The Gambler: Chapter 4 (Patreon)

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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Blake’s pride was falling apart at the seams as his eyes scanned through the various diaper options at his disposal. His first thought was to go for one of the plain white diapers on the top shelf. Something about the idea of choosing a patterned or colorful diaper felt extra childish to him. However, the downside to the plain white diapers on display was that they were all ridiculously massive. As much as he hated to admit it, many of the more infantile diapers also had the advantage of being slimmer.

After careful deliberation, Edan decided to aim for the thinnest-looking diaper, regardless of the pattern. “Th-That one,” he stuttered as he pointed his finger towards the shelf, “The one on the bottom left.”

Bending down in front of the changing table, Clara gestured to the diaper that she believed Blake was referring to, offering him a cheerful smile as he nodded yes while blushing up a storm. Snatching a large from Blake’s diaper stack of choice, her eyes lit up with unending joy as she gazed upon his selection.

In Clara’s hand sat a powder blue diaper with pink and white teddy bears and hearts decorating both the front and back. Blake felt nauseous. If he’d seen the diaper unfolded beforehand, he never would’ve picked it. Of course, he had to choose one of the sissiest diapers available. One look at Clara’s face told him that there wasn’t a single good idea swirling around in that scheming head of hers.

Sure enough, Clara was already imagining all the sissy fun that she could have with baby Blake. She was on the fence before, but after choosing such a pretty nappy, how could she possibly resist. Not wanting to scare him more than he already was, she decided to keep that one a secret for now. If she played her cards right with his training, she could have him begging to be her sissy diaper slut by week’s end. Such a naughty thought had her pussy moistening and her mind racing.

“Alright, Blakey-poo, it’s time to get you ready for your first changing!” exclaimed Darla, who gleefully lifted Blake up by his armpits and deposited him safely atop the large, padded changing table, “If you wouldn’t mind, Clara, I can give you a hands-on tutorial. This is your first time too, is it not?”

Clara nodded enthusiastically as she said, “Mhmm! That would be lovely! I want to be able to do this on my own next time, so any tips and tricks you got for me are more than welcome.” Stepping up to the table beside Darla with the unraveled diaper in hand, her heart throbbed as she gazed upon her helpless and pathetic rival. This was all so thrilling. No wonder Martha couldn’t get enough of it.

Unable to take his eyes off of Clara’s domineering expression, Blake could feel every pair of eyes that were staring at him. Quite the gathering had formed since they stepped up to the center-most diaper table, all of whom were eager to see someone’s first. As much as he couldn’t stand how humiliated staring at his new Mommy was, it was definitely better than locking eyes with a random stranger who saw him as little more than a piece of property.

Flattening out the diaper, Clara laid it down on the table in between Blake’s legs. “Lift up for me, sweetie,” she said, lightly tapping Blake’s inner thigh with two fingers.

Blake flinched from the pleasurable ripple effect that Clara’s touch had on him. Already hard from the moment Clara stripped him, his twitching cock was growing thicker and more bulbous by the second; a fact that did not escape the notice of his two female caretakers.

“Oh, my word! This boy is gonna love it here if he’s already getting this erect!” said Darla as she prodded Blake’s girthy meat stick. She then turned her head to Clara with a knowing expression “I think I heard you mention this was only for a week, correct?”

A little caught off guard by the question, Clara responded with complete honesty, “Um, yeah. It was just a silly bet we made at the casino. Why do you ask?”

“Because if buddy boy is already this stiff before his diapering has even truly started, there’s no way he’ll want to stop at one week,” Darla stated, turning to Blake with a knowing expression, “I’ve seen your type too many times. You’ll crack. They all do.”

Biting his tongue, Blake wasn’t about to let this diaper bitch’s taunting get the better of him. The first key tactic of bluffing was to enrage your target and there was little doubt in his mind that Darla wasn’t aware of this fact. He really couldn’t let his guard down for even a fraction of a second in this place. Instead, he donned his trademark poker face. If they thought he’d be easy to break, they had another thing coming.

“Ooh! This one’s a fighter too!” shouted Darla as she nudged Clara with her elbow, “You’ll have your hands full with this one for sure.”

Chuckling, Clara ran her fingers through Blake’s hair. “I think I’ll manage. After all, I’ve studied every move he’s made since we were amateurs,” she said with more confidence than she’d ever felt in her life. The bet may have been decided at the poker table, but clearly, there was a grander psychological game at stake. This wasn’t just about embarrassing Blake anymore. If he was going to be this defiant, she’d have to step up her game. “Well, shall we get started?”

