Trust Fund Baby Pt. 01

That night, as I sat enjoying my cocktails, I forced Olivia to masturbate for me until she could come no more. When I realized that she was completely satiated, I made her crawl into my kitchen on her hands and knees, enjoying the grimace on her face as the hard marble tiles assaulted her kneecaps with every tentative step. Once she reached the center of the huge kitchen, I told her that I wanted to watch her come once more, on her knees. As she struggled to get comfortable on the rock-hard tiles, I sat on a barstool next to the expansive island, sipping my cocktail.

It took her nearly ten minutes to reach her last climax, and she was sweating profusely when she finally tensed up and cried out my name. After she came, she collapsed onto the kitchen floor and curled up in the fetal position.

"Are you done?" I asked coldly, reminding her who was in charge.

I watched with amusement as she tried to get back up to her knees, her jelly-like legs struggling to support her, even in the kneeling position.

"Relax, Olivia," I said authoritatively, "take a break."

Olivia slumped onto the hard kitchen floor and remained virtually motionless in the fetal position, for several moments until I rose and stood over her. Her submission to me had aroused me immensely, and I wanted to fuck her again. However, there was something on my bucket list that I was going to do first. You have to remember that I was an inexperienced eighteen year old boy. I was so scared of never seeing Olivia again, that I wanted to do everything to her, on this one night. Emboldened by the four vodkas I had consumed, I unzipped my pants, and extracted my cock.

As she lay there in the fetal position, I didn't give her any warning, but I aimed my cock at her ass, and started to urinate on her. Tentatively, at first, due to being way out of my comfort zone, and expecting immediate and furious pushback from Olivia.

I let a small trickle of piss out first, and when it splashed against her tight little ass, I waited with baited breath for her reaction. It couldn't have been more different than my expectations. There was zero pushback on her part, only an immediate attempt to get into a position that would be more conducive to me giving her a thorough soaking.

Olivia had apparently made the decision to enjoy my golden shower, in an attempt to secure my repeat business. In her mind, the seven hundred dollars I had given her, more than compensated her for the ignominy of being pissed on. She maneuvered into the doggy-style position, which was the perfect choice for my first time. She faced me too, raising her head up high to look me in the eye, as I defiled her.

I started to slowly circle her, ensuring that I could soak every part of her. I purposely delayed wetting her hair, not out of respect for Olivia, but rather to preserve her femininity as I defiled the rest of her. I had seen a lot of golden shower videos on YouTube, and often noticed that wet hair often transformed a beautiful woman into a drowned rat.

For this reason, I peed over the rest of Olivia first. I got her ass first, as she posed doggy-style for me. Then I directed my stream onto her lower back, wetting just the tips of her long black hair. I didn't even need to ask Olivia to change positions, she did it of her own volition, every few seconds, thus creating variety for me.

I urinated on her tits as she knelt before me, then all over her pussy as she cavorted on her back. When Olivia got back into the doggy-style position, I waited until she lifted her head and made eye-contact with me, then I aimed my urine stream right for the tip of her nose. Olivia squealed excitedly as I soaked her face, fulfilling my fantasy of an enthusiastic recipient of a golden shower. Saving the best for last, I told her to lower her gaze, and pissed all over the top of her head, soaking her straight black hair.

When I had finally emptied my bladder, I flicked my cock in her direction, ensuring that every last drop of my piss ended up on Olivia. Then, as I zipped up I gave her the next set of instructions.

"Take a shower, Olivia, you dirty slut. When you are done, get back here naked except for your collar. Lube your asshole for me."

Judging by the look on her face, Olivia was able to compartmentalize the physical requirements of the job, going through the humiliating repertoire with relative ease. However, it was the verbal abuse which shocked her, and she winced when I called her a dirty slut.

For my part, I had nothing against Olivia. She seemed like a nice enough young lady, regardless of the fact the she paid her bills by being a sexual plaything for men. I was just using her as a vessel, a warm orifice into which I could deposit my load. It was Madison I wanted to punish, Madison's face I imagined when I closed my eyes and pissed on Olivia. Madison's ass I wanted to fuck.

Several minutes later, Olivia emerged from the bathroom, smelling much less offensive, and completely naked except for her collar. She walked towards me trying to act composed, but I could tell I had got under her skin.

"Get on all fours like the bitch you are," I ordered.

Olivia obeyed reflexively, although I saw the grimace on her face again, in response to the verbal abuse. I think I was probably the youngest client she had ever had. Most of the men she entertained were in their forties and fifties. They would be absolutely enthralled to be with a twenty something girl, content to enjoy a blowjob or sex in the doggy-style position, before coming inside her young pussy. With a much longer refractory period to contend with, Olivia could snuggle with her benefactor until he was ready to go again, for the last time. She considered those encounters to be relatively easy money, and for the most part, a respectful enjoyable experience.

Older married clients often dated her repeatedly, cultivating a relationship as they wined and dined her, as an equal. This was in stark contrast to the way I made her earn her money, an eighteen year old boy with an extensive check-list of fetishes gleaned from watching porn, and a refractory period of fifteen minutes.

