The Sissy Investment Ch. 04

Colleen shuddered. Judge DeVon Carver was one of her regular and most sadistic private clients. The in-person private appointments with her as a submissive whore saw Justus charge a jaw-dropping 2K per session, with each encounter lasting a full two hours.

The good Judge had taken to using Colleen twice a month, and combined with her other at-home clientele, Colleen was pulling in an extra 10-16K monthly for Daddy J on top of what he made from her on-line subscribers.

In all, Justus was now earning a little over 20K per month from monetizing Colleen's body, with only a tenth of that being declared as actual income. He'd always known she'd be his money making machine - getting her fired from her office job was just a way of getting some severance pay added to his growing pile of cash while freeing up her time to live as his permanent whore.

"Come in Judge, come in..." Justus said jovially as he waved DeVon Carter into the loft.

"It's wonderful to see you again Your Honor, and I know Colleen is looking forward to spending some time with you this evening."

Surly and ill-tempered, the cruel Judge simply grunted and inquired if the slut was ready for him and if she had any other clients for the evening. When the answers came back affirmative and negative respectively, DeVon Carver slammed down 4K in cash and announced that he was taking a "double" tonight, as he'd had a shitty week at work. The slut needed to pay for it good if he was going to have any hope of effectively working out his frustrations.

Justus smiled, pocketed the cash, and kindly said to his paying customer... "Judge...you've been such a loyal client that I want you to just take your time with Colleen this evening...consider her yours until dawn if you like."

Justus Hill knew from his drug-dealing days how to keep an addict coming back for more, and it wasn't like he was going to make any more money off the cunt's body that night even if Judge Carver left after two hours, so it was good business to offer the bitch up for the entire night.

Plus, he knew that meant the little White whore was going to get fucked into next week which made him hard as a rock in his jeans.

When Judge Carver let himself into Colleen's bedroom, he found the little minx displayed exactly as he had requested as if from a menu at a restaurant.

On Colleen's feet were a pair of brightly shined patent leather MaryJane buckle-up shoes, two sizes too small to pinch and painfully squash her feet in the restrictive unforgiving material.

She sported knee-high white socks, a black and red plaid micro-mini skirt that barely covered half of her ass when she was standing upright, a thin white cotton t-shirt which read "SLUT" across the chest in stylized script, a pink rubber studded dog collar around her neck, and her hair was tied into two excruciatingly tight pig tails at the sides of her head...tied off with pink and yellow ribbons.

On her dick-slurping lips a thick coating of glittery gloss had been applied, and she had thick black liner around each eye.

Colleen was not standing upright to greet her client as DeVon had also pre-arranged that she be restrained in a specific bondage position for his arrival.

Colleen's upper limbs were stretched directly behind her by a long arm binder made of thick black leather. The D-ring at the end of the binder had been hooked to a rope and pulley system, and Daddy J had yanked and yanked on the rope pulling the slut's arms up behind her and forcing her to bend over at the waist.

Her ankles were tied together with a short leather belt, similarly her legs were strapped to each other in this manner just above the knees. This decreased her base of support and placed most of her weight off balance pulling even harder at her shoulders which were in total agony by the time Judge Carver arrived.

A bright pink ball gag was stuffed into the sissy's mouth, and thick strings of drool were stretching their way down to a puddle on the floor that had been created over the last 45 minutes that Colleen had been kept in this torturous and stressful position.

Her giant boobs were not supported in a bra and so they hung down in front of her chest like two dangling melons, ripe for the picking. As the slut wheezed and gasped and struggled to keep her balance the enormous tits dangled and swayed from side to side like giant pendulums, keeping her unsteady and ratcheting up the stretch on her shoulders.

When Judge Carver closed the bedroom door and announced "Hello Colleen...it's time for your punishment" the little sissy nearly wet herself. Judge DeVon Carver was extremely sadistic with a chip on his shoulder, and he liked nothing better than to abuse the smaller, weaker, Colleen to work out his frustrations.

"Look at me when I'm talking to you, whore!" DeVon roared as he laid a thunderclap of a barehanded spank onto Colleen's left bum cheek.

