The Betting Pool

In a high-rise deep in the business district of Los Angeles, an innocuous conference room had been rented out for its four attendees. A large bald man sat at the head of the table with a suitcase and began to speak.

“You’ve all followed your instructions and not spoken to one another at all, and you should understand the rules now. Each of you will draw lots and then leave with a chaperone to complete your end of the arrangement.” He said cooly as he clicked open the suitcase, retrieving manila envelopes.

“The shortest straw will receive the largest reward of $1 million dollars. The medium length straw will receive the medium reward of $500K, while the longest straw will receive the smallest reward of $250K. Each of your rewards are contingent on the completion of your challenge and you’ll be given opportunities to earn more as well.” He said calmly. “Let’s begin.” He said retrieving a small cup with deceptively similar looking lengths.

A short and slight man with blonde hair sat to his left and drew a straw. It was very short based on the depth of the cup he drew from and he couldn’t stop himself from smiling. He was probably in his early twenties, but very slight and small. In the middle seat of the table sat a red-haired woman who looked very agitated. She had moderately sized breasts and looked upset at this first draw. When she drew her straw it was clearly longer than the first and she was visibly upset. Last, a black-haired man that was 6’ even sat on the right and drew out the longest straw by far. He seemed fine with this development.

The bald man handed out the manila folders as 3 well-dressed men entered the room to direct the contestants to their vehicles.

“Thank you for playing, you may read your folders on the way to your destinations.” He said calmly.

~~~

Justin had a history of sex work. He didn’t love to work and he didn’t exactly prostitute himself, he would just find long-term relationships with whoever would support him financially which progressively became men more than not. After his latest long-term relationship had ended he’d been contacted for this bizarre gambling thing and figured he’d try it out. Why not? Seemed like good money without the complexities of maintaining a relationship.

As his black head of hair disappeared into the non-descript black van and it was closed he started to read the manilla folder. The van immediately left him completely disoriented as the inside windows hid his view entirely.

REWARD: $250K

DURATION OF SERVICE: 6 MONTHS - OPTION TO EXTEND

MODIFICATIONS: INTALLED CHASTITY CAGE, TATTOOS, ORGASM BLOCKER. ADDITIONAL MODIFICATIONS FOR ADDITIONAL PAY AT SPONSOR DISCRETION AND CONTESTANT AGREEMENT

NATURE OF SERVICE: PROSTITUTION – LIGHT SERVICE

This was… straightforward? Okay… He had a couple small tattoos on his ankle and wrist, but he didn’t have anything else too crazy. There were additional pictures and explanations in the portfolio. Apparently he’d be “working” in an apartment deep in Seattle and outside of his work he’d be able to live his life like normal. For every day that he worked he’d get a days’ worth of his reward. But if he gave up or failed to perform then it would all be rescinded. Pretty hardcore.

Finally, the van came to a stop and he was let out and went into a non-descript office building that became clear that it was an off-grid surgical site. They loaded him in with lots of visual obstacles to him being seen from outside and he found himself waiting in a simple doctor’s office.

After waiting for longer than he’d like, a tall woman with black hair and a lab coat came in. She was looking through some papers. “Hello Justin?” She said questioningly.

“Yes, that’s me…” He said sheepishly.

“Undress.” She said flatly. “We’re going to be putting you into a very thorough chastity cage and giving you several tattoos. Once we’re done I’ll let you review an additional set of modifications that your sponsor will increase your reward for.

“Y-yes…” Justin said concerned as he got undressed. He had a moderately sized dick but was otherwise very plain.

“We’ll be shaving you as well, you may want to get in the habit of keeping yourself well-shaven.” She said. She brought out a cart with a tattoo gun, a strange looking chastity cage, and a series of needles.

She first started with numbing Justin entirely with an injection into his lower pubic area followed by another shot to his taint and right ass-cheek. She started quickly in with the tattoo gun. The sensation was very strange as he couldn’t feel any pain from the new changes to his body, but he couldn’t help his cock getting hard from time to time as she operated so quickly.

“Hmmmm, that looks great.” The woman said, clearly started to get excited herself. She handed Justin a hand-mirror.

The first thing Justin noticed was the barcode on his right ass-cheek in the shape of a heart. He’d have to look into what that was in the future… Above his dick and beneath his belly-button there was the word USELESS in large block letters. Between his balls and Asshole there was the word TOY going from his ass down, so it would be read when he was on his knees. Finally, and the most shocking, he had two words going around his asshole, PUBLIC USE.

His face went blush and he was close to protesting… but if he resisted too much he may give up the cash prize. And $250K made a lot more sense when he saw how intense these changes were.

“Now for my favorite part…” the woman said as she helped Justin onto the table and started to apply the chastity cage. It had 4 needles attached to it that seemed designed to go deep into his pubic mound and into his taint. It cupped beneath his balled and left them exposed while his cock was pressed into a small steel cap. With very little clearance. It would be impossible to get an erection with how small it was.

“This will completely block your ability to orgasm by anal, nipple, or vibration stimulation.” The doctor said with a flushed face. “However, a part of your sponsors offer gives you some opportunities. I will give you some time to look that over.” She said as she left.

Justin started reading over the offer… $200K more, get to orgasm once a month… but then… jeeze, this was pretty extreme stuff… Justin pretended like he was thinking hard about this decision, but deep down, he knew this was the sexiest thing to ever happen to him. He called back in the doctor and they got to work.

