Trust Fund Baby Pt. 15

"That's my Celibacy Club t-shirt," she exclaimed with a giggle. "Now covered in your semen."

"Oh, Jesus," I said apologetically, as I held up the light-blue garment for closer inspection. "I will run this down to the concierge for dry-cleaning," I offered.

"Perfect, Papa," she said with a grin. "Check into a five-star resort with a teenager, and in the morning give a semen-stained article of clothing, emblazoned with the words "Celibacy Club" to the dry-cleaning center. I am going to brush my teeth and then shower again, Papa," she whispered, as she reached for her toothbrush. "Toss my t-shirt on the floor and I will rinse it out later."

I exited the bathroom to make a quick call to check in with Olivia, and a few minutes later, as I sat in the hotel suite, Jessie appeared at the door. Still naked, with my semen having dried on her chest and stomach, she was a picture of happiness.

"Shower time," she said cheerfully. "Care to join me?"

I should have taken a quick shower and left the young girl alone, but as soon as we were back in the warm environment of the enclosure, Jessie's playful side emerged, and after an extended frolic under the water, we rolled out of the hotel bathroom, both still wet, and practically fell onto the King Size bed.

I knew exactly what she wanted, even before she began to push my head down her body. I imagine experiencing her first ever orgasm had a profound effect on Jessie, because she seemed very eager for a repeat performance. Enjoying the effect I was having on her, I started to tease her, in a similar manner to the previous day. Jessie tolerated it for a few minutes, before wrapping her fist in my hair and gently guiding my tongue between her legs.

As Jessie got progressively more comfortable around me she relaxed, and predictably her orgasms became easier to induce. In fact, as soon as I grazed her clitoris with the tip of my tongue, she arched her back and let out a contented whimper. Jessie quickly self-lubricated as I licked and sucked her clitoris, and after just a few minutes I noticed her stomach muscles tighten, a sure sign that she was fast approaching orgasm.

Jessie enjoyed five very powerful orgasms courtesy of my eager tongue, and once she was done, she coaxed me from between her legs, by inviting me to make love to her.

"I have only had sex twice before," she said innocently. "Two, young, premature ejaculators," she added derisively. "I want you to show me how it is done, Papa."

I got up off the bed, and went to wash her vaginal secretions from my face, as she continued to engage me from the hotel bedroom.

"Does doggy-style really hurt, Papa?" Jessie asked, presumably confusing it with anal sex.

"Not if done carefully," I replied, wondering if I was going to get a crack at her virgin ass.

When I returned to the bed, holding a condom, Jessie was laying on her back, ready to be taken. Her legs were splayed apart, and I could see the evidence of her arousal, as her juices were all over her labia and inner-thighs.

"You don't need a condom, Papa," she assured me. "I am on birth-control, and it has been months since my last sexual activity. I am clean."

I hardly ever used condoms for sex, my vasectomy at eighteen years old indemnifying me from the risk of pregnancy. However, I wanted Jessie to be comfortable and was planning to secure her consent for every single thing we tried. That said, it was music to my ears when she invited me to enter her bareback.

Predictably, having only had two very brief sexual encounters, she was tight as fuck. Even though she was extremely well-lubricated, it still took me several moments to get balls-deep inside her, and she whispered words of encouragement the whole time I eased my way into her tight pussy. As Jessie looked up at me, her bright blue eyes twinkling as she smiled, her youthful innocence caused my nuts to ache with desire. It was as if I was in a time-warp, such was her resemblance to her mom, Jody, who I had fucked over two decades ago.

Jody had been just eighteen years old the night we fucked. Even though Baldwin had paid Jody to seduce me, knowing that the blowback from Madison would derail my impending nuptials to my fiancée, and Jody disclosed that fact to me, before I got balls-deep inside her, I still couldn't resist her. Jody sucked me off first, before inviting me to enter her clean-shaven, teenage pussy, in the exact same position that I was currently coupled with her daughter, Jessie. The resemblance between mother and daughter was uncanny, although Jody possessed way more sexual experience at eighteen, than her daughter did.

