Trust Fund Baby Pt. 15

The dealership had a Bugatti Chiron sitting on the showroom floor, surrounded by velvet ropes and "do not touch" signs. I knew that the Bugatti was one of the world's most desirable automobiles, and I casually asked the beautifully-attired floor manager what the lease payment would be on the Bugatti, in case I decided to switch cars at the last minute. My enquiry was met with a certain amount of derision from the stunning looking woman, and while the nice thing for her to do would have been to let me down gently, she elected to go and crunch the numbers.

When she returned a few moments later with a smirk on her face, and presented the quote on her iPad Pro, I realized quite why she had shown me disdain. At sixty five thousand dollars per month it was way out of my league financially, and it was at that point in my young life that I recognized that there were men worth one hundred times what I was.

"Our exotic car financiers typically want an automotive debt to income ratio of less than fifteen percent," she said coldly, continuing my education. "So they would expect a verifiable income of just under four hundred thousand dollars per month," she added dispassionately. "For you and your co-signatory," she concluded, with a fake smile.

Now, as I was facing the harsh reality that I couldn't afford Jody, that was a much bigger kick in the nuts. The whole Bugatti thing had been a minor embarrassment, the floor manager getting her jollies putting me in my place, as my uncle looked on in amusement. However, when it came to Jody, I wanted to possess her more than I wanted anything on earth, but I just couldn't swing the fifty grand a month entrance fee. The thought of her kneeling before that fat fuck Baldwin, as he blew his wad across her exquisitely fabricated, lace bridal-veil, was eating me alive.

The months turned into years, and even though Jody and I both remained within the city limits of Newport Beach, I ran across her very infrequently. We were just in completely different social circles, as she had kids in primary school, and I was still fucking college freshmen. I think I maybe saw her a dozen times over the course of two decades, and by time I turned forty years old, I had got her completely out of my system.

At least I thought I had, until she showed up one day at my strip-club. "Top Shelf Pussy," as my club name suggested, specialized in the higher end of the strip-club market, catering to the sophisticated wealthy men who were willing to pay much more for the attentions of a perfect ten.

Jody hadn't aged a day when she breezed into my club, a testament to her blessed genes, and the remarkable anti-aging characteristics of plastic surgery and cosmetic enhancements. She was fashionably attired, as always, her stylish clothing befitting the wife of a multi-millionaire. The finishing touches, a red beret and some dark, oversized Gucci glasses, made her look European.

I felt the familiar surge in my pants the second I saw her, and I walked excitedly towards her to give her a hug.

"Jesus Christ," I exclaimed loudly. "How long has it been Jody?"

"Jessie," she corrected me. "I am Jessie Baldwin. Jody is my mom."

Instinctively I began to apologize for my mistake but Jessie remained gracious, removing her sunglasses and flashing me a broad smile.

"No apology necessary, Pete," she said sweetly. "I know I am the spitting image of my mom when she was younger. She told me all about your history with her."

"Does she know that you are here today, Jessie?" I asked cautiously. "Did she send you?"

"Hell no!" Jessie responded. "My parents wouldn't approve of me being here at all. In fact, you are the only thing that they ever argue about. My mom is not even allowed to mention your name in our household."

I couldn't for the life of me figure out why this young girl was here, and a thought appeared that maybe she was setting a trap for me. So, I did the one thing that I needed to do to protect myself.

"How old are you Jessie?" I asked the young woman.

"I imagine that you will be needing a copy of this," she said sweetly, as she thrust her California Driver's License towards me.

I must have breathed a palpable sigh of relief as I viewed her license and ascertained that she was over eighteen years of age.

"I want to work in your club," she said, with a smile on her face. "I can't think of a better way to piss off my parents."

I knew it was wrong on so many levels, and I recognized the likelihood of severe blowback from Steve Baldwin if I allowed his teenage daughter to showcase her wares at "Top Shelf Pussy," but even as I weighed my options, my slowly stiffening cock had already made the decision for me.

