ACT I, CHAPTER 21

“Caterpillar!” shouted Connor, as he stared at the slab of pink-painted timber with pretty red hearts drawn lovingly on its sides. He exhaled hard, believing that his safe word would be the end of it.

However, Latasha could only snicker at poor, helpless Connor. She leaned in close, whispering, “You know, safe words can get you out of almost anything. I never want you to feel unsafe or uncomfortable here…”

Connor didn’t like the tone of Latasha’s voice. Unlike with his previous use of Caterpillar, she still spoke with a deep, dominant voice that made the hairs on the back of his neck stand up.

“...but, the one thing it can’t get you out of is punishment,” said Latasha, forebodingly tapping Connor’s rear with the sturdy plank. “So get ready ConCon, because your ass is mine.”

Kicking his legs, Connor did everything in his power to get away, which regrettably wasn’t much. He knew he couldn’t force his way out. He had no choice but to reason with his strict mommy domme, “Please, I-I really don’t like pain!”

“Good,” said Latasha, her devilish smirk only grown, “Then the lesson should sink in even more.”

Wincing, Connor knew there was only one thing left he could do, “I...I wet myself!” Latasha’s giggling seised. The room went silent. Connor wasn’t sure what was going on, but his confession had at least stopped Latasha for the time being so he continued, “I’m sorry. I was just trying to hide it. During the nap, I had a dream where you pour warm water doing my diaper, and...when I woke up I was-”

“PFFFFF! AHAHAHAHA!!”

Latasha couldn’t hold it in any longer. She keeled over, becoming short of breath due to how vicious her mockery was. “Yeah! Haha! No shit!”

“Wait...y-you knew?” stuttered Connor, “Th-then, why didn’t you say anything?!”

Taking a deep breath, Latasha calmed herself down enough to speak again, “So I could let you know what a good girl you were for Mommy, telling her all about your sleepytime accident.” She petted his head, and slowly started to unravel him. “To be honest, Connor, I’m starting to get a little offended. You think so low of me to believe I can’t sniff out a wet diaper?”

Connor was blushing up a storm, cursing himself for being so stupid. Of course, she would know. As his limbs felt air for the first time in several hours, he hung his head, feeling immense guilt. “I’m sorry, M-Mommy Tasha,” he said, hoping his apologetic obedience would be enough to avoid a hefty spanking.

“Mommy forgives you, ConCon. I’ll spare you the paddling for today. Besides, now you know what awaits you if you misbehave again,” said Latasha, her sentence immediately followed by a sigh of relief from Connor. She smiled, waiting for him to get comfortable before delivering the rest of the news, “But! You will still be punished. I’m afraid you’re out of warnings, my sweet ConCon.”

Connor’s anxiety returned, as his mind went frantic over what she had planned for punishment 2.0. After all that had happened today, his heart couldn’t take the stress anymore. He grabbed onto Latasha’s hand, tears forming in the corners of his eyes, “Please don’t hit me. I’ll be extra good! I promise!”

Latasha’s already huge heart grew another size bigger. Not for his begging, but for how innocent he was acting. Looking deep into his eyes, she knew how pure his intentions were. She brought him in for a big hug, rubbing his back. “Oh, sweetheart! Don’t worry, I’m not gonna hurt you.” She separated enough that she could talk directly to him, “But, you have now wet your diaper three times without asking, one of which you just confessed was fully accidental.”

Connor opened his mouth to protest. Her count of wet diapers was correct, but she knew, well and good, how each of them got wet. He wouldn’t get a word in edgewise, though, as Latasha shoved a binky back into his mouth.

“Now, now, don’t go making a fuss,” said Latasha, booping him on the pacifier, “You are to be padded 24/7 until you can prove to me that you’re potty trained. During the day, you will wear pull-ups, and for sleep, you will wear nighttime diapers.”

Again, Connor tried to speak, but Latasha held his pacifier firm, “You told me to make all of your decisions for you.”

Connor was sunk. He had no argument and no way out. Caving to his defeat, Connor begrudgingly nodded his head, accepting his diapers would become a more permanent fixture of his day-to-day life.

Grinning, Latasha lifted him up, “Great, then let’s get you all changed for a relaxing evening.”

