The Gambler: Chapter 7

Heyyo! Thank you to everyone from the Interactive Story Club for helping to put together another amazing chapter. Make sure to vote in this week's poll and don’t forget to comment if you have any additional ideas for chapter three and beyond! I hope you enjoy!

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Despite the little time with which Clara had to make Blake’s wardrobe selection, she found herself caught between two very blushy options. One was the Princess Package, which was by far the most feminine clothing package in the bunch. It came with a short, bright pink princess dress with big, poofy shoulders, a pair of sparkly high heels, and a tiara to top off the regal ensemble. The other option was the Humiliation Package, which made Clara blush just looking at it. It was made up of a tiny crop top that said “Sissy Slut”, a massive waddle spreader, and locking mittens and booties to ensure the wearer would be bound to their misery.

If Clara had a coin, she would’ve already resorted to flipping it. Instead, she decided to press both at the same time and let fate decide. Hovering a finger above each option, she closed her eyes and pushed forward. When she re-opened them, she was beyond shocked to see that the screen listed both options as selected. “Well, this oughta be interesting,” she snickered as she pressed the confirm button.

*WOOSH!*

The moment Clara locked in her selection, a glass tube suddenly shot down from the ceiling and surrounded the circular cubby that Blake had been hiding in. As it sealed around him, he pounded his fist against it, hoping that Clara would find him before something bad happened. However, he was shocked to see that not only did Clara know where he was hiding, but she was also the one to activate the glass case. Smiling viciously, she gave him a subtle wave before turning to exit the room.

“Clara, w-what did you do?! Get me out of here!” screamed Blake, unaware that the soundproof casing made certain that no sound would escape its boundaries. All he could do now was wait and see what Clara had activated.

“Hello and welcome to the Sissy Dressing Chamber,” said the machine in a feminine, monotonous voice, “Please stand in the center of the circle and keep your arms and legs tucked in. Dropping in 3, 2, 1…”

Still on his hands and knees, Blake quickly tried to stand up in order to obey the robotic voice's instructions. Unfortunately, the countdown was so sudden that he was only halfway up when the floor dropped out from under him. This resulted in an uncomfortable landing on a very slippery slide that gave him no opportunity to correct his positioning. He rolled and tumbled through the tube until he was finally spat out into the padded room he’d seen earlier, landing with a big “Umf!”

“Initiating cosmetic sequence!”

Before Blake could get a grasp on his new surroundings, a set of mechanical arms with soft, white-gloved hands descended from the ceiling and plucked him from the padded floor. The arms held him in such a way that any slight resistance put him into an agonizing position. He was left with no choice but to let the robot hands do whatever they wanted with him.

Another pair of hands came out of the walls holding various cosmetic items. Blake whimpered softly, realizing exactly where this was going. “C-Clara please, I’ll be your baby for the week, just please don’t make me a- MMF!” He yelled, his words cut off as a hand grabbed his cheeks tightly to puff out his lips. A slathering of pink lipstick was layered onto his lips as other hands moved in with blush, eyeliner, and other horrid make-up tools that Blake wouldn’t be able to name with a gun to his head. Things only got worse when his makeover became painful as both his eyelashes and eyebrows were plucked to perfection.

Looking ahead, Blake was forced to see a dull reflection of the cartoonishly feminine mess his face was becoming. Adding fuel to the fire was the round, metallic dome that dropped down from the ceiling and covered his entire hairline. Part of him was curious about what they were planning to do, given how short his hair was. He cursed himself for his curiosity as the dome lifted back up, unveiling his ear-length hair had been forced to grow out until it reached midway down his back. Not only that but his locks were given bouncy, little curls that made him look as though he was trying to cosplay Sherley Temple.

Mercifully, after his hair was finished, the hands around his face retracted, giving him a moment of reprieve. His eyes grew watery as he stared at his new reflection, barely able to see his masculine feature buried under pounds of gaudy makeup. He was no beautician, but his face appeared as though two widely different makeup styles were at play, with his eyes looking soft and petite, while his lips and cheeks were bright and bold. Whoever programmed this crap must’ve had a terrible eye.

“Cosmetic sequence complete! Initiating dressing sequence!”

Then, as abruptly as his rest period had started, Blake was thrust back into the next stage of his torment. Out from the walls came more hands, only this time, they carried with them something much more terrifying than makeup. He was helpless to stop the hands as they placed a big ball of pink fabric below his feet and began to lift it up onto his legs. The material was soft and silky, which had an instantaneous reaction on his exhausted man meat. His cock perked back up, its intense throbbing threatening to burst the tapes off of his diaper as the dress reached his pelvis and began to unravel.

