Diary of a Diaper Boy

Chapter 26: The Diaper Boys

We finished the movie and got ready to sleep. My diaper was nearly leaking at this point and I got a change from my mom. Dillon was waiting in the hallway.

"What's up?" I asked.
"Hey... so..." he said, "I'm not too good at diapering myself at night. Any chance your mom would be willing to?"

"I don't see why not. I'll ask." I replied, going back into the room.

"Hey, mom." I said, "Dillon wears diapers for bed as well, he was wondering if you could change him too."

She hesitated for a minute, "If it's okay with his parents, I don't mind."

I asked Dillion and he said that they were fine with it. He followed me into the room and my mom was waiting. I left to give him some privacy and headed to my room to find Jacob getting his spot ready on the floor.

"Where's Dillon at?" he asked.

"Between you and me," I lowered my voice, "Dillon wets the bed like me and has to wear diapers at night. My mom is changing him right now."

Jacob looked shocked. "Don't say anything to him." I said, "He is kinda embarrassed by it. This is his first sleepover."

"Really?" He said.

"Yeah," I replied in a whisper.

Jacob thought for a minute, and then he spoke. "How about I put on a diaper tonight as well? It would make him feel less weird about it."

I paused to think for a minute as well. "That might be a good idea," I said. "If he walked in to find both of us in diapers, he might feel more comfortable."

"Let's do it," Jacob said with excitement. "Let's get me diapered up too."

I grabbed a diaper from my drawer. Jacob and I were not the same size but it would fit well enough. I handed Jacob the diaper and he looked at it in his hands.

"Well, go put it on before Dillon gets in here," I said.

"You think I know how. I've never diapered myself," he replied.

"I guess your right," I replied.

Jacob and I sat there in an awkward silence for a few minutes. "You can put it in me right?" Jacob asked. "I don't want to ask your mom to do it, that would be super weird."

"You're right." I said, "I guess I could try. I'm probably better at diapering someone else than I am myself."

Jacob handed me the diaper and laid down. He started to pull down his pajama pants. I looked away quickly. "Oh come on," he said. "We've both got one. And you've seen it before."

I looked over to see my friend in just a t-shirt, butt naked on the floor waiting for me to change him. "Well, mine is a bit bigger than that," I said jokingly.

"You dick." He replied with a slight laugh, "Just put the damn diaper on me."

I slipped the diaper underneath Jacob and started to get a funny feeling. I hurried as fast as I could and continued to put the front of the diaper over him and fasten the tapes. "All done." I said, "Feel good?"

Jacob got up and adjusted the diaper. He was grinning from ear to ear. He felt the front and back of it and looked at me. "I kinda like it. It feels nice and comfy. It's like you are trapped in a pillow." he said as he started to check himself out.

That's when Dillon walked in. Jacob still hadn't got his pajama pants back on. Dillon stood in the doorway, staring at Jacob. Jacob's started to get red, then I started to giggle.

Dillon then took his pajama pants off, threw them at the wall, and stood there, exposing his fresh diaper as well.

Jacob started to laugh, like really laugh. Dillon started to as well. I then stood up, and ripped off my shorts, exposing my diaper along with my friends. They stopped laughing, looking at me. Then the three of us burst out laughing. Dillion and I were in tears, doubled over. Jacob was on the floor in tears as well.