The Club Ch. 03

JAMESTON HALL

PROLOGUE

Anthony's childhood and early adolescence had been difficult, both emotionally and physically. He was the youngest of three siblings, the two older being girls. His grandfather and father were partners in owning three nationally franchised stores. The family was elated when Tony arrived, as the expectation was that he would inherit these lucrative businesses, and, expand the family's franchise holdings.

Simply stated, Tony was a pretty boy. He had those jaw dropping facial features that made passersby look twice when he was on outings with his mom. Over his dad's objections, Tony's mom enrolled him in child modeling classes. Successful photos shoots then became an integral part of his childhood.

His older sisters tolerated their younger brother, until Tony's "borrowing" his sisters' clothing items got seriously annoying. Despite being yelled at and tattled on by his sisters, plus a stern lecture from his dad, sneaking into his sisters' bedroom continued. He would pilfer clothing items, particularly blouses and skirts, and try them on in the privacy of his upstairs bedroom. Tony instinctively knew he was wrong, but just couldn't help himself.

When hormonal changes began to rock his adolescent body, he tried like hell to suppress his effeminate mannerisms, and earnestly studied -- and tried to emulate the "jock behavior" he was witnessing in high school. That created even more conflict in his young life, and his prom night date with a favorite female friend turned into a real disaster! He hated close dancing and kissing her. He hated it. He hated himself.

Tony was sent out of state for his first year of college. It was a large, public state university with a hugely diversified student body. That is when he discovered other men similar to him, but Tony did not trust the "gay" scene. Just before reaching his twentieth birthday, Tony went into full mental crises and dropped out of college. That probably shoved his dad over the edge, causing that poor soul to have a heart attack.

Now Tony was really on his own, cut off from family and, of course, funding. He worked a number of menial jobs, but knew this wasn't the life that he wanted for himself. So, Tony made amends with his family and went back for his bachelor's degree. After college, his job provided him with sufficient money to begin his outward transformation from man to woman. Tony began with hormonal injections and straight on faced his deepest desire for transgender transformation. He wanted the outward appearance of being a woman, but to retain his male genitalia. Pricey breast augmentation surgery followed.

Over time, Tony evolved into Antonia, called "Nina" for short. Coincidentally, she moved to the same city as where "The Club" was located. Now Nina was drop dead gorgeous, with a figure to die for, perfect make up and coiffed "to the nines" as the saying goes. Nina dressed in a sexy, impeccable style all her own. Eight-to-five jobs were far, far behind her, as her reputation as a she-male on the porn scene widened.

That was Nina's income source -- and she became a really high dollar earner, catering only to wealthy male clientele. Nina had heard rumors regarding "The Club" and its membership, including their fabulous country estate, but had never quite made the connections for an introduction into this realm of high society. That was all about to change, as the Procuress of the Menu initiated a contact through Nina's manager.

ONE

Since his retirement from that Fortune 500 company, Bizz Man has been investing his portfolio into a sizeable fortune. Now, passing his 75-year-old mark, he's thinking about the future, and, of course, his most unfulfilled bucket list of prurient desires. His wife continues to "do her own thing." With kids and grands pretty much out of the house, Bizz Man has the luxury of time to entertain himself in randy reveries. Even in his 70's, burgeoning lust is consuming him!

He and his long-time Money Man are the only two people that really track his financial profile in excruciating detail. So, Bizz Man now places a call to Anil.

"Anil, this is Bizz Man. I'm wondering what you would say if I wanted to purchase a special country property away from city life-- say, as a getaway for the family, and hopefully, a place that will be passed down through my family? I don't know if I can make it happen, but sure would like to try!"

Anil was silent for what seemed like the longest moments in phone call history. He cleared his throat and then addressed Bizz Man. "Are you freakin' serious?"

"Dead serious" was Bizz Man's answer.

"This will be a couple of mil out of your portfolio. Are you OK with that? I don't think it will much affect your monthly income streams, but it certainly needs checking out" was Anil's comeback.

"Anil, let's do it" and Bizz Man ended this call before Money Man could even respond.

