ACT I, CHAPTER 8

“Good night, Skye,” Connor said as he tucked Skye into her crib, kissed her on the forehead, and locked the bars into place. Skye couldn’t help but squirm and blush at Connor’s display of affection.

It had been a week since Connor had started at the Padded Palace, and his routine was already feeling natural. The girls could certainly be a handful, but they’d all taken a liking to him, which made his job much easier. Latasha was always patient with him and so willing to teach him anything he needed to know. Now if he could master Stacy’s cloth diapers, he’d be all set!

However, it was Skye that seemed to be the closest and farthest away. When it was just the two of them, she was always sweet and playful, while still being a little shy at times. But when she was with the other girls, she always kept her distance from him and was even shyer.

To Connor, it was obvious as to why. He wasn’t so naïve that he wouldn’t catch her staring at him constantly. She had a crush on him, and no doubt had no idea how obvious she was making it. Unsure of what to do, he decided to keep that knowledge to himself unless it became a problem in the future.

Outside the door, Latasha watched Connor finish Skye’s bedtime duties and turn off the lamp, leaving only a small night light tasked with the job of illuminating the darkened room. “Don’t let the bed bugs bite,” he said, causing Latasha to chuckle. What a good caretaker Connor was turning into.

Latasha entered the room just before Connor made his exit. “Everything all good?” she asked, pretending like she wasn’t spying.

Connor nodded his head, “She’s all tucked in.” He stretched his arms and gave out a small yawn.

“Sounds like Skye isn’t the only sleepy baby here. Head on to bed, Connor. I’ll see you tomorrow,” said Latasha, enjoying Connor’s blushing face. Once she’d found out how easy it was to make him all rosey, she just couldn’t help herself anymore.

Connor, on the other hand, couldn’t tell whether he hated or loved the new attention that Latasha had started showing him. Ever since Carol had said all that stuff to him about Latasha wanting her victims to be “unsuspecting,” he couldn’t help but think that with all this teasing, maybe she was right...but, that’d be silly! She said so herself, she doesn’t want boy babies anyway.

Shaking off his embarrassment, Connor responded, “Have a good night, Latasha.” He turned and exited, waving to Skye one last time before heading off to his own room.

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Dressed in only a t-shirt and a pair of boxers, Connor spread himself out on his bed. He had gotten used to just how plush his mattress was. He was so used to sleeping on stiff dorm mattresses and couches that his new bed was like resting on a cloud. As luxurious as it sounds, it was quite the adjustment.

Connor held his phone above his head as he felt the cool, silk sheets with his free hand. The sensual fabric grazed past his fingertips. He just couldn’t get enough of it. He stopped paying attention to his phone as he looked at the closet across from his bed. All week, he’d avoided temptation. There was no lock on his door, so he had no way to stop Latasha from entering his room. And no, she didn’t knock. What if he got caught at the wrong moment?

Connor was snapped out of his mental spiral when his phone slipped from his hand and bonked him on the head. He rubbed his head, agonizing at the minor pain.

Standing up, Connor tiptoed to his door and peeked out into the hall. The coast was clear. He twisted the door handle and closed it quietly, so as not to alert the hawk-like hearing that Latasha possessed.

Sliding open the closet door, Connor once again stood in front of the set of cardboard boxes, each one filled to the brim with adult baby clothes, toys, and accessories. Looking back towards the door one last time, he reached into the top box and pulled out the silky, pink babydoll dress with poofy sleeves and lots of ruffles. He had no interest in the other baby stuff that was in there. All he wanted was the dress, closing his eyes in bliss he pressed the dress against himself.

There was just something about the way Connor felt when his skin came in contact with a frilly dress like this that made his heart flutter. At the same time, there was an abstract shame that lingered in the back of his head. Why did he enjoy this so much? What was wrong with him? It was as if two halves of himself were at war with each other.

Connor was so distracted by his thoughts that he failed to hear Latasha’s footsteps until she was already at the door. Reacting quickly, Connor dove into bed, hiding the dress under the blankets with him. Just in the knick of time too, as Latasha opened the door immediately after he settled himself into place. She held something behind her back.

“Hey Connor, I have a surprise for you!” said Latasha, in sort of a half whisper-half shout. She pulled her hand out from behind her back, unveiling a small, pink frosted cupcake with a big “1” candle in its center. “Happy first week!” She mimed blowing a party streamer, making a tiny trumpet sound.

Connor chuckled at Latasha’s gesture, happily accepting the delicious-looking pastry. “Thank you, Tasha. I wouldn’t have made it without you.”

“Oh, hush! You’re a natural at this. You’ve done so much that I could never have taught you,” said Latasha. Her voice trailed off at the end of her sentence as she noticed the closet door ajar with the lid on the top box cracked open. What have you been up to Connor? Oh, how she wished she could push him to confess what he was up to, but she knew she needed to restrain herself.

Instead, Latasha gave Connor a warm smile and moved towards her exit, “Well, I won’t keep you up. Have a good night, Connor.”

“Good night,” Connor said as he waited for his door to click shut. He let out a sigh of relief, having nearly been caught once more. It was like Latasha had a sixth sense or something. He was so focused on not getting caught that he hadn’t even realized that his bare legs were covered in the hidden dress. His little buddy instantly rose to attention, pitching a tent in his boxers as he lifted the blanket and gingerly swished his legs underneath the childish dress.

Suddenly, an idle thought entered his head. A small, arousal-fueled thought that would change his life forever. Without thinking, he pulled the dress up his legs until it was brushing over his stiffened crotch. He needed to know what it felt like to be directly on him.

Connor removed his shirt and scooted the dress up to his stomach, melting in its tender embrace. It was everything he’d hoped it would feel like. He had only one step left. He hooked his thumbs on the sides of his boxers and stripped himself of them, leaving him naked with the dress.

His hands shook ever so slightly as he reached down and lightly caressed his cock within his silk-coated mitt. It was as if he’d been struck by a bolt of electricity. His body instantly reacted, sending signals of pleasure rippling throughout his body and up to his brain. Masturbating with a lotion-filled sock had nothing on the smooth, liquid-like clothing that conformed around his throbbing phallus and gyrating hips.

Connor stroked himself up and down furiously, quickly bringing himself to the edge of a climax. He then slowed down his hand and let himself rest. He never liked to cum too soon, savoring the tingly sensations.

In his head, Connor was on cloud nine! His thought drifted to Latasha, whose intimidating, yet kind presence permeated his mind. “What would she do if she caught me?” he thought as he felt his internalized arousal begin to rise once more. “Would she tease me? Punish me? Make me wear some ridiculous diaper like Skye and the others? Or...would she force me to wear this dress, seeing as it brought me so much pleasure?”

That was the thought that tipped Connor over the edge. He was so lost in thought that he didn’t even realize he’d gone past the point of no return until it was too late. His eyes widened as he lost control and exploded a massive load of semen from the head of his penis. It was one of the biggest climaxes of his life. He felt weak and his arms collapsed at his sides afterward, refusing to move.

As he slowly escaped his euphoric aftershock, Connor tilted his head up, noticing the dress was still covering his deflating dick. Nervously, he pulled back the dress, revealing to himself what he already knew to be true. He wasn’t able to control himself. He’d been too careless.

In the center of the dress was a large, sticky cum stain.

“Uh oh.”

TO BE CONTINUED...