The sissy screamed in pain through her gag but got the message and immediate strained her neck backward to maintain eye contact with her customer. As the force of the blow rippled through her body her hanging breasts swayed back and forth like two over-filled water balloons.

Judge DeVon Carver was 59 years old, wiry thin with grey hair that looked like steel wool and was the only Black man Colleen had met who was under-endowed when it came to penis size.

Not that it mattered what size his cock was -- the Judge, was impotent. He did, however, make up for Mother Nature's stinginess by amassing a staggering collection of diabolically large strap-on cocks that he liked to use among other things to dilate Colleen's gurl-cunt.

After fully inspecting his merchandise for the night to make sure her clit was securely caged and that her boi-labia were nicely plumped and primed, DeVon set his duffel bag down on a low table in full view of Colleen where she was doubled over in agony so she could see him emptying its contents.

"His Honor brought you three of his cocks to satisfy you this time bitch" DeVon announced, as he laid out the gigantic rubber invaders on the table as well as the leather harness that held them suspended in between his thighs.

"Two of them of course you've had the pleasure of making love with already...but this one cunt...this one is brand new just for tonight. It's called the Touchdown!...you'll understand all in good time. For now, though, I guess I better mix up some lube for that tasty hole of yours so we can get started. I know you're eager to get fucked and all stretched open for my pleasure."

Judge Carver placed a large shaker cup on the table and added a healthy amount of j-lube powder as well as some warm water and began to shake and mix the cocktail until it was thick and goopy...just the way he liked his pussies to be -- sloppy.

He then took a small bottle filled with a reddish liquid and added a few drops of it to the lube before shaking and mixing it again, giving the whole container just a hint of a cloudy murky coloring. Tabasco sauce. Not enough to really burn the whore's pussywalls...but enough to cause a delicious amount of inflammation which would help her cunt become puffy, engorged, and swollen.

Since he was only using rubber cocks on the bitch instead of his own penis, he didn't have to worry about the fire-lube as he called it affecting him. Colleen was the only one who would be overheating tonight.

Filling a large, oversized syringe with the lube, DeVon place the tip of the loaded weapon at Colleen's lips and then by depressing the plunger ever so slightly expressed enough lube to moisten her outer ring and allow the thick plastic cylinder to slide home into her cunt.

Colleen grunted into the gag as Judge Carver stuffed the entire 10-inch device into her anus, and then slowly withdrew it all the way, depressing the plunger as he did so, coating the slut's insides with viscous lubricant the whole way.

Two more times she was loaded up in the same fashion and failed to see the humor in the Black man's joke when he said next time, he'd probably need to use a caulking gun to slick the cunt up before he worked it over.

Judge Carver however thought his joke way hilariously funny and laughed out loud as he ordered Colleen not to lose a drop of her pussy-juice while he was busy getting his first erection strapped into place.

Cock number one was realistic looking, but ominous. A twelve-inch hard rubber truncheon in chocolate brown that was a scaled-up version of a porn star's real-life appendage. At three inches in diameter, it was a formidable starting point for the sissy-gurl, who was just starting to feel the warming effect of the spicy additive to the slop that her client had injected up her cunt.

As DeVon slathered a little more lube around on the shaft of his cock, he pulled another couple of small items out of his duffle.

The first was a small, two-pronged metal hook with blunt ends that was attached to a foot-long leather lanyard. The second, was a short length of rope.

The sadistic Jurist positioned himself behind Colleen, and with a slow steady pressure dilated her around the head of his cock, feeling it pop inside of her with a satisfying sound of suction. Allowing her to get used to the girth of the invader, DeVon reached forward and pulled the slut's head back by using a handful of her hair in one hand, while he inserted the two prongs of the hook one into each of her nostrils with the leather lanyard pulled back over her forehead between her eyes.

Running the short length of rope through the leather lanyard, DeVon wound the ends around his fists and pulled back gently, effectively creating reins with which he could control Colleen's body as he mounted her and worked his rubber cock deeper and deeper into her cunt.

"OK slut...time to take this fine White pussy for a ride!"

Thickened lube was beginning to bubble out around the circumference of the rubber cock as DeVon pulled back with his hands while pushing forward with his hips -- all at once arching the slut backward and sinking twelve inches of hard rubber up her cunt.

