Trust Fund Baby Pt. 16

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The finale: I get taught a lesson I will never forget.
13.9k words
3.27
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Part 16 of the 16 part series

Updated 06/10/2023
Created 05/12/2021
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The loss of Jody Baldwin really hit me hard, and for several days I mooched around my house feeling sorry for myself. It was ridiculous really, as I was a young, healthy multi-millionaire with a multitude of options for casual sex. I didn't have an orgasm for several days which was highly unusual for me, and once I snapped out of my funk, I realized that I was in an elevated state of arousal, and desperately needed to bust a nut.

It was Kat, the MAC make-up artist, that I turned to for release, the inherent asshole within me completely taking advantage of her interest in my sexual prowess, having witnessed me put the wood to Jody.

In my usual authoritative style, I didn't even really ask the young woman, electing to send her a very forthright text.

"I have an opening at 10am tomorrow at the club if you want to audition," it read. "Wear your special rim-job make-up."

I didn't even sign off as Pete in the text, deciding to close with my preferred salutation, Papa. I didn't even really care if Kat showed up or not. I was going to be at work anyway, having let over a week go by without showing my face in there. If Kat did arrive at the appointed time, it would be a sign that she was willing to submit to me, particularly as I had made no attempt to sugarcoat my lewd expectations.

I had zero intention of hiring Kat. She certainly was attractive enough, and she possessed the playful, flirtatious manner that is a necessity within the manipulative environment of a strip-club. Kat was however, lacking the key ingredient that I required all of my employees to possess.

My stage manager, Jade, had mastered the art of private dancing, where the girls are looking to remove the maximum amount of cash from the punter's wallet, and the guy is looking for as much action as possible, for the least amount of cash. Jade had extracted seven hundred dollars from me, in the middle of a job interview, for fuck's sake. That was truly impressive, the benchmark by which I judged all subsequent auditions. Maybe Kat possessed a similar level of manipulative allure, you could never really judge a book by its cover, as the saying goes.

Whatever attributes Kat did bring to the table, the key required ingredient that she lacked was desperation, which was an absolute requirement for a position in my pussy club. Kat had graduated Cosmetology School, had a full-time job at the MAC counter in Nordstrom, and free-lanced for extra cash. While she might have been impressed with my Bugatti that I drove to work most days, and had certainly reacted positively to my inducement of multiple orgasms from Jody, it was the lack of desperation in her life that gave me cause for concern.

Without the overriding, crushing pressure of some unyielding outside force, such as impending bankruptcy, job loss, or threat of foreclosure, young women would go with my program until they were faced with some sexual act that they deemed repugnant, at which point they would throw in the towel.

Truly desperate women, however, those for whom life presented no alternate options, would suppress their disgust, force a smile onto their faces, and suck it up. Without this desperation, Kat wouldn't be forced outside of her comfort zone, and the encounter would lack the young girl's abject revulsion, something that I needed in order to experience a fulfilling climax.

The following morning I was pleasantly surprised to see Kat sitting in the waiting room completing her application package, which included the employment application, the non-disclosure agreement, and the various consents to sexual activity, being filmed etc. Olivia checked Kat's paperwork, scanned her California Driver's License into my database, and then escorted her to the large walk-in closet where the club stored its vast collection of fantasy and fetish wear.

"Paperwork is all in order, Pete," Olivia said over the intercom.

A few minutes in front of the mirror as the hair stylist attended to the last minute touches, and Kat was ready to be used as a cum-receptacle for my six-day load. Olivia knocked quietly on my office door, announced the arrival of "Pussy," my latest aspiring dancer, and Kat crawled in on all fours in a black latex catsuit, complete with a long black tail and some cute kitten ears.

However alluring her previous boyfriend might have found this hyper-sexualized costume, it left me cold. I had enjoyed hundreds of lovers by this point in my life, and had been through the submissive pussy-cat scenario maybe a dozen times. In fact, just about the only memorable encounter of this nature, was when I forced the college Freshman, Gina, to lap up the entire football team's ejaculate from a saucer, as if she were a kitten.

