Daily Free-Write January 21, 2021

Continued from November 25, 2020 “Diaper-Training My Boyfriend”

“Hey,” said Percy, greeting us as we returned from Tommy’s discreet diapering. “Ready to play?”

“You know it,” I said, taking at the game table. Tommy quickly took a seat next to me, to make sure his diaper had less chance of being detected, I was sure. Of course they were obvious the moment we walked to join our friends and the ones I’d told gave me a knowing look. But I would let Tommy come out about his diapers in his own time, or at least think he was coming out. It really was almost impossible to ignore the large bulge and the crinkle that followed him around everywhere. And would it really be fair to keep that all to myself? It was just too cute for one man to handle.

“Sweetie, why don’t you get us a couple drinks,” I asked. Tommy looked back at me like I’d asked him to swan dive off the top of the building. “C-can’t you get it yourself?”

“No, you know how terrible I am at choosing. You pick.”

He looked down at his lap, his soft curls falling over his eyes.

“Is somebody going to get themselves in trouble?” I asked, raising my hand. His eyes went wide, and I knew he understood that I had no compunction about threatening to spank him in front of friends.

“Uh oh!” said Cassie, our group’s resident ‘mom’. “Better do what your boyfriend says there, Tommy. Sounds like he means business!”

Tommy stood up stiffly and quickly scooted off to the fridge.

*Crink* *Crink* *Crink*

He returned with two sodas.

*Crink* *Crink* *Crink*

“See? Was that so hard?” I asked, giving the front of his diaper a little squeeze under the table once he sat down. Instantly his face went red. It was too adorable and had me rock hard.

“N-no, guess not,” he said, quietly.

Of course Percy knew exactly what was happening, and Cassie has likely figured it out and was watching our every move with keen interest. At least half the table was in on it, while the other half was happily oblivious, chattering away as we got our game tokens.

“Okay. So each of you are members of the cookie security team, and you are in charge of building and maintaining a state of the art cookie vault. Pull out your cell phones because you need to download the app to find out the security updates. At least one of you will also get a message informing you that you are the cookie thief. It is your job to set yourself up to steal cookies, but don’t get caught, or you’ll be sent to cookie Jail, and have to work off your debt in the cookie factory. Okay, let’s get started.

The game was silly. It was fun. It was perfect for getting Tommy to relax and be his goofy self. He turned out to be the first cookie thief, though he sort of gave himself away with his mischievous grin and adorably dorky bad guy voice.

“Oh my, this is just terrible. Look’s like someone stole the cookies! I wonder who it could be?” He said, trying and failing not to smile. He was quickly sent to cookie jail to learn to reform his cookie thieving ways, and made a big dramatic speech for cookie court about how he’d learned his lesson and he wouldn’t do it again. Of course, with all his gesticulations and hand waving, it was inevitable that his shirt would ride up just enough to show a peek of plastic. I grinned as the back of his shirt got caught on the back of his diaper and stayed there as the shirt settled. He would now be flashing everyone whenever he wasn’t facing the group. Of course I wouldn’t say a word about it. I did ask him to get us another drink, though. I wanted to keep him well hydrated throughout the night.

After a couple rounds of cookie security, I noticed that my boyfriend was squirming.

“What’s wrong honey,” I said, quietly.

“I have to go to the bathroom,” he whispered back. Just like a little kid. He looked at me with a sense of urgency, like he was seeking permission. And that’s what I planned to give him.

“It’s okay, buddy,” I whispered back. “Just relax.”

He looked down at his lap and back to me with a look that said ‘are you joking?’.

I shook my head.

He cleared his throat nervously, shifted a bit, then held his breath a few seconds. He let out a sigh and sat still for a good 30 seconds. It was obvious to me that he had just peed his pants and I was so proud of him for taking this big step. I gave him another squeeze under the table and kept my hand there to feel the spreading warmth.

He tried to push my hand away, but I wouldn’t budge.

“Not here,” he whispered, looking worried.

“What’sa matter, little Tommy?” I whispered, rubbing harder. “Don’t you like your diapers? Are you shy about your diapers?”

I emphasized the D-word with another squeeze each time, knowing that he was already beginning to associate that word with pleasure as I kept up this reinforcement throughout the day. This was just the first time it was happening around others. And of course I knew exactly how to be discreet even if he felt as we were broadcasting his little problem to the whole world.

I ‘let him off the hook’ by letting him go get us some more drinks, and he was more than happy to scoot off back to the fridge, flashing the group with his bright white sticking up over the back of his pants.

No one said anything, or gave any indication to him of what they had seen. Instead we all passed a lovely night of games and merriment, and I was glad to see him feeling comfortable around others in his padding. Of course that wouldn’t last once he found out about his wardrobe malfunction.

At the end of the night, we said goodbye to everyone. “Good luck,” said Percy, giving me a wink. Cassie pulled me aside to ask what was going on and I filled her in. The looked at me dead serious and said, “Call me if you need a babysitter.”

I was pleasantly surprised, but I agreed to call her at some unspecified time in the future. She later sent me text that simply said, “Seriously, I want to do it.”

Once everyone was gone, I told Tommy to go brush his teeth.

“And then we’ll check your diaper to see if you need a change before bed.”

“Aww, do I hafta go to bed so early?”

