Daily Free-Write April 10, 2021: Stupid Bet Pt. 5

Continuation of March 31, 2021, “Stupid Bet Pt. 4”

Hunter woke up bright and early next to a soggy boy in his bed. He was glad Nicky’s next shipment of diapers was already on the way. While he told Nicky he had ‘won the bet’ and would ‘get to wear undies again’, he saw it as just another opportunity to reinforce the fact that Nicky needed diapers. Not only that, he thought, holding up the buzzy wand and smiling to himself. He would do everything he could to make sure Nicky loved his diapers as well.

Nicky woke up to the sudden shock of a buzzer on the front of his crotch. He opened his eyes and saw hunter standing above him, a soft smile on his face, the familiar massage wand pressed into his obviously soaked diaper. When he tried to move, he found that he was stuck.

“Hey! What’s going on?” he said. Or at least that’s what he tried to say, but he found his mouth stuffed with a pacifier and he was unable to spit it out. He groaned in pleasure as his bigger boyfriend began moving the massage wand all around his diaper bulge. “Mmm….”

“That’s it, baby boy. Just relax and enjoy. Enjoy your didees…”

Nicky groaned again, this time at his boyfriend using Mom’s pet name for diapers. He knew getting them in the same room together was a bad idea. He turned his head to see a familiar set of blue hospital restraints on his hands and ankles. He sighed and rolled his eyes, first in annoyance, then in pleasure as Hunter bumped up the intensity of the buzz buzz.

“You’re not going to get out of this until you cream your night didees, so you’d best just give in and let it happen,” said Hunter.

His voice of authority turned Nicky on, and he found himself relaxing and getting into the feeling as his boyfriend attentively worked his dick through the diaper. He had to admit there were some nice aspects to being in padding all the time as well.

“There we go, sweetie. You’re doing so good. So proud of you for being a good boy yesterday and letting Daddy dress you even though you earned your big boy pants back. You behaved at Mom and Dad’s house and didn’t even fuss when I put your cute little plastic pants on. You deserve this little treat for being a good boy. You deserve to enjoy your night diapers. Yes. Oh, there we go. There we go. Make stickies for Daddy like the good boy you are. Yes, you love to make stickies and you love to do it in your didees. You love your didees….” With Nicky’s mouth plugged, there was no way for him to argue when Hunter told Nicky what he loved or called himself ‘Daddy’.

“MMMffffffffff!!!” Nicky squeezed his eyes shut as Hunter’s suggestions entered his mind along with a final surge of pleasure that spilled over into an intense orgasm, straining against the restraints as he screamed into his pacifier, his balls and prostate pumping baby batter all over the inside of his didees.

“Gooood boy…” cooed Hunter, as he watched his boyfriend achieve yet another orgasm in a used diaper. “Good boy!”

He made sure to shower his boy with lots of affection after his orgasm. He wanted him to feel so nice about those special moments and connect them to being secure and padded. As Nicky’s breathing slowed to a normal rate, Hunter unclipped the mitts and ankle cuffs, and cuddled Nicky close for some after care. He petted Nicky’s head and talked about their day to come.

“Shhh…. Shhhh… there we go. Wasn’t that nice? I think from the state of your diaper, we’re going to have to keep you diapered at bed time for a while yet. Don’t worry, shhh, calm down. You won’t be diapered all the time. In fact, after your shower, we’ll get you back into your big boy undies and big boy pants, just like yesterday. Yes, they’re all clean now. And if you can keep them dry for the whole day, I’ll get you another pair. Aww, my little boy likes that, doesn’t he? Yes, he does! Okay, sweetie. I’m gonna take out your paci now and we can get ready to go to the store for some more candy, since you were just so good after your accident yesterday.”

Hunter unfastened the buckle at the back of Nicky’s head, loosening the paci strap and allowing Nicky to speak.

Nicky was going to comment on how Hunter was having too much fun with his ‘baby things’ from Mom, but instead another thought took priority and all he said was, “Candy!”

“Yes, sweetie. Candy. Now, go on and get your butt in the shower so we can get you dressed.” Hunter himself was already fully dressed compared to little Nicky who was in nothing but a Diaper.

“Y-you mean I can take it off myself?” asked Nicky, in awe.

“That’s what being a big boy is all about, little one. You get to do lots of stuff by yourself now!”

Nicky liked the sound of that. He excitedly hurried over to the shower once Hunter unfastened his mitts and ankle cuffs. He was going to be the biggest boy today, Hunter would see!

After a quick shower, he ran back out into the bedroom, almost slipping on his way out of the bathroom.

“Careful, baby boy,” said hunter, who heard the boy stumble and slam into the door. “Don’t make me regret letting you try big boy things.”

Nicky looked sheepish as he made his was slowly over to his boyfriend, who had laid out his outfit for the day. He didn’t want to blow his chances at being big!

Once again, Hunter held open Nicky’s training pants and Nicky stepped into them, followed by his crotch snap jeans, and a tight Tommy the Freight Engine T-Shirt.

Nicky was a little disappointed he still had to wear the childish T-shirt, but he wasn’t about to complain. Not at the risk of losing his big boy pants, or worse, candy!

“Okay, big boy,” said Hunter, ruffling Nicky’s hair and leaving it messy like a little boy’s. “Let’s get some breakfast in you and practice our concentration so you can stay nice and dry this time, alright buddy?”

Nicky nodded. “Yeah! I can do it!”

Hunter chuckled. Before the bet, Nicky would have rolled his eyes and said something like ‘come on, that’s easy,” but not now. Now he really saw it as a challenge that he could meet – if he tried real hard. Something that he had to prove. It was Hunter’s job to make sure he didn’t meet that challenge. That was all he had to do until Nicky gave in and asked for his safe and comfy diapees back full time. He smiled indulgently at his boyfriend.

“I know you can, baby boy! And even though you’ll probably have a few slip ups, we’re gonna keep trying until you’re sure you can too. But never forget – if you ever want a diapee, all you have to do is ask, kiddo. Okay?”

“Okay, Daddy. But I won’t need to, because I can control it.”

Hunter hid his elation at hearing Nicky start to use the D-word for the first time. This was going to be an easy win for him.