~~~

A day later, Justin found himself in his new, extremely nice flat in Seattle. He was wearing a new black hoody and jeans to hide his new appearance. He was going to have a week of time to rest from his modifications before he’d have his first guest, and he’d need it. He took off all of his clothes to inspect himself in the full-size mirror.

Spreading his ass-cheeks, he revealed a large buttplug. It was much larger than he was used to, but he’d have to start getting used to it… It was inflated and he couldn’t remove it without texting his sponsor. There was a chain connecting the butt-plug to his chastity cage. In addition, he had a latex covering further hiding his caged cock and making it look smooth. A white lock symbol was printed onto the chastity cage. One of the hardest changes for him to accept was the catheter put into his urethra which forced him to text his sponsor whenever he wanted to relieve himself in any way. He now had belly button piercing and nipple barbell piercings. Additionally, he had two new tattoos around his nipples in large text. His right said ‘SHUT UP’ while his left said ‘OPEN WIDE’. These corresponded to new inserts he’d gotten in his jaw that would magnetically force himself to keep his mouth open or closed, based on which nipple his partners chose to pinch. He experimentally pinched his own nipples and felt the strange sensation of his mouth opening and closing against his will. On his back he had a new tattoo, ‘SATISFIED CUSTOMERS’ It said, clearly denoting that the space beneath the line would be filled in. A part of his sponsors’ deal was additional tattoos, piercings, and even bondage each month. Finally, he had a thick latex collar around his neck that he couldn’t remove. Thankfully it was very normal to dress warm in Seattle.

His new appearance… turned Justin on so much. It was wild to him how fulfilling it was to have been so drastically modified. He had cut ties with his life from before to be ready for whatever outcome came when he pulled his lot, but he had no idea it would be so intense…