As Jessie and I got into a rhythm, we began to talk about her sexual history, or rather her lack of it. At my age, my second release was going to take a while, and the close connection that the missionary position provides, was conducive to a little personal revelation.

"You are really tight, Jessie," I said, as we started to get to know a little more about each other.

"I have only had sex twice before, Papa," she said quietly. "Almost a virgin."

"Have you ever given a man a blow-job?" I asked, enjoying the way this conversation was heading.

"Prior to last night I had never given or received oral-sex," she said candidly. "Now that I have enjoyed receiving oral, I can't wait to reciprocate. I feel like I really owe you one, Papa."

We ended up making love for nearly an hour, tenderly rocking together as we whispered sweet nothings to each other. I was aware of the fact that my time with Jessie Baldwin would be short-lived. Eventually, her father would figure out where she was, and come gunning for me. I wanted to enjoy as much play from her as I could, and then return her to her nest, so that Steve Baldwin could ruminate over my violation of his little Celibacy Club President.

Jessie came twice more as we remained coupled in the missionary position, although the releases paled in comparison to the ones she experienced from oral sex. It was a very tender and satisfying experience, and after I blew my load deep inside her teenage pussy, we remained coupled until my cock softened.

After our first time making love, there was a much deeper connection between the two of us, and despite the age difference we had a lot in common. I hadn't gained the maturity that typically comes from attaining the grand old age of forty, and having spent the last twenty years in the company of teenagers, I understood their slang, was familiar with their music, and felt right at home hanging out with them.

Jessie shared her dreams and aspirations with me, and as she continued to receive hostile texts from her father, she eventually decided to show them to me. Steve Baldwin was known to be a controlling prick, and it was eating him alive that his sheltered, Catholic Schoolgirl daughter, President of the Celibacy Club, was on birth-control and had just charged eight hundred dollars of fetish wear to his credit card.

In his rambling texts he referred to her as a worthless slut, a whore, and a cocksucker, which seemed wildly inappropriate correspondence between a father and his only daughter. He also made some reference to an upcoming Debutante's Ball, telling her that he had no intention of going with her, and to ask her new boyfriend to take her instead. His last text, which caused Jessie to burst into tears, said that he was ashamed to be her father. I could tell that she was really hurt by his mean texts, and as she sobbed quietly, I hatched a plan to bring Steve Baldwin to his knees.

Jessie and I stayed together in that luxurious hotel suite for nine days, coming up for air to eat, shower and the occasional walk on the beach. I fucked her in every conceivable position, was the proud taker of her anal-cherry, and enjoyed multiple blow-jobs over the protracted fuck-fest. Jessie was literally down for anything I desired, and even though there were things that she obviously didn't particularly care for, she never said no to any of my requests.

In exchange I provided her a safe, loving environment in which to make some important life-decisions, and got her off multiple times a day with my tongue. When it became apparent that I needed to go home, I invited her to join me, and was ecstatic when she agreed. I contacted Olivia and asked her to clean house, depositing eight young runaways onto the streets of Newport Beach, which probably doubled the homeless population of the well-heeled enclave. Olivia gave each of the young women two grand in cash, and the offer of a plane ticket to anywhere in the country, although they all elected to stay in the beach-front community.

When Jessie and I returned to my mansion, she took it all in her stride, not exhibiting any of the open-mouthed awed reaction that most homeless teenagers showed. Jessie had grown up very rich, and her father's current home was far more opulent than mine.

A few days after it became apparent that we were going to live together, I took Jessie shopping again. As new lovers this was a much more intimate experience, and Jessie tried on multiple outfits as I sat and watched, reminiscent of the scene in the movie Pretty Woman. Deferring to me on just about every thing she chose, she finally announced her desire to submit to me.

"I just want you to decide what you want me to wear, Papa," she said seductively as she pulled me into the dressing room, lowered herself to her knees, and sucked me off.

Once Jessie was settled in, I reached out to Steve and Jody Baldwin individually, to inform them that their daughter was living with me, which was immensely satisfying. Jody called me back, and after an extended conversation with her teenage daughter, didn't exactly give her approval, but wasn't overtly hostile. Steve Baldwin, in contrast, was livid, alternating between threatening my life, and disowning his "slut of a daughter." When the subject of the upcoming Debutante's Ball was raised, he was adamant that he would not attend.

