Trust Fund Baby Pt. 01

By the time I pulled my Lamborghini into the valet-parking area of the bar, I had my libido under control, and I scanned the patio area, as I handed the valet-parking attendant a twenty dollar bill, and told him I would keep my keys. I noticed several good-looking young women looking in my general direction, but no sign of Madison. I entered the patio area, to make sure I hadn't missed her, and as I turned to head into the bar, a beautiful young Asian woman asked me for the time. I was wearing my Apple Watch, eschewing the typical Rolex or Patek Philippe showstoppers, favored by the Newport Beach crowd. She noticed right away, and before I could answer her question, she placed her slender hand on my wrist.

"I love your understated watch," she began. "It takes a lot of confidence to break from the crowd and leave the house with something other than a Rolex on your wrist. I admire that in a man," she added, leaving her hand on my wrist, the entire time.

"Thank you," I replied politely, continuing to scan the room in search of the lovely Madison. "It's eight-fifteen," I added, answering her original question.

"Early," she remarked, to no-one in particular. "I am Olivia," she added, "I think I've seen you here before."

I felt flattered that this hot young girl recognized me, until I realized that it was not me she recognized, but my car. There was nothing instantly memorable about me. I am not especially handsome, do not possess any notable physical traits such as a Mohawk, or tattoos on my face. I am a regular-looking, average height and weight, mainstream dressing teenager, and would not inspire a gorgeous single woman to remember me, after casually observing me from a distance, two nights ago.

I wish whatever self-protective radar that this gorgeous young Asian had evoked in me, would emerge and protect me from Madison, when the need arose. My defenses were unnecessarily up around this young Lucy Liu lookalike, and I felt bad as she stood expectantly for me to tell her my name.

"Where are my manners, Olivia?" I said politely. "My name is Pete, can I buy you a drink?"

"Cosmos," she replied without hesitation. "Thank you Pete."

I made my way to the bar, and was two-rows deep, awaiting bar service when George made eye-contact with me.

"What can I get for you, Pete?" he asked politely.

I ordered a Cosmos and a vodka on the rocks, and watched carefully as George made Olivia's drink. After he handed me her cocktail, he poured chilled water over a glass full of ice, and passed it to me.

"One Cosmos and a vodka on the rocks," he repeated, demonstrating his capacity to follow instructions by making me a non-alcoholic drink.

The crowd parted slightly to let me pay George, and I sidled up to the bar for any intel on Madison.

"She was here last night," he informed me. "In the patio area. She stayed about three hours, allowing several guys to buy her a drink, before leaving on her own."

"And tonight?" I asked, trying not to sound too eager. "Was she here tonight?"

"She just left," he informed me.

"Alone?" I asked, not knowing what good it did me to find out.

I didn't have her phone number, and I didn't know where she lived, so who she left with was immaterial.

"No," George said, to my consternation, "she left with two Asian guys, in a limousine."

"Thanks, George," I said, trying to remain cool, despite having the wind knocked out of my sails.

I handed George a twenty dollar bill, and headed back to Olivia with our drinks. She thanked me profusely and proceeded to down it within about five minutes. My uncle's words were ringing in my ears, as I went back to the bar to get Olivia another Cosmos.

"Cut your losses before you spend any real money," he had warned me.

While this was probably sage advice to some poor schmuck working a minimum-wage nine to five, I was a trust-fund baby, and I could afford to buy the entire bar a round of drinks, if I so desired. For this reason, I handed Olivia her Cosmos with a smile. She tapped the edge of her glass against mine, and drank about half of it in one swig. Olivia enjoyed three more Cosmos before she made her attentions clear, and propositioned me.

Prior to meeting Madison, I would have appreciated Olivia's no-bullshit, direct approach, but after the sensational evening I had just spent with Madison, I found it jarring, to say the least. Olivia offered to spend the night with me for five hundred dollars, and being an inexperienced eighteen year old, who had never paid for sex before, I questioned what that entitled me to.

I was expecting a general set of ground-rules, such as wearing a condom, or understanding that Olivia would leave after I fell asleep, but I got a detailed itemization of exactly what was on Olivia's menu.

