Trust Fund Baby Pt. 15

As it turned out, it was a very subdued and contrite Steve Baldwin that slinked into my strip-club that morning, hat in hand, and looking to make peace. After a brief exchange of pleasantries, my security crew patted him down, and offered him a seat. I sat behind my large imposing desk, which incidentally had been the location of my most recent sexual encounter with his daughter, and probably still had her scent emanating from it.

"How can I help you Steve?" I started, wanting him to do all of the work in this conversation.

"Is it Jessie?" he began, apparently struggling to contain his emotions.

"Is what Jessie?" I responded, thoroughly enjoying his turmoil.

"TOY," he said, barely able to verbalize the word. "Is my baby girl Jessie the star of the Make Daddy Proud event?"

"That is the question on everyone's lips these days," I said calmly. "Most of the guys with eighteen year old daughters have reached out to me over the last few days. I told them all exactly what I am going to tell you. Show up at the event and prepare to be shocked."

"Pete, please," Baldwin begged me. "This will ruin me if TOY is Jessie. I will never be able to show my face around town again. What can I do to prevent you following through with this?"

As he capitulated to me, I felt an intense feeling of satisfaction, an almost euphoric surge of emotion at finally getting one over on my long-time nemesis.

"I will think about it, Steve," I said quietly. "Give me a few days and I will let you know my terms."

"Can I talk to my daughter?" he added softly. "She refuses to answer my texts and calls. Please. One brief chat. FaceTime preferably."

Without committing to anything, I nodded my head to acknowledge his request, and then dismissed him, telling him that I had another meeting scheduled.

"Another desperate young woman looking for work," I added, as he rose from his seat.

I had engineered what happened next and it really couldn't have gone any better. The young woman "looking for work" was actually from an exclusive escort service. I made Baldwin wait three days for a meeting with me, to buy enough time to find a virtual clone of his daughter. Standing together, Jessie Baldwin and the teenage blonde escort wouldn't have been indistinguishable, but they were undoubtedly very similar in appearance. I had dressed the young girl in Jessie's clothes too, just to evoke a response from him.

Scheduled right after him, she was waiting in the lobby and under instructions from Olivia, approached Steve Baldwin as he was leaving.

"Hi Papa, I am Amber," the young escort said, as she extended her hand to greet Steve. "I am here for the rehearsal."

Steve recoiled reflexively as he took in the startling similarities between Amber and his daughter, Jessie. Amber was wearing an unusual tartan t-shirt that Steve had purchased for his daughter on their visit to Warsaw, Poland, and the unlikely co-incidence of her attire seemed to shock him to his core. When he didn't take her pro-offered hand, she moved in for a hug, and I watched his nostrils flare as he recognized that Amber was wearing his daughter's perfume.

After their awkward embrace, which Amber held for way too long, Steve finally verbalized what was on his mind.

"Are you a friend of my daughter, Jessie?" he asked nervously. "Jessie Baldwin."

"I'm her understudy, Papa," she beamed. "I am here to run through the Make Daddy Proud routine, in case Jessie can't make it for some reason."

Baldwin struggled to process what was going on, and as Amber hung all over him like an over-zealous groupie, he appeared to change his mind about leaving.

"Why don't you just use Amber as your Toy for the show?" he asked me. "I will pay her whatever she wants if you agree to leave Jessie out of it."

"I am open to that, Steve," I lied. "Stay and have a beer and let's chat about it."

Steve hesitated briefly, before nodding his head agreeably. As we went towards the bar, Olivia intercepted us and took our drink orders. Years prior, Olivia had suffered tremendously under the sadistic tendencies of Steve Baldwin, and was salivating at the thought of him getting his comeuppance.

"The male escort who is standing in for you in the rehearsal is ready, Pete," she said cheerfully, as she handed us two ice-cold beers. "His name is Ethan if you need anything from him."

Steve Baldwin and I were never destined to be friends. Even as we sat next to each other at the end of the bar, looking out onto the dance floor, I could feel the tension between us. However, I wanted him to view this rehearsal of the Make Daddy Proud event, knowing that his daughter was going to be the main attraction on the actual night.

