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
https://linktr.ee/chicagoshowoff
Pinned
I think my bulge wants love pats and kisses. What does my manhood make you wanna do?
Reposted by Chicago Showoff
November 4, 2025 at 10:11 PM
Pucker up and give’em a kiss
throne.com/chicagoshowoff
throne.com/chicagoshowoff
I just received Nutsack Kiss from Anonymous via Throne. Thank you, good sub, for funding my lifestyle. throne.com/chicagoshowoff
December 1, 2025 at 8:06 PM
Pucker up and give’em a kiss
throne.com/chicagoshowoff
throne.com/chicagoshowoff
Reposted by Chicago Showoff
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 🤭
friend-of-dorothy.co.uk/chicagoshowoff and use discount code CHICAGO10.
I think my nuts are getting heavier already 🤭
September 20, 2025 at 5:51 AM
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 🤭
friend-of-dorothy.co.uk/chicagoshowoff and use discount code CHICAGO10.
I think my nuts are getting heavier already 🤭
Reposted by Chicago Showoff
On your knees admire my engorged sex. Open wide for your gag reflex test #FatCockFriday #CockWorship #Exhibitionist #DongExposure #PenisSex #FCF
November 14, 2025 at 11:07 PM
On your knees admire my engorged sex. Open wide for your gag reflex test #FatCockFriday #CockWorship #Exhibitionist #DongExposure #PenisSex #FCF
On your knees admire my engorged sex. Open wide for your gag reflex test #FatCockFriday #CockWorship #Exhibitionist #DongExposure #PenisSex #FCF
November 14, 2025 at 11:07 PM
On your knees admire my engorged sex. Open wide for your gag reflex test #FatCockFriday #CockWorship #Exhibitionist #DongExposure #PenisSex #FCF
Reposted by Chicago Showoff
Don’t worry babe. I’m still a slut for you. All these winter layers make for an obscene meaty and sweaty hang
January 12, 2025 at 5:37 PM
Don’t worry babe. I’m still a slut for you. All these winter layers make for an obscene meaty and sweaty hang
November 4, 2025 at 10:11 PM
Today is my birthday!!! Buy out my wishlist or ding me on cashapp $ChicagoShowoff to make me feel special throne.com/chicagoshowoff 🎁🥳🎉🎈
Chicago Showoff - Wishlist | Throne
Send Chicago Showoff gifts via Throne. Browse Chicago Showoff's wishlist and support your favorite creator safely.
throne.com
November 4, 2025 at 9:27 PM
Today is my birthday!!! Buy out my wishlist or ding me on cashapp $ChicagoShowoff to make me feel special throne.com/chicagoshowoff 🎁🥳🎉🎈
Reposted by Chicago Showoff
We just can’t help ourselves. Me and my hairy dong are hypnotizing boys and draining wallets tonight
November 18, 2024 at 5:05 AM
We just can’t help ourselves. Me and my hairy dong are hypnotizing boys and draining wallets tonight
I just received Nutsack Kiss from Anonymous via Throne. Thank you, good sub, for funding my lifestyle. throne.com/chicagoshowoff
October 14, 2025 at 10:50 PM
I just received Nutsack Kiss from Anonymous via Throne. Thank you, good sub, for funding my lifestyle. throne.com/chicagoshowoff
Sperming on Soles and Wiggling my Toes: A Self Foot Worship Video www.manyvids.com/Video/692363...
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.
www.manyvids.com
October 7, 2025 at 9:51 PM
Sperming on Soles and Wiggling my Toes: A Self Foot Worship Video www.manyvids.com/Video/692363...
Reposted by Chicago Showoff
Sometimes you just have to expose your genitals on the internet.
What’s up, Bluesky?
What’s up, Bluesky?
November 13, 2024 at 6:24 PM
Sometimes you just have to expose your genitals on the internet.
What’s up, Bluesky?
What’s up, Bluesky?
Reposted by Chicago Showoff
A very sexy guy who is proud to serve my penis has been sending me gifts off my wishlist
December 17, 2024 at 8:55 PM
A very sexy guy who is proud to serve my penis has been sending me gifts off my wishlist
Reposted by Chicago Showoff
Rub on your penis like me bro
August 17, 2025 at 4:53 PM
Rub on your penis like me bro
I just received Jock Strap from Anonymous via Throne. Thank you, good sub, for funding my lifestyle.
October 1, 2025 at 3:31 AM
I just received Jock Strap from Anonymous via Throne. Thank you, good sub, for funding my lifestyle.
If we spent a day together I wonder what we’d get up to?
September 28, 2025 at 5:17 PM
If we spent a day together I wonder what we’d get up to?
Aww he made me his home screen and then he emptied out his wallet
September 24, 2025 at 10:54 PM
Aww he made me his home screen and then he emptied out his wallet
The guys at @friend-dorothy.bsky.social wanted me to try some of their sexual wellness products and I got my hands on the first one today.
It’s a daily dietary supplement that increases semen volume + enhances ejaculation for a more intense and healthy orgasm.
💪🏼🥴🍆💦💦💦
It’s a daily dietary supplement that increases semen volume + enhances ejaculation for a more intense and healthy orgasm.
💪🏼🥴🍆💦💦💦
September 20, 2025 at 5:40 AM
The guys at @friend-dorothy.bsky.social wanted me to try some of their sexual wellness products and I got my hands on the first one today.
It’s a daily dietary supplement that increases semen volume + enhances ejaculation for a more intense and healthy orgasm.
💪🏼🥴🍆💦💦💦
It’s a daily dietary supplement that increases semen volume + enhances ejaculation for a more intense and healthy orgasm.
💪🏼🥴🍆💦💦💦
No way, boss, that’s not a waistbanded boner and I’m definitely not mindlessly rubbing it at work 😵💫🍆
September 19, 2025 at 6:05 PM
No way, boss, that’s not a waistbanded boner and I’m definitely not mindlessly rubbing it at work 😵💫🍆
Reposted by Chicago Showoff
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
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
December 4, 2024 at 7:14 AM
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
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
If you're not afraid of public penis pleasure join me in my secret spot www.manyvids.com/Video/686340...
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...
www.manyvids.com
September 15, 2025 at 7:21 PM
If you're not afraid of public penis pleasure join me in my secret spot www.manyvids.com/Video/686340...
Bush, balls and feet makin’em weak. Submit to hairy hog $end your hard earned cash to me
September 9, 2025 at 6:52 PM
Bush, balls and feet makin’em weak. Submit to hairy hog $end your hard earned cash to me
Didn’t continue the live updates today but we ended with 6 callers (1 video) and 7 cumshots. Lots of sexting off and on, and one personalized small penis humiliation video. Not a bad day
September 4, 2025 at 3:43 AM
Didn’t continue the live updates today but we ended with 6 callers (1 video) and 7 cumshots. Lots of sexting off and on, and one personalized small penis humiliation video. Not a bad day
Made a man bust this morning with just my voice. Happy September gay people on my phone
September 2, 2025 at 12:39 PM
Made a man bust this morning with just my voice. Happy September gay people on my phone
How to Shoot Cummies: A Masturbation Encouragement Video www.manyvids.com/Video/679336...
ChicagoShowoff - How to Shoot Cummies - ManyVids
Oh shoot, bubba, you caught me trying to sperm my penis. Since you're here you might as well masturbate with me. I'll show you how it's done. I'll show you how to shoot your cummies
www.manyvids.com
August 17, 2025 at 4:35 PM
How to Shoot Cummies: A Masturbation Encouragement Video www.manyvids.com/Video/679336...