Diaperpup Chicago
@diaperpupchicago.bsky.social
Just a pup looking for fun times and new abdl adventures. And probably a diaper change!
Last nights diaper before changing for bed! I was so droopy.
January 4, 2026 at 3:00 PM
Last nights diaper before changing for bed! I was so droopy.
Happy New Year Everyone! Hope everyone gets just as soggy as me today!!
January 1, 2026 at 4:52 PM
Happy New Year Everyone! Hope everyone gets just as soggy as me today!!
My new shorts don’t leave much to the imagination, but they allow daddy to quickly see how full I am!
December 31, 2025 at 10:24 PM
My new shorts don’t leave much to the imagination, but they allow daddy to quickly see how full I am!
Merry Christmas and Happy Holidays from my soggy butt to yours!!
December 25, 2025 at 5:16 AM
Merry Christmas and Happy Holidays from my soggy butt to yours!!
So which one of you is gonna get down there and check this diaper?
December 20, 2025 at 3:26 AM
So which one of you is gonna get down there and check this diaper?
Rocked both my big boy undies and my little guy diapers today!
December 7, 2025 at 11:38 PM
Rocked both my big boy undies and my little guy diapers today!
The aftermath of daddy waking up and deciding my diaper was the best spot to pee!
December 7, 2025 at 8:15 PM
The aftermath of daddy waking up and deciding my diaper was the best spot to pee!
Daddy may have made me a little excited!
December 6, 2025 at 11:49 PM
Daddy may have made me a little excited!
Did I need to go to the bathroom, yes. Did I need to use the airplane bathroom to do so, no! But how else am I to prove that im being a responsible good boy and keeping my pants dry?
November 29, 2025 at 12:03 AM
Did I need to go to the bathroom, yes. Did I need to use the airplane bathroom to do so, no! But how else am I to prove that im being a responsible good boy and keeping my pants dry?
I’m all about a good view!!
November 28, 2025 at 5:15 AM
I’m all about a good view!!
Somebody come change me before I leak everywhere! But diaper squeezes first because it feels so good!
November 24, 2025 at 12:32 AM
Somebody come change me before I leak everywhere! But diaper squeezes first because it feels so good!
When that morning light hits right and highlights both my super soggy diaper and bed head!
November 22, 2025 at 11:34 PM
When that morning light hits right and highlights both my super soggy diaper and bed head!
Trying out a new diaper! And so far I really like the feel and the look! Teddy bears really do it for me.
November 16, 2025 at 5:30 PM
Trying out a new diaper! And so far I really like the feel and the look! Teddy bears really do it for me.
Hope everyone else enjoyed their BDF as much as I did! I also may have leaked all over the kitchen floor before changing.
November 15, 2025 at 12:49 AM
Hope everyone else enjoyed their BDF as much as I did! I also may have leaked all over the kitchen floor before changing.
Reposted by Diaperpup Chicago
Wish I had some help getting diapered up this morning
November 12, 2025 at 2:30 PM
Wish I had some help getting diapered up this morning
So update on the pull-up situation. I ended up with a small wet spot on my shorts, and then proceeded to flood them in the shower because I knew they were full.
November 11, 2025 at 1:23 AM
So update on the pull-up situation. I ended up with a small wet spot on my shorts, and then proceeded to flood them in the shower because I knew they were full.
Trying some pull-ups, going to see if I can make it to the end of my work day in 3 hours without leaking! Anyone wanna place a bet?
November 10, 2025 at 8:05 PM
Trying some pull-ups, going to see if I can make it to the end of my work day in 3 hours without leaking! Anyone wanna place a bet?
Reposted by Diaperpup Chicago
Unlike kindergarten, grad school weirdly doesn’t demand potty training as an entrance requirement
November 9, 2025 at 9:38 PM
Unlike kindergarten, grad school weirdly doesn’t demand potty training as an entrance requirement
Daddy interrupted my gaming session and made me get my diaper changed!
November 10, 2025 at 3:56 AM
Daddy interrupted my gaming session and made me get my diaper changed!
My daddy I need a diaper on look!
November 8, 2025 at 9:48 PM
My daddy I need a diaper on look!
Someone ended up a very soggy boy on his flight home!
November 7, 2025 at 4:05 AM
Someone ended up a very soggy boy on his flight home!
After a thorough sogging! I have to say I’m a fan. I like the design, the wetness indicators are cool and it held up like a champ, you can definitely soak a lot. I did have to readjust the tapes quite a few times as my belly loosened the top tapes which is normal for hook & loop for me.
October 8, 2025 at 6:04 PM
After a thorough sogging! I have to say I’m a fan. I like the design, the wetness indicators are cool and it held up like a champ, you can definitely soak a lot. I did have to readjust the tapes quite a few times as my belly loosened the top tapes which is normal for hook & loop for me.
Last night versus today. I’ve almost unlocked all the hidden items!
October 8, 2025 at 3:55 PM
Last night versus today. I’ve almost unlocked all the hidden items!
Guess it’s time to go game! Kinda really dig this new diaper!
October 8, 2025 at 1:38 AM
Guess it’s time to go game! Kinda really dig this new diaper!
My BDF submission! No boosters today.
October 3, 2025 at 10:42 PM
My BDF submission! No boosters today.