Closing his eyes, Blake decided not to watch the inevitable unfold, hoping to spare what little remained of his male ego. Unfortunately, this only made the sensations of having the smooth, foreign fabric rubbing across his bare chest even stronger. He didn’t want to admit it, but he didn’t mind how light and airy the dress actually felt. That idle thought didn’t get far, though, as he started kicking himself for even contemplating an upside in all of this feminine chaos.

As much as Blake didn’t want to open his eyes to see the nightmare that was befalling him, the moment that he felt his left hand become encased in the same silky fabric as his dress was alarming enough to force his eyelids up. Sure enough, his fists were being shoved into two thickly padded mittens, making sure he would be unable to use them for basically anything. Unfortunately, opening his eyes to confirm this only made it possible for him to see how his wardrobe was developing. Needless to say, he was less than thrilled.

Blake was now wearing a fluffy, puffy princess dress with enormously poofy shoulders. The bodice was incredibly form-fitting, giving his flat chested torso a bit of curviness, while the skirt was pushed up by a wide crinoline, keeping the hem well above his diaper. Combined with his hair, makeup, and plushy mittens, he failed to find even a hint of her former male self that had walked into this establishment only a couple of hours ago.

Finishing off Blake’s wardrobe was a pair of sheer tights that erased any traces of leg hair that he had and a pair of pink sequined high heels. The heels were not for the faint of heart, either, given that they stood at nearly six inches. With the heels in place, several more hands came toward him, each holding tiny padlocks. One by one, the dress, the heels, and the mittens were all locked onto his body, making it clear that he would not be getting out of this outfit on his own.

Blake assumed that the locks meant an end to his torture at the mercy of the dressing hands. Looking across the room at the two-way mirror, he had a complete, if not slightly mismatched ensemble. He wiggled a bit, hoping that the hands would release him shortly. As fate would have it though, his wardrobe was nowhere near finished.

Two more arms sprouted up from below, making it hard for Blake to see what was happening. He looked back at the mirror, his heart stopping as he saw what was coming up between his legs. It wasn’t a diaper, it was something much bigger and far more ridiculous. The thing looked more like a caricature of a diaper than a real one. Its PVC outer lining shined brightly, taunting him with its presence. Slowly, his feet were guided into the leg holes, which felt like having his legs swallowed up by a pillow monster. The soft, cotton interior was so plushy that it took well over a minute to lead his toes through the whole thing.

“S-Stop! I-I’m already diapered! I don’t-Mmmmmmf!” he shouted before his mouth was stuffed full with a large binky that was promptly tied around his head. There was nothing he could do. No one he could plead to as the outrageously thick waddle spreader absorbed his already large diaper, combining their girth to make an impossibly huge super-diaper!

With the cherry on top of a tiara being placed delicately on his curly hair, Blake was finally lowered to the ground as the machine said, “Dressing sequence complete. Testing will begin momentarily. Please stand by.”

Returning to the padded floor with a soft *pomf* as he landed on his diaper butt, Blake was shell-shocked by what he had become. He looked like some sort of slutty princess sissy baby! As the hands around them disappeared, he began trying to remove anything he could to lessen the humiliation he was feeling. Sadly, he couldn’t even get the tiara off of his head, much less get any other aspect of his wardrobe to budge. It was the damn mittens that prevented him from taking any action. If he had control of his fingers, this would all be a different story.

Giving up on removing his sissy princess attire, Blake decided to spend his free time looking for an exit. He naively tried to stand, resulting in him faceplanting down on the spongy floor as both his high heels and the padded ground made it beyond unfeasible for him to do anything more than crawl. It was embarrassing, but he was determined to escape this mess. Slowly but surely, he made his way back to the panel that he entered the chamber through. He tried to push and paw at it, but the blasted thing didn’t budge so much as an inch. Looking around the room, he failed to see any other exit, so he continued to try his best to dislodge the entry panel.

“Okay, baby girl! Are you ready to learn how to be the best sissy ever?!” said another robotic-sounding voice, only this one seemed far more upbeat than the voice used during his makeover.

Blake didn’t like the sound of whatever was about to happen. Clearly, Clara had enrolled him in some sort of sissy course without sticking around to see how it went. Grunting into his pacifier, he folded his arms and flopped back onto the padded floor, feeling a strangely noble sense of defiance in his defeat. So long as he held onto that defiance, he knew he’d be alright.

“Excellent, I knew you’d be excited, sissy baby! Let’s not waste any time and get started!”

TO BE CONTINUED…

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