>Be 9yo, already social outcast at school
>best friend is a 7yo girl (we'll call her Jenny), mom's best friend's daughter
>whatever, she's still cool, we play vidya and she keeps up with Teenage Mutant Ninja Turtles and X-Men animated so we can talk about it and play pretend
>she goes to a different elementary school (probably fortunate in hindsight)
>we play together every Saturday and half the Sundays too
>Mom has something planned, her friend agrees that I can just stay the night with Jenny
>Jenny does not like the sound of this; do not understand why, we do everything together - more time is fun time, we're both only kids
>Have a lot of fun in the afternoon, she starts getting pensive after dinner
>time to get ready for bed kids
>I take a shower first, go get my pajamas and hang on the couch watching a movie.
>Jenny comes out in a nightshirt, but I can see the diaper bulge underneath, it crinkles a little.
>"Anon, I just have to wear these because I wet the bed sometimes, okay?"
>Ask her if I can see it
>Never seen someone turn bright red before, she lifts up her nightshirt and reveals princess pullup
>Immediately obsessed, no idea why
>Ask her if she's embarrassed, she nods
>"Jen's mom, she's embarrassed about the diaper thing, I'll wear one too..."
>Jen's mom goes along with it.
>Jen was all worried when I asked but in way better mood once we're both wearing one.
>Don't bother to put my pajama bottoms on, just wear the princess pull-ups
>Watch T.V. for an hour, go to bed, I sleep on the floor in Jen's room.
>Jen wakes me up the next morning, had forgotten I was in a pull-up until I sat up on my sleeping bag.
>Have to piss like a race horse
>"Hey, can I pee in it?"
>Don't know why I asked Jen. She giggles and nods
>Flood that sucker
>Jen had peed during the night too
>We got out, have cereal and watch cartoons in wet pull-ups
>Jen's mom wakes up, comes out, and sees us on the couch in visibly wet pull-ups
>"You two are going to leak on the couch, at least change into new ones"
>"But I'll miss the good part"
>Almost laugh at Jen's whining
>Her mom comes back with fresh pull-ups, pack of wipes
>Jen stands up, hikes up her nightshirt
>Mom tears sides of pull-up, it hits the ground with a light thud. She's wiping her daughter, like, two feet from me
>Huge frog in throat
>Jen steps into new pull-up
>Jen's mom steps in front of me
>Hesitantly stand myself up, both wanting and dreading this happening.
>Jen's mom rips the sides, my willy meets cool air and shrivels but Jen's mom just goes to town wiping the piss off my junk. Feels cold but good.
>Step into the new pull-up, also feels good
>Jen's mom lightly slaps the bottom of my pull-up, I'm pretty embarrassed but force a smile as I sit down. Really did enjoy it.
>Fast forward three years
>Been having sleep-overs practically every week for ages
>Mom thrilled to have Saturday nights to herself
>Jen's mom happy to have us there, in retrospect I think she might've been into shotas a bit... but she never did anything illegal... just made sure she really cleaned my junk.
>She switched us to tape-diapers a few weeks in, said changes would be easier and she'd be less worried about leaks
>Mom never asked about diapers, don't know if she ever knew, I certainly didn't tell her.[Expand Post]
>I never thought much of it, but Jen's mom must've been special ordering diapers for us as they never stopped fitting; they did have two tapes.
>In warmer months we'd play outside in just diapers
>Jen's 11 and a half now, I just turned 14
>She actually has breast buds, they don't exactly jiggle but they're not flat anymore either.
>Getting straight painful erections when she's going around in just her diapers
>Think I'm being subtle rubbing one out in my diaper every now and again, doesn't take much for me to cum in a wet diaper while watching her titties.
>Rubbing the front of my diaper, watching cartoons with Jen on the other arm of the couch
>Realize she's rubbing the front of her's too, and she's looking at me.
>Does she know what she's doing?
>"Wanna snuggle?"
>I couldn't believe I dared to ask that, I hadn't in awhile. >She nods, snuggling into me on the couch, but stops touching her diaper.
>Casually (not at all) drop a hand onto her diaper, her hand ends up on mine, with both start moving a bit, quickly turns into vigorous rubbing with us both looking straight ahead at the T.V.
>Start cumming, turn to Jen, she's looking at me big doe eyes.
>I kiss her right on the lips, she tenses up, jerking against my hand
>In the afterglow, both of us are kind of shocked.
>We'd always been super close, like brother-sister, but never like that
>Jen's mom came in for a diaper check soon after that, I was pretty wet so I headed back to the bedroom with her
>Yeah, she still changed me at 14, though I didn't have any hair down there - she shaved it off for me
>Made poopy diaper changes way easier, that's another story I guess
>This time, Jen follows us back. It wasn't like she wasn't always allowed, we'd just been giving each other our privacy for changes for the last two years.
>Jen's staring at my junk hardcore while her mom wipes me down, powders me, and tapes up a fresh diaper.
>Her turn next, I spent the whole time staring at her vulva, all red from arousal.
>Next week when I come around she's wearing a t-shirt and a diaper
>Says mom told her to cover up as she's getting breasts
>Jen's mom must've noticed something
>Doesn't matter though, it would take more than that to stop the direction of fate
>That night, sleeping on the couch (Jen's mom had moved me out of her room when I started 7th grad), Jen wakes me up in the middle of the darkness.
>She straddles my midsection, our diapers crinkling together, puts a finger on my mouth to shssh me.
>We hump and feel each other up, I came in like 2 minutes, and again in about 7. It took her 10.
>We're hugging each other for dear life on that couch as we kiss.
>I force a little tongue (I'd read about it on the internet) and she goes with it.
>After what feels like only another minute, she breaks it off and returns to her room.
>Want to sleep in her room and snuggle again so bad.
>Next day, Jen's mom sits us down at the table
>"What's going on between you two?"
>We feign ignorance
>"I heard something in the living room last night."
>Jen and I are caught
>I didn't know what to say. Jen does, says she's always loved me, I'm her boyfriend, and mom should just let us sleep in the same room again.
>Mom says she doesn't want to be a grandmother so early.
>"Gaah, we keep our diapers on," Jen says, incensed.
>Line so strange both Jen's mom and I crack up.
>Jen's mom says she needs to think
>Crazy worried whole next week
>Weekend sleepover comes
>Jen's mom cool with it, as long as, like Jen promised "we keep our diapers on" during that stuff.
>Fuck, I'm down, basically given permission to frot on her daughter.
>Spend, like, half the day making out on the couch. Hump in diapers to completion on her bed twice, once with each of us on top.
>Awkward as Jen's mom coming in for a diaper check with both of us napping her bed, but also hot.
>I'm wet, Jen's basically dry, she's still cuddling me a little as her mom untapes my diaper.
>Little guy is at half mast thanks to Jen's bare titties against my arm
>Weird having my legs in the air while my girlfriend snuggles with me
>Realize how completely my mom would probably not be okay with any of this and, also, that no one is ever going to tell her.
>Ask Jen out on a date next week, she says yes
>We decide on Friday, Jen's mom agrees to give us a ride, mom is okay with two-day sleepover.
>I run by my house to grab my bag then bike over to Jen's, her mom's still at work but Jen's school gets out earlier than mine.
>Ask her if she wants to wear diapers.
>We'd change each other once in a blue moon when Jen's mom was busy but she liked doing it so we almost always left