The Perfect Opportunity - Chapter 3 (Patreon)

Commissioned by an anonymous Patron.

"So," the woman behind the desk looked over her glasses at Glenn, as he squirmed in his seat, "you don't have any real experience."

"N-No," Glenn lied, feeling his cheeks warming up, betraying him. Maybe she'd take it as him being embarrassed about his lack of a job history... Or, maybe, she'd suss out the truth. As she leaned forward, staring harder at him, he couldn't help suspecting it would be the second, as he fought not to stare down the front of her dress at her ample cleavage.

"It's funny," Ms. Beesley mused. "I can't help feeling like I've seen you somewhere before... Now, are you certain there's nothing? I know it might not seem like it, but even a fast food position would be beneficial... I know it's only an entry level job, it's just that our other candidates have experience, so, to be frank, there's nothing to entice us to hire you over them, as nice as you seem..."

Glenn bit his bottom lip, not knowing what to do. It sounded like this was exactly what he was searching for, the start of a real career... If she knew what he'd been doing to earn money up until now, however, he wasn't sure she'd be willing to hire him. It felt far more likely that she'd laugh him out of her office!

"Well..." he chose his words carefully, "I have done some work at parties..."

"Okay," she nodded. "That's something! So, were you a DJ, or...?"

He shook his head. "No, nothing like that. I was, uh... the entertainment."

"Oh, a performer," she smiled. "A pirate? I know those are big."

He chuckled nervously, fidgeting. "S-Something like that." It started with the same letter, at least, and he knew that most of the guys who worked at the company did that sort of thing, or teamed up with the girls to be princes to their princesses... Not him, though.

Ms. Beesley tilted her head, then, to Glenn's horror, a look of recognition crossed her face. "Wait, I remember where I know you from!" she exclaimed. "I didn't recognize you without the wig or the dress, but you were at one of my friends' daughter's birthday parties!"

Glenn's cheeks burned as he scrambled to his feet, wanting to run for the door. "Uh-oh!" the woman teased. "My friend said she found a diaper in her garbage after the party... She assumed it was from one of the girls, but she thought they were all over that phase... I guess she was right, huh?"

Glenn froze, staring down at himself, horrified to see a wet spot forming on the front of his pants from the humiliation of being recognized as a former party princess, which, of course, only embarrassed him further. "I-I don't..." he stammered. "I-I'm not... I-I'm sorry!" He didn't know what to do, standing there, bladder continuing to empty itself into his underwear, helpless.

"I will say," the woman smirked, standing up herself, towering over him, "normally, this little display would be enough to take you out of the race... You really were an adorable little princess, though. And I do have a party of my own that I need some entertainment for..."

"I-I don't do that anymore," he told her meekly.

"Do you want to work here?" she asked simply, earning a timid nod. "Then I think you do."

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*

He tried to get her to tell him, at the very least, who he was going to be for the party, but he was never able to get a straight answer out of her, only being told that she would handle everything, and all he needed to do was show up.

When he went to the address he was given, he found a huge, beautiful house, with a number of cars already parked outside, that made him feel extremely intimidated, and made it hard for him to argue when his new boss - he hoped - led him to a spare bedroom, where a diaper was waiting on the bed, spread out, powder and lotion sitting on the bedside table. "The cleaning crew at the office took care of your last little accident," she told him, "but I won't have you leaving any puddles here."

"I-I won't," he promised, although he could hardly blame her for deciding that wasn't good enough, and making him strip down. "C-Can't I put it on myself?" he sniffed.

"I'd feel better if I handled it," Ms. Beesley said. "I don't want any leaks."

Glenn self-consciously shuffled out of his underwear, covering his crotch with his hands for all the good it did him, since the woman quickly brushed them aside so she could powder and lotion him up before pulling the diaper up between his legs. It had been a while since he'd had to wear one... It felt even thicker and bulkier than he recalled, and the flower design was so girly, so babyish... Instantly, he was taken back to all his other misadventures, and, automatically, he began to dribble.

"Wet already?" Ms. Beesley chuckled, turning back around from the closet, not missing the slight discoloration of the diaper's design. "Good thing I have plenty of these, huh?" she patted the front of the diaper. "Now, sit up... Let's get you dressed.

