LINKS: | PART 1 | PART 2 | PART 3 | PART 4 | PART 5 |
The next week went by relatively uneventfully. Jessica ensured that Rocky was diapered at all times. She did let him use the toilet to handle number 2 activities, much to Rocky’s relief, but she did make him hold it until she had to change his soggy bottom. This helped her ensure that he wasn’t cheating the system.
Rocky was starting to get very used to the routine and just peeing when he needed to. This worried part of him, but the other figured that he had no choice but to go with it for the week and that he might as well as take advantage of it. He did enjoy the extra attention his girlfriend gave him, but it was a different form of being intimate than he was used to. They had not had sex since the diapering began, but Jessica did enjoy exciting him by rubbing the front of his diaper while cuddling and watching TV together. She was careful not to get him to the point of finishing, though, as keeping him on edge only made him more submissive.
Sunday came and Rocky was excited as his week of diaper punishment from losing the bet was ending. The evening was winding down and Jessica had just finished changing him into a thick night time diaper and a snappy onesie.
“Why did you order all this stuff?” Rocky asked. “It was only for a week and today’s the last day!”
“Yeah… I was going to bring that up.” Jessica replied. “You’ve been soaking these diapers all week. I don’t think it’s a great idea to put you back in big boy undies.”
“Hold on! I’ve only been peeing them because I have to! You won’t let me use the toilet” Rocky argued.
“I’m not so sure about that. Didn’t you admit that you wet in your sleep Friday night? I don’t want you wetting the bed with me sleeping next to you.”
“No! I said I don’t remember going! I probably woke up, went, and went back to sleep without fully waking up! I do that all the time with the actual bathroom.”
“Hmmm… I don’t know. I don’t think I can trust you to go the whole night. And it’s just more fun keeping you in them all the time.”
“Well that’s ridiculous. You know I won’t have an accident!”
“Wanna bet?” Jessica asked with fire in her eyes.
“Ummm.” Rocky began. His betting spirit put him in this position to begin with. “There’s no need to make a bet. We’re still finishing the punishment from the last one.”
“See? You’re scared!” Jessica fired again. “You know there’s a real chance that you’ll pee yourself again! If you’re too scared to take that bet, then I think you need to stay in diapers! I’ll make you a deal and say you only need to wear them to bed.”
“I don’t need to wear them to bed! I don’t need them at all!”
“Fine. Prove it then.” Jessica said slyly. She had him right where she wanted again. She knew his pride would take over again. “Take the bet.”
“Okay, then. I will!” Rocky declared as confidently as he could, but deep down he felt pretty nervous. “What are the terms?”
“It’s simple. If you wake up and that diaper is dry, you don’t have to wear a diaper ever again. We’ll get rid of them all as well as all these cute onesies. You can be a big boy again!”
“It’s a deal!” Rocky said right away.
“Hold on.” Jessica snapped. “You didn’t hear what happens if you lose. Which I think there’s a real possibility of happening.”
“Fine. I’m not going to, but what would happen if I somehow lost?”
“If you wake up wet, we’re keeping you in diapers full time for the foreseeable future.”
“No way!” Rocky yelled. “That’s ridiculous!”
“I know, I know. You’re scared you’re going to wet the bed tonight. I don’t blame you. We don’t have to do the bet, but you’re going to wear diapers to bed until you can prove you don’t need them.”
Rocky bit his lip. He felt like Jessica was getting her way no matter what he did. The bet was really risky as the stakes were so high, but it was the only way that he could get back in the driver seat as soon as possible.
“Alright! We’ll do the bet!” Rocky declared, partially regretting it as the words came out as he stuck his hand out to his girlfriend.
“Alright baby, we’ve got a bet!” Jessica said with a huge grin as she shook his hand. “We can go to bed early tonight, but why don’t we have a night cap first. There’s only one episode left in this season.”
“Fine! But I’m not drinking any beer or wine. I’ll just have a little bourbon, straight.” Rocky replied. He wanted to limit his fluids before bed, but he figured that a little bourbon would go a long way to help him relax so he could sleep through the night and not have to worry about his bladder the whole night.
Once again, Rocky’s vices got the best of him and the single glass of bourbon turned into three as he let the bet slip to the back of his mind. Before he knew it, Jessica was leading him to bed as he stumbled down the hallway, crinkling with every step.
The morning came as quick as well. As the alarm blared, Rocky tried to ignore it. He could sleep a little longer. Jessica wasn’t suffering from any grogginess, though. She shot up with excitement. She was a little worried that Rocky may have won the bet and her week of fun was now over, but there was still a chance.
“Okay baby boy!” Jessica exclaimed in a sing-song voice. “Did you stay dry last night or do you have a soggy butt?”
Rocky’s eyes shot open. The bet. How did he forget about the bet. He didn’t remember waking up to pee in the middle of the night, which was a good start. But as he moved his legs, it was clear that he was soaked. Did he really wet himself in his sleep? How did he turn into a bed wetter in a single week?
