my place. Even though we had some history, and were comfortable around each other, our relationship was definitely a professional one, that of client and provider. For this reason, she didn't come in until I extended my hand and asked her to wait inside.

My hair was still wet as I had dressed hurriedly, in an effort to ensure that Olivia was not kept waiting. She ruffled one hand playfully through my hair.

"Let me fix that for you, Pete," she offered sweetly. "You need to look your best for Madison."

Once we entered my bathroom, and I could see Olivia reflected in the ceiling to countertop mirror, I realized just how cute she was. She had straightened her hair, and had applied her makeup in a more feminine, less goth manner. The dog collar and leather pants were gone, replaced by a short, pleated, plaid mini-skirt, with matching tights. She had on a tiny black spandex crop-top, over which she had worn a black mesh top that was completely see through. Knee-high black leather boots completed the ensemble, and made her look dominant, in a feminine way.

Olivia twirled slowly, allowing me to check her out, and presumably trying to secure some future business.

"Hairdryer?" she asked, once she was done displaying her wares.

"Top drawer," I responded, pointing towards my bathroom cabinets.

As Olivia dried my hair, we chatted amiably, although I developed, and maintained an erection the entire time. This was a very good sign, as I had been so totally consumed with thoughts of Madison that I wondered if I would ever feel sexual attraction to another woman again. After Olivia dried my hair, she opened the top drawer of my cabinets to return the hairdryer, and emerged with my styling paste.

I felt a strong connection to her, as she stood in front of me and teased and styled my hair, the way I always imagined a girlfriend would. My hair looked great when she was done, a little edgier than I normally would have chosen, but we looked like a stylish, chic couple. Olivia placed the gel on my countertop, and under the guise of a few last styling tweaks, positioned her petite body between mine and the countertop.

"Perfect," she said quietly, as she moved between my legs. "You look hot, Pete."

We were inches apart as she spiked the front of my hair, and I reflexively leant into her. I felt my lips graze hers, in the lightest of touches that sent a shiver of excitement through me, and caused my cock to dance around in my underwear. Olivia responded in kind, returning my amorous advances by putting one hand behind my head and extending her tongue into my mouth.

I definitely felt the chemistry as we kissed, and even though I was acutely aware that she was an escort, I think she experienced the connection too. Olivia was a fantastic kisser, tender and gentle, but at the same time able to transmit her desire for me. She drew in closer to me, and I parted my legs slightly to encourage her. As our genitalia touched, albeit through our clothes, we began to rock slowly against the countertop, simulating the motions of sex. We engaged in a gentle grinding movement, which seemed to impart much more respect and mutual admiration than the more aggressive, purely sexual, dry-humping typically favored by young people.

Once she knew she had my undivided attention, Olivia withdrew her hand from the back of my head, and placed it on the shaft of my erect cock. I let out a whimper, and emboldened by my response, Olivia gave my cock a gentle squeeze. I felt an immediate expulsion of pre-cum into my underwear, and an overwhelming desire to make love to her. I moved closer to her, encouraging her to continue teasing me through my jeans. The vodka was starting to really take effect, lowering my inhibitions and defenses against this seasoned courtesan.

At the time, at eighteen years of age, with four sexual partners to my name, I didn't have the experience to realize that Olivia was not acting as a courtesan in that exact moment. She was reacting candidly to an unexpected moment of tenderness and mutual attraction between two young adults. Unbeknownst to both of us, money would exchange hands between us in the future, and we would have several fantastic paid encounters. However, as my cock throbbed, and my breathing quickened under her delicate touch, I viewed her more as my equal, and vowed never to treat her disrespectfully again.

I let out another quiet moan as she rubbed the palm of her hand along the length of my cock.

"You make me so excited, Olivia," I whispered, as our lips parted briefly. "I think you are a very beautiful and sexy woman."

Olivia smiled broadly, and in that moment I could tell the feelings were mutual. We were two, young, reasonably attractive kids, and we were into each other. Just in case I had any doubts that Olivia was experiencing the same response to our make-out session, she removed her hand from my cock, and it disappeared under the hem of her mini-skirt. A few seconds later, her hand emerged from between her legs, and she rested her middle finger on my top lip, right under my nose.