Gawd! A sense of arousal that he hadn't felt in quite some time washed over Bizz Man. He was going after that property next to The Club's country estate. That was his fantasy. His libido was suddenly awakened and he was craving sex -- all kinds of erotic S-E-X --maybe even to try something entirely new to him! He hankered after the possibility of owning that special place for fulfilling some of his more exotic dreams.

TWO

Bizz Man was obsessed. He took action and engaged a savvy real estate broker to approach the estate's current owner. At this point, my cousin didn't care about the repairs certainly required on this four-bedroom cottage and its six-car garage with the above living quarters. He coveted Jameston Hall. In fact, when sipping drinks from the club's country estate veranda, even the four bad boys had favorably remarked on several occasions about that cottage's idyllic setting.

Was it meant to be? Maybe.

It took some finessing, but, over the course of several months of negotiating with the present owner, it was a DONE DEAL! At last, Bizz Man owned Jameston Hall. He couldn't wait to break the news to his cousin over drinks and dinner. In the back of his mind, he was also planning on how he would announce this property acquisition to his wife and family. But, that was later. That just wasn't important right now. It was Bizz Man's secret acquisition. He would engage a property manager and, thus, become the hands-off, absentee owner.

THREE

As his first cousin, as well as Procuress of the Menu, I had a zillion questions. It was a lively conversation between cousins in this small, intimate Italian restaurant with the best shrimp scampi under God's green earth. I wanted him very much to describe Jameston Hall in great detail. Bizz Man did me one better. He suggested that the two of us tour his new estate over the coming weekend.

We provisioned a carry out deli order and a couple of bottles of champagne. The drive took about an hour. As our car turned into the long driveway sentineled with magnificent oak trees, my mouth stood agape. The grounds and buildings were indeed picturesque. I could see excitement flickering in Bizz Man's eyes. My cousin was thinking.

We paused inside the front door and you immediately pulled me tightly into your embrace. This certainly was not our first cousin-to-cousin tryst. Your tongue kissing was far in and wanting. Then I heard you unzip and I fell to my knees, directing your hard-on into the wetness of my mouth. When I glanced up, you were intently watching downwards at your own in-and-out movements penetrating my lips. "Don't be such a prick-teaser." With that statement, your hands grabbed my hair, ram rodding my head to best satisfy your joystick. You can be a bit rough at times, Cousin Dear!

"Please stand up" were your breathy words to me. And, I complied.

"Pull your leggings and panties down just to crotch level, as I desire my cock to touch your clit and to cream all over the inside of those lacey black panties" was my cousin's direction. Standing face to face, it didn't take long for you to give yourself a hand job and ejaculate, as I arched my back and stretched my panties further out to catch your warm semen. Your right hand immediately pushed the cum ladened panties up against my clit, slathering your moistness into my womanhood. I climaxed and fell into your arms. Hence, we two cousins christened Jameston Hall right at that entryway.

FOUR

After our deli lunch and some touring of the property, my Cousin delicately approached a subject that was very much on his mind. He wanted a date -- not just an ordinary date, but something very special in the realm of erotica.

I had to wonder what THAT could entail. After all, I had made all the arrangements for the Lusty Four Gentlemen of the Club. I had also heard about my Cousin's teenage redheaded nurse fetishes and, early on, developing a voracious appetite for oral sex. Now I really didn't know what to expect Bizz Man to say. But I was listening.

"Dear Cousin, a close friend of mine died very unexpectantly. It was a freaking shock and wake up call to me. Life can end at any moment and if there is anything you want to do, you had better do it now" was the next emphatic statement by Bizz Man.

"Go on, Cousin, tell me exactly what you have in mind" was my reply.

"I want my Procuress to arrange a secret date for me with a talented she-male. I've often wondered what it would be like to suck a dick and give a blowjob. Does this shock you? No, I'm not turning gay, but this is a huge unanswered question in my life. That is a large reason that I bought this property -- for discretion and privacy -- and to fulfill my verboten fantasies.

It will also be perfect for the Foursome's Fuck-Fest already on everyone's calendar. It's good not be tethered to the Club's social events calendar and schedules. I can't wait to see my buddies' faces when driving directions lead them here --rather than to the Club's next door country estate," so my cousin's explanation rambled on. "I have not breathed a word of this property acquisition to any of my Club gang," he added "nor should you."

