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Chicago Showoff

@chicagoshowoff.bsky.social
3.8K followers 3K following 167 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 · 04/11/2025
a fidget toy to help you relax #TesticleTuesday #BullBalls #LowHangers
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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
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Reposted by Chicago Showoff
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.
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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.
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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.
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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.
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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.
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Reposted by Chicago Showoff
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
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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.
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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
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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
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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
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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.
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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.
214311
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
41575
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
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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.
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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.
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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!
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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.
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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.
114710
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.
51383
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
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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
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
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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.
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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.
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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
2958
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.
316813
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.
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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
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Chicago Showoff @chicagoshowoff.bsky.social · 13/03/2026
I just received Bator Grease from Anonymous via Throne. Thanks for keeping me slick, sub.
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Chicago Showoff @chicagoshowoff.bsky.social · 13/03/2026
I just received EliteMan Celestial Trunk from Anonymous via Throne. Thank you for keeping me comfortable, sub.
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Chicago Showoff @chicagoshowoff.bsky.social · 13/03/2026
I just received Backpack - Obsidian Black from Anonymous via Throne. Thank you, good sub, for funding my lifestyle.
010
Chicago Showoff @chicagoshowoff.bsky.social · 13/03/2026
I just received Barefoot Training Shoes from Anonymous via Throne. Thanks for the gear, sub.
011
Chicago Showoff @chicagoshowoff.bsky.social · 01/01/2026
52 songs for 52 well lived weeks
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Chicago Showoff @chicagoshowoff.bsky.social · 01/12/2025
Pucker up and give’em a kiss throne.com/chicagoshowoff
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Chicago Showoff @chicagoshowoff.bsky.social · 14/11/2025
On your knees admire my engorged sex. Open wide for your gag reflex test #FatCockFriday #CockWorship #Exhibitionist #DongExposure #PenisSex #FCF
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Chicago Showoff @chicagoshowoff.bsky.social · 04/11/2025
a fidget toy to help you relax #TesticleTuesday #BullBalls #LowHangers
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Chicago Showoff @chicagoshowoff.bsky.social · 04/11/2025
Today is my birthday!!! Buy out my wishlist or ding me on cashapp $ChicagoShowoff to make me feel special throne.com/chicagoshowoff 🎁🥳🎉🎈
throne.com
Chicago Showoff - Wishlist | Throne
Send Chicago Showoff gifts via Throne. Browse Chicago Showoff's wishlist and support your favorite creator safely.
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Chicago Showoff @chicagoshowoff.bsky.social · 14/10/2025
I just received Nutsack Kiss from Anonymous via Throne. Thank you, good sub, for funding my lifestyle. 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.
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Chicago Showoff @chicagoshowoff.bsky.social · 07/10/2025
Sperming on Soles and Wiggling my Toes: A Self Foot Worship Video www.manyvids.com/Video/692363...
manyvids.com
ChicagoShowoff - Sperming on Soles and Wiggling my Toes: Self Foot Worship - ManyVids
Spread legs. Spread toes. Big, hard boner. Watch me enjoy my size 12 stompers before shooting cum all over the soles. It's a toe wiggling good time.
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Reposted by Chicago Showoff
Chicago Showoff @chicagoshowoff.bsky.social · 17/08/2025
Rub on your penis like me bro
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Chicago Showoff @chicagoshowoff.bsky.social · 01/10/2025
I just received Jock Strap from Anonymous via Throne. Thank you, good sub, for funding my lifestyle.
Gift image
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Chicago Showoff @chicagoshowoff.bsky.social · 28/09/2025
If we spent a day together I wonder what we’d get up to?
Account owner takes a front facing selfie of their body standing in little, thin, light blue house shorts, inviting you to imagine what you’d like to do together.
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Chicago Showoff @chicagoshowoff.bsky.social · 24/09/2025
Aww he made me his home screen and then he emptied out his wallet
Screen shot of a conversation between account owner and a financial sub. 
sub: I want to so bad daddy {proof of making my bulge his lock screen} You’re so hung 🤤🤤
account owner: you’re a good girl for daddy’s fat cock
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Chicago Showoff @chicagoshowoff.bsky.social · 19/09/2025
No way, boss, that’s not a waistbanded boner and I’m definitely not mindlessly rubbing it at work 😵‍💫🍆
Account owner (in business casual activewear) shows off a thick, veiny erection flipped up and pinned down by an elastic waistband while sitting in an office chair.
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Chicago Showoff @chicagoshowoff.bsky.social · 15/09/2025
If you're not afraid of public penis pleasure join me in my secret spot www.manyvids.com/Video/686340...
manyvids.com
ChicagoShowoff - Cum Outside with Me. I Have a Secret Spot - ManyVids
I know a spot for the real bate bros. We can let our balls hang and be one with nature. I know a spot for the real exhibitionists. Those who aren't afraid of public penis pleasure. Would you let me ta...
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Chicago Showoff @chicagoshowoff.bsky.social · 09/09/2025
Bush, balls and feet makin’em weak. Submit to hairy hog $end your hard earned cash to me
Naked account owner stands wide stance at the top of an ocean blue yoga mat showing off their feet, hairy legs, low hanging balls, semi-erect, veiny penis, and full bush. The cock and balls hang heavy and aromatic after yoga practice.
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