Daily Free-Write November 25, 2020: Diaper-Training my Boyfriend

I could feel his diaper pressing into my right butt cheek as he twined his legs around my thigh. The puffy plastic protruding out from his waist was such a familiar sensation that it felt wrong to have him in bed without it. In fact whenever Tommy and I snuggled, I’d insist he be diapered.

The alarm went off and he fumbled to pick up his phone and turn it off. When he put it down, he noticed me staring.

"Oh, did I wake you?"

"No, love. You didn't."

Without asking I slid my hand under the sheets and cupped his diaper.

"Somebody's a soggy guy this morning. It's a good thing I keep you diapered for bed." I gave him a half-lidded smile.

"Oh my gosh, Cyrus! Stoooooop!" Even in the morning light I could see him blushing.

"You're so cute when you're embarrassed. Come on, buddy, let's get you into the shower."

I pulled him into the bathroom and untaped his tapes, letting the diaper fall to the ground with a loud thud.

Imagine my surprise when I learned that my boyfriend was a bedwetter. But it was darn cute, too. It took a while to get him comfortable with letting me take care of his changes, but eventually he stopped complaining and just let me take charge.

"Into the shower with you, soggy butt." I smacked his rear to hurry him up and raised an eyebrow as a few more drops of pee hit the bathroom floor. Today was shave day so I brought in a razor and cream for after we washed up.

Warm water streamed down his body. He was soft and small with feminine features, especially since we'd let his hair grow out more. I started with his hair, running my fingers through the soft blonde curls. I rinsed and moved on to the rest of his body.

"Arms up, bud."

He sighed and put them up.

"Don't get huffy with me. I know you like getting washed in the shower."

"Sorry, I do, it just feels a little childish. I don't know."

"Nobody here but us, love. If you enjoy it, then just relax and let me give you some personal attention. And smile."

"Okay," he said, smiling a goofy smile. "Thanks for washing me Mr. Man!"

"Dork." I chuckled.

"Okay, your all done, now it's time to shave your diaper area."

He winced and blushed.

"Can we not call it that?"

"Why not? That's what it is. Your diaper area. The place where your diapers go when I put them on you."

"Aw geez." He covered his face with his hands.

"Hey, you need them for bed. So what? That's nothing to be ashamed of.”

"I guess you're right..."

"I know I am, so shut it. Now let's get your little bits and your tush nice and smooth for your diapers."

Every time I said diapers I played with his cock. I wanted to condition him to get hard every time I said the word, and from what I could see, it was working. I held up his penis against my own and noticed the pronounced size difference.

"Such a little guy down there."

"Cyrusss!" he whined. "You know I can't help that."

"It's good. I like it small. Saves me time shaving."

I gave him a little kiss on the forehead and then creamed him up as I told him how much I liked him just the way he was.

[detail]

"Okay, love, you're all done. Go ahead and dry off.”

As soon as he was out of the bathroom, I began to jack off furiously. I never told him just how turned on I was when I did things for him like diaper him up or shave him. I'm sure he could have guessed by the extra helpings of dick juice I'd been feeding him since I started.

I imagined taking charge of his changes during the day as well, keeping him in diapers and locking the bathroom so I could control his potty schedule, showers, and anything else he needed to do in there. I thought about how I started cutting up his food. How he looked embarrassed but said nothing when I did it in front of his friends last week. About after, when I scolded him for cursing and warned him, he'd get a spanking. I thought about how I encouraged him to drink more before bed and then cuddled him with my hand against his crotch til I felt it getting warm. Whispering him to sleep as he continued to pee. I thought about how much more he was wetting, how we had to switch to even thicker diapers for night-time use. And then I thought about what I planned for him later. I screwed up my eyes and came. [description]

"Oooohhhhh, holy mother of... wow." I opened my eyes and watched the last white spurts of semen paint the floor of the shower.

"Oh gods that was good," I said to myself, leaning against the wall and catching my breath.

I shut off the shower and went into the bedroom. He was already dressed for work.

"Be home by four tonight, yeah?"

"Of course. I won't be late." We were having some of our friends over for our weekly dinner and game night.

He gave me a quick peck on the cheek and left. After he left, I checked my online orders. A new package was arriving today. Perfect timing.

Later that night we finished dinner a littler later than usual. It was almost eight by the time everyone was done because we were having so much fun just talking. There were seven of us, and we'd been doing this game night for a while now, so someone was already clearing off the table before I had the chance, and Percy, our resident game guru, was setting up tonight's game.

"It's a bluffing game called cookie security. We have to guard the cookie vault, but one of us is the cookie thief."

"Sounds exciting! Tommy and I just have to step away for a second and take care of something in the other room."

"Sure, take your time." He said. "Looks like Cassie and Jorge are still busy with the dishes anyway."

Tommy gave me a questioning look but I just led him over to the bedroom. His diaper was already waiting for him on the bed.

"Up up!" I said, patting the bed.

He looked at me with his mouth hung open.

"You can't be serious. Not now! There are people here."

"You remember what we agreed to 8 o clock, no exceptions."

"But it's not even bedtime!"

"This is about developing good habits, buddy. We've been over this before. Now up on the bed or they're gonna hear me making good on my threat of a spanking."

"I still haven't forgiven you for that, you know."

"Yeah yeah, keep it moving."

He relented and parked his butt right on top of the diaper where it belonged. I smiled as I powdered him and taped him up. He got squirmy when he saw I was going to use the scented baby powder on him, but he knew he couldn't stop me. At least not quietly.

This was good. I had slowly been bumping back his diaperings earlier and earlier knowing that eventually it would overlap with nights when we had company.

I checked the leg guards to make sure there would be no leaks and patted his diaper. I had added two stuffers into the diaper to account for the longer duration and his diapers looked extra thick and poofy because of it. It was adorable.

"This is really thick, Cyrus. There's no way I can keep this hidden."

"Don't worry bud. You'll be wearing pants. No one will see.

"And what about the noise? These diapers are really loud. And the smell of the baby powder?"

"Your mouth is louder than the diaper," I said, pulling up his pants and zipping them. "Now stop worrying! just go on out there and let's play some games and have fun with our friends."

I pulled him up off of the bed and gave his thickly padded butt a pat. It made a 'whoof' sound and he walked forward a few steps, then hesitated. He looked down at his pants and twisted around to look at his butt.

"You really think they won't notice?" He seemed doubtful.

"You can hardly even tell," I lied.

I hurried him out to the living room to rejoin the group.