The Trapped Boytoy

Dave was a slacker and always had been. Breezing through life, everything came easy to him as he was a firm believer in the philosophy of taking the path of least resistance (and least work) to achieve his goals. Now many might want to live this responsibility-free life themselves but can't quite make it happen as pulling this off does require some skills. Dave was lucky though as he was fortunate enough to be able to pull this off as he was blessed with the good looks and a certain charm with women that served him quite well over the years and made his Bohemian lifestyle possible. Never holding a steady job for more than 3 weeks at a time, he casually drifted through his twenties, shacking up with waitresses, aspiring actresses, and an endless parade of overly inked very adventurous art girls. He had a gift no doubt, and his good looks gave him an amazing ability to always be able to charm his way both into their panties, and then eventually into their apartments.

Usually it would take a few months, sometimes more, before these girls would realize that they had inadvertently taken on a huge drain on their finances when their handsome boy toy moved in. Never paying for anything and constantly was borrowing money he was an extravagance few could afford. Accusations would be made, fingers would be pointed and Dave always would leave. It was always time to move on to his next conquest, and bank account, once the bitching got too extreme and the free food and frequent sex dried up.

As he got a little older, his needs changed, and he moved upscale a bit. He no longer had the energy required to move constantly so his new "girlfriends" had to be wealthy and hot. His youthful good looks and stunning body allowed him now to become a perpetual erotic diversion to a series of very wealthy, usually newly divorced women who loved having a young, attractive, (and well hung) stud around the house. The pattern was very predictable and followed the same standard script as before although now he was getting kicked out of high rent Upper West Side condos instead of cramped Brooklyn efficiencies.

He was a taking odd jobs as a "handy-man" now, and specialized in fixing various things in those high rent condos on the Upper West side where the MILF hunting was most productive. When a good target would come into his crosshairs he would crank up the charm (and show a little skin at the right time) and more often than not it would work.

"Oh Mrs. Johnson, do you mind if I take off my shirt to work on your Kohler Carbon special ordered gold plated Shower nozzle with the custom designed needle spray attachment?" he would say, batting his steely blue eyes and casually flexing his impressive guns under his usually too tight cotton t-shirt.

Mrs. Johnson, or any of a number of women just like her, never minded AT ALL and were usually quite enthusiastic about his getting more "comfortable" so he could work. His "job" would usually end at the same time his relationship with the client would blossom, and the owner of the handyman company always had an asterisk by his name when making out the work schedule for the next week.

Once he had the client properly interested, it would not take long before he would shack up with this gorgeous yet naive older woman who he would then sponge off of for as long as he could. The pattern for these ladies was not that dramatically different than the waitresses from his early twenties, except that instead of his borrowing $20 and not paying it back, he was borrowing $2,000 and not paying it back.

These women usually would tire of his moochy crap after a few months and begin to demand things from Dave. That was usually when their sensitive and sexy handy man would flee into the night, never to be heard from again. He had to admit to himself, he had a pretty sweet setup. Little did he know how this little world he had created was about to come to a dramatic and unexpected end.

One of the ways Dave was able to pull this scam off as long as he did was not just because he was handsome. There are no shortage of hot studs in New York so to set him apart he had become quite skilled in the art of seducing women and keeping them relatively happy with minimal cash. He was a good listener, knew how to cook and give good massages and was always willing to go to whatever boring ass Opera or Symphony his current Sugar Momma wanted to attend. He also was a master of perfectly tailoring his schtick to whatever situation he was in. If the lady in question liked Opera, he would polish up on his Toscanni. If she liked politics he would spend weeks reading back issues of either the "Nation" or "The National Review" depending on the political persuasion of the MILF of the day. This would always set him apart from just any old brainless gold-digging meat stick. Looks would get him INTO their bedroom, but to stay there would require more.

It was also in that arena where he truly shone. Amongst his many skills that allowed him such leeway was his impressive ability in the fine arts of love. He learned early on in life that pleasing women, especially orally and often, would cover up for a lot of his "sins" in other areas of his life. Women rarely stay too mad too long at a man, no matter how worthless he is, if he is buried facedown in their pussy often and long enough. This is especially true if he knows what he is doing. And boy could Dave perform in this area as as over the years he had had a lot of practice.