"You can fuck me in any position, vaginally or anally, as long as you wear a condom," she began, with a level of detachment that was intriguing, to say the least. "I am okay giving you a blowjob without a rubber, and fine with a facial. You can titty-fuck me and come in my mouth or on my face. No rough stuff or choking, until I get to know you better. Once we are done, you can urinate on me in the shower if you want, for two hundred extra."

I stole another look at Olivia as I processed her offer. She was truly a beautiful young woman, although I suspect, like me she was operating in the bar scene on a fake ID. She couldn't have been much older than me, although our respective starts in life had given her a greater degree of street-smarts. She was about five foot five, barely one hundred pounds, toned and lean from hours spent in the gym. She had perfectly straight jet-black hair that flowed down her back and rested on top of her upturned butt-cheeks.

"You like?" she teased, as she rotated in front of me. "I am worth every penny."

There was no doubt in my mind that Olivia was worth every penny, and as she turned slowly in front of me, I admired her tight little ass, encased as it was in a pair of skin tight leather pants. The high-waisted pants rode up her ass-cheeks, lifting and separating them, as if to reiterate that anal-sex was included in her "all you can eat buffet price."

As she rotated around to face me again, I took in her upper body. She was wearing a black leather bustier with no bra, that lifted her perky tits skyward. A black leather collar was fastened around her neck, and as I asked her to spin one more time for me, I noticed an 'O' ring on the back of it. This would come in handy in case she had been a bad girl, and she needed to be hooked to a leash.

Once Olivia was done gyrating for my visual pleasure, she offered me her wares once again, at a slight discount.

"I will throw in a Golden Shower, for the original five hundred dollar fee," she offered cheerfully.

I knew nothing about negotiating with a lady of the night. I had seen a documentary once about a brothel in Nevada called the Bunny Ranch. They didn't film the explicit sex acts, but much of the negotiations were shown in the film. The most successful escorts set their prices sky-high and refused to negotiate, stating that it implied a financial need to lower your prices. As Olivia began to lower hers, I wondered how much of a need she had for cash, and for what purpose. Did she need drugs? Her rent money? A car payment?

Even though I was horny, much of that was due to the fact that I was eighteen. Also, as undoubtedly hot as Olivia was, it was Madison that made my cock throb. In her absence, I would be just as happy to go home solo and jerk-off, while sniffing her panties. For this reason, I declined Olivia's advances.

"I will buy you another drink though," I offered politely.

Olivia was taken aback by my declining her offer of sex. She had practiced her delivery time and time again, and from the moment she identified me as both single, from my solo entry into the bar, and able to afford her services, from my exit from a bright orange Lamborghini, she assumed I would fold like a pack of cards.

Olivia was irresistible, and under most other circumstances, I would have been powerless to say no. However, I lusted after Madison, and all of these other women were a mere distraction.

"Cosmos?" I asked cheerfully.

Olivia nodded her head, but I could tell she was annoyed. In this crowded bar, there were few ways to tell who the players were. I stood out, due to the fact that I had arrived solo, in a four hundred thousand dollar car. Olivia had spent a considerable amount of time with me, not thinking for one second that I would be able to resist her. She knew I was single and receptive to a hook-up, because she had seen me leave with Madison two nights ago. Now, with time running out, and her cards on the table, I wasn't playing her game.

When I returned with her Cosmos, she had regrouped and come up with a "plan B."

"Don't just say no," she teased, "counter."

This was the wrong thing to say to me. She had a service that she was trying to sell and I wasn't that interested in buying it. By inviting me to propose a counter-offer, she was opening herself up to a lowball. This reminded me of buying custom-made chess-sets in Mexico, where the initial price was in excess of two hundred dollars, and the final transaction price occasionally dipped to below fifty.

"I don't want to offend you," I began.

"You won't offend me baby," she said sweetly, as she sidled up close to me and rested her hand on my ass. "It's just business. What are you in the mood to spend?"

I wanted to tell her that I would pay her a thousand dollars finder's fee, if she could locate Madison and magically deposit her in my bed. However, it appeared that Madison was hooking up with two guys in a limo, and that thought made me very jealous.

Olivia twirled slowly one more time for me, showcasing her wares as we negotiated the purchase price. She shook her tight little ass as I ran my hand across her leather pants.

"Grade 'A' American ass," she teased, "tight as fuck. How much?"