Perhaps the flowers on the diaper should have tipped him off, but he couldn't quite figure out who he was supposed to be even after he was in the dress. It was purple, and laced up the front, though he suspected the skirt was not the same as it had been in whatever movie it was from. Here, it was a fluffy, translucent tutu, one that ended not far under his diaper... As he sat there, however, anxiously squirming on the bed, it certainly looked like that wouldn't matter, because he could see the diaper through the fabric!

It wasn't until Ms. Beesley put the wig on him that he put it all together, the long, blonde hair, braided, with flowers tucked into it, tying it all together for him. "I-I'm Rapunzel?" he squeaked.

"That's right," the woman smiled down at him. "Which means you need to remember one thing, sweetie... Mother knows best. Isn't that right?"

"I-I guess," Glenn gulped, being helped to his feet, looking down at himself. "B-But..."

"No buts," she interrupted him. "You want the job? This is where your life begins."

Glenn wasn't sure it was exactly legal for her to make him go through all this, but he was hardly in any position to do anything about it now. He'd agreed to this, and he'd shown up here... He'd let her diaper him, and dress him up... It was a little too late to start resisting now. "Y-Yes, ma'am," he nodded. "I-If I could, though... H-How old is the birthday girl?"

If he'd learned one thing from his time as a party princess, it was that the age range that his little act was suitable for was very limited... At a certain age, the girls thought they were too old for it, even if their parents hadn't realized it yet. And, if it went too far above that, there was a chance they would notice his diapers and tease him for them; now, when the diapers were on full display, that might happen regardless, unless the partygoers were young enough to still need them themselves.

"I never said it was a birthday party," the woman grinned, leading him by the hand to a completely different part of the house, where, as he approached, he could hear the party was already underway. "Here she is, girls!" she exclaimed, pushing Glenn through the doorway first, into a room full of women around her age, one of whom was sitting in the middle of them, looking very pregnant. "Our little princess!"

Glenn blushed as he was passed around the room, practically, being cooed and fussed over, everyone wanting to tell him how adorable he was, giggling and patting his diaper, commenting on how soggy it was, not giving a second thought, apparently, to giving the padding a squeeze. He wouldn't call them old, exactly, but they were definitely older than him, and taller, and dressed much more nicely than anything he could afford, even if he had been able to choose his outfit for today.

"Yes, she's sweet, isn't she?" Ms. Beesley said, once everyone had gotten their turn. "If anyone would like to be first at the diaper changing competition, I have everything set up."

Sure enough, there were the rest of the diapers the woman had said she had, next to a changing pad, more powder, lotion, wipes, and oil waiting, along with a stopwatch and a clipboard. "D-Diaper changing competition?" he blushed, looking around at all these women, his diaper growing warmer imagining any of them changing him. "I-I thought..."

"I told you, silly," the woman patted him on the head. "You're the entertainment."

"B-But I thought you just wanted me to sing, or..." he protested.

"Oh, you can do that, too," Ms. Beesley promised. "We're not little girls, though, we need a bit more than that to keep us amused. And I think you'll do perfectly for that, my little princess. After all..."

He didn't get it at first, not until she gave him a swat to his padded bottom, reminding him of his role, and what she'd told him earlier. "Mother knows best," he finished her thought for her, getting a round of laughter before one of the women stepped up, leading him over to the changing mat, getting him into a dry diaper as quickly as possible, scrawling her time down on the clipboard.

"I think the princess needs a refill," the woman chuckled, leading the blushing Glenn back to the others. "Are you ready, Sybil? We can use the bottles if not..."

The pregnant woman smiled. "Believe me, I'm ready," she started to slide the shoulder of her dress down, exposing her nursing bra. Glenn looked over at Ms. Beesley in a panic, but she did nothing to prevent him from being taken to Sybil, his face pushed to her breast, warm, sweet milk filling his mouth...

This was going to be a long day, he thought, his diaper beginning to warm again, knowing that, through the tutu skirt, the women would notice right away when he was released from his breastfeeding, and the next contestant would probably want to try her hand at the competition. If he got hired, maybe it would all be worth it... But, from the way Ms. Beesley was looking at him as she watched this, he had a feeling the job wasn't going to end up being quite what he'd hoped for when he'd gone in for the interview... And, after all the diapers he was bound to go through before this party was over, it would be awfully hard to argue he didn't deserve whatever the new position would end up being.