Once fully seated, he kept Colleen impaled on him like that for nearly five minutes before he began to slowly saw in and out of her...opening her up...and reaming out her asshole.

The slight friction of the giant rubber cock inside of her despite the lube she had been filled up with, was enough to start activating the tabasco additive and it was really beginning to make her inner walls sweat and swell in response.

Colleen let out a low, constant, gutteral groan as Judge Carver set up a comfortable rhythm of yanking her back toward him to stuff her to the hilt followed by letting some slack into the reins as he allowed her to slide forward and nearly off of his cock...long-dicking her as he watched her lips turn crimson in color and begin to really thicken up.

Judge Carver, knowing that he could use Colleen all night if he wished, took his time and rode his bitch in this manner for a full thirty minutes before pulling out and marveling at the distended swollen hole left behind after his exit.

Colleen's eyes were blurry from the strain on her nose due to the hook, and her insides were radiating heat. Engorged, her anal lips looked like someone had placed a bright red donut on the outside of her sphincter.

DeVon took the opportunity to change both his erection, and the position of his bitch so she could enjoy his next cock in a whole different way.

Sweet relief of having the arm binder finally removed and being allowed to stand upright was short lived, as DeVon manhandled Colleen over to the bed and forced her down on her hands and knees.

He then pulled her wrists back between her legs and secured them to each of her ankles. Colleen was hobbled, and displayed with her pussy-hole aimed upwards practically begging Judge Carver to open her up and stretch her even more.

Colleen's cumhole was bubbling with spiced lube that had been nearly churned into butter by a thick column of rubber hammering in and out for the last half hour.

Having replaced his porn-star replica with an even longer torpedo that the manufacturer had dubbed the "Battle of the Bulge", all Colleen could do was wait to be speared like a trussed-up piece of meat.

The fourteen-inch monster was jet black and consisted of a flared head that immediately expanded out to a bulbous knot of thickened rubber measuring four inches in diameter, before immediately slimming back down to an almost amateur-hour diameter of two-inches.

Three inches of length continued that way until the dildo once again flared out to a second bulge spanning an eye-watering six-inches in diameter before narrowing again so the entire volume of the beast could be lodged inside the sub's ass-cunt provided they were able to dilate to such proportions.

In Colleen's case, she was not being given a choice as to whether she could tolerate the entire mass of DeVon's second cock in her pussy...he was going to stuff her to the bursting point come hell or high water.

Back and forth the judge worked the double-bulged monster, delighting at the way Colleen's lips were riding its surface as they clung to it as it sliced in and out of her.

The judge was floating on a cloud of euphoria, his endorphins began to release from the pain he was inflicting on the submissive White sissy. Colleen on the other hand had more-or-less mentally checked out.

In exquisite pain, she was now drooling and mumbling around the brutal ball gag with unfocused eyes and the sound of the air in her lungs being forced out of her with every inward thrust of her lover.

DeVon pummeled Colleen in this position for almost an hour before offering her any relief whatsoever, dripping his own sweat on her back as he levered himself in and out of her with his massive rubber weapon.

Needing a rest himself, he decided to enjoy a large glass of ice water from the pitcher Justus had provided, picking up a second empty glass and holding it between his thighs as he gulped down the refreshing water.

The man was pissing while he was drinking, urinating out what would become Colleen's refreshment which she would have no choice but to accept with gratitude.

Placing her warm glass of fresh piss on the nightstand, DeVon untied the slut's wrists. Not wanting however to lose any of her hard-fought dilation, he inserted one of Justus' larger butt plugs into her cunt as a place holder for his third and largest erection of the night.

"Drink up whore" DeVon ordered...

"I'm gonna rest a few minutes before pleasuring your hole with my new cock, so you have plenty of time to savor that delicious nectar I just pissed out for you. You be sure to tell me how much you enjoy it and how lucky you are to be allowed to drink a Black man's piss. Be believable now...if the Judge don't believe you, it means you're gonna get punished."

With the ball gag removed, DeVon basked in the humiliation of this young White she-male entertaining him with how much she loved drinking his piss...how lucky she was to be getting it...how she would like nothing more than for him to piss out another big glass of it for her to gulp down.