A light flicked on in my head, as I spontaneously decided that I wanted to ass-fuck Olivia. It wasn't about the money, it never was. This was about getting even with Madison for her encounter with two guys in the limousine.

"Let's go," I said assertively, "finish your drink. I will pay your price."

Olivia did a double-take when I agreed to her five hundred dollar fee. She smiled sweetly at me, slammed her Cosmos and leaned in to kiss me gently on the cheek.

"I promise you won't regret it," she said quietly. "I am going to rock your world."

Olivia was hanging all over me as we made our way across the patio. When we entered the bar on our way out, I made eye-contact with George, and he gave me the thumbs up. In the last forty-eight hours he had seen me leave his bar with two insanely hot chicks, and he was paying his respects. When we got to the Lambo, Olivia had no clue how to open the scissor-door, highlighting for me, once again, the gulf in sophistication between her and Madison. I opened the door for the increasingly inebriated Asian, and she fell into the low-slung bucket seat, with a giggle.

When we got back to my place, Olivia ran around it excitedly, admiring the clean modern lines, the unobstructed views and the general minimalist vibe of the place. I poured her another drink, and put on some sensual music. I wasn't sure if it was because she was a prostitute, or if it was because I wasn't enthralled with her, the way I had been with Madison, but I felt much more confident tonight.

I had been feeling it ever since I declined her services, the shift in the power-dynamic evident the second I said no. It felt good to be in control, and I decided to push my luck. Excusing myself to use the restroom, I went to my wall-safe and withdrew seven hundred dollars in cash. When I returned, I placed it on my coffee table, in full view of Olivia. I fanned out the crisp, one hundred dollar bills, and watched her intently as she counted them out from a distance, and processed the fact that I had just paid her the extra for a Golden Shower.

"Let's take a shower first," I said assertively, as I turned towards my bathroom, desperately hoping that Olivia would follow me.

When I got into the bathroom, I turned to face her and we started to kiss. Olivia was a few inches shorter than Madison, and I leaned down slightly to engage her lips. She was a very sensual kisser, although I didn't feel quite the same connection as I did with Madison.

What I did feel though, was a stiffening of my cock as Olivia began to caress me through my jeans. As my body responded to her gentle touch, I tried to forget about Madison. It wasn't easy, especially as I kept seeing mental images of her getting team-tagged in the back of a limousine. If she got impregnated in the back of that Cadillac, which one of those two would she sue for child-support, I mused.

Eventually, as Olivia extracted my cock from my underwear and knelt before me to suck it, Madison evaporated from my mind, and the young Asian had my full attention. I had never experienced oral-sex before, and as Olivia licked and nibbled my cock-head it felt otherworldly. Olivia teased me incessantly, bringing me to the edge of orgasm several times before offering me release.

"Why don't you bust a nut before we shower, baby?" she offered.

I didn't feel the need to respond to her invitation, so I just nodded agreeably. Olivia took my cock back between her lips and sucked me to completion for the very first time. At eighteen years of age, I knew a few people with serious girlfriends. I had heard the spit or swallow conundrum, and I knew that it was considered a bonus to have a girl swallow your load. For this reason, and because I expected very little push-back from a hooker, when I erupted in Olivia's mouth, I intentionally kept my cock buried in it. Olivia seemed surprised initially, but adjusted on the fly, and swallowed my load.

After I came, she nursed my cock with her lips for a few moments until I went soft.

"Did you enjoy that, baby?" Olivia asked, as she looked up at me from her kneeling position.

I stammered and stuttered a brief inaudible word in amazement, and Olivia immediately recognized my lack of experience.

"Oh my God," she said with a smile, "was that your first blowjob?"

As I admitted my lack of prior sexual encounters, Olivia told me not to be embarrassed. Once she learned that I had only ever had sex with three women in my life, she relaxed the condom requirement, telling me that she wanted tonight to be memorable for me.

Then she stripped off, undressed me and we entered the shower enclosure. Up until the events of two nights ago, I had been fairly self-conscious about my body and my sexual prowess. However, I had fucked Madison three times over the course of the night, and she had enjoyed multiple orgasms, courtesy of my cock, so I had some measure of confidence, as Olivia and I started to soap each other up.

