Diapered sleepover

How It Started

Dan was packing a bag for his sleepover tonight. His friend Oliver was moving out of town and this was their last night to spend together. He packed pajamas and made sure to pack his dino stuffy. It was a bit embarrassing that he still slept with a stuffed animal but Oliver already knew about it. He packed everything and started walking to Oliver's house. Oliver opened the door when he heard Dan knocking and greeted him. Dan smiled and followed Oliver to his room most of it was already packed the only things left was the tv and an air mattress. "It looks so empty in here it's gonna suck when you leave." Dan said as his smile started to fade. "I know but mom said you could come visit us and the new house has a pool" Oliver said trying to cheer him up. Dan nodded "What do you want to do?" he asked. "How about Truth or Dare?" Oliver asked. Dan nodded and they played for awhile before Oliver's mom told them to get ready for bed. Oliver looked at Dan "One more before bed Truth or Dare?" "Dare" Dan said. Oliver smiled "I dare you to wear one of my brother's pull ups to bed" Dan blushed as Oliver handed him a pull up. "Turn around" Dan said as he got changed. He put the pull up on and smiled a bit feeling how soft it was. Oliver turned back around "You look kinda cute in that" Dan blushed and quickly put his pants back on "Let's just go to bed" He said. Oliver nodded "Don't forget Rexy he's in your bag right?" Dan nodded and grabbed his dino stuffy and laid down in his sleeping bag.

Dan woke up the next morning and really needed to pee. He was about to get up but remembered he was wearing a pull up and for some reason really wanted know what it would feel like to use it. He looked over to make sure Oliver was still asleep and started to pee. He felt the pull up getting warm and smiled. Oliver started to wake up and Dan quickly got up and ran to the bathroom. He took off the wet pull up and threw it away putting his undies back on. Dan noticed his underwear was a lot thinner than the pull up and for some reason wanted to wear another one. He looked under the bathroom sink where he knew they kept a couple pull ups and put on another one. He smiled and spent the rest of the day helping Oliver and his family finish packing.

A week later Dan was getting ready for his birthday party and his mom told him there was a gift on his bed from Oliver. He quickly ran to his room and grabbed the present. There was a card on top of it he opened it and read it. "Sorry I couldn't make it to your birthday party but I thought you might like this present. I saw the wet pull up you left in the trash can and noticed you were wearing another one while we packed so I hope you enjoy pull up boy." Dan unwrapped the present and it was a pack of dinosaur pull ups. He put one on and texted Oliver "Thanks" with a blushing emoji and went back to start the party.

Continued in Little Friends Chapter 13