I felt the wetness about the same time that I smelled it. As she brushed her finger across my lip, there was a transfer of her vaginal secretions, and her scent of arousal permeated my nostrils. She slowly moved her finger down across my upper lip, and as I opened my mouth slightly, she inserted the soaking wet digit inside it, and instinctively I began to suck it clean.

"You make me wet, too, Pete," she whispered. "More than you know. However, I need to get you to the bar. You have some unfinished business to attend to."

Holy shit! Madison! I had completely forgotten about her under Olivia's tender advances. I reluctantly withdrew from my embrace with Olivia, and we shared a moment as she wiped her vaginal fluids from my lips.

Once we got into her car, I buckled up, and as Olivia shuffled in her seat, I found myself staring at her toned legs. Her plaid mini-skirt had ridden up her thighs, and it was then that I noticed that Olivia was wearing stockings and a matching plaid garter-belt, not tights.

"You like?" she asked seductively, as she lifted the hem of her skirt a couple of inches higher.

"I love!" I responded, looking every bit like the horny teenager that I was.

Olivia smiled appreciatively, any self-doubt that I had seen in her eyes the night that I dominated her, having seemingly evaporated.

I voiced no objection when she rested her hand on my inner-thigh as she drove me back to the bar. I was already in a heightened state of arousal, and I continued to whimper quietly as Olivia raked her nails up my inside leg and began to gently squeeze my nuts through my jeans. Her tender caresses felt fantastic.

As we pulled into the bar, she rubbed the palm of her hand across my erect cock, expelling some more pre-cum into my underwear.

"Are you ready for Madison?" she asked sweetly, skillfully suppressing any jealousy she might have been feeling.

Arousal is an interesting beast, especially in an eighteen year old male, because under Olivia's sustained and expert teasing, I had once again forgotten about Madison, and I contemplated asking Olivia to suck me off in her car. My immediate sexual needs were at the forefront of my mind, and the alcohol had lowered my resistance. In addition, I justified enjoying a little play from Olivia as a way to take the edge off, so that I would be less desperate around Madison.

Her dainty hand danced around in my crotch, squeezing, rubbing and fondling my nutsack, before she raked her manicured fingernails up the shaft of my cock. I let out another moan of desire and leaned in to kiss Olivia again. Even though she initially responded, a few seconds later we parted lips, and she refocused on the task at hand, delivering me to Madison.

The alcohol was kicking in now, the last vodka that I had pounded surging through my veins. I got out of her car, a little uneasy on my feet, and made my way into the bar. Olivia had apparently fulfilled her duty because she disappeared, leaving me to fend for myself. I entered the bar and made a beeline for the games area. When I arrived at the pool table, there was no sign of Madison, and I moved out onto the patio to try and find her.

She wasn't there either so I did a quick check of the bar area, with no success. Olivia showed up a few moments later, and handed me a vodka on the rocks. She had a Cosmos in her hand and we clinked our glasses together, before I took a large swig of my drink. Apparently she hadn't told George, the bartender, that this drink was mine because it was very strong, not the usual non-alcoholic beverage he typically pours me. As I sipped my drink and surveyed the bar for signs of Madison, Olivia disappeared into the crowd.

Long story short, as the reality that I had just missed Madison sank in, and the alcohol continued to affect my judgement, I began to consider my other options, principally Olivia, wherever she had gone.

I made small-talk with a couple of Newport Beach babes, but they didn't give me the time of day. In fact, one hottie completely ignored me, which was very uncharacteristic of the way I was normally treated in this place. It dawned on me that arriving in a Lamborghini probably drew the attention of girls in a bar like this, but having arrived in the passenger seat of an older Nissan Sentra, I was invisible to most of these gold-diggers. So, I finished my drink and having made my decision to leave, I went to find Olivia.

As it happened, she was looking for me too, and when we bumped into each other near the main entrance, I started to ask her for a ride home, but she cut me off.