Once Olivia was on all fours, I approached her continuing to issue directives.

"Throw your head back, so that your hair spills down your back. Big smile!"

After Olivia made the requested adjustments, I laid my hands on her, continuing to alter her body position, until she was exactly the way I wanted her. I inserted one finger into her wet pussy and lifted her ass up slightly, at the same time pushing down on her lower back, which had the effect of arching her back. I kicked her knees apart, lewdly exposing her vagina and anus, thus facilitating my entry, into either orifice.

It was Olivia's ass that I took first, although it should have come as no surprise. I had ordered her to lubricate it, and what other reason would there be for that? As I forced my way inside her tight anal-passage, I closed my eyes and thought of Madison.

Even though Olivia was a beautiful girl, desirable in every way, it was Madison that got me hard. She had intimated that anal-sex was available, the first time we hooked up, but I never did get to butt-fuck her. So, as I got balls-deep in Olivia's anus, I fantasized that it was Madison that I was sodomizing. To her credit, Olivia remained in my desired position, ass up, back arched, head thrown back, until I unloaded into her ass.

Anal sex didn't feel much more satisfying than regular vaginal penetration, from a purely physical standpoint. However, my views on women had been shaped by my misogynistic uncle, who had mentored me since the untimely death of my parents, and my copious consumption of pornography.

For this reason, next up on my bucket list was ass to mouth. This disgustingly degrading act, depicted with increasing frequency on hard-core porn sites, involved the female cleaning her partner's cock with her mouth, right after it emerged from her anal-passage.

Years later, after a few disgusting experiences, I learned to give women ample warning before engaging in anal-sex, and the inevitable ass to mouth clean-up, that turned me on so much. This allowed them the opportunity to use an anal-cleanse, to make the whole encounter more sanitary.

Olivia was not afforded the courtesy of such warning, and as I watched her wrinkle her nose and fight the urge to gag, I almost felt sorry for her. Not sorry enough to allow her to stop the ass to mouth act, but a little empathy, none the less.

By the time I finally deemed my cock clean enough to put back in my briefs, she had a look of abject misery on her face, and I felt like I had truly got my money's worth. She had completely drained my nuts, rendering me incapable of another erection in the foreseeable future.

"I am completely satisfied. Go and brush your teeth, Olivia," I told her, as she slinked naked out of the room, my semen leaking from her asshole.

As I heard her freshen up, I got dressed and I recapped our session. Feeling like she had done an excellent job, I decided to tip her. I went to my wall-safe, and after determining that a three hundred dollar tip would be appropriate, I withdrew the cash in fifty dollar bills. I also pulled out a crisp, one hundred dollar bill for her cab fare, which I stuck in my pocket. Once I had the six fifties in my hand, I had a devilish idea to make Olivia work for her extra money. I crumpled them up, so that each fifty was balled up and sat in my chair, sipping my cocktail.

When Olivia returned to my living room, she was still naked, except for her collar. I pointed at the floor by my feet, and she lowered herself slowly to her knees in front of me.

"That was fantastic, Olivia," I told her condescendingly. "Would you like the opportunity to earn your tip?"

I could tell that Olivia was completely over it, but she forced a smile on her face and looked up at me adoringly.

"I would love that, Pete," she said softly. "What do you want me to do?"

In retrospect, I should have handed her the three hundred dollars, given her a hug and sent her home. However, because I was an eighteen year old asshole, and Madison's unavailability was driving me insane with jealousy, I wanted to punish all women, and Olivia happened to be right in front of me.

So, as the young working-girl knelt naked before me, I picked up the first fifty dollar bill, crumpled as it was into a small ball. Greed appeared in her eyes as she processed the amount of my gratuity, quickly replaced by dread, as she contemplated what she had to do to earn it.

I tossed the crumpled up fifty dollar bill across the room, and we both watched as it rolled right next to my piano. Olivia looked up at me expectantly, awaiting my instruction. I paused for dramatic effect, enjoying the power I had over her.

"Fetch!" I commanded

Olivia was willing to play my game, she just didn't quite understand the rules. She started to get to her feet, apparently intending to run and collect her prize.

"Like a dog, Olivia," I added for clarification. "Fetch it the way a dog would."

I saw the shame in her eyes as she made a split-second decision. Her options were to leave with her seven hundred dollars, and some of her dignity, or to allow me to continue to toy with her, for a tip. Olivia took off like a greyhound, scampering across my living room on all fours, in pursuit of the fifty dollar bill. When she reached my Steinway, she lowered her head, picked up the crumpled bill with her teeth, and crawled back to me, like an obedient puppy.

I held out my hand and she released the bill from her mouth, dropping it into my palm.

"Good girl," I said derisively, as I patted her on top of her head.

"Again?"

Olivia hesitated, perhaps under the impression that she was required to make several retrievals to earn the fifty dollars. I unraveled the crumpled bill, and placed it next to her purse, the inference being that she had earned this extra money, even if she chose to leave now.