I hesitated a minute, then quizzed my cousin on his "special date" desire.

"My 'she' date has to be feminine, good looking, with an average size cock. Most importantly, this she-male has to be very experienced and an exceedingly talented Fellatrix" were Bizz Man's stated conditions back to me. "Of course, discretion is of the utmost importance to me" was his final guidance. "I am willing to pay whatever it takes to make this happen."

After staring at my Cousin and thinking about what he had said for a moment or two, "I accept this challenge" was my response. I can't believe that I was actually saying that! At that very moment, I was enjoying the sensation of my Cousin's cum exuding against my inner thighs.

FIVE

With Bizz Man's request in mind, I wanted to error on the side of caution in making discreet preliminary inquiries for a she-male to fulfill my cousin's wishes. Through another source, I did make contact with the manager of girls selected for the Foursome. Remember the likes of Cyber Man's Caramel Brulée; Vanilla Sweet Cream chosen by Legal Man; Chrysanthemum Tea who partnered with U Man; and, of course, the pregnant Desiree for you, my dear cousin? I also recollect that there were other women included in the two previous libidinous evenings enjoyed by the Lusty Foursome. There were certainly no complaints from any of you gentlemen!

I can make this happen for my cousin.

"What? You already have a connection for me," I remarked with a surprised tone of voice when answering my phone. "Of course," responded the husky voice at the other end of the mobile phone call. "The way this works is that you will need to set up an initial meeting in a public place, so that the two parties involved can get comfortable with each other, before the actual date, location and fees are set."

I responded with an "OK."

You, Dear Cousin, acted like a pubescent teenager when I told you about the phone call. This initial meeting was arranged in an upscale venue with one of those glitzy mirror-walled bars lined with liquor bottles of every shape and description. I sat next to you, awaiting entrance of the manager and your potential "date."

That twosome did make a grand entrance, and this "she-male" was a gorgeous brunette with her cosmetically injected lips. Her lipstick color was a jazzy red. At that moment, I had to privately wonder how such prominent lips would feel wrapped around a pecker --or even a clit.

Shaking myself out of my reverie and back to business, I sensed that my cousin was getting a case of major jitters. Your past inhibitions about touching a man's privates came, unwittingly, to perch homophobically alongside you! Small talk around the table felt forced. I also sensed negative vibes slicing through the air like javelins hurled in the heat of the hunt. After an uncomfortable half hour, we paid their bar bill and graciously excused ourselves.

"I'm not going through this again" is what you muttered repeatedly in the car. "Really?" was my Disappointed-In-My-Cousin response. For the rest of the return trip, silence entombed our ride. Before slamming the car door shut, all I could think to say was "What about your frickin' fantasies?"

I was pissed.

SIX

In this past month or two, my cousin was busy introducing his personal touches into Jameston Hall. Being a techie kind of guy, smart home technology installations were a must! He also sprang the ganga surprise of property acquisition on his family. Several summer weekends were enjoyed at the newly acquired country estate. He had no regrets about purchasing this parcel of historical real estate, even if his most secret aspirations were not yet being fulfilled.

As the Procuress of the Menu, I was actually quite surprised for his phone call -- particularly after the first bar scene and his evident "homo" jitters. I really didn't know if my contact would deal with him -- or me, again.

"Why hello, Dear Cousin" was his upbeat phone greeting.

"I'm very surprised to hear from you" came my somewhat cool response. "What's up?"

"I've given serious thought to my bucket list fantasy, and would like to try this "date" arrangement again," were his next words to me. He went on to add, "In my bathroom, I have a dildo suction-cupped to my shaving mirror. And, "yes", I have been grabbing that bad boy, and giving it my best moves. It's practice, cousin, it's practice! Now I'm ready."

"Are you absolutely sure? Are you serious this time around? The porn world is pretty much underground and we have made my contact extremely nervous" came my hesitant response.

"Please, Oh Fabulous Procuress, let's try again" was his next pleading sentence. "Don't whine!" was my reply.

SEVEN

This time it was Nina who was contacted and scheduled for the initial public rendezvous with Bizz Man. Time and place arrangements between the two parties were made, certainly at a different location from the first she-male disastrous introduction. I was asked by Nina's manager for some background on this prospective client [i.e. my Cousin Bizz Man], with retracted surnames and/or addresses. After a bit of research and editing know-how, I provided a general bio, in hopes that this meeting would go more smoothly.