As if being a hopeless slacker and mooch was not bad enough, among his other irresponsible habits was he was a hopeless gambler. Like so many other people with gambling problems, he always thought that he was just one more shot away from striking it big. Billion dollar hotels are built in Vegas on just such faulty math, and Dave had it in spades. This fictional big score would then allow him to finally be able to pay off all of his debts and go clean with a nice nest egg. Like most plans of gamblers it of course never worked out that way and soon he found himself stupidly $35,000 in hock to some Italian-American gentlemen from New Jersey that were not the most understanding of creditors. Being straight men they also were quite immune to his natural charms so he would have to pay them back.

Given his current situation of being in-between cougars and his alarming debt situation with the mob, Dave decided it was time to cast his net again into the sea of Rich Manhattan MILFs and called his old friend Shelia up at the Manhattan Handyman service for a job. Shelia, the owner, just shook her head when he dragged in asking if there were any odd jobs available. She too was attracted to Dave but also felt a bit protective of him, knowing him to be a lovable (and sexy) fuckup.

He was kind of a kid brother to her rather than a potential romantic conquest, so when he asked for a favor, she was almost helpless to resist. She knew the kind of clientele Dave "preferred" so she directed him to go to 720 Park Avenue and meet Victoria de Simone who had called just that morning needing help in her spectacular Penthouse.

Dave kissed and thanked Shelia, and despite her knowing he was a hopeless flirt, she was very happy about giving the assignment to him. He may be a gigolo, but he was not a pure gigolo and so did have some redeeming qualities. All of the women he hooked up with were ones he was genuinely attracted to, so he was not only pimping himself out for money, although that was obviously a big consideration. He genuinely was in lust with these women, having a soft spot for ladies of all ages. Watching his tight ass bound out of her office, she sighed and wondered how long it would before Victoria succumbed to his charms just like all the others.

Taking the subway into Manhattan Dave daydreamed all the way from Brooklyn about his new prospect. This new potential sugar mama was in a class of her own, as the wealth at that address was legendary. The apartment house he was traveling to was as far away in luxury from his Brooklyn walkup was as Versailles is to a trailer park featured on Honey Boo Boo. Despite the relatively short distance he traveled (less than 10 miles) he might as well have crossed several oceans for the different world he was entering. Stepping out of the subway as he rode the escalator up to street level he thought to himself how so many guys his age (30) missed out on the joys of ladies over 55 and grinned at his potential good fortune if he could make this work. More for him he chuckled more for him.

Entering 720 Park Avenue, the doorman looked very suspiciously at Dave as he had seen his kind before. Tall, muscular, smooth talking boys lke him were always on the hunt for rich pussy and were always sniffing around and he was constantly shooing them away like pests. As he was preparing to send this new boy packing, he grimaced as Dave presented his appointment card indicating he was legitimately there on business. Reluctantly he was let into the lobby and as he stepped inside he gasped.

This was truly plush, he thought, and was well beyond the realm of the 1%. This was home to the .00000001%. Marble was everywhere and he was astonished as he looked around the room and saw museum quality fine original oil paintings hanging on the walls and solid gold sconces for the lighting imbedded in the ceiling. Completing the Taj Mahal motif was a large tinkling fountain in the middle of the floor, an original Bernini statue planted in the center, and this was simply the lobby. Escorted by the doorman to a private elevator off of the main lobby, for the first time Dave began to feel nervous as he was shown inside. Stepping into the gold and oak lined car, there was only one button on the panel, which he pushed.

"Holy fuck!" he thought to himself as he rocketed up to the 18th floor. "If you have your own elevator in this rather expensive part of Manhattan you are a whole different level of loaded." Straightening his longish but still stylish hair in the shiny brass on the walls, he waited to arrive.

As the doors opened and he entered into the apartment foyer he was met by Victoria already waiting for him in her own lobby. As his eyes met hers and he took in her form he was beyond impressed. She was as stunningly beautiful as her insanely luxurious surroundings were and seeing her full up close, Dave was instantly highly attracted to her.