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Connor didn’t realize how much he missed t-shirts and pajama bottoms until he was finally able to wear them again. Sure, they were female cut and he already had his nighttime diaper on underneath, but after an entire day in dresses, he’d almost forgotten how it felt to dress casually. He lounged on the couch, waiting for Latasha to join him with snacks for the movie.

“ConCon!” Speak of the devil! Latasha zoomed into the living room, ferrying a bowl of popcorn mixed with M&M’s, along with two opaque baby bottles. She set them down next to Connor and handed him the TV remote. “...I’m gonna run upstairs and change into my jammies for a second. Why don’t you go ahead and pick us something out!”

Leaving Connor once again alone, Latasha jogged upstairs and headed for her bedroom. Connor had been so good today, but she wasn’t through seeing his rosy cheeks just yet.

Flipping through Netflix, Connor contemplated what movie Latasha would like best. Would she expect him to pick a kid’s film? Or would she laugh at him for not picking something more adult? His anxiety about this decision sent him doom scrolling through the endless number of options. Becoming self-aware for a moment, he chuckled, remembering why he wanted Latasha to choose everything for him now.

Still, Connor’s time to pick something was rapidly running out. He knew he’d be teased for failing to do such a simple task. He needed to choose something quickly!

“Alright ConCon, have you picked out what we’re watching?” said Latasha as she re-entered the room, holding back her instinct to blush as much as she could.

Out of time, Connor turned to Latasha, ready to face the music. But as he laid his eyes upon Latasha, all words left him.

Standing before him was Latasha, wearing a matching set of silk lingerie and lace panties. His jaw dropped at how gorgeous she was. His sore buddy sprang back into action, unable to help itself.

The giggles returned for Latasha, as she soaked in his loving, awe-inspired gaze. She knew he’d lose it when he saw her like this. She looked up at the TV, which only increased her jubilation. “Is that what you want to watch, ConCon?”

Not yet out of his stupor, Connor turned toward the TV. Call it twisted luck or fate or whatever you want to, but somehow, the cursor happened to land on Barbie’s Dreamhouse Adventures. His face turned crimson, “I...uh…”

“That’s awesome!” shouted an excited Latasha as she playfully jumped onto the couch, “This is one of Skye’s favorites, and honestly, mine too. It’s super funny. You’re gonna love it, girly!”

Connor once again relaxed as he listened to Latasha, a woman who had seemed so beyond his level mere seconds ago, gush over a children’s TV show. As the theme song started to play, he couldn’t help but feel incredibly comfortable with all of the femininity surrounding him. He leaned into Latasha, nuzzling against her warm body and smooth, silky outfit. The sensations caused further throbbing in his diaper, which he did his best to quell by stuffing his stiffy between his thighs.

Latasha placed her arm around Connor, snuggling him closer to her. She picked up a baby bottle and handed it to him, “It’s orange juice.”

Plopping the bottle between his lips, Connor savored the yummy orange juice, his favorite kind. He looked over to Latasha, “Thanks for the juice, Mommy Tasha.”

Latasha chuckled, squeezing him tightly, “Ooh! You’re such a cutie. It’s really sweet that you’re still calling me Mommy Tasha.” She paused the episode just before the theme song ended, “By the way, do you like me calling you ConCon?”

“I do!” said Connor, thinking about how much he loved all the adorable pet names he’d been given. However, there was one nickname Latasha didn’t call him, and yet, he’d heard it twice today. Despite not remembering everything from his infantile dreams, one thing stood out from everything else, “But...um...would it be okay if, when I’m dressed as a girl...you called me Connie?”

Latasha’s face lit up. She squealed and pulled Connor into her lap, “Sure thing, Connie.” She pulled the blanket over the two of them and picked up the remote. “Now that we’ve got that settled, let’s settle in! We’ve got three whole seasons to binge!”

The show resumed with Latasha wrapping her arms around Connor and holding him close. He couldn’t explain it, but it was like he was floating on a cloud. He felt so cozy and so loved. He just couldn’t help himself, “I love you, Mommy.”

Latasha was on the verge of tears hearing that. It had been a rocky day at times, but it was all worth it for this moment.

“I love you too, Connie.”

TO BE CONTINUED...