That Bizz Man was financially sound to pay the four-hour sex play session fee, with an expected gratuity, was also to be checked out by Nina's manager. A payment of half the total fee would have to come up front. At last, everything appeared to be a "go"!

I and my cousin nervously awaited the 7:00 PM cocktail meeting time, and I asked Bizz Man to stop looking incessantly at his watch! "They will come -- guarantee it!" was the best way my words could sooth his immediate anxiety.

At that point, the restaurant door opened. Nina strolled in ahead of her manager and absolutely took command of the whole bar area. Eyes of every single patron -- both men and women, were immediately focused on this stunning specimen of a woman. Nina strolled over to Bizz Man directly, then came around the table to buss his cheek and offer my cousin the softest, most sensuous, throaty voice greeting imaginable. "So delighted to meet you, my dear!"

With Nina's tanned figure eight body at about 5' 6" in height; her shoulder length white-blondish hair pulled severely to the side with a glistening rhinestone barrette; alluring eye makeup fringed with those in-style lush fake eye lashes; and, wearing a beautiful, bust-cinching mid-thigh black and white sheath and matching heels, my cousin 's jaw just dropped. He took --what seemed like several moments, to acknowledge Nina greeting him directly.

Nina was the one who led my cousin into conversation and seemed to ease his apprehension. God! What an entertaining communicator she turned out to be. Bizz Man was enthralled --now much more relaxed, smiling, and anticipating his most erotic dreams actually coming true. At those moments in the bar, I surmise my dear cousin forgot that this absolutely amazing woman possessed -- should I say most indelicately, a C-O-C-K! As the Procuress, my inner thoughts were "This is going quite well!" And, that initial meeting certainly did!

Arrangements were then made for the four hour she-male play session at Jameston Hall. Nina would be chauffeured to the site, and her escort would wait for her in the guest quarters above the garage. Of course, I would also be on property to take care of the financial end of this dalliance.

EIGHT

Even in retirement, Bizz Man had interests that required travel. He made excuses to his wife that out-of-town business took him away for the coming weekend, beginning Friday. My cousin was anxious to get to Jameston Hall a day early to be sure everything was perfect for the upcoming Saturday four-hour she-male fellation session. Yes! He was most eager and ready for this amatory experience. The arresting Nina would be his guide.

Alone in the master bedroom suite that evening, my cousin retired with his fantasy, causing an unexpected boner. Bless that man! He then wanked his way into slumberland.

NINE

Bizz Man belted down a couple of scotch whiskeys before the appointed date time of 6:00 pm. When he heard automobile tires rumble down his tree lined driveway, my cousin quickly retreated to the sitting area and waited. Just to hurriedly double check, his "Turn down lights" and "Play soft music" voice commands were tested. Everything was in working order! He would set the mood for whatever Nina desired. Then the much-anticipated door knock came.

"May I come in?" was her sultry, posed question.

As Nina moved past him into the foyer, she was beguiling in her signature thigh high mini dress; ample breast cleavage peeping out of her key hole neckline secured with ties behind her neck; the most exotic dangling earrings my Cousin had ever seen; and, the piece de resistance, those ultra-suede over-the-knee boots. Surprisingly, Bizz Man's arousal was set in motion at that front door, catching a waft of her Amyris flower fragrance.

"Please, let's kiss" was Nina's coaxing invitation. Without hesitating for even a moment, he drew Nina tightly to him and gifted his date with an amorous French kiss. "She" was drop dead beautiful, and my cousin was immediately drawn to her, as a butterfly anxious to suck in this she-male's private nectar. Several impassioned kisses followed, before he escorted Nina to the sitting room and offered her a libation from his well-stocked bar.

Sitting closely together, this twosome chatted about what my cousin desired, and, as importantly, what would make him uncomfortable. Anal sex, at least for this first time around with a "tranny" date, was quickly found to be off the table. A wonderfully long session of foreplay and reciprocated fellatio it would be! Nina then invited Bizz Man to shed his sport coat, kick off his shoes, unbutton his shirt, and get comfortable. In that moment, she took charge!