I needed more from this current sexual encounter. Kat was in front of me, but it was Jody that I yearned for. As Kat crawled around my office floor, purring and mewing like a kitten, I watched on in amusement. Olivia's assurance that Kat's paperwork was in order meant that for the duration of her audition, I could take complete liberties with the young job applicant.

Written by a team of highly experienced labor-law attorneys, my interview process disclosure was quite graphic. It stated quite clearly, that due to the physical interaction inherent in giving somebody a lap-dance, the job applicant should expect some incidental touching, groping, caressing, genital contact and the likelihood of inducing an erection, possibly even a climax.

When I first read the document that the lawyers proposed we had all applicants read and sign, I thought it was a joke. It seemed so unnecessarily blatant in its disclosure of what could occur during the audition. However, several thousand job interviews later, with the courts having ruled in favor of "Top Shelf Pussy" on multiple occasions, against accusations of sexual harassment, the document was an indispensable part of the application process.

Kat had signed it, acknowledged that she had read and understood its contents, and she was mine, ripe for the taking.

"I want to watch you bring yourself to climax first," I ordered the bewildered-looking young woman. "There are some toys in the ottoman in front of you."

Kat bit her lip first, a seemingly universal sign among young women that they are struggling with the idea of something. Fortunately for me, Kat's internal battle was brief, and she lifted the lid of the large, leather foot-stool. Extracting a "Magic Wand" personal vibrator, she looked at me for direction, her indecisiveness immediately losing her points.

"On the floor, on your back," I instructed. "Maintain eye-contact with me."

Kat fired up the vibrator, slid the crotch of her catsuit to one side, and lowered the wand to her genital area, before finding the correct placement to stimulate her clitoris. A smile crept across her face as the personal massager began to work its magic. I was barely hard, going through the motions as I tried to imagine Jody in the same situation.

As I slowly undressed I closed my eyes, and accessing the recent image of Jody sucking me off from my short-term memory banks, I finally got an erection. I watched dispassionately as Kat brought herself to climax five or six times, before I gave her my next directive.

"Stay on your back," I said firmly. "Are you wearing your rim-job make-up?"

As she nodded nervously, I walked towards the prone woman and straddled her body, placing my feet either side of her breasts. Without any attempt to secure her consent, I lowered myself to my knees and leaned slightly forward, which put the tip of my cock just in front of her face.

"Suck my cock," I ordered, as Kat raised her head slightly, and parted her lips to facilitate my entry into her warm mouth.

It wasn't really a blow-job as much as a face-fucking, as I took advantage of Kat's passivity and indecisiveness. If she chose not to fight my advances, I was going to push her up to, and over, her limits. As Kat lay there, I used her mouth as if it were a pussy, thrusting deeply into her oral cavity in an attempt to trigger her gag reflex. She seemed a little perturbed by my aggressive behavior but still voiced no objection.

It had been six days since my last orgasm, as I had wallowed in my misery after losing Jody for the final time in my life. Even though I was ready to bust a nut, I wasn't going to blow my load without experiencing Kat's analingus skills, so I withdrew my erect cock from between her lips, and scooted slightly forward. In my new position, with my nuts resting on Kat's chin, my intention was obvious, and I lifted my cock up by its tip, thereby exposing my scrotum for Kat to pleasure.

While she didn't seem enthralled with this one-sided encounter, the look on her face didn't suggest that she found anything actually repugnant, so I kept moving forward.

"Suck my nuts," I ordered her.

Obediently extending her tongue, Kat began to lap away at my nut-sack.

"Good pussy," I said condescendingly. "Meow."

And there it was, the first flash of resentment as my disparaging comment had presumably touched a nerve. After a protracted ball-licking session, during which Kat sucked, nibbled and licked my swollen nuts, she scooted further beneath me, and began to lap away at my taint.

I love having my undercarriage attended to. It just never gets old, particularly if it is a new girl who is having their first taste of my nether regions. On the day of Jody's demeaning performance, Kat had been quite open about her willingness to perform analingus, jokingly making reference to her transfer-resistant foundation being well-suited to such sexual activity.

However, as I had discovered on multiple previous occasions, there was quite often a disconnect between the sexual bravado of a young girl, and her actual reaction to the act when it was required of her, in the flesh. I was ready for my rim-job, and was interested to gauge Kat's reaction, when I verbalized my desire. Rising up slightly onto my knees, so that I could see her face as she lay beneath me, I issued my next directive.