“Well! I’m dry!” Rocky lied as confidently as possible. It was his only shot. “I guess I won the bet!”
“Hmmm. Is that so?” Jessica responded suspiciously. “I should probably check just in case.” Before Rocky could stop her, she unsnapped his onesie in one smooth motion, revealing a very soggy nighttime diaper.
“You liar! You are absolutely soaked! I can’t believe you!”
“I’m sorry!” Rocky apologized, sensing he may have put himself in more trouble. “I didn’t know I was wet. I slept through the night!”
“So you wet in your sleep? You would’ve ruined the mattress if you weren’t wearing a diaper! It’s a good thing we’re keeping you in them from now on! Look at this damage!” Jessica grabbed Rocky’s ankles and lifted them above his head, showing off his soggy bottom.
Rocky’s stomach dropped. It seemed like his girlfriend was on a warpath. The only thing is that he couldn’t tell if it was in anger or in excitement. She seemed to be enjoying this too much. Regardless, he felt powerless to do anything as he laid there in a wet diaper, which he was already too comfortable with.
“You know what?” Jessica said. “I don’t think I can trust you with this. You tried getting out of wearing protection you obviously need last night and then you just lied to me.”
“I didn’t lie!” Rocky interjected.
“If that’s true, I don’t know if that’s any better!” Jessica snapped back. “I have an idea. Wait here, diaper boy.”
Jessica left the room and came back a minute later holding a white trash bag and shoved it into his hands.
“What’s this for?” Rocky asked. he guessed it was for his wet diaper, but they usually just threw those in the trash can. Why would she bring an empty trash bag into the bedroom?
“That’s for your big boy undies.” Jessica said matter-of-fact, a slight smile broke through her stern face as she failed to hide her enjoyment.
“Oh. I’m serious, Mr. Pissy Pants. You clearly won’t be needing them anymore and we need the room in your dresser for your diapers! After all, they will be your underwear from now on!”
“I’m not going to throw out my underwear!”
“I would really think twice before you disobey me again. You’re really testing my patience. If you make this difficult for me, I will not put much effort in keeping your padded ass a discrete secret. Maybe more people need to know about your potty problems. Maybe your mom has some advice!”
“I don’t know. It might be a good idea. You obviously are having some issues. You must’ve been a hard boy to potty train. I think she’d have some good ideas!”
“Fine! I’ll do whatever you want!” Rocky gave in, on the verge of tears. “Just please don’t tell anyone!”
“There. That’s a good boy.” Jessica’s stern face flipped to a giddy one almost instantly. “I think we can keep it a secret as long as you behave. Besides, we still have auntie Kylie and Samantha in case we ever need a babysitter. Now get to work throwing those ugly big boy undies away. We don’t want you late for work!”
Rocky begrudgingly took the garbage bag and waddled over to his dresser. He opened the underwear drawer and looked down at the last remnant of his manhood one last time. His face was burning with embarrassment and tears started rolling down his face as he grabbed pairs of underwear from the drawer and stuffed them into the bag.
Jessica saw that Rocky was crying and felt a little bad, but she knew it was for the best. She loved how close they had gotten over the last week. He might not want to admit it, but he needed to be the submissive one in the relationship and diapers were the perfect vehicle to make that happen.
Jessica took a bag of diapers out from the closet and instructed Rocky to fill his underwear drawer with them. He noticed that Jessica had gradually moved away from the plain white, medical style of diapers that were easier to hide discretely, and had replaced them with thicker, more crinkly diapers with babyish designs.
When Rocky finished filling the drawer with diapers, Jessica pulled a pair of underwear out of the garbage bag and looked at it mischievously, confusing Rocky. What was she thinking of now?
“Do you want to wear big boy undies one last time?” Jessica asked.
“Ummm. Yes.” Rocky answered, cautiously. This must be a trap, but he couldn’t get in trouble if he accepted something that she offered, could he?
“Okay. Kneel on the floor and put your hands behind your back!” Jessica ordered, gleefully.
Rocky was too defeated to question this odd command and just did as he was told. Jessica wasted no time in putting the underwear over his head and telling him to stay there.
Rocky supposed it could have been worse, but it was still a bit humiliating. He had to admit that part of him did enjoy letting his girlfriend order him around and have fun at his expense. It did appeal to some part of him that he didn’t realize that he had until the past week. Maybe he really did crave all of this deep down. Maybe that’s why he regressed to the pissy pants state that he was in so quickly. He didn’t even react when he heard the sound of Jessica’s phone taking a picture of him in this vulnerable position. At least his face was hidden.
Meanwhile, Jessica was filled with joy. She had never admitted it to anyone before, but this was a dream come true for her. This all started as a soft probe to see if her boyfriend would be willing to play along with her most secret fantasy. She was surprised how quickly and easily she could turn him into a submissive diaper boy. She wondered if her plan was that good or if she just got lucky. It was probably a bit of both. Her boyfriend may have a lot of accidents in his pants now, but all of this was no accident.
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