23 UK Middle

“Alright spidey, let’s calm down and go to bed.” Damien said with a sigh, looking across the room at Andrew as he flexed in his little boy spider-man pajamas, his goodnites pull-ups peeking out and bulging through. It was all too good. Damien had spent so long on getting to know Andrew, finding out why the relatively cool senior in high school still seemed to be obsessed with super heroes and was only seen in tighty whities in the locker room. The answer? He was just a total baby. A bedwetter his entire life, had never touched any other big boy underwear but underoos and whities to his tiny pinkie dick. Damien couldn’t even pity Andrew, the “kid” seemed to love it. In fact, he felt a boner start to pop up in his boxers at the certain knowledge Andrew would wake up soaked and unbothered the next morning. Call it his spidey senses.

Maybe I should talk to him about your behavior and see what he thinks appropriate underwear for a little bully like yourself should be?

And anyways I’m too big for diapers, I was dry last night 😁 and @mr-talbot-tutor likes my undies he picks them out himself 😎

First time I took off my cage all month and it went straight back on 🔒

But it’s the opposite with the cage… I can’t fill one this big anymore 😭

I’m actually a little embarrassed about how cool I feel, I used to wear even cooler undies all the time but now… I’ll just enjoy being allowed to nap and play in my super cool Star Wars underoos😖

And now I’m getting dressed for the day so it’s back to my REAL undies again 😖 atleast they’re Star Wars too…