"Eat my ass, girl," I said firmly, looking down at her face as she lay beneath me.

Kat flashed me another look of resentment, wrinkled up her nose to transmit her disdain for the way I was addressing her, and then disappeared from my view as I lowered my buttocks onto her face. Seconds later, as I squatted on her face, I felt her tongue licking around the entrance to my ass.

"Yeah, Pussy," I said appreciatively. "Right there. Perfect."

Like I said, I love rim-jobs, considering them to be the perfect mixture of physical and visual stimulation. As Kat lapped away at my asshole, like the little kitten she purported to be, the sustained teasing started to get the best of me, and I began to whimper appreciatively.

I have no clue what Kat's expectations were when she decided to attend the audition, but I imagine she had hoped for us to fuck, seeing as how she had witnessed me pound Jody into a completely satiated state, about one week prior. Unfortunately for the young woman, I wasn't planning on spending much time with her this morning, and shortly after her tongued entered my anus, I reached for my lube and began to coat my erection with a liberal dose of it.

Even though it had been six days since I last came, it took me quite a while to jerk myself off. It was to the image of me butt-fucking Jody that I turned, closing my eyes and trying to recall her in the Patriots Cheerleader Uniform, bent over the chair, with my dick in her perfect ass. Finally, as Kat continued to rim me, I blew my load, most of which landed in her hair and the black kitten ears that she was wearing.

Shortly after my cum-shot, I got back onto my knees, and then I stood.

"Olivia will let you know if we have any available slots on the roster," I said, as I headed towards my shower.

Kat glared at me from her prone position, her look as she realized that I had used her as a cum-receptacle one of disgust, and our brief encounter shattering any illusions that the young MAC make-up artist had about my sexual prowess.

At that point in my life, I just didn't give a fuck. Without Jody, I felt lost and empty, and no amount of fresh pussy was going to change the way I felt. I went slowly downhill after my encounter with Jody, drinking more, working less, and becoming much more dependent on drugs.

I ceded the day to day control of the strip-club to Olivia and Jade, and basically partied all day and night, fucking most of my dancers in their off-hours, and as many young college co-eds as Olivia could persuade to come to my house. There were some crazy nights at my mansion, most of which were documented on social media.

My uncle intervened finally, after suspecting that my drug use was no longer recreational, and seeing a few of the lewd photos that circulated the internet. I knew that I was in too deep with the drugs and partying, and I offered him zero resistance when he asked me to check into rehab. My uncle picked up the tab for my three month stint in recovery, and when I got out I was clean, sober and over half a million dollars richer, my expenses having slowed to a halt during my time in the facility.

When I got out, my plan was to stay away from the strip-club and the college kids. I just didn't want the additional temptation in my life, especially as I was committed to a sober lifestyle.

One day at Alcoholics Anonymous was enough to steer me in a completely different direction. There were some pretty fucked-up chicks in the meetings, and I got talking to one young blonde who attended fifteen meetings a week, between AA, Narcotics Anonymous and Sexaholics Anonymous. We exchanged numbers and the following day I attended my first ever sexual addiction meeting.

In retrospect, I should have realized how this would turn out, twenty five young adults with a compulsive desire to fuck that was strong enough to derail their lives. There were some beautiful girls in that group, and after the meeting, as they crowded around my Bugatti, I invited two of them back to my house for coffee.

Mary and Joanne squeezed into the front bucket-seat of my hyper-car, and within moments of feeling their flesh pressed tight against another human, all of the lessons imparted in the Sexaholics Anonymous meeting, seemingly flew out of the window, and they began to kiss each other tenderly.

By the time we entered the electric gates of my mansion, they were deeply engrossed in each other, and had somehow managed to virtually disrobe, within the confined space of my Bugatti front seat. As the three of us entered my home through the garage, we didn't even make it to the master suite, such was the desperation of the two sexual addicts.