“Shit…” He said quietly, and pulled out his phone to text his sponsor.

~~~

The week had passed without incident and mostly involved him exploring the city and getting used to his nice flat, which held a prominent king size bed which made him feel tiny. He was expecting his first “client” tonight and had carefully shaved and painted his finger and toenails black in preparation. He’d stopped short of using make-up but he considered it. The doorbell rang.

He came out to the door and did his best to be sweet and welcoming, “Hello!” Justin said cheerfully to the two individuals at his door.

In front was a taller, blonde woman wearing a nicer fur-lined coat. “Oh my you’re adorable!” She said happily, “See Charlie, I said this would be fun!” She said with some bubbly energy.

The other figure, Charlie, was an imposing man that was easily six foot four. He came in silently, closing the door behind him as he took off his coat.

“Hmm…. We’ll see. Get naked.” Charlie ordered simply. Justin acquiesced, exposing his body in its entirety.

“Damn, that cage is some serious work. Can’t imagine, giving that up…” Charlie said inspecting Justin’s body.

Stepping into the conversation the woman spoke with the now naked Justin as he crawled onto the bed. “You see, sometimes I just can’t satisfy Charlie enough, and I need a break. That’s where you come in sweetie!” She said happily.

Justin was at a loss for words, but tried to show some eagerness. “Yes-“ And was immediately shushed as he was gently thrown on the bed.

“Don’t need you to say anything.” Charlie said as he undressed, revealing a much larger cock than Justin had beneath his cage. After applying a bit of lube and removing the deflated plug from Justin’s ass he entered Justin.

Justin gasped with shock at the size of the intruder and did his best to stay on his knees and elbows as Charlie slowly began to increase his pace with each pump. He tried to lean into his partner, giving himself to them more fully, but either way it didn’t matter much with how strong and thoroughly Charlie was fucking him. Justin was shocked by how impossibly hot sex was with the cage on. He was frustrated that he knew he wouldn’t be able to climax but he felt his arousal rising quickly.

“Fuck, you make that look fun…” The woman said. Taking off her pants she slid in front of Justin, forcing him to lick her out, which Justin did happily.

Finally Charlie came explosively, bottoming out into Justin’s ass causing him to squeal as he did his best to lick up his female partner in front of him. His inexperience was showing and she was helping herself get there with her hands.

Impatiently, Charlie flipped around Justin so that his head hung over the corner of the bed. “Let’s see if these actually work.” He said eagerly as he pinched Justin’s left nipple, forcing him to ‘open wide’. Charlie made short work of slipping his entire dick into Justin’s throat causing him to splutter and choke. He wasn’t ready for this! And he started to panic, but held back. He would hate for his first clients to be the reason he lost out on his huge payout.

Charlie brutally used his throat as Justin’s arms and legs twitched and convulsed involuntarily. Due to his inexperience, Justin passed out before Charlie had finished. But, when he woke up he found a note on the bedside table. “You were a ton of fun!” The note said with a drawn “<3 -Charlie and Bess”.

One Month Later

Justin looked in the mirror and admired his new back tattoo telling him he had successfully pleased 35 partners. At a steady pace of 1-2 partners per night, he had found his groove. He’d spent ample time improving his ability to pleasure woman, as well as to how to deep-throat men and had improved substantially, although he still struggled occasionally.

This month he had gotten a large septum piercing and latex cuffs on his wrists and ankles. Each month had a special surprise but they were all generally pretty tame. The last month was what scared him. That was when he didn’t know what the modification would be. But, if he managed to serve more clients each month, he would be given an opportunity for more money at the end of the six months. He didn’t necessarily need the money, but it was exciting to him to try for it.

This was the most sexual he had ever been and it resonated with him more than he had expected. Being unable to cum had been very frustrating at first, but now he felt like he enjoyed getting aroused even more. He received a text. He had 30 minutes.

Rushing to the bed, he retrieved a vibrator and got to work making himself cum. After about 2 minutes, he realized it wouldn’t be enough. Retrieving a dildo he started pumping up and down on it on the floor as he held the vibrator to himself. Finally, he came, harder than he ever had in his entire life. Clearly the month of denial had heightened his sense substantially making him cum much harder than he expected. Justin could get used to this.

Three Months Later

Again, looking in the Mirror, Justin saw his new tattoo denoted that he had serviced 45 clients last month and 65 clients this month, his personal record. His collar and cuffs now represented a full body suit that covered everything besides his chest and private and was sleek and tight. It had him feel extremely sexy and he often snapped the latex on himself. By now, his butt plug had been exchanged for a much larger plug that visually distended his stomach, where he also had a new tattoo around his belly button, ‘ANAL SLUT’. Sticking out his tongue he admired his new tongue piercings, creating a smooth textured experience when he pleasured his partners.

Justin was a pro at this point. He enjoyed his job immensely and being paid $2,500 a day didn’t hurt either. He’d had a couple return clients at this point, picked out his favorites and his least favorite, and even started to perfect his own special services. He was especially proud of what he could do for his female client’s with his tongue. He even had a handful of female clients that would come to him exclusively to get head all night.

Still the fifth month loomed. His phone pinged, sweet release again.

Five Months Later

