Chicago Briefs @chicagobriefs.bsky.social · 09/05/2026Underwear that matches the marine layers at sunrise #bikinibriefs #calzones #mutande #slips 🩲: N2N Bodywear 151
Chicago Briefs @chicagobriefs.bsky.social · 12/04/2026These skies over Lake Michigan can’t be beat #thong #manthong #tanga #string 161
Chicago Briefs @chicagobriefs.bsky.social · 11/04/2026Inside vs out 🩲: Box Menswear #thong #tanga #manthong #string 151
Chicago Briefs @chicagobriefs.bsky.social · 09/04/2026“Boxing” at the gym 🥊 🩲: Box Menswear #tanga #manthong #thong 171
Chicago Briefs @chicagobriefs.bsky.social · 08/04/2026Chicago Riverwalk briefing 🩲: Intimissimi Uomo 131
Chicago Briefs @chicagobriefs.bsky.social · 25/03/2026@petitqunderwear.bsky.social thong for me this morning 272
Chicago Briefs @chicagobriefs.bsky.social · 12/01/2026🌴🌴🌴🌴💪🏻💪🏻💪🏻💪🏻 🩲: @petitqunderwear.bsky.social 1102
Chicago Briefs @chicagobriefs.bsky.social · 08/12/2025Orange’nt you glad it’s Monday? 👖: DSG 🩲: Dietz 131
Chicago Briefs @chicagobriefs.bsky.social · 04/12/2025Gym to the streets in yellow 💛 👖: Nike 🩲: Dietz 131
Chicago Briefs @chicagobriefs.bsky.social · 28/09/2025Hot and that smile again. I would be on my knees in a second to put my face in that thong 000
Chicago Briefs @chicagobriefs.bsky.social · 07/09/2025Pushing though the cool autumn weather 🍂 👖: Nike 🩲: GX3 121
Chicago Briefs @chicagobriefs.bsky.social · 03/09/2025Late summer Chicago mornings ☀️ 👖: Nike 🩲: Bikkembergs 362
Chicago Briefs @chicagobriefs.bsky.social · 29/08/2025Keep going into autumn 🍂 👖: N2N Bodywear 🩲: Box Menswear 121
Chicago Briefs @chicagobriefs.bsky.social · 14/08/2025Wearing my two favorite brands to workout in. 👖: N2N Bodywear 🩲: @petitqunderwear.bsky.social 141
Chicago Briefs @chicagobriefs.bsky.social · 13/08/2025Taking advantage of these spectacular summer sunrises 🌅 👖: Puma 🩲: N2N Bodywear 121
Chicago Briefs @chicagobriefs.bsky.social · 04/08/2025Monday morning 🤦🏻 👖: GX3 Underwear 🩲: Propaganda Tokyo 031
Chicago Briefs @chicagobriefs.bsky.social · 25/07/2025Would you still consider them shorts if you can see through them 👀? 👖: @GX 🩲: @petitqunderwear.bsky.social 131
Chicago Briefs @chicagobriefs.bsky.social · 23/07/2025Stopped at the end of my run to drop trou and take some lakeside sunrise photos 🩲: @cocksox.bsky.social 161
Chicago Briefs @chicagobriefs.bsky.social · 23/07/2025Chicago can be a beautiful city when the light is just right. 👖: N2N 🩲: Mundo Unico 051