Moments later, as the lights dimmed and the music started, Amber and Ethan began to dance seductively together. From a distance, under the soft lighting of the stage, Amber bore a startling resemblance to Jessie Baldwin, and as the routine became progressively more risqué, I could see Steve getting pissed.

The two understudies went through a series of simulated sex-acts, as they slowly disrobed each other, and once they were both naked, Ethan developed an erection and forced Amber to her knees. As she began to fellate him, Steve looked down in abject misery.

"Jesus, Pete, please," he said forlornly. "What do I have to do to change your mind?"

I made Steve Baldwin sit and watch the whole sordid rehearsal, as Olivia periodically refilled our beers. Amber extracted three cum-shots from Ethan during the ninety minute performance, and as he took her in every conceivable position, I peppered Steve with questions and my own personal observations.

"You don't really get the same atmosphere in an empty room," I taunted him. "When we have three hundred and twenty five guys packed in here like sardines, it will be a completely different experience."

I thought that Steve was going to throw up when Ethan began to ass-fuck Amber, as he imagined his little girl, fresh out of High School, getting sodomized on stage.

"Amber and Ethan don't know each other," I added with a chuckle. "That's the only reason that he is wearing a condom for the anal scene. I certainly won't be on the big night."

Once I was satisfied that I had extracted my pound of flesh from my nemesis, I took my foot from his throat, and signaled the DJ to cut the lights and music. Amber and Ethan stood there awkwardly as I gave them some direction.

"The anal scene needs to be much more aggressive," I said firmly. "Amber, you need to transmit fear and pain in equal measure. You are losing your anal-cherry. It needs to appear to be a traumatic experience. Steve, any thoughts?" I added, just to be a prick.

Steve shook his head in silence, the whole sordid event having beaten him down.

"Ok, guys," I said cheerfully. "Let's skip to the rim-job scene."

Steve excused himself upon learning that his daughter would be performing analingus on stage at the big event. Olivia escorted him to the door, and I saw the look of defeat on his face as she handed him Jessie's tartan, Warsaw t-shirt, and he exited the club.

It felt so good to get one over on that prick Baldwin, and while I had zero intention of letting him off the hook, I did follow through on his request to talk to Jessie. She was reticent at first, but when I presented it as an opportunity for her to rub her Dad's face in the fact that we were fucking, she loved the idea.

"Why don't you let me give you a facial first?" I suggested, as we both cracked up. "Then we can FaceTime him."

Jessie ended up lubing her pert breasts for my enjoyment, and I tit-fucked her to completion, blowing my load all over her neck, lips and chin. After a perfunctory clean-up, which left visible dried semen stains on Jessie, she donned one of my "Top Shelf Pussy" T-shirts, and called her Dad.

I stayed out of the camera's view, but judging by Steve's uncomfortable start to the brief conversation, he could tell I had just blown my load on his daughter's face.

"But I love him," I heard her say at one point, trying to piss her Dad off.

As he begged his daughter to reconsider her upcoming appearance at the "Make Daddy Proud" event, she reiterated that it was merely a public demonstration of our love. I was enjoying every moment of their excruciatingly awkward exchange, but when I signaled her to wrap it up, she saved the best for last.

"Gotta go, Daddy," she said cheerfully. "Pete is just getting out of the shower and is probably ready to go again. Night, night."

As the day of the "Make Daddy Proud" event approached, I had significantly increased the marketing budget, and I had a dozen promotional bulletin billboards, strategically located in the places where wealthy men gathered. Every night, under cover of darkness, my event management team changed the picture on each of the twelve massive billboards, the new image which measured a gargantuan fourteen feet by forty eight feet, creating additional excitement in town.

The latest picture, taken from behind Jessie to hide her identity as she leaned over the top of my Steinway Grand Piano, showed off her new Henna tattoo. The oversized temporary inscription, situated as it was in the classic tramp-stamp position, read "Top Shelf Pussy Debutante," a clever play on words as it paid homage to Jessie's upcoming Debutante's Ball. Jessie's long blonde hair cascaded down her tanned back, the latest clue as to the hidden identity of the future stripper.

Once the picture was up on the bulletin billboards, I imagine there was a collective sigh of relief from every one of the Debutantes' fathers whose daughter had black, brown or red hair, and an exasperated groan from the guys with blonde daughters. As an additional kick in the nuts to the guys who had not been able to positively eliminate their eighteen year old baby girl from the potential list of strippers, the words "Pete's latest Toy" were emblazoned above the beautifully constructed image.