As an eighteen year old, my refractory period was about as long as it takes to smoke a cigarette, and before long I was hard again. Seven hundred dollars was nothing to me, but as a matter of principle I wanted to get my money's worth. As soon as I was erect I wanted to fuck, and emboldened by her total lack of push-back when I came down her throat, I wanted to get behind Olivia.

I figured I was paying for the privilege, so I didn't need to be overly considerate, the way I had been with Madison. Once Olivia's ass and lower back were soaped up, I span her around and shoved her into the corner of the shower enclosure. I wouldn't characterize my action as using force, but I definitely manhandled her into my desired position. Once her movement was curtailed, by virtue of her position in the corner of the shower, I moved behind her.

Her upper-body was flush against the shower wall, and I rested my forearm on her shoulder blades to hold her in place. With my other hand, I scooped up some of the soap suds from her ass, and after kicking her legs further apart, I used them as a makeshift lubricant. After I had soaped up her vaginal canal, I lined my cock up with the entrance to her pussy.

Olivia wasn't fighting me, but it wasn't loving, consensual sex, either. There was a certain amount of coercion on my part, but I figured I was paying for it, so I was going to get it the way I wanted it. Had I been more experienced, I would have recognized that Olivia had not self-lubricated, but in my youth and desperation to bust a nut, I didn't really consider her pleasure, and I tried to force my way in.

The soap did a reasonable job of facilitating my access to her pussy, but I am sure that she didn't experience a great deal of pleasure, as I fucked her up against the shower wall. I didn't feel the same connection to Olivia as I had to the multi-orgasmic Madison, and even though I was pounding her from behind, it took me a long time to orgasm. When I felt my nuts constrict, I pulled out from Olivia's pussy and ejaculated all over her back and ass.

It was a copious load that I shot all up her lower back. Three or four ropes of semen splattered across her rear, pooling just above her ass-cheeks. After I was done coming, I scooped up a large glob of it and told her to face me.

I forced Olivia her to her knees, and held my hand out in front of her face. She took one look at my ejaculate and gave me a quizzical look.

"Eat," I said, as she tentatively lowered her lips to my palm and began to eat my jizz.

I kept her on her knees for several minutes, and made her lick my hand completely clean. Then, as she washed my semen from her ass, back and lips, I exited the shower and went to dry off, and get dressed.

I don't know why paying for sex evoked such a mean response from me. I wanted to belittle Olivia, teach her a lesson for taking my money, and as she continued to offer me zero push-back, I elevated her level of humiliation.

She looked a little sheepish when she emerged from the shower. Even though Olivia talked a big game, I think deep down she was a good girl, and felt dirty when she was forced to do certain things. She seemed to realize that I was planning on getting my money's worth, because she approached me with palpable trepidation.

"I want to watch you masturbate, Olivia," I said, as if she was my toy.

I watched her face redden as she processed my directive. I maintained eye-contact with her, offering her no way out.

"Whatever you want, baby," she said sweetly. "How do you want me?"

I positioned Olivia on her hands and knees to start with, asking her to put her hand under herself, so that she could stimulate her clitoris. Then, I poured myself a cocktail, and got myself in a comfortable position to watch the show.

I don't think Olivia had masturbated in front of a client before, but after a few moments, I could see the arousal on her face, as she got comfortable in this compromising position. It took Olivia a few minutes to rub out her first orgasm but when she came it was intense, and very real. The difference between Olivia's orgasm and the ones experienced by Madison was very noticeable. Olivia's entire body shook and tightened as she reached her climax, and she slumped forward, resting her weight on her elbows, as she struggled to control her breathing. I allowed her two or three minutes to compose herself, before resuming control of her.

"Again," I said, impassively, "come for me again."

This happened several years ago, and I now know that digital stimulation of the clitoris is not the easiest way for a woman to have multiple orgasms. In my subsequent dalliances with Olivia, I always encouraged her to bring sex-toys with her. During my ever-growing refractory periods, I would watch her masturbate using either a vibrator or a Sybian Chair, that I purchased for communal use by my bitches. I allowed them each their own set of attachments, to keep things sanitary. However, that black leather vibrating cock-mount, nearly got worn out, as I incorporated masturbation into all of my sexual encounters, paid and unpaid.