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Chicago Showoff

@chicagoshowoff.bsky.social
3.8K followers 3.1K following 169 posts

belligerently bisexual, big-dicked nonbinary loverboy most likely edging and exposing fat leaky dong | respond to messages + go live on paid platforms ⬇️⬇️⬇️ linktr.ee/chicagoshowoff

PostsRepliesMedia
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 15/06/2026
Looks like it’s deep dish and deep dick for you
The account owner flopped out their hairy semi-engorged sex parts in front of a fresh-baked deep dish pizza cooling in a 10in round pie pan.
421511
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 17/03/2026
Babe I cooked us dinner but first we gotta fuck
Account owner displays an engorged erection with unruly pubes in the kitchen while waiting for oven roasted veggies to cool Pictured is a large-batch weekly meal prep of pan roasted cabbage and chicken sausage
61349
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 15/04/2026
Hey cutie we’re having taco bowls with sweet potato instead of rice and a side of hairy ballsack
Account owner displays roasted sweet potato chunks and fresh-prepared guacamole in two different sized bowls which strangely resemble the size of their hairy testicles
2998
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 05/05/2026
Hey goober it’s time to eat again
Account owner shows off their hairy cock and balls and a green crunchy broccoli and snap pea salad
233123
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 25/09/2026
We’ve got 25 minutes
The account owner is naked in the kitchen again preparing to reheat fried fish sticks and bake thinly sliced and seasoned yellow summer squash to crispy perfection. Their veiny heavy dick and low hanging balls are partially covered by the sheet pan of food but their unruly curly bush of pubes is on full display.
21155
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 07/09/2026
Lake Michigan is gorgeous this time of year
The account owner pictured from the knee down dangles their legs off the edge of a rock jetty, dipping their toes in the surf against the backdrop of clear blue sky and clear blue water stretching toward a white horizon.
2391
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 02/08/2026
If you wanted to see the printmaker all you had to do was ask
Account owner pulls open the waistband of black shorts to expose a wrist thick veiny erection surround by curly brown pubic hair. A sizeable portion of their dick remains pinned down in the shorts. The prominent main vein down the center of its shaft is often visible through fabric garnering attention.
216413
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 09/05/2026
cock and also balls
Account owner is showing off an obscenely large engorged erection after sneaking off for an edging session of penis rubs in the bathroom
441236
Chicago Showoff @chicagoshowoff.bsky.social · 09/10/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
i kiss the sky by CS on Apple Music
Playlist · 8 Songs
030
Chicago Showoff @chicagoshowoff.bsky.social · 09/10/2026
It’s ready to be devoured
In the kitchen wearing only a old T-shirt with the sleeves cut off, the account owner shows off a bean and squash tostada and their juicy round ass.
4942
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 21/06/2026
I inherited this from my father. Pretty cool appendage I must say
Account owner pulls back their shorts and boxers to give you a Birds Eye view of their penis and pubes. This is what their hairy sex looks like on any given day when forced to wear pants.
742335
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 07/09/2026
Meet me at our picnic spot if you know what’s good for you
POV: you’re sitting across from the account owner at their secret waterside picnic spot with top tier views
2593
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 04/11/2025
a fidget toy to help you relax #TesticleTuesday #BullBalls #LowHangers
1780488
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 13/08/2025
Happy Toe Tuesday, buddy. Now suck this stomper🦶🏻
Account owner’s size 12 foot is sole up with toes spread. The whole foot appears wet and shiny from oil or slobber
2394
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 13/11/2024
Sometimes you just have to expose your genitals on the internet. What’s up, Bluesky?
A proud masturbator is spreading their legs on the couch exposing a side profile of their rock hard, veiny erection. The bator’s hand can barely reach around the base of the girthy sex rod surrounded by a forest of bushy, dark brown pubic hair.
633716
Chicago Showoff @chicagoshowoff.bsky.social · 25/09/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
don’t be shy by CS on Apple Music
Playlist · 8 Songs
030
Chicago Showoff @chicagoshowoff.bsky.social · 25/09/2026
We’ve got 25 minutes
The account owner is naked in the kitchen again preparing to reheat fried fish sticks and bake thinly sliced and seasoned yellow summer squash to crispy perfection. Their veiny heavy dick and low hanging balls are partially covered by the sheet pan of food but their unruly curly bush of pubes is on full display.