It was all the locals could talk about, especially the guys who had eliminated their own Debutante from the running. One of the colossal billboards was situated right in front of my club, and I thoroughly enjoyed looking out of my office window at the ever-changing advertisement. I even got a call from the Police Chief informing me that he had to deploy additional patrol units to keep the traffic moving on Pacific Coast Highway. Apparently, drivers were stopping to admire and photograph the huge billboard, situated on the congested main route of Newport Beach.

The following day, as Jessie cavorted topless in my swimming pool, the photographer captured several natural-looking shots of her, before she agreed to pose for a more seductive billboard image. Jessie came up with the provocative notion of spilling suntan lotion on her stomach, but as we brainstormed some ideas, we decided to squirt the milky white cream on her tits. The billboard went up overnight, and in the morning the lewd image assaulted the town.

I knew I was going to get some blowback as the huge photo of Jessie laying topless on a sun lounger with suntan cream pooling all over her tits and neck, created the visual that she had just been tit-fucked. Jessie was wearing a black sun visor, pulled down in such a way as to shield her face, thus protecting her anonymity. The caption above the provocative image read "Cum and see me dance at Top Shelf Pussy."

I did get a call from the City Public Affairs Officer asking me to take down the offensive billboards, but by the time my team arrived to remove them, it was already dark, and the damage had been done. The local news did a live report on the lewd billboards, although they blurred Jessie's chest, which predictably created more interest in the image. They say there is no such thing as bad publicity, and as the image went viral on social media, there were some educated guesses as to the identity of the young blonde, and Jessie Baldwin's name was mentioned on numerous posts.

The following day, I needed city approval before I was allowed to post my advertisement, and on Jessie's instruction, we selected a very inoffensive image. Jessie was photographed exiting a large shower enclosure, with a towel concealing her naked torso, and a second towel wrapped around her head. Jessie raised her arm to her head to hold the towel in place, and with her upturned arm obscuring her face, the photographer snapped a few dozen shots. It was very innocent, and as we reviewed the options, Jessie pointed to one particular shot and told us to use it.

I didn't think much more of it and predictably it passed the scrutiny of the city official, whose job was to censor any offensive images. We pushed the line a little with the caption, but as it was more innuendo than graphic, it passed the inspection too.

The next morning as I sat in my office looking out at the gargantuan billboard featuring Jessie Baldwin under the caption, "I love getting wet," I heard a commotion at the entrance to my strip-club.

As I approached the front door, I saw Jody Baldwin wrestling with one of my security guys. She was furious, screaming at the top of her voice for me to take down the images of her daughter. It took a few minutes but she finally composed herself and we moved our conversation into my office.

"What the fuck, Pete?" she asked me angrily. "Why would you embarrass Steve and I like that? That is my baby girl plastered all over town."

I tried to deny that the image was of Jessie, but apparently Jessie had a small, light colored birthmark under her right armpit, which is precisely why she had chosen to adopt this pose, and select this particular image.

"Steve will fucking kill you when he finds out," Jody threatened.

The look on Jody's face was priceless as I informed her that her husband had already been to see me, cap in hand.

"He practically begged me not to allow Jessie to appear in a live sex-show," I said with a smirk. "It was one of the highlights of my life to have Steve Baldwin capitulate to me. He even asked me if I could arrange a brief FaceTime with Jessie, as she wouldn't take his calls."

"Bullshit," Jody retorted. "Steve wouldn't beg you. He hates your fucking guts."

"Call him," I invited her. "Ask him the sordid details of the FaceTime call. Ask him what your daughter was wearing. Clothing wise, and on her face," I added cruelly.

Jody appeared to process the evaporation of her leverage, and then began to offer up some compromises.

"Pete, I can almost come to terms with you and Jessie being intimate," she began softly. "But we have been friends for years. Please, don't fuck my daughter on stage. I am begging you."

"Friends is a bit of a stretch, Jody," I responded. "All I remember is you derailing my wedding to Madison. Oh, and the last time I showed an interest in you, it was going to cost me fifty grand a month."