Tall, very curvy and pleasantly plump, her long dark hair had streaks of silver peppered throughout giving her a very regal appearance. As he glanced down her body and soaked in her full womanly curves (covered in Versace of course) he smiled. He was delighted to see that her glorious figure was perched on top of a pair of incredibly long legs that he could already imagine kissing. Even more delightful to his senses were her delightful, beautiful painted toes peeking out of some rather expensive Jimmy Choos on her feet that he already imagined in his mouth.

Her queen-like appearance perfectly matched her palatial surroundings, from her black and white marble foyer entrance, to the 800-pound crystal chandelier in the dining room, past the original Monets hanging over the fireplace and finally ending at a full private balcony overlooking Central Park. This was luxury on a scale that would make Trump look subtle and his usual MILF hunting grounds on the upper west side paled in comparison to this upper EAST side palace. This wasn't just money but it was old old money, and from the looks of the place, lots of it.

As Victoria eyed her new handyman, she too was impressed. Tall, over six foot three inches tall, it was obvious that he hit the gym often. Dressed in simple jeans and a white t-shirt, both a bit too tight, they highlighted his impressive abs as well as a delicious ass that she wanted to sink her newly whitened teeth into. His hair was a bit on the longish side, but swept off of his face like a mane and overall he was gorgeous. Glancing him up and down she ached to feel those ruffled locks entangled in her well-manicured fingers. With his hair hanging down a bit in his face coupled with his gym sculpted body he just exuded sex and it seemed obvious to her that he would be a very gentle and giving lover. When she spied a genuine look of lust in his own eyes, her designer Jean Yu panties instantly grew wet.

Snapping back into her normal cool diffident demeanor, she directed him to the main bathroom where she was having a problem with one of her designer Italian marble sinks. As she saw him bend down to begin to work, she got a better view of his incredible ass and ripped back and decided to stay and "supervise". Supervising turned to chatting and chatting turned to flirting as he kept asking her more and more questions, seemingly very interested in hearing her life story.

As they talked, Dave heard the sad but familiar story he had heard from so many gorgeous ladies of her class. Wealthy ex-husband, Hedge fund manager on Wall Street, traded in old wife for new younger trophy wife, big settlement, yada yada yada. One interesting side note to her particular story though was that despite an eye popping 9 figure settlement from her ex, Victoria had lots of money independently from her family through their cosmetics business in Europe. The combination of the two fortunes put her at the absolute pinnacle of wealth in America.

Hearing her talk about her situation, Dave could almost salivate as he quickly realized how rich this woman was. Knowing this and seeing her gorgeous body he knew he had hit the jackpot of all times. Equally in lust with her gorgeous body as much as her equally beautiful bank account dangling before his eyes, he put on the charm extra thick.

As he peeled off his shirt to work, he could feel her dark eyes studying his body as he made sure to flex as much as possible. This had worked before and he was hoping it would work again. Asking for a glass of water, when Victoria brought him into her kitchen and poured him a glass herself, he knew she was checking him out. He feigned getting overheated, and purposefully spilled his drink down his bare chest.

When he felt her grab one of her insanely high thread-count tea towels and begin to dry him off, he knew she was interested. Seeing a room off to the side with clays and other tools of the sculpting trade, and then noticing some of her own statues on the shelves he realized that among her fine qualities, she was also quite a talented sculptor. Sensing a way to move his charm offensive up a notch, he delved into his mind to scoop out all of the old art history subject matter he had been able to absorb from the countless art school girls he had banged in his twenties. Luckily for him there were a lot of memories to recall.

His memory must have served him well since soon they were discussing abstract expressionism and the relative merits of modern pop art in her studio like two art critics at a MOMA opening. He jumped but smiled when he felt her hand run over his back as he was bending over to inspect her current project.

"So, Mr. Jaconi" she began to ask.

"Call me Dave."