“Good habits, remember, Tommy?” I asked, sending him off to the bathroom with a swat on the butt. I followed behind, allowing him to get there ahead of me, so he could try to use the restroom.

“I’m glad they stayed to help with the cleanup,” he said as he entered the bathroom. “Hey, give me a second, I need to… hey what’s this?”

“Oh, I said, smiling and leaning in the doorway. “That’s just a potty lock. It’s to keep naughty little boys from trying to use the potty before they’re ready.”

He blushed bright red and I could tell he had a little tent going on in his diaper.

“Cyrussss!” he whined, and I moved in for the kill, circling my arms around him from behind and swaying him back and forth as I hugged him, my front hand reaching into his pants and cupping his diaper. He struggled weakly, but clearly wasn’t trying too hard. A few moments and he was peeing himself as we both stared at our reflections in the bathroom mirror.

“Told you you wouldn’t make it,” I said, teasing him. “You need these now. I’ve noticed you dripping on the bathroom floor. From now on you come to me if you want to use the potty, got it?” He closed his eyes and nodded.

“Look at yourself when you agree. And tell me what you agreed to.”

“I-I…” He made a funny face as he looked at himself, a thick diaper under his pants and his boyfriend cupping his padded crotch from behind. “I need diapers and I’ll come to you if I want to use the potty…”

“Such a good boy,” I said. “Now go brush your teeth.”

With no more need to use the potty, he went and grabbed his toothbrush.

“Wow, Cyrus. I have to admit, that was really hot,” he said with a smile, before stopping.

I saw the moment of recognition in his eyes as he caught a glimpse of white sticking up over the back of his pants. His eyes widened as he turned to get a better view of his butt.

“Oh my god, was this…..”

“Uh huh.”

“In front of everyone?” he asked, looking even more worried.

“Uh huh.” I said, smiling and moving back in to hold him from behind once more.

“…The whole time?!” he squeaked.

“That’ right, sweetie. The whole time. And nothing happened, at all, did it? You did just fine.”

“Just fine?! No. This is terrible! Now they all know!”

“Know what? That you need diapers, buddy? Because you do. You know we need to pad you up before bedtime or you could fall asleep and wet your pants.”

“But it’s so embarrassing! And the diaper rubs are nice, but what if they saw that too? They’ll think I’m a freak!”

“So what if you enjoy them?” I said, firmly. “They don’t have to know that. Unless you want them to…”

“Nooooo” he said. “Please don’t tell them, Cyrus!”

I unbuttoned his pants, and let them fall to the floor so the diapers were in full view.

“Oh? I shouldn’t tell them that my little boy loves his little diapees and has to wear them because I keep you in them? I shouldn’t tell them that you are just an adorable little boy who is a goof and a dork and who is no longer allowed to use the potty without adult supervision?”

He was moaning now, as I rubbed the front of his soggy diaper.

“Don’t tell them that?” I asked.

“Yes,” he said, quietly as he leaned back into me and closed his eyes.

“Alright,” I said, picking up the pace of my rubbing. “But only if you admit to me that it’s all true. Repeat it after me and I’ll even let you put on your own diaper tonight.”

He just nodded in response.

“Repeat after me, little one.” I said. “I need diapers at night so I don’t wet my pants or bed.”

“I need diapers at night so I don’t wet my pants or bed. Ohhhh….”

He moaned as I rubbed a little faster and harder.

“Don’t cum yet baby boy, we’re not done. Say, “I’m just a little boy who wears diapers because my boyfriend keeps me in them, and I need his permission to use the potty.”

He repeated what I said.

“Good boy. You’re almost done. If you cum too early you’ll be getting a spanking, so listen carefully.” There wasn’t a real danger of him cumming. At this point I had gotten very good at edging him, backing off just enough whenever he got close to having an orgasm. “Say, I’m a little cutie who is no longer allowed to use the potty without permission.”

“I-I’m a l-little… huff… cutie who is… no longer allowed to… ohhh…. Use the potty without… permission.”

I was going all out now. Feeling his orgasm coming fast, I gave him one last thing to say.

“Say, I love my diapers, Cyrus, and I want you to keep me in them from now on.”

“I love my diapers, Cyrus and I want you to keep me in them from now on,” he screamed, as the noise of plastic being jostled back and forth filled the bathroom, faster and faster, ripping the orgasm from his body. He convulsed and went weak in the knees, but I was there to hold him. Of course he would want them off now, but I  stuck my fingers in the legholes of his diaper and declared them dry enough to sleep in. My fingers came back with a healthy dollop of cum on it, and I made him suck it off my fingers before allowing him to brush his teeth.

“Such a good boy,” I said, petting his head once he finished. I couldn’t wait for the next game night. I promised myself we’d make more progress by then so he’d be ready.  Maybe I’d have him go pantsless. The possibilities made me hard as diamonds, and I pressed my tented pants into the back of his diaper. “You’ve made your boyfriend very happy. Now you have to finish what you started.”

After all the events of the day, I needed to get one out as well. I hauled my blushy boy off to the bedroom for a nice hard fucking, opting to only pull down the back of the diaper to give me free access to his hole.

“No, no. the diaper stays on. You peed last time we did this, remember?”

He buried his red face in the pillow as I plowed him nice and deep. Nothing could compare to the feeling of babying my boyfriend, and I made sure to fill him to the brim with bubbling seed before kissing him goodnight.