"Pete, I found her," she said excitedly. "I found Madison. Follow me."

Instinctively I followed Olivia as she led me through a set of double doors marked "Staff only." We ended up walking through the coat-check area, which was barely utilized in the balmy climate of Newport Beach, and down a corridor that led to a gender-neutral restroom.

I smelled her scent before I even opened the door. The intoxicating smell of her preferred perfume permeated the air, evoking memories of Madison spraying her LaPerla panties with copious amounts of my favorite fragrance. My cock throbbed in my pants as I entered the large restroom, and to my surprise Olivia followed me inside.

The lights in the restroom were lowered prompting me to realize that they must have been on a dimmer. Madison was leaning over the marble countertop, bent at the waist and supporting her weight on her elbows. She was facing away from me, her long blonde hair cascading down her arched back. Her skirt was hiked up several inches, exposing the straps of her garter-belt where they attached to her expensive color-coordinated silk stockings. The stockings were Cuban style, a single thick line extending down the back of each leg, in a dead straight line, from the garter-belt strap to the heel of her Louboutins.

As I admired her toned calves, I noticed that she had already removed her panties, or at least lowered them to her ankles. The tiny piece of silky material was stretched between her legs, her vaginal secretions clearly visible in the crotch.

She couldn't have made herself any more available to me, at least until she began to shake her ass seductively. As the alcohol surged through my veins, I threw caution to the wind and stepped forward to take what I perceived to be rightfully mine. Olivia reached around from behind me and unfastened the top button of my Levi's. She snuggled in behind my ear and nibbled my lobe.

"Madison wanted to apologize for her aloofness," she teased. "Go on, Pete. Give it to her. You know you want to."

As Olivia slowly lowered the zipper to my jeans, I averted my gaze upward to take in Madison's reflection in the counter to ceiling mirror. She had her head bowed slightly towards the mirror, positioned in such a way that I couldn't see her beautiful face.

I can't tell the exact moment that I realized that the girl bent over the bathroom counter wasn't Madison, but by the time I had figured it out, it no longer mattered. Olivia had apparently engineered this surprise to take my mind off Madison, and it was working. Olivia had my jeans down around my ankles, and was busy lowering my underwear. Once my briefs were just below my knees, she placed her foot in the crotch and pushed them down to my ankles. Then in one fluid motion she grabbed the base of my T-shirt and pulled it over my head. Tossing my T-shirt onto the marble countertop, she sank slowly to her knees and untied my sneakers. She slipped them off and then slid my jeans and underwear over my feet.

"Who are you?" I said tentatively, as Olivia lined my cock up against the anonymous, already lubricated vagina.

"My name is Samantha, and I am Olivia's gift to you," she began, in a girly voice. "I am over eighteen years of age, and you have my consent," the young girl added, the latter of which were really the two answers I was looking for.

Samantha raised her head and made eye-contact with me. Whoever she was, and however Olivia had procured her, she bore a very close resemblance to Madison, both in facial structure, eye-color and hairstyle. I thought momentarily about declining this freebie, but the alcohol had diminished my judgment, and I wanted to ejaculate inside this young girl, especially as my vasectomy indemnified me from the risk of any future involvement with her.

Money had apparently already exchanged hands, and Olivia had purchased Samantha's teenage pussy for my enjoyment. In addition to this, they had dolled her up in some fancy designer clothes for my visual delight. I shot Olivia a look of gratitude, and she smiled broadly at me, as if to give her approval.

"My treat!" she mouthed silently, and at that moment I made up my mind, and I thrust my hips forward slightly.

Olivia grabbed the tip of my leaking penis and having lined it up at the entrance to this girl's pussy, eased me inside her. She was very wet, warm and extremely tight, and as we started to fuck, she looked me right in the eyes in the mirror, with a huge smile on her face. She was a very beautiful young woman, about Olivia's age I guess. She had very light blonde hair, blue eyes and a cute upturned nose. She was too young to have had any cosmetic surgery, and too pretty to have needed it, and as she smiled agreeably at me, she began to egg me on.