Now in my forties, I wasn't as prone to involuntary erections as I had been in my late teens and twenties. However, as Jessie nestled right next to me, I inhaled her scent, and immediately recognized that she was wearing her mom's perfume, which caused my cock to fully harden. Jessie looked up at me, her bright blue eyes the mirror image of her mom's, her tanned skin contrasting beautifully with her incredibly white teeth, and it felt like time had turned back twenty years, and it was Jody standing next to me.

"There is an audition process, Jessie," I said quietly, as my desire began to overwhelm me.

"Olivia told me all about it," Jessie said confidently. "I know exactly what you expect of me, when we get to the VIP room, Papa. The only question I have for you is do you want me to dance as a Cheerleader or as a Schoolgirl?"

Jessie Baldwin was an incredibly alluring young woman, her model-quality looks virtually assuring her an easy ride once she found herself an appropriate benefactor. Newport Beach was full of eligible bachelors, successful attractive men in their thirties and forties who would have made a perfect husband for this young goddess. Jessie must have known that she was a perfect ten, so it was a little disconcerting that she had selected one of her mother's ex-lovers, and her Dad's nemesis as the target of her seduction.

"Did you decide, Papa, or shall I surprise you?" Jessie asked sweetly, resting her dainty hand on my forearm.

"Surprise me," I stammered, in awe of the effect this little hottie was having on me.

"Ok, Papa," Jessie said, as she raised herself up on her tiptoes and brushed her lips against my earlobe. "I will be a few minutes. Why don't you take a shower?"

As I watched her tight little ass head for my office door, my head was spinning. Was Steve Baldwin's daughter really going to dress up for me and dance? Was it some kind of trap? Why on earth did she want me to take a shower?

I did have some concerns that it was a trap, but as I tried to organize my thoughts, I came to the conclusion that as long as Jessie was eighteen, and a consenting party to any sexual activity that occurred between us, I wasn't opening myself up to any potential legal action. I had seen her California Driver License, which served as her age-verification, and the multitude of security cameras that existed in and around my facility would provide incontrovertible proof that Jessie had driven to my strip-club of her own volition. Just to be sure, I rang Olivia.

After a brief conversation, during which Olivia assured me that she had scanned Jessie's license, which created a digital copy and verified its authenticity, I began to feel a little less worried.

"Jessie has already signed her paperwork," Olivia added, referring to the employment application form, the non-disclosure agreement, and the consent to be filmed during the audition. "All of the loose ends are tied up."

After thanking Olivia for her efficiency, I took a shower in the private bathroom within my office. As I lathered myself up, I replayed Jessie's words in my head. In my perverse universe, there was only one reason why a woman would ask a man to shower, and as my cock throbbed and danced before me, I raised one foot and began to clean my nut-sack, taint and asshole.

Despite having had several hundred sexual partners, Jessie's mom was the one that got away. Even though I had fucked Jody, the fact that she hadn't given me a rim-job was my principal regret, sexually. There was nothing I could do to change that sad situation, but if I could persuade her daughter, Jessie, to eat my ass, it would go a long way to filling the void.

After I was satisfied that my undercarriage was squeaky clean, I dried myself off, and made myself presentable. I knew that Jessie was totally out of my league looks-wise, and that the only reason that I might get some play from her, was to piss her parents off, but I was at peace with that. My plan was to push her as far as I could during the audition, and then reject her employment application on some technicality.

As long as I sought her consent for each individual sex-act, and recorded the entire audition, I should be indemnified from any claims of impropriety. With my plan firmly cemented in my mind, I asked Olivia to bring in Jessie's employment package, just to ensure that the important forms had been executed correctly.

As I perused her application, my nuts ached with desire. This was either the first job Jessie had ever applied for, or she was fucking with me, because the entire four page disclosure was riddled with sexual innuendo.

In the box designated for the applicant's birth date, she had disclosed her date of birth, and then added the words "Barely Legal" right next to it. Under her education history, she disclosed that she had attended an all-girls private school, before inexplicably adding "designed to keep me pure until I came of age."

Similarly, her vocational history, which was predictably light considering her youthful age, detailed her experience as a volunteer underwear model, with the words "after I turned eighteen, just for my boyfriend" in the additional details section.