Perhaps this had gone too far, Justin thought, looking in the mirror. On his back a 70 and 75 now graced his back, while all the preceding numbers had an additional strikethrough. Sticking out his tongue, he revealed that he now had a modified split tongue which had made his cunnilingus prowess just more intense. His latex collar had been replaced with a much thicker latex collar that covered his entire next from below his chin and down. Lip piercings now stood out from his lips and his shaved head held a beautiful flourish of tattoos. His stomach was even more distended by his butt-plug and he had a new tattoo right around the rim of his rosebud of an asshole, made even easier to see and tattoo by his permanently stretched asshole. His cock remained neutral and unchanged.

A ping went to his phone and Justin went to take care of himself eagerly. In the back of his head he was confused… This wasn’t enough? Surely his sponsor wanted more from him in his last month of service. As soon as he had climaxed he had his answer. His door knocked and familiar suited men appeared. Helping him into street clothes and collecting what few personal affects he had, they took him away.

Some transport later with a hood over his head and a pit in his stomach, Justin found himself in a dark, premier looking nightclub. “Where are we? What’s-“ Justin said before his mouth shut against his will. The attendant explained.

“For the last month of service, your mouth will be either forced open or shut. We don’t care what you have to say. Period.” He said bluntly. Another one of the men produced strange latex bags. Two went onto his feet and created a perfect seal with his existing feet. After forcing Justin’s hands into fists, the other two bags went on his hands forcing them closed.

Justin looked at them in panicked confusion, until one of the men forced him to his knees. After producing several belts they further trapped his hands by binding his forearms to his biceps.

“If you manage to serve over 75 clients in the next month, you’ll be offered an extension. That is all.” And they were gone.

The next month was a blur for Justin. Each morning and afternoon he would be mostly alone, relying on the staff at the club to tend to him from time to time. Then as soon as the afternoon turned to evening, he would be worked hard.

Sometimes he would just lick up women as they requested it, other times he would be fucked brutally by several men in a row while women laughed at him and pinched him to watch him squeal and squirm. Sometimes he would be the center of attention, being fucked by a sturdy cock while blindfolded and disgraced in the center of the club. Other times he would be fucked quietly in a private room or corner of the club. Whenever that happened he would do his best to overperform to get back to the group as quickly as possible. He surprised himself with how much of a slut he had become. The lewd sound of his butt plug being removed and shoved in throughout the night was commonplace.

The depravity increased over time until Justin was usually reduced to a little rubber pet as his legs were also tied up and wine bottles were put in his ass like some depraved beverage holder.

When he wasn’t entertaining, his bondage was obnoxious and frustrating, but the second he was getting fucked it turned him on even more. With how much sex he was having, his inability to orgasm was more of a benefit to his sexual stamina than it was annoying. Maybe he just hated to lose, but he was going to have his 75th client no matter what.

End of the Sixth month

It was the end of the sixth month. The only way he could tell was that the TVs in the bar that showed the news in the morning helped me keep track of time. Otherwise Just would have had no idea at all. The club was extremely busy tonight. By this point I had been on my knees and elbows exclusively for over 15 days and was used to being mute entirely. It was especially frustrating when playmates left his mouth open at night and he had to awkwardly beg a staffmember to pinch his nipple and let him close his own mouth.

One of the staff put a collar around Justins mouth and guided him into a private room.

Here, he saw a woman silhouetted in the dark. He couldn’t see any of their features besides this in the darkness but he knew immediately, this was his sponsor.

“Congratulations Justin, You’ve serviced over 100 clients this month. You must be very proud.” She said. Her voice dripping like honey. “How you are right now is perfect, exactly how I like my men.” She said.

Justin’s erection usually only responded in the middle of intense fucking now from its training in its cage, but now, hearing the woman’s voice he felt his member strain against it’s cage again. He moaned in appreciation.

“You have a choice now Justin. You can leave. You will be given the $450K you came here for, and we will reverse as many of the modifications as you like. You’ll be able to cum at will again and can live your normal life. This is your first option.” She said, still covered in shadow.

“Or, you can choose to extend your contract with me.” She said calmly. “You would not be paid anymore and you’d truly give up all of your control to me. I wouldn’t call you by your name Justin anymore. No one would. You may be freed in several years, or never again. At which point you’d still be entitled to your money. I would make further modifications to your cute body, and bondage would become a more consistent part of your life. Cumming will become even more rare for you and slowly I would introduce more humiliations to your life and clever, painful modifications as well. Frankly, I never want to hear your voice ever again after I ask you this question.” She leaned forward, exposing vibrant red hair. “I’ll be honest Justin, I wouldn’t recommend it, it’s a very intense life.”

Justin was trembling in anticipation. About 3 months ago, he realized he would have done this even without the money, it made him so happy to be used so constantly. This last month had been heaven after he had gotten used to his dehumanization… But to give up that much control? To be at this woman’s mercy? Intoxicating…

“So, I’m going to let you speak for a moment. After which you’ll either escorted out, or spend the night with me.” She said. “Yes to stay, No to leave.” She pressed a button on her desk and Justin felt control of his mouth return.

“YES!” He immediately eagerly said, and felt his mouth go slack again as the magnets opened his mouth.

“Good boy.” The woman said, negotiating him to her sex where he’d stay serving her for the remainder of the night.

Perhaps we’ll return to Justin’s fate in the future. For now, the reader will have to imagine