21155
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 14/04/2026
If you see my penis on a Monday you’re destined for a great week. It’s science #exposedpenis #bushtok #porn #monochromemonday #mcm
Account owner is holding back their big bush to expose a semi-flaccid veiny penis with a downward curve. This is the view you would see if the account owner was taking a piss next to you in a public toilet.Zoomed in for detail to further expose the account owner’s big curly bush, the low hanging nutsack and the veiny shaft.
316913
Chicago Showoff @chicagoshowoff.bsky.social · 08/09/2026
——> the beach playlist music.apple.com/us/playlist/...
music.apple.com
juicy like lemon//needed a shoulder by CS on Apple Music
Playlist · 8 Songs
030
Chicago Showoff @chicagoshowoff.bsky.social · 07/09/2026
Meet me at our picnic spot if you know what’s good for you
POV: you’re sitting across from the account owner at their secret waterside picnic spot with top tier views
2593
Chicago Showoff @chicagoshowoff.bsky.social · 07/09/2026
Lake Michigan is gorgeous this time of year
The account owner pictured from the knee down dangles their legs off the edge of a rock jetty, dipping their toes in the surf against the backdrop of clear blue sky and clear blue water stretching toward a white horizon.
2391
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 17/12/2024
A very sexy guy who is proud to serve my penis has been sending me gifts off my wishlist
Someone holds the packaging of a magic bullet blender they received as a gift from their Amazon wishlist while wearing a pink thong, also a gift from the wishlist. The backside of the pink thong
216910
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 04/12/2024
I love to make a cocksucker happy by spreading my legs Cock drunk😵‍💫 and obedient🫡 @dcthroat.bsky.social made love to my whole package 💪🏻😎 And there’s nothing better than that tongue action on my nuts while my pole is getting throated. That’s skill
136440
Chicago Showoff @chicagoshowoff.bsky.social · 04/08/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
it didn’t stop me by CS on Apple Music
Playlist · 8 Songs
000
Chicago Showoff @chicagoshowoff.bsky.social · 04/08/2026
I will feed you and I will fuck you. It’s how I show I care 🫶
In the photo the account owner is approaching you naked with a big, heavy, swinging cock to offer a plate with a halved shrimp roll/po’boy on it because you’ve been working too hard again and need a food break.
518512
Chicago Showoff @chicagoshowoff.bsky.social · 02/08/2026
If you wanted to see the printmaker all you had to do was ask
Account owner pulls open the waistband of black shorts to expose a wrist thick veiny erection surround by curly brown pubic hair. A sizeable portion of their dick remains pinned down in the shorts. The prominent main vein down the center of its shaft is often visible through fabric garnering attention.
216413
Chicago Showoff @chicagoshowoff.bsky.social · 18/07/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
the same way, indeed by CS on Apple Music
Playlist · 8 Songs
030
Chicago Showoff @chicagoshowoff.bsky.social · 18/07/2026
On the back porch tonight with pesto and penis. Only thing missing is you
Account owner displays a big bowl of pesto pasta salad with their big veiny cock resting on the rim of the bowl
41735
Chicago Showoff @chicagoshowoff.bsky.social · 15/07/2026
Boy math is pretty simple. I spread my legs. you simp, serve and send gifts. throne.com/chicagoshowoff
0793
Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 28/05/2026
I just received a Nutsack Kiss from Anonymous via Throne. Your obedience will be rewarded, son, but first submit to my superior sex. throne.com/chicagoshowoff
Account owner is flexing while sitting on the edge of a bed with their heavy sex dong and bull balls hanging free through the fly of light blue Calvin Klein boxers.
114910
Chicago Showoff @chicagoshowoff.bsky.social · 21/06/2026
I inherited this from my father. Pretty cool appendage I must say
Account owner pulls back their shorts and boxers to give you a Birds Eye view of their penis and pubes. This is what their hairy sex looks like on any given day when forced to wear pants.
742335
Chicago Showoff @chicagoshowoff.bsky.social · 20/06/2026
I just received HARD WOOD | Boy Smells Candle from Danny via Throne. Keeping me bricked up and smelling fresh. Thanks, bud!
070
Chicago Showoff @chicagoshowoff.bsky.social · 15/06/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
everything twinkles by CS on Apple Music
Playlist · 8 Songs
040
Chicago Showoff @chicagoshowoff.bsky.social · 15/06/2026
Looks like it’s deep dish and deep dick for you
The account owner flopped out their hairy semi-engorged sex parts in front of a fresh-baked deep dish pizza cooling in a 10in round pie pan.