My situation was completely different from most of the other attendees of the SA meeting. I wasn't actually a sex addict. I was a forty year old, single, multi-millionaire who just had a lot of options. I think most men in my situation would have fucked as many exotic dancers as I did, had they owned a strip-club. I didn't think I had a problem with sex. I freely admitted to being a drug-addict, and an alcoholic, and after I kicked those two vices, my road to recovery encouraged me to address any other of my addictive behaviors, and the subject of casual sex reared its ugly head.

Encouraged by the staff at my outpatient recovery center, I agreed to continue to attend the sex-addicts meetings, but I quickly discovered that most of them, especially the women, had way worse problems than me. The room was full of twenty and thirty year olds, most of whom had sucked or fucked a random stranger for their drug fix. These young women were ripe for the taking, and with my extensive experience of manipulating the fairer sex, it was a ridiculously easy proposition for me to work my way through the group.

The co-eds of my youth, at Saddleback College, had basically been nice young women, fueled on the weekends by alcohol, peer-pressure and the sexually permissive environment of the dorms. The runaways were a bit more desperate, and were often fueled by hunger and fear. By contrast, the female sex-addicts in my group session were a truly deranged bunch, hanging on to life by the skin of their teeth. Some of them had their lives shaped and destroyed by drugs, and were willing to perform just about any degrading act for a fix.

However, for some, including Mary and Joanne, as they ate each other out in the sixty-nine position, sex was their drug of choice. It had been a while since I had enjoyed a sober sexual encounter, and I wasn't as authoritative as I usually am, as I stripped off and sought their consent to join. They had their faces buried in each other's pussies, but as Mary brought Joanne to her third climax, she looked up at me, her face slick with her partner's secretions and spoke.

"Fuck my ass, Pete," Mary practically begged me. "I like it rough."

Mary's vaginal secretions were all over her inner-thighs, and I used the viscous fluids to lube up my cock. As soon as I entered her anal-cavity, I could tell that she was no stranger to getting butt-fucked. Her asshole had been stretched open from being sodomized on numerous occasions, and it was with minimal effort that I got balls-deep.

I had enjoyed what I considered to be rough sex, a few times in the past, although I got my jollies from humiliating young women, not beating them. However, not averse to a few playful swats on the ass, or some gentle hair-pulling, I began to periodically slap Mary's butt-cheeks as I fucked her ass.

"Harder," Mary insisted several times, before I was spanking her with much more force than I was comfortable using.

As she kept begging me to hit her with more intensity, Joanne finally emerged from beneath Mary's pussy, and after grabbing my pants, removed the leather belt. Folding it in half, she handed it to me.

"Use this," Joanne said coldly. "That will get the bitch off. Trust me."

Realizing that the two of them had a sexual history, I raised my arm and gave Mary a fairly solid whack across her right ass-cheek. A red welt appeared immediately on the young girl's ass and she let out a plaintive wail, which led me to believe that I had overdone it.

Before I could make my apologies, Mary took a deep breath, turned her head over her shoulder, and in an obvious highly aroused state, spoke quietly.

"Harder," she begged. "Hit me harder."

That was my first clue to the fucked-up backgrounds of many of these sex-addicts, and I laid the belt on the floor, and withdrew from her much abused asshole.

"I need to take a shower," I informed them, as Joanne picked up my belt and raised her arm skyward.

The first whack with the belt would have been enough for me to throw in the towel, but despite inducing an anguished howl from her friend, as soon as Mary caught her breath, she begged for more.

"Again, Joanne," she begged. "Hit me again."

It was tough to watch, but Joanne beat Mary's ass and its environs until there were red welts all over her ass, lower back, and upper thighs. Mary had three orgasms under the sustained assault before she slumped to the floor in tears.

"Now you can butt-fuck her," Joanne said, as Mary struggled to get on all fours, wiggling her ass to signify her consent once she was in position.

I wasn't a fan of the violent nature of their coupling, but apparently that is what it took to get Mary off. With the two younger women having been satiated, they turned their attention to me, and predictably I ended up fucking both of them in the ass, before turning the subject towards rim-jobs.

They had both been in some pretty fucked-up relationships, and thought nothing of eating my ass, alternating between the two of them, as the other one blew me. Mary, Joanne and I had a few more encounters after that, spread over the course of several weeks, but Mary's desire to continuously escalate the violence scared me, and after a few more sessions, we parted ways.