I found myself getting increasingly aroused at her sexual bravado, and hurriedly turned to the last page, which contained the section in which to detail any additional skills or hobbies. Jessie had listed her hobbies as nude-sunbathing, entering wet t-shirt contests and playing the trombone, although she had added the word "rusty" in parentheses right next to the name of the musical instrument. The duality of the word left me wondering whether her playing abilities were rusty, or whether she enjoyed playing the "rusty trombone" which, of course, were two very different things. I had to chuckle at her clever double-entendre, and while I had no desire to hear her butcher Arthur Pryor's famous brass piece, "Blue Bells of Scotland," I was very much interested in her "rusty trombone" technique.

Under additional skills, she had written, "I can tie a cherry stem into a knot using my tongue," which I took to be a self-assessment of her oral skills.

In the final section, marked other accomplishments, she seemed to focus on the more wholesome things in her life. I learned that she had been a Girl Scout, a Cheerleader for the all-girls school soccer team, and President of the Celibacy club in her senior year. When I finally put her employment application down on my desk, I was totally confused. Jessie Baldwin seemed to have presented two diametrically opposed images of herself, and I was hoping to find out which was the true her.

I hadn't anticipated an audition this much for years. I had an endless stream of hot chicks parading through my office, looking for work. Nearly every interview culminated in sexual release for me, and I often found myself balls-deep in some twenty-something year old erotic dancer, as she demonstrated her VIP menu. Today, however, I was about to be treated to the sight of Jessie Baldwin, who was not only the spitting image of the woman who I fell for twenty years ago, but was also the teenage daughter of my nemesis, Steve Baldwin.

There was a light tap on the door, which snapped me back into reality. I knew I needed to regain control of this young hottie, so I spoke in a commanding voice.

"Enter."

Jessie peeked around the corner of the solid mahogany door, her face transmitting a combination of shyness, and the need for my approval. I could only see her head, but she had arranged her hair into a high ponytail, and her platinum blonde tresses were held up in place with a red silk ribbon.

"Come in Jessie," I said in a softer tone, trying to make her feel more at ease.

Jessie flashed me an appreciative smile, and shyly entered my office. She looked phenomenal, dressed as she was in a Japanese schoolgirl uniform. The authentic-looking sailor uniform, as they are referred to in Japan, was in the traditional colors of white and blue, although the silk bow-tie was in the same shade of bright red as her hair ribbon.

I had spent a lot of time in the Far East in my twenties and thirties, and while Bangkok and Manila were my preferred destinations for paid sexual encounters, Tokyo escorts were renowned for their sexy schoolgirl uniforms, and I enjoyed the services of many a young courtesan dressed that way. Of course, amongst the homogeneous population of Japan, black hair is the norm, with the vast majority of women possessing darker colored tresses. To see the platinum blonde Jessie dressed up in the authentic-looking uniform, was incredible. In fact, I had only ever seen such an alluring sight in the world of anime porn, and that particular young woman's look was undoubtedly achieved using a white wig.

"Wow," I said reflexively. "Jessie, you look phenomenal. Come on in. Don't be shy."

As she walked towards me, I had the opportunity to fully check her out. The silk sailor-top that she was wearing was the perfect size for her petite frame, and was pure white with blue and white striped cuffs. The front of the sailor collar matched the blouse cuffs, the blue with white stripes contrasting beautifully with the bright red silk bow-tie, loosely tied in the nautical style. Her pleated blue skirt was also a perfect fit, although it was several inches too short. Jessie may have been able to get away with this skirt length in the red light district of Shinjuku, Tokyo, but no public school system would have allowed her to attend class in such a provocative uniform.

Lastly, eschewing the knee-high socks that are often worn with the sailor schoolgirl uniform, Jessie had elected to wear white, silk stockings with elasticated tops. She had pulled them up to just above her knee and they accentuated her toned legs beautifully.

"Are you comfortable turning around for me?" I asked her softly, trying to get her to relax.

With a shy nod of the head, Jessie rotated one hundred and eighty degrees, and stood motionless with her back to me. I could see her shoulders rise and fall as she took in deep breaths, presumably from the stress of our interview.