421511
Chicago Showoff @chicagoshowoff.bsky.social · 28/05/2026
I just received a Nutsack Kiss from Anonymous via Throne. Your obedience will be rewarded, son, but first submit to my superior sex. throne.com/chicagoshowoff
Account owner is flexing while sitting on the edge of a bed with their heavy sex dong and bull balls hanging free through the fly of light blue Calvin Klein boxers.
114910
Chicago Showoff @chicagoshowoff.bsky.social · 25/05/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
follow your <3 by CS on Apple Music
Playlist · 8 Songs
030
Chicago Showoff @chicagoshowoff.bsky.social · 25/05/2026
If I invite you to brunch you gotta be my munch
Account owner in the kitchen shows off a made to order omelet with dill, carrots, pickled purple onion and turkey bacon as well as a big ole slab of hairy dong.
51493
Chicago Showoff @chicagoshowoff.bsky.social · 09/05/2026
cock and also balls
Account owner is showing off an obscenely large engorged erection after sneaking off for an edging session of penis rubs in the bathroom
441236
Chicago Showoff @chicagoshowoff.bsky.social · 05/05/2026
I just received Sexy Swimwear from Danny via Throne. Thanks for assisting my show off, sweet sub.
040
Chicago Showoff @chicagoshowoff.bsky.social · 05/05/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
bring you my way by CS on Apple Music
Playlist · 8 Songs
120
Chicago Showoff @chicagoshowoff.bsky.social · 05/05/2026
Hey goober it’s time to eat again
Account owner shows off their hairy cock and balls and a green crunchy broccoli and snap pea salad
233123
Chicago Showoff @chicagoshowoff.bsky.social · 30/04/2026
Big hairy wiener with prominent main vein needs a slutty tongue to lick up the leakage #throwback #thirstythursday #tbt
Account owner kicks back on the bed to unbutton denim shorts allowing their fully rock hard cock to breathe. The glorious erection shows off the veins, curly pubes and a precum dripping mushroom head.
632632
Chicago Showoff @chicagoshowoff.bsky.social · 22/04/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
and baby, the sky is too by CS on Apple Music
Playlist · 8 Songs
020
Chicago Showoff @chicagoshowoff.bsky.social · 22/04/2026
Hurry home princess we’re having bbq beef and peanut noodles
Account owner shows off thin-shaved beef and a colorful (green and orange) cold noodle salad near their hairy nude lower half.Account owner shows off thin-shaved beef and a colorful (green and orange) cold noodle salad near their hairy nude lower half.
31438
Chicago Showoff @chicagoshowoff.bsky.social · 15/04/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
woke up thinking about you by CS on Apple Music
Playlist · 8 Songs
010
Chicago Showoff @chicagoshowoff.bsky.social · 15/04/2026
Hey cutie we’re having taco bowls with sweet potato instead of rice and a side of hairy ballsack
Account owner displays roasted sweet potato chunks and fresh-prepared guacamole in two different sized bowls which strangely resemble the size of their hairy testicles
2998
Chicago Showoff @chicagoshowoff.bsky.social · 14/04/2026
If you see my penis on a Monday you’re destined for a great week. It’s science #exposedpenis #bushtok #porn #monochromemonday #mcm
Account owner is holding back their big bush to expose a semi-flaccid veiny penis with a downward curve. This is the view you would see if the account owner was taking a piss next to you in a public toilet.Zoomed in for detail to further expose the account owner’s big curly bush, the low hanging nutsack and the veiny shaft.
316913
Chicago Showoff @chicagoshowoff.bsky.social · 06/04/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
that 1 1 1 1 1 by CS on Apple Music
Playlist · 8 Songs
010
Chicago Showoff @chicagoshowoff.bsky.social · 06/04/2026
Come over here and get you some
Account owner flops out veiny dong and heavy ball sack in the kitchen to tempt you to come over for dinner. Pictured is a large-batch weekly meal prep of pan roasted Brussels sprouts, cauliflower and chicken legs.
41375
Chicago Showoff @chicagoshowoff.bsky.social · 17/03/2026
—> the kitchen playlist music.apple.com/us/playlist/...
music.apple.com
between the now & then by CS on Apple Music
Playlist · 5 Songs
010