Olivia nodded her head, giving me consent to continue my game, and I pulled out the second fifty dollar bill and launched it across the room. To her credit, Olivia's enthusiasm didn't wane, and she pursued the final bill with as much gusto as the first five, even as it landed clear in the hallway. In fact, as she appeared to learn what I was enjoying about this game, she adjusted her gait slightly, becoming more "puppy-like" with each retrieval.

As she dropped the final wadded bill into the palm of my hand, I acknowledged her efforts with a final command.

"Good girl. Stay," I said, as she remained motionless by my feet, on all fours.

Thoroughly enjoying the control I had over her, I stood up and positioned myself in such a way that she was in the "heel" position. Without issuing any verbal commands, I began to walk slowly around my living room with Olivia crawling obediently at my side. After a few laps of my entertainment space, I entered the kitchen. I approached the large island in the center of the room and coming to a halt, I rested my hand on top of Olivia's head, as if she were a dog.

I withdrew the crisp, one hundred dollar bill that I had earmarked for her cab fare from my pocket, allowing her to view it as her next tip. She gave me a flash of acknowledgement, which I interpreted as her desire to earn it. Generously willing to accommodate her, I crumpled it up into a small ball, placed it atop the marble island and, in a slow deliberate movement, flicked it skyward from the countertop.

Olivia tracked the flight of the wadded-up hundred dollar bill, and I watched the look on her face change from anticipation to disgust, as it landed in the middle of the urine puddle.

"Fetch, girl," I said enthusiastically, as the crumpled bank note began to absorb my piss.

Whatever was going on inside Olivia's head as she processed this humiliating scenario was hidden behind the huge smile on her face, which I assume was there for my benefit. A few seconds later, she emerged from the large puddle of piss with the soaked hundred dollar bill between her lips, and traces of my urine on her hands, knees and nose, from where she had dipped her face into the pool of liquid to retrieve her tip.

She crawled over to me, still trying to appear cheerful, and dropped the money at my feet. I wasn't about to handle the defiled bank note, and kicked it gently in her direction with a word of praise.

"Good girl," I said condescendingly. "That is yours now. You earned it."

As the words "you earned it" hung in the air, we exchanged a knowing look and I saw abject defeat in Olivia's eyes. I am sure that once she reached the sanctity of her own home, she replayed the night's events back repeatedly, trying to see if I had given her any obvious way out of the humiliation. In truth, I hadn't. I had fucked the crap out of her every orifice, before urinating on her for the agreed amount of seven hundred dollars.

Once our business transaction was completed, as agreed, I had allowed her the option of earning a tip, that amounted to more than fifty percent. I slowly escalated the humiliation, so as not to shock her into refusing my ever-increasing debasement of her. If I had suggested in the bar that I wanted to piss on my kitchen tiles and have her retrieve a soaked hundred dollar bill with her lips, she would have undoubtedly told me to fuck off. However, for the grand total of eleven hundred dollars, she was willing to allow me to take her reins, bring her to heel and subject her to my humiliating puppy play.

As she knelt before me, her cute little button nose bore the telltale signs of having been submerged in my urine, and I wondered if she could smell its foul odor, as close as it was to her olfactory nerves.

"You may get dressed now Olivia," I said gently, "playtime is over."

Olivia got up from her knees, and exited the room in silence.

I heard the shower run again, as Olivia washed the stain of the evening from her.

A few minutes later she returned, looking none the worse for wear, and with a smile back on her beautiful face. She was fully clothed but missing her collar. Apparently she was done with the puppy play.

"I ordered you a cab," I informed her, "I have had a few too many drinks to drive you home."

"Thank you, Pete," she said gratefully, as she gathered up her purse and the eleven hundred dollars she had earned.

Olivia and I chatted amiably, as we waited for her taxi to arrive. Now that the fun and games were over, the balance of power was restored, and we chatted like we were friends. There was only two years between us, and in another universe we probably could have dated. I was feeling very relaxed as Olivia had completely drained my nuts. I couldn't tell how she was feeling deep inside, but she counted her money twice, and had a huge smile on her face as she processed the fact that she had earned eleven hundred dollars tonight.

"Let me give you my number," she offered. "Now that I know where you live, I can be here anytime, with two hours notice."

We exchanged numbers, although I knew I would never see her again. This was a spontaneous one-off session, done to help me get over Madison, which I had done.

After Olivia left, I took a shower and reflected on the events of the evening. It had been eleven hundred dollars well spent for me, and judging by the fact that she was up for a repeat, Olivia apparently felt the same way. My cock didn't stir, even as I played the night's events over in my head.

I was very tired by the time I turned in for the evening. The combination of several vodkas and several orgasms had wiped me out. I pulled the covers back on my bed, and lying on top of my sheets were Madison's panties. They were covered in semen stains, although they had finally dried. I picked them up and sniffed them, her aroma still emanating from the expensive undergarment.

My cock twitched as I sniffed her scent, and as I watched on in astonishment, slowly stiffened and rose into a throbbing hard-on. I ended up jerking off twice before bed, torturing myself to the thought of Madison getting spit-roasted in the back of the limousine, by the two Asian guys.