“I think we’ve made our audience wait long enough,” responded Darla, acknowledging the onlookers around her with a performative smile. Goddess, she loved her job. “Okay, so the steps to changing a diaper are relatively straightforward. All you have to do is clean off his diaper area, load him up with plenty of power and lotion, and tape him up. However, as simple as may seem from the onset, dealing with an infant of any age is never as easy as marking off a checklist.”

Snatching a sanitizing wipe from a nearby container, Darla grabbed Blake’s exposed penis without hesitation, catching both him and Clara off-guard. “Male genitalia needs to be thoroughly wiped, so don’t be shy when it comes to cleaning every nook and cranny,” she said in a surprisingly no-nonsense manner.

“Of course!” affirmed Clara, who was giving Darla her undivided attention. Watching how she handled Blake’s naughty bits with almost no emotion made her realize how normalized this was for her. The male phallus had always seemed so forbidden and imposing to her, but Darla treated it like a silly toy that boys got to play with. Such a raw display of dominance only served to stoke her caregiving ambition.

Such admiration was not shared by Blake, who couldn’t bodily decide whether Darla’s sterile touch was insanely arousing or painfully ticklish. Slamming his head back on the table, he felt weakened by the professional caretaker’s penile prowess. Caught between wanting to cum and wanting to disappear from this plane of existence, his mind was lost in a tailspin by the time Darla was discarding the well-used baby wipe and moving on to the next step.

“Now that the baby’s all squeaky clean, it’s time to move on to the fun part!” said Darla as she took up a large bottle of baby lotion in her hand and proceeded to squirt a large helping directly onto Blake’s genitals, “Here at the Auction House, we believe there’s no such thing as too much lotion. Just be prepared, your baby slave may want to hump everything in sight if you go overboard, so know your Little’s limits.”

Just like with the wipes, Darla was exceedingly clinical when it came to spreading out the lotion with her hands. Even still, Blake’s erection grew to its maximum length as she lathered up his cock and balls. Hearing giggles from all directions in response to his arousal, he buried his face in his hands and silently whimpered to himself.

Unfortunately, Darla was having none of his shyness. Pointing to his arms, she motioned to Clara, “He needs to learn there’s nowhere to hide on a changing table,” she said sternly, prompting Clara to grab both of his arms and pry them away from his face.

The moment Blake reopened his eyes, he was greeted by his own cock being rolled towards him as Darla placed her arm under his knees and lifted his rear end high. “Make sure his backside gets equal attention as well. Baby slaves are whiney enough without adding a diaper rash into the mix, unless, of course, they really earn it,” she said, emphasizing her last point with a small smack across Blake’s butt.

With lotioning now complete, the next step was powdering, which mercifully was nowhere near as harrowing as the baby lotion had been. “When it comes to baby powder, just make sure to get an even layer on any part of his body that’s going to be inside of the diaper,” stated Darla as she sprinkled baby powder across Blake’s crotch and bum as if she were a five-star chef seasoning a prime cut.

At last, the grand finale was here. Straightening out the diaper under Blake’s butt, Darla looked over at Clara and said, “Why don’t you go ahead and do the honors? I’ll do the tapes while you hold it down.

Clara was ecstatic as she took the reins from Darla. Soaking in another of Blake’s priceless expressions, she wanted to paint this image of him in her mind. His quivering lips. His furrowed brow. His clenched jaw. The tiny droplets of sweat on his forehead. The look of utter panic in his eyes. It was the antithesis of the public persona Blake had cultivated for years and she couldn’t get enough of it.

Folding the diaper over his pulsating cock, Clara made sure to engulf his privates within the soft walls of the padding with her palm. This nearly caused an eruption of epic proportions to occur.

Blake’s poker face was barely holding on by a thread at this point. He didn’t want Clara or Darla to know just how close to an orgasm he was. Given how close his diaper change was to being finished, he couldn’t let himself lose control now.

Unfortunately, Darla had more than caught on by this point and had been planning on this moment from the start. “Oh, one other thing,” she said, attempting to sound as unassuming as possible, “You can mix and match sex toys with every change. Now I know he hasn’t had any anal training…well, yet anyway…but if you’d like, we show him just how much fun wearing diapers can be.” She opened a drawer that was on the far end of the changing table, showing off the wide selection of butt plugs and buzzers for Clara to choose from.

Clara’s ears perked up at the sound of Darla’s suggestion. How could she resist such a tempting offer, especially after sneaking a peek at the options? Tapping her chin, she carefully considered the options laid out before her.

TO BE CONTINUED…

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