"Ok, DAVE, and YOU can call me Victoria. Pardon me if this is embarrassing, and it may seem like an odd question, but have you ever done any modeling? You see, you have the most fascinating back, and I would love to see it memorialized in bronze."

Smiling he said no, but in reality he had, many times for former arty girlfriends. Now it was indisputable that she was interested and he definitely knew his charms were working. As she ran her fingers over his back and inspected each cut of his lats, his skin tingled under her touch, the smell of her Clive Christian perfume making his head spin. Victoria was an artist so this wasn't as cheesy as it sounds, but it did indicate a certain level of lust, and she certainly had feelings of lust flooding over her from Dave.

Before long he was posing with his shirt off so she could model his powerful chest. This proceeded to him going fully naked in her studio for a life study. From the obvious look on her face as he dropped his drawers and sat on the posing stool, she approved of what she saw.

Dave liked what he saw too as she was even more gorgeous dressed down then she was in her Versace and jewels. Now donning a plain white shirt, artist smock and being barefoot in black leggings he had a hard time maintaining a soft cock for his nude modeling session. Victoria hit all of his erotic buttons, even if she was nearly 30 years his senior.

By the end of that afternoon they were having a glass of Chateau Lafite on her terrace. By the end of the evening, his face was buried in her silvery pussy, as she was groaning and scratching the back of his neck to pieces as her slender blue blooded fingers also ran through his thick wavy long hair. When she asked him to stay the night, he grinned, kissed her feet (which she loved) and agreed. By the end of the week, he had moved in and was hired as her live in personal "trainer" and life study model.

Everything again went right according to script and would have been absolutely perfect if Victoria did not have one peculiar trait which disturbed him. She was gorgeous, and certainly enjoyed his expert worshipping of her body (which he enjoyed too) so the frequency of loving was not a problem. The sticky point was she was the most selfish Lover he had ever known.

He would always diligently spend hours massaging every inch of her body, paying special attention to her legs and toes, which she seemed to enjoy the most. After this he would then eagerly eat her out for hours, as she seemed to have an insatiable sex drive and would not allow him up from her lap until she had at least nine back clawing full on howlers. The problem was, that once she was satisfied she would decide it was time to go to bed and as soon as his lips left her pussy she would pass out and go to sleep.

She said she preferred oral to penetration (although she did enjoy watching Dave's erect cock bouncing around the apartment) so full release fucking was off the menu. To Victoria even the SIGHT of cum made her gag which made lovemaking definitely one-sided. This did not prevent her riding him into a froth every once in a while, but because of her almost insane aversion to the male seed, this made that prospect very difficult to pull off as he had to hold back his flood behind a quivering dam.

This Spermaphobia also of course eliminated the possibility of blow-jobs or even pity hand-jobs and it was obvious she thought of a penis more as an attractive appendage for artistic study than something that needed care and feeding itself. This sadly meant that Dave was pretty much on his own for satisfying his natural urges and spent many a morning in the shower using LOTS of extra overpriced conditioner.

After a few months with Victoria, and his growing romantic relationship with his left hand as his only source of sexual release, he was beginning to sympathize with her Ex as he now knew the probable unstated reason for his departure. Now normally, he would have bailed at this point in a second, but he was stuck.

He still owed a lot of money to the mob, and although Victoria gave him a generous weekly allowance, it was not enough to pay off the debt fast enough. His calculations indicated that it was going to take at least 4 months for him to get out of trouble and payment was severely complicated by their terms. The interest rate one gets from the Mob was not one you would get at the bank so the hole he was in only kept getting deeper. Twenty five percent per month kept Dave seriously under the gun (both literally and figuratively) and trapped into his current circumstances.

He tried all of his charms to get Victoria to allow him to release into her, or even to just jack him off out of pity, but every time the subject came up, she would get quite upset and he would back off. Knowing his precarious situation, and being genuinely interested in Victoria, he certainly did not want to screw up his situation now despite his fast bluing balls. He especially could not afford to leave until he paid off his debt. For the time being, he would have to be happy with satisfying his needs on his own and regular masturbation at least kept him somewhat balanced. Other than this (which was a BIG problem) life with Victoria was otherwise very pleasant.