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Chicago Undies Guyℒ️

@chiundiesguy

πŸ”ž NSFW Gamer Probably just want to see you in briefs or a singlet

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08.01.2025
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Latest posts by Chicago Undies Guyℒ️ @chiundiesguy

Sondheimslut poses in his underwear in the mirror

Sondheimslut poses in his underwear in the mirror

Offering some counter-programming to hump day

04.03.2026 14:27 πŸ‘ 202 πŸ” 2 πŸ’¬ 7 πŸ“Œ 1
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Part 2 for the day

06.03.2026 02:55 πŸ‘ 58 πŸ” 2 πŸ’¬ 1 πŸ“Œ 0
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I cut my hair and worked out

05.03.2026 22:12 πŸ‘ 90 πŸ” 3 πŸ’¬ 0 πŸ“Œ 0

Repost you in a singlet πŸ˜›

03.03.2026 00:14 πŸ‘ 46 πŸ” 2 πŸ’¬ 1 πŸ“Œ 0
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Everyone having a good Monday?

02.03.2026 21:06 πŸ‘ 41 πŸ” 1 πŸ’¬ 2 πŸ“Œ 0

God damn, good for you!! I loved this set initially but it kinda dropped off the face of the earth in the past couple weeks. If I played a good chunk I’d probably still only hit diamond though 🫑

02.03.2026 22:58 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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i see y’all posting your singlets and i just love a bandwagon to jump on

02.03.2026 19:03 πŸ‘ 1856 πŸ” 104 πŸ’¬ 58 πŸ“Œ 3

Mizuki mains rise up 🫑

27.02.2026 20:06 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

If their monetization wasn’t completely outrageous it would (kind of???) make sense but it genuinely is insanely expensive with the worst user experience. The amount of bots on that platform vs any others I’ve interacted with and constant ads are absolutely awful to deal with.

26.02.2026 05:19 πŸ‘ 5 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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ignore my messy dresser and look at my butt

25.02.2026 22:41 πŸ‘ 38 πŸ” 0 πŸ’¬ 5 πŸ“Œ 0
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can’t remember my login for the patrickalt and got locked out ☹️ so have to post this here ☹️ you understand ☹️ for humpday ☹️

25.02.2026 22:16 πŸ‘ 1514 πŸ” 63 πŸ’¬ 52 πŸ“Œ 5
Me showing my big ass in s’mores undies

Me showing my big ass in s’mores undies

Undies pulled down brow my bulbous ass

Undies pulled down brow my bulbous ass

Me flexing my back slightly showing my ass

Me flexing my back slightly showing my ass

My undies had s’mores on them 🍫 which bares the question would my ass be as tasty as a graham cracker marshmallow chocolate confectionery treat? Much to consider this #HumpDay #Gay

25.02.2026 22:23 πŸ‘ 94 πŸ” 3 πŸ’¬ 11 πŸ“Œ 0

I support this for you despite the nerfs

25.02.2026 22:36 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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How boys who play jetpack cat hang out

25.02.2026 19:52 πŸ‘ 1761 πŸ” 88 πŸ’¬ 35 πŸ“Œ 3
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Lunch break

25.02.2026 22:10 πŸ‘ 5070 πŸ” 818 πŸ’¬ 71 πŸ“Œ 23

Silent hill townfall probably comes out in a month and I cannot wait!!!!!!!!!!

22.02.2026 17:27 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

LMFAOOOOO get his ass

18.02.2026 00:48 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Hbd!!!

15.02.2026 05:32 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
White man reclining on brown couch wearing black vest and black jockstrap

White man reclining on brown couch wearing black vest and black jockstrap

This jockstrap has to be 12 years old at this point

14.02.2026 13:56 πŸ‘ 386 πŸ” 28 πŸ’¬ 5 πŸ“Œ 0
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Look at this unflexed pic my bf took of my ass

13.02.2026 20:13 πŸ‘ 815 πŸ” 25 πŸ’¬ 15 πŸ“Œ 3

JPC is WILDLY fast. I was so surprised playing them :1

10.02.2026 22:16 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Not mad about my arm side profile at the moment.

04.02.2026 21:46 πŸ‘ 154 πŸ” 6 πŸ’¬ 9 πŸ“Œ 0
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07.02.2026 18:51 πŸ‘ 52 πŸ” 1 πŸ’¬ 2 πŸ“Œ 0

hit all star in my final role in overwatch stadium for the season. 🫑

07.02.2026 06:19 πŸ‘ 8 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
White man flexing back muscles wearing jockstrap

White man flexing back muscles wearing jockstrap

Ok yes I did find a nice patch of light by the window yesterday, you caught me

05.02.2026 17:27 πŸ‘ 570 πŸ” 34 πŸ’¬ 8 πŸ“Œ 1

🀭🀭🀭 get her ass, show her who has the better glock

03.02.2026 02:42 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

I need this singlet

31.01.2026 22:47 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Plenty of room in this big butt

31.01.2026 09:01 πŸ‘ 506 πŸ” 60 πŸ’¬ 5 πŸ“Œ 1
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here’s some butt/bulge

31.01.2026 19:17 πŸ‘ 65 πŸ” 0 πŸ’¬ 2 πŸ“Œ 0