Chicago Showoff's Avatar

Chicago Showoff

@chicagoshowoff.bsky.social

belligerently bisexual, nonbinary loverboy + sex-positive bator most likely edging and/or exposing fat leaky dong | respond to messages on paid platforms ⬇️⬇️⬇️ https://linktr.ee/chicagoshowoff

2,885 Followers  |  2,312 Following  |  129 Posts  |  Joined: 13.11.2024  |  2.3187

Latest posts by chicagoshowoff.bsky.social on Bluesky

Video thumbnail

a fidget toy to help you relax
#TesticleTuesday #BullBalls #LowHangers

04.11.2025 22:11 — 👍 222    🔁 23    💬 4    📌 1
PLUTO - Show Haters (Visualizer) ft. Quavo
YouTube video by PlutoNotDaBrattVEVO PLUTO - Show Haters (Visualizer) ft. Quavo

48. PLUTO - Show Haters (feat. Quavo) youtu.be/P2r0BswN1QQ

03.12.2025 00:17 — 👍 0    🔁 0    💬 0    📌 0

Pucker up and give’em a kiss
throne.com/chicagoshowoff

01.12.2025 20:06 — 👍 14    🔁 0    💬 0    📌 0
Account owner is holding next to their giant hairy cock and balls an aluminum canister of 120 CUM 2.0 male enhancement tablets from Friend of Dorothy Supplements for an influencer ad campaign.

Account owner is holding next to their giant hairy cock and balls an aluminum canister of 120 CUM 2.0 male enhancement tablets from Friend of Dorothy Supplements for an influencer ad campaign.

If you want to try CUM 2.0 along with me follow this unique url
friend-of-dorothy.co.uk/chicagoshowoff and use discount code CHICAGO10.

I think my nuts are getting heavier already 🤭

20.09.2025 05:51 — 👍 98    🔁 7    💬 2    📌 0

On your knees admire my engorged sex. Open wide for your gag reflex test #FatCockFriday #CockWorship #Exhibitionist #DongExposure #PenisSex #FCF

14.11.2025 23:07 — 👍 71    🔁 3    💬 2    📌 0

On your knees admire my engorged sex. Open wide for your gag reflex test #FatCockFriday #CockWorship #Exhibitionist #DongExposure #PenisSex #FCF

14.11.2025 23:07 — 👍 71    🔁 3    💬 2    📌 0
T-Pain - Club Husband (Official Visualizer)
YouTube video by T Pain T-Pain - Club Husband (Official Visualizer)

47. T-Pain - Club Husband youtu.be/_wXd68UXgOE

10.11.2025 01:35 — 👍 0    🔁 0    💬 1    📌 0
Account owner is exposing a thick veiny pink dong out of the fly of thick gray winter pants while wearing gray wool socks and a warm coral top layer. The cock looks heavy, stinky and grateful for fresh air

Account owner is exposing a thick veiny pink dong out of the fly of thick gray winter pants while wearing gray wool socks and a warm coral top layer. The cock looks heavy, stinky and grateful for fresh air

Don’t worry babe. I’m still a slut for you. All these winter layers make for an obscene meaty and sweaty hang

12.01.2025 17:37 — 👍 403    🔁 29    💬 5    📌 1
ITZY「Algorhythm」Music Video
YouTube video by ITZY JAPAN OFFICIAL YouTube Channel ITZY「Algorhythm」Music Video

46. ITZY - Algorhythm youtu.be/8ExNmYax-ms?...

07.11.2025 04:29 — 👍 1    🔁 0    💬 1    📌 0
Preview
Pay me on Cash App Instantly exchange money for free on Cash App

😵‍💫😵‍💫😵‍💫 give in and press send cash.app/$ChicagoShow...

05.11.2025 02:34 — 👍 1    🔁 0    💬 0    📌 0
Video thumbnail

a fidget toy to help you relax
#TesticleTuesday #BullBalls #LowHangers

04.11.2025 22:11 — 👍 222    🔁 23    💬 4    📌 1
Preview
Chicago Showoff - Wishlist | Throne Send Chicago Showoff gifts via Throne. Browse Chicago Showoff's wishlist and support your favorite creator safely.

Today is my birthday!!! Buy out my wishlist or ding me on cashapp $ChicagoShowoff to make me feel special throne.com/chicagoshowoff 🎁🥳🎉🎈

04.11.2025 21:27 — 👍 1    🔁 0    💬 0    📌 0
Preview
Chicago Showoff - Wishlist | Throne Send Chicago Showoff gifts via Throne. Browse Chicago Showoff's wishlist and support your favorite creator safely.

throne.com/chicagoshowoff Check out my profile on Throne. You can purchase things I want and need, treat me to cash or something special, or send a surprise gift of your choice

04.11.2025 21:19 — 👍 1    🔁 0    💬 0    📌 0
Drop Dead {Visualizer}
YouTube video by Tei Shi Drop Dead {Visualizer}