"You take the slut," he screamed down the phone, as Jessie listened on in tears. "Put the bitch on the main stage of your pussy club for all I care. See if she can make her new daddy proud."

After he hung up on me, Jessie was catatonic. It was one thing for her dad to be pissed at her cavalier attitude towards her celibacy, but the Debutante's Ball was the biggest father and daughter event on the social calendar. It was her opportunity, having just turned eighteen, to be presented to the elite of Newport Beach, as an eligible young socialite, and she desperately wanted her dad there.

The following morning, Jessie appeared to have come to terms with her father's decision to boycott the Debutante's Ball, and I agreed to accompany her, as her chaperone. This was laughable really, given that the intended purpose of the chaperone was to make sure the young lady's welfare and safety was protected, and Jessie had already made it quite clear to me that she wanted to fuck in the limousine on the way to the event.

As it turned out, Steve Baldwin calmed down after a few days, but the long-term damage to his relationship with Jessie was done, and after telling him to go fuck himself, she wanted retribution.

One night, as we laid in bed snuggling, after a prolonged love-making session, she whispered softly in my ear.

"Let me dance in your strip club, Papa," she begged. "One night. Hold a special event just to piss my dad off."

"I can't sell alcohol, and have performers under the age of twenty-one at the same time," I replied, trying to deflect her request.

"Paradise just did it," she responded, referring to one of my competitors. "They had an alcohol-free event, which enabled them to feature eighteen year old dancers, and also allowed the performers to be totally nude."

"Jessie," I countered, "while I would love to see your tight little body rocking naked on my stage, it would cost me a fortune in lost revenue. We make fifteen grand a night from alcohol sales."

"Charge a premium for entry that night," she offered. "I know tons of guys at Saddleback College who would pay fifty dollars to watch me dance naked."

"Jessie, this is not a good idea," I said, approaching it from a different angle. "Someone will undoubtedly smuggle in a camera or use their phone to take some lewd picture of you. With the advent of social media, if your images go viral it will haunt you forever."

"But I really want to fuck with my dad, Papa," she said despondently. "I would love to see the look on his face when he finds out that his baby girl is the featured performer at Top Shelf Pussy."

As I absorbed her words, I realized that fucking with Steve Baldwin would be the highlight of my life. That asshole had caused me countless humiliations over the last twenty five years, and payback was long overdue.

"I think I have an idea to rub your dad's face in your new-found sexuality," I said cheerfully. "Hear me out."

As I detailed my plan to upturn her dad's life, Jessie listened on intently. The idea was to promote a one-night, special event featuring Jessie Baldwin naked on my main stage, without actually naming her. As we brainstormed, we came to the conclusion that Jessie could dance naked wearing just a mask.

"Like at a masquerade ball," she said cheerfully. "You should come on stage after I dance, reveal my true identity, and force me to suck you off, Papa," she added with a giggle.

"Fuck yeah, Jessie," I said excitedly. "Great idea, although why stop at a blow-job. We should go through all of our sexual repertoire, anal, rimming, the works. After everyone is blown away at how nasty you can be, we could remove your mask. Half the fun will be the big reveal. Your dad will shit himself."

Once Jessie was on board, I ran prominent advertisements all over Newport Beach. Utilizing a multi-media strategy, that incorporated bill-boards outside all of the exotic car dealerships in town, an aerial banner towed behind a small Cessna plane along the entire Newport Beach coast, and several radio spots on the local classical musical station, I focused my efforts on the older, wealthy men of my beloved city.

I never mentioned Jessie Baldwin by name, but promised an alcohol-free evening featuring an eighteen year old, recent High School graduate. This young mystery woman, a daughter of one of the most prominent men in Newport Beach, was set to appear in the upcoming "Debutante's Ball" next week, followed by her debut at "Top Shelf Pussy."