So delighted was Judge Carver with Colleen's performance, that he allowed her to simply continue the verbal adoration for several minutes before shutting her up with another of Justus' gags that had been provided as part of the service for which he had paid.

The silencer DeVon had opted for was an inflatable butterfly gag with a detachable bulb. Once seated behind her teeth, with every squeeze of the bulb the bladder inside her mouth expanded to fill every nook and cranny of her oral-cunt. Unable to spit it out, Colleen had no choice but to endure whatever size the Judge decided to make the gag before he detached the inflation device.

Bigger, and bigger...pump, after pump, DeVon sealed off Colleen's mouth with the gag expanded to such proportions that she thought her jaw was going to dislocate.

Colleen was rendered completely mute.

Arms and legs now free, the only bondage DeVon applied to the slave for the next round of fucking was a steel collar around her neck, bolted to the bed frame by a long thick chain.

Collen could run, but she could not hide. DeVon would have no need to chase her as he could simply reel her back in toward him by yanking and pulling on the chain secured around her neck.

She was so weak from the meagre Daddy J kept her on as well as the abuse she had already suffered tonight that the Judge knew she was going nowhere anyway, and that she would be unable to fight him off.

Securing his final cock of the night into his harness, DeVon figured it was time to show Colleen why her next boyfriend was called "The Touchdown".

Colleen's eyes nearly bugged out when Judge Carver showed her another inflation bulb, this one attached to his latest rubber erection. While only 10-inches in length, as DeVon began to pump the entire length of the dildo began to thicken and swell, mostly in the middle section of the cock.

By the time the demonstration was over, it looked like the Judge had a big black football hanging in front of his crotch.

"I counted whore...it takes fifty squeezes of the bulb for my cock to reach its full girth...10-inches long...and 8-inches wide at its thickest point. When we get all the way to your fifty squeezes, you're gonna hear your man yell Touchdown!...and you'll know you've been stretched out beyond all recognition bitch."

"This cock is going to stretch you slut...and I'm going to love every second of fucking and blowing up your pussy with it while you try to scream through that big rubber balloon you've got filling that filthy mouth."

By the time Judge Carver was at forty squeezes, Colleen was crawling and clawing in vain at the bedsheets, trying to get away from a sadistic man she was now tied to by an enormous knot of inflated rubber.

With every hiss of the bulb re-filling, she let out a silent scream thought the butterfly gag. As DeVon roared out "TOUCHDOWN" and spanked both of Colleen's butt cheeks she began to spasm while mounted on his crotch like she was having a seizure.

"Hold still whore!" DeVon ordered as he slapped Colleen's ass harder. "We ain't even gotten to the fucking part yet."

It took a lot of strength but by placing both of his hands on Colleen's hips and pushing them forward as he leaned his body weight back, Judge Carver began to draw the rubber football out of Colleen's cunt, dilating her anus to epic proportions as he did so.

4, 5, 6, 7, and then 8 inches of diameter were holding open Collen's cuntlips as they blanched and became taut as rubber bands around the inflatable erection.

By just releasing his pressure against her hips she immediately was sucked back onto the huge dildo with the entire football-like shape of it buried inside of her.

Colleen thrashed from side to side each time Judge Carver drew the widest part of the dildo level with her outer lips and relaxed slightly as he allowed it to sink back into her ever-deepening hole.

She was drenched with sweat and began to cry when she heard DeVon's voice from behind her saying that he thought a good thirty minutes of making love to "The Touchdown" would be a good start...so she should just take it like a good sissy-whore and let a superior Black man have his way with her and get his money's worth.

When it was over, as Judge DeVon Carver stood in the hallway outside of Colleen's bedroom he said to Daddy J... "When is she available next week...I want to use and stretch her before I leave on a business trip. I'll be gone a couple of weeks and it's going to be stressful, so some relaxation time fucking your whore would do me good before I leave."

After settling on a date, and seeing the good Judge to the door, Justus went back to check on Colleen.

Colleen was nearly unconscious, still secured to the bed frame by the padlocked steel collar. Now with her body fully relaxed, Justus marveled at how opened-up Judge Carver had made her pussy.