Jody and I went back and forth, as she vacillated between threatening me and offering me incentives to cancel the show. After I laughed at her offer to pay me, she changed tactics and began to cry and beg me. It was still two hours until opening time of my club, and truth be told Jody's persistence was wearing me down. However, I remained stoic and resolute in my insistence that I was going to fuck her teenage daughter in front of the majority of our peers.

Jody had used her sexual allure to manipulate men since the day she turned eighteen, and I was surprised that it had taken this long. However, in typical Jody style, she dried her crocodile tears and asked to use the restroom. After a prolonged bathroom break, Jody returned to my office, with her make-up refreshed, a friendly smile on her face, and heavily scented with my favorite fragrance.

Walking in as if she was here to audition for a dancer's position, Jody locked the door as she closed it, and headed towards me. She knew the sexual attraction I harbored for her, and had evidently decided to use it to her advantage.

"There must be something I can do to persuade you, Papa," Jody said, as she rounded my desk.

Jody was on me before I had time to react, invading my personal space as she sought to use my obsession with her to manipulate me into getting with her program. It worked too, my cock stiffening immediately as she put her lips to my ear and began to promise me the world. As I inhaled her scent, I was reminded of our last encounter, nearly twenty years ago.

As a Trust Fund Baby, I was used to getting my sexual needs met, and it was a pretty rare occasion for me to jerk off. However, over the last two decades, every time I masturbated, it was to the memory of my brief hook-up with Jody.

Years before they eventually married, Baldwin had paid Jody to seduce me, in an attempt to derail my upcoming marriage to Madison. Jody had warned me that it was a trap, even going so far as to tell me how much he had paid her, but I was unable to resist her, despite being fully apprised of the potential blowback. Jody had sucked my cock that night after we shared a Chinese takeout, bringing me to an embarrassingly quick orgasm, before allowing me a second release, inside her tight, teenage pussy. It was the seminal sexual encounter of my life, the memory of which I would resurrect, anytime I jerked off.

It was also the regret of my life, on two accounts. Firstly, it cemented Jody as the love of my life, the one that got away, if you will. Secondly, despite Jody having promised me a two-girl rim-job with the lovely Rachel, they left me high and dry as I showered for the encounter, and this had haunted me for twenty years.

Now as she had drifted back into my life, and was in desperate need of my benevolence, I knew that whatever happened today, I was going to get that high-maintenance bitch's nose between my ass-cheeks.

Jody had taken control of the situation, and it was obvious to me that she had matured over the last two decades. She had accumulated a mountain of experience when it came to manipulating men, and as her dainty hand brushed across the front of my pants, she flashed me one of her heart-stopping smiles.

"You are hard, Papa," she whispered, as she nibbled my earlobe. "I have missed you, baby."

As she flattered and teased me, my mind began to spin, my focus disappeared, and I started to lose sight of the goal, a rim-job from my dream girl. Jody caressed my cock through my pants, and once I was leaking pre-cum, extracted my erection, knelt before me, and began to suck me off.

I hated Steve Baldwin with a passion, but as Jody demonstrated her other-worldly oral skills, I started to envy that fat fuck. I was receiving the best blowjob of my life, and if Baldwin was enjoying that service even once a week, he was the luckiest man alive. Predictably, despite having sky-high expectations for this unexpected encounter, I was unable to resist this goddess, and with a guttural moan, I exploded in her mouth.

After I came, Jody looked up at me with her angelic-looking face, opened her mouth, and with a huge smile, swallowed my load. The juxtaposition between her innocent looks, and her willingness to perform lewd sex-acts, was overwhelming, and I found myself unable to focus on my game plan. Jody was well aware of the power she wielded, and after I composed myself, she began to flatter me.

Rising from her knees, she placed her lips against my ear, and whispered into it.

"I love you, Pete," she began. "I guess I always have. In a different universe you and I would have been together. It is one of my lifetime regrets that I ended up married to another man. It should have been you and I. We are soulmates."

As I processed her words, I felt a deep sense of melancholy, coupled with immense relief. If Jody really did consider me her soulmate, maybe there was hope for us in the future. Maybe she would leave that asshole Baldwin, and be mine. As we shared a tender embrace, Jody began to weep quietly, and in an uncharacteristic show of vulnerability, started to detail the perverse nature of her relationship with Steve Baldwin.