The back of the sailor schoolgirl uniform was no less alluring, and even as her high ponytail prevented her long platinum hair from reaching the top of her skirt, I wanted to bend Jessie Baldwin over my imposing looking desk, and get balls-deep inside her teenage pussy. Lust is a very powerful emotion, and I wondered briefly if Jessie Baldwin was trying to use mine to make me do something that I would regret.

As I checked her out, a barely legal High School graduate, all dolled up to audition for a spot on stage at my strip-club, I could see her heavy breathing. I knew it was nerves rather than arousal, and I wondered if she may have exaggerated her sexual experience on her innuendo-filled application.

The rear of the sailor collar was solid blue, although it had white stripes running around its outer edge. Her white, stay-up, silk stockings were adorned with a matching blue bow attached just behind each knee, which was a cute embellishment. Lastly, in place of the regulation black or brown flat shoes that Japanese schoolgirls are expected to wear, Jessie had a pair of white stripper heels, modified slightly to include a tiny blue bow on the back of each pump, which was a very feminine touch.

"You look beautiful, Jessie," I said, as I shuffled in my chair, trying to conceal my erection. "Absolutely spectacular."

Having garnered the approval that she so desperately needed, Jessie appeared to loosen up slightly, and lowered her shoulders in a more relaxed manner. Inexplicably, she didn't turn back to face me, and I realized that she was waiting for my next directive.

"You may turn around now, Jessie," I said quietly. "Have a seat."

Jessie turned around slowly and flashed me a broad smile, before moving gracefully to the chair on the other side of my desk. As she lowered herself into the leather seat, she grabbed the hem of her skirt to try and pull it down, in a failed attempt to gain some modesty from the tiny pleated garment. I was treated to a very brief flash of her underwear, just enough to ascertain that they were the same shade of bright red as her hair ribbon.

"I am sorry, Jessie," I began. "The club provides a multitude of different sexy costumes for the dancers and I am sure if I had allowed you more time to browse, you could have found a skirt in your size."

"This is my own personal uniform, Papa," she said shyly. "I bought it after Olivia told me you liked schoolgirls. I also brought a cheerleader uniform to my audition today."

The way that the sexy Japanese schoolgirl uniform fit her upper body so perfectly, made sense that she had custom-ordered it. I had to smile at the thought that the obscenely short, pleated, micro-skirt was intentional, and as we made eye-contact I wanted to fuck this little vixen even more.

"Well," I began, "first thing is first. You signed a consent form to allow me to film today's audition and I want you to know that there are two cameras running at the moment."

Jessie nodded her understanding and consent, as I pointed to the two 4K cameras that were strategically placed, in order to film the entire office.

"The audition will probably last about an hour, and will consist of a brief conversation, followed by some still photos, and a quick look at your dance moves and stage presence. Any questions or concerns, so far?"

"When do I get to entertain you in the VIP room, Papa?" Jessie asked seductively. "Olivia told me that this is where the decision to hire is really made."

I was trying to proceed in a calm, measured manner, so as not to spook the young girl, but as her confidence seemed to be growing with every passing moment, I answered her question.

"We will at some point visit the VIP room," I said with a smile. "However, I need you to be completely comfortable with that first. Fair enough?"

Jessie gave me a relaxed smile, her demeanor suggesting that she was already comfortable with whatever direction this meeting took. Leaning back slightly in her chair, she crossed her legs, which had the immediate effect of causing the hem of her already comically short, pleated skirt, to rise up her upper thighs.

"Fair enough, Papa," she whispered, as my erection throbbed in my pants.

"I looked over your employment application," I began, as I struggled to take my eyes from her toned legs. "Not too much work experience, but you are very young so that makes sense. Were you in the school band?"

This was my subtle way of addressing the trombone playing situation, but Jessie called me on it right away.

"I put that in there as a joke," Jessie giggled. "Olivia told me that your thing is rim-jobs, and I wanted to pique your interest. I would feel much more comfortable if you asked me exactly what is on your mind, Papa," she added flirtatiously. "Instead of beating around the bush."

As I sat there opposite this little temptress, with my raging boner, and my nuts aching with desire, the VIP room, and its luxurious leather chair with the removable seat was all that was on my mind. However, trying to maintain a semblance of decency around this hottie, I changed tact.