By designating the event as alcohol-free, the dancers in my club would be permitted to dance naked. Also, under California's complex licensing laws, I was able to turn a section of my strip club into an adult book store, which in turn allowed for a live sex-show. I often featured lesbian sex-shows at the club, but the inclusion of strap-on phalluses meant that they were deemed to be "simulated shows" under the law. My event permit would allow me to run Baldwin's teenage daughter through a series of progressively lewd sex acts, before revealing her true identity in front of a few hundred carefully selected guests.

This change of use application required one permit, and the approval of the Newport Beach Police Department. My club was a second home to the rank and file officers of NBPD, and the Police Chief was happy to rubber-stamp my request. In addition, the Fire Department inspected the premises, and after determining that we had adequate fire suppression equipment installed, and an emergency exit, signed off on a maximum occupancy of three hundred and twenty five guests for the one-night event.

The Fire Chief approved the event, telling me privately that the biggest headache that it caused him was trying to accommodate the requests for that day off from his young firefighters.

Once the day was etched on my calendar, I set about trying to ensure that I had the right mix of clientele for the event. I had no interest in filling my club with horny college guys, some of whom would surely smuggle in alcohol, which would contravene the rules of my permit. I wanted the elite of Newport Beach to witness Jessie Baldwin submit to my every whim.

After consulting with my tax accountant, it became apparent that it was more financially beneficial to the club to give the tickets away, and claim the charitable donation on my tax return. I set aside twenty-five tickets for the Police and Fire Departments, and then gave out three hundred free tickets at at local charity fund-raiser.

The caliber of gentlemen that attended the charity event were exactly the sort of guys I needed at Jessie Baldwin's unveiling. I wasn't interested in making money for this particular evening, but rather in the complete humiliation of that prick Steve Baldwin. Over the years he had tormented me and systematically emasculated me, first through his sadistic treatment of my best friend Olivia, and then through his debasement of my fiancée, Madison.

Lastly, as a final kick in the nuts, he had taken the love of my life, Jody, and turned her into his fuck-toy. Not content with flexing his financial superiority over me, Baldwin also periodically sent me lewd photos of his sexual conquest of all three of the most important women in my life. Even as Jody entered the last trimester of her pregnancy, almost nineteen years ago, Baldwin ass-fucked his young bride regularly, and sent me photographic proof of his continued domination of the object of my desire.

I was salivating over the prospect of my payback, particularly as it would be witnessed by all of our peers. It was all the local guys would talk about, and with no other personal information divulged, they were trying to identify the debutante, by a process of elimination. Every wealthy man in Newport Beach with an eighteen year old daughter wore a furrowed look on his brow, as he contemplated the reality that it might be his baby girl who was going to dance naked on stage in front of his contemporaries.

The "Make Daddy Proud" event as it was advertised, received an inordinate amount of attention from the Newport Beach millionaires, and there was a palpable excitement when our advertising blitz attached the stage-name "TOY" to the young debutante.

Baldwin had used the moniker "TOY" for decades to demean young women, and identify them as his playthings. Jody, Madison and Rachel had driven exotic cars around Newport Beach with personalized license plates that incorporated their name with the word "TOY," for the whole world to see. The rumors floated around town that it was Baldwin's beautiful young daughter, Jessie, who was to be outed as a wannabe porn-star at the upcoming event, and it was clearly ruffling his feathers.

However, I never expected him to capitulate so quickly, and it was a very satisfying moment when he called me and wanted to talk. I was very lightly scheduled but I wasn't going to put him out of his misery so quickly. I made him wait three days for the opportunity to speak to me, and in an overt act of control, I instructed him to meet me at "Top Shelf Pussy," first thing in the morning, before we opened up for business.

On the day of our meeting, I got to the club early intending to rub my subjugation of his daughter in Baldwin's face. Making sure that there was an abundance of "Make Daddy Proud" marketing materials displayed around the venue, I instructed my security crew to pat Baldwin down upon entry. I never really considered him a violent man, but who knew how he would react to the news that I was going to fuck his teenage daughter, on stage, in front of the entire Newport Beach upper echelon.

Truth be told, I didn't think that Steve would be packing a gun to the meeting, but my security crew thought that he may be wearing a wire in an effort to get me to implicate myself in a crime. This wasn't a concern for me, having ensured that I examined the identification of every single one of my sexual conquests, to ensure that they were old enough to consent.