ACT I, CHAPTER 14

“Upsie Daisy!”

With Connor lying on the changing table, Latasha grabbed onto his ankles and lifted them high, sliding the unfolded, bright pink diaper under his bottom. There was no turning back now.

As she lowered him onto the surprisingly spongy padding, Connor’s eyes looked anywhere they could avoid seeing Latasha or anything she was doing. After realizing that would be easier said than done, he decided to cover his face with his hands, too embarrassed to watch as his brand-new caretaker began to wipe him down. His heart was beating like a snare drum in a marching band.

“Aww. There’s no need to be scared, little one. Mommy’s done this hundreds of times,” said Latasha, as she sanitized his diaper area. Normally, she might spend a little extra time cleaning the sensitive bits, something that clients always enjoyed immensely. However, seeing how obviously nervous Connor was made her resist the temptation to play with him, for now anyway.

Discarding the wet wipe, Latasha picked up a bottle of lotion and squeezed a hardy amount onto her hand, and lightly slapped her hand down on Connor’s pelvis, near his genitalia. He jumped and let out a small “Eeep!” in surprise, bringing forth a boatload of giggles. “Seriously Connor, relax. This is supposed to be therapeutic, after all.”

Connor slowly rested his head back, doing his best to calm down. He didn’t want to admit it, but he’d never...had a girl...down there...which only made this experience even more humiliating! His first time being naked with an attractive woman and she was diapering him. If anyone who knew him from college saw him like this, he’d die of shame on the spot.

Closing his eyes, Connor tried to take his mind off of the negatives, concentrating on Latasha’s soothing hands that rubbed the lotion into his diaper areas until every square inch was coated with a healthy layer of baby lotion. Perhaps he really did need to relax and let things fall into place. Latasha knew what she was doing, and he did tell her to make all the choices for him from here on out, even if he did shoot from the hip on that one.

“Uh oh! I think someone’s getting excited!”

Connor had never wanted to escape his body more than he had when Latasha said those words. He was so focused on how good everything was feeling that he didn’t even notice his little buddy was reacting to all the stimulation. His hands shot down to cover himself, but Latasha smacked them away.

“Nuh-uh! No playing with yourself during changies! Maybe if you’re good, I’ll let you play with some of Skye’s buzzy toys in a little bit,” said Latasha, knowing fully what Connor’s intentions were. Not that it mattered though. There was no way his hands would wander south during diaper changes ever again after that. Plus, she greatly enjoyed watching him squirm, finding herself getting slightly aroused at his helplessness.

With no idea what to do or say, Connor once again found himself burying his face in his hands, as the gentle sprinkling of baby powder only seemed to make things worse.

What he didn’t know was that Latasha was about to sprinkle more than just baby powder onto him. He was so flustered, cute, and obviously horny that it got Latasha thinking. While Connor buried his eye’s behind his hands, she reached down and grabbed the hidden bottle of X-lube that she kept tucked away for special occasions. She dusted him with the powdery substance that need only to get wet in order for the fun to start. She smiled deviously, recapturing that wondrous feeling she used to get when she was a domme full time.

Finally, it was time for the big moment. Latasha straightened out the front of the diaper, ready to lock in her new Little. She grabbed onto his stiffened shaft and held it flat against his waist, causing a tiny yelp from Connor, as she folded the diaper over him. She made quick work of the tapes. “There we go, sweetie. All taped up,” she cooed, patting the front of his diaper and feeling him throb beneath the palm of her hand.

Connor shifted his fingers, peeking out at the bulk between his legs. He could’ve handled a thousand of Skye’s diaper changes. It never would’ve prepared him for how large and poofy it looked and felt to have one secured to his hips. He pressed his legs together as much as he could, finding that Skye’s special diapers made it impossible for his knees to ever touch. As confounding as that was, Connor’s focus was almost wholly dedicated to the sound that emitted from his dry padding. The crinkling of diapers was a sound that was always present in this nursery, but now that it was coming from him, it sounded like someone hooked a megaphone up to his diaper.

Latasha corralled him off the diaper table, placing her hands under his armpits again as she helped him down. She reached under the table and pulled out a pair of clear plastic panties. “Okay, Connon, step on in.”

This was another part of the process that Connor knew was coming, but he still felt unprepared for. At least the diapering was passive. He had to actively step into a piece of clothing called “plastic panties.” His male ego looked like a beaten, pulpy mess at this point. He lifted his right leg and stepped in, then his left. With both feet in place, he felt the rustling pants crackle their way up to his legs until they snapped snuggly onto his waistband.

The plastic pants managed to make Connor’s diaper seem even bigger. At this point, his blush never seemed to die down. It was as permanent a fixture of his face as his nose or eyes were at this point.

Latasha grabbed Connor by the hand and lead him to the wardrobe once more. He couldn’t explain it, but his penis seemed even harder than it was when he was getting changed. The soft diaper material mixed with the intense craving to wear everything in that closet seemed to be having quite an effect on him.

Throwing the doors open wide, Connor was able to see the various pastel dresses, onesies, and other infantile outfits that all seemed to make his heart flutter. He couldn’t believe he’d get to choose from this fabulous selection.

“Hmmm...what to choose for you,” said Latasha, her words reminding Connor that it wouldn’t be him getting to choose. That thought only drove home just how much he was at Latasha’s mercy. He looked at the lineup of dresses once more, seeing several that looked far too daring or revealing for him. He bite his lip and did his best to stay calm.

Thumbing through the rows of sissy attire, Latasha had fun imagining Connor dolled up in so many of these lovely dresses. His small frame wasn’t far off from Skye’s. Sure he was taller, but that just meant short dresses would ride up even higher on him and overexpose his diaper; a thought that forced her to stifle a giggle.

At last, though, Latasha came across the perfect dress to usher Connor into a new way of life. She turned back towards Connor, “Close your eyes and lift your arms for me, sugar bee.”

Connor obeyed without question. As hard as it would be to keep his eyes closed, he had a strange desire to please Latasha.

His fingertips traced across the soft ruffles that brush against him as the dress slid past his head, then his chest, then his stomach, before finally reaching its resting point. With his eyes still closed, Latasha pulled him over towards the mirror next to the wardrobe. He felt the outfit behind tugged and pulled on to straighten it out. Latasha’s breath grazed his ear as she leaned in close, “Go ahead and open your eyes now. I think you’re gonna like what you see.”

Connor wanted nothing more than to open his eyes and look at the dress Latasha had chosen for him, but he was simultaneously terrified to see himself. Sure, he masturbated with a dress, but he had never worn one before. He wasn’t sure he was prepared to see himself...like that.

Latasha took hold of Connor’s hand, hoping that it would serve as a gesture that no matter what, she’d be here for him. Luckily, her action seemed to have the desired effect, as Connor appeared to calm down.

With one last deep breath, Connor opened his eyes.

TO BE CONTINUED...