45. Tei Shi - Drop Dead - youtu.be/SxxZe5QfNyw

26.10.2025 03:31 — 👍 0    🔁 0    💬 1    📌 0
Demi Lovato - Little Bit (Official Lyric Video)
YouTube video by Demi Lovato Demi Lovato - Little Bit (Official Lyric Video)

44. Demi Lovato - Little Bit youtu.be/1U2g66Dpyb0

25.10.2025 22:21 — 👍 0    🔁 0    💬 1    📌 0
An enormous, meaty, hairy penis at full erection is being displayed by a horny masturbator.  The cock and balls are flopped over the waistband of sweatpants and the beer-can-thick boner is being gripped by a big muscular hand (the cock dwarfs the hand). The penis head is flared and mushroom shaped and a giant main vein runs down the middle of the thick shaft.

An enormous, meaty, hairy penis at full erection is being displayed by a horny masturbator. The cock and balls are flopped over the waistband of sweatpants and the beer-can-thick boner is being gripped by a big muscular hand (the cock dwarfs the hand). The penis head is flared and mushroom shaped and a giant main vein runs down the middle of the thick shaft.

We just can’t help ourselves. Me and my hairy dong are hypnotizing boys and draining wallets tonight

18.11.2024 05:05 — 👍 519    🔁 33    💬 9    📌 2
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.

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.

I just received Nutsack Kiss from Anonymous via Throne. Thank you, good sub, for funding my lifestyle. throne.com/chicagoshowoff

14.10.2025 22:50 — 👍 116    🔁 5    💬 0    📌 1
Elmiene - Ode To Win (Official Audio)
YouTube video by Elmiene Elmiene - Ode To Win (Official Audio)

43. Elmiene - Ode To Win youtu.be/UeFYDtWDN6g?...

12.10.2025 03:13 — 👍 0    🔁 0    💬 1    📌 0
Señales - Simon Savi (Video Oficial)
YouTube video by Simon Savi Señales - Simon Savi (Video Oficial)

42. Simon Savi - Señales youtu.be/5yf5pVH6R3g

12.10.2025 00:11 — 👍 0    🔁 0    💬 1    📌 0
Lily Rose - Of Course I Do (Official Visualizer)
YouTube video by LilyRoseVEVO Lily Rose - Of Course I Do (Official Visualizer)

41. Lily Rose - Of Course I Do youtu.be/wLVTIPHhjsw

12.10.2025 00:01 — 👍 0    🔁 0    💬 1    📌 0
Video thumbnail

I was having a toe wiggling good time playing with myself 😵‍💫🦶

07.10.2025 21:56 — 👍 39    🔁 1    💬 0    📌 0
Preview
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.

Sperming on Soles and Wiggling my Toes: A Self Foot Worship Video www.manyvids.com/Video/692363...

07.10.2025 21:51 — 👍 13    🔁 0    💬 1    📌 0
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.

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.

Sometimes you just have to expose your genitals on the internet.

What’s up, Bluesky?

13.11.2024 18:24 — 👍 260    🔁 10    💬 6    📌 1
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.

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

The backside of the pink thong

A very sexy guy who is proud to serve my penis has been sending me gifts off my wishlist

17.12.2024 20:55 — 👍 123    🔁 8    💬 1    📌 0
Video thumbnail

Rub on your penis like me bro

17.08.2025 16:53 — 👍 60    🔁 3    💬 3    📌 0
Gift image

Gift image

I just received Jock Strap from Anonymous via Throne. Thank you, good sub, for funding my lifestyle.

01.10.2025 03:31 — 👍 6    🔁 0    💬 0    📌 0
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.

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.

If we spent a day together I wonder what we’d get up to?

28.09.2025 17:17 — 👍 113    🔁 2    💬 2    📌 0
A screen cap of the CashApp transaction history between the financial sub and account owner showing a total of $1,895 sent in tribute payments.

A screen cap of the CashApp transaction history between the financial sub and account owner showing a total of $1,895 sent in tribute payments.

My cash magnet cock said submit and $end

24.09.2025 23:15 — 👍 5    🔁 0    💬 0    📌 0
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

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

Aww he made me his home screen and then he emptied out his wallet

24.09.2025 22:54 — 👍 16    🔁 0    💬 1    📌 0
Account owner is holding next to their giant hairy cock and balls an aluminum canister of 120 CUM 2.0 male enhancement tablets from Friend of Dorothy Supplements for an influencer ad campaign.

Account owner is holding next to their giant hairy cock and balls an aluminum canister of 120 CUM 2.0 male enhancement tablets from Friend of Dorothy Supplements for an influencer ad campaign.

If you want to try CUM 2.0 along with me follow this unique url
friend-of-dorothy.co.uk/chicagoshowoff and use discount code CHICAGO10.

I think my nuts are getting heavier already 🤭

20.09.2025 05:51 — 👍 98    🔁 7    💬 2    📌 0

@chicagoshowoff is following 20 prominent accounts