ChiTownHole @chitownhole.bsky.social · 14/10/2026Thank you. I am told it looks even better when balls deep in it 😈😘 010
ChiTownHole @chitownhole.bsky.social · 13/10/2026Also I had a fun encounter with another bottom who made out with my hole so deeply and passionately it caught the attention the many voyeurs. 030
ChiTownHole @chitownhole.bsky.social · 13/10/2026static.klipy.comDavid Rose's Iconic 'Obviously' MomentALT: David Rose's Iconic 'Obviously' Moment 0120
ChiTownHole @chitownhole.bsky.social · 13/10/2026I do love getting pounded to within an inch of my life by an anonymous guy but I also love making out with a guy as we bate together. 040
ChiTownHole @chitownhole.bsky.social · 13/10/2026Fear of this exact scenario is why I bought a denim apron because I am always naked at home. 110
ChiTownHole @chitownhole.bsky.social · 13/10/2026Woke up today and my hole is not sore at all. The human body is amazing! 000
ChiTownHole @chitownhole.bsky.social · 13/10/2026Oh my that was an intense night at the bathhouse. I was fucked by some of the largest cocks I have encountered in a while, back-to-back. I had 3 prostate orgasms, thereby losing all coherency of speech to the poundings I was taking. I became a babbling gaped hole. It was amazing. 280
ChiTownHole @chitownhole.bsky.social · 12/10/2026This weather has me feeling feral as f**k. Thinking of going to @steamworkschi.bsky.social tonight for the @cumunion.bsky.social party. Any others of #gaychicago going? 050
Reposted by ChiTownHoleJohn Coons/Teo @johncoons.bsky.social · 11/10/2026CHICAGO! We're bringing our show Double InDUMBnity back to the Newport Theater 11/19 for a victory lap! If you missed out last time because we sold out, this one is for you! www.eventbrite.com/e/john-jonah...eventbrite.comJohn & Jonah in Double InDUMBnityFollowing their shows BLEAK! and Nocturnal Omissions, your favorite adult cabaret clowns, John and Jonah are back at the Newport Theater! 2101
ChiTownHole @chitownhole.bsky.social · 11/10/2026Getting fucked with a view of the ocean is next level. 180
Reposted by ChiTownHole𝗕𝘂𝗹𝗹𝗕𝗼𝘀𝘀𝗝𝗼𝘀𝗵 @bullbossjosh.bsky.social · 10/10/2026During my lectures we explore every inch of your slutty black hole 🕳️ 361387189
ChiTownHole @chitownhole.bsky.social · 08/10/2026True cumraderie is taking turns holding the bottoms cheeks apart so your fellow top can get in deeper. 030
ChiTownHole @chitownhole.bsky.social · 08/10/2026This #Jocktober it seems nobody is posting what should be the official song of the month: youtu.be/h5kw9xqEed4?...youtu.beJockstrapYouTube video by HungerFF - Topic 020
ChiTownHole @chitownhole.bsky.social · 08/10/2026These cakes’ gravity pull is too strong for this world.static.klipy.comFat Tony Fat Tony Dies In A Black HoleALT: Fat Tony Fat Tony Dies In A Black Hole 120
ChiTownHole @chitownhole.bsky.social · 08/10/2026static.klipy.comSisqo - Thong Song Music VideoALT: Sisqo - Thong Song Music Video 010
Reposted by ChiTownHoleSunday Bunday @sundaybunday.bsky.social · 07/10/2026Help me, Bluesky! You’re my only hope! *sound on* 8246
ChiTownHole @chitownhole.bsky.social · 07/10/2026static.klipy.comMadonna Getting Wet in Water SplashALT: Madonna Getting Wet in Water Splash 020
ChiTownHole @chitownhole.bsky.social · 07/10/2026I have a special tool that can be used to get an objective answer to this question. 020
ChiTownHole @chitownhole.bsky.social · 07/10/2026Magnificent. As a man who likes suits do you like me also wear a jockstrap with a suit? 010
ChiTownHole @chitownhole.bsky.social · 07/10/2026Wasn‘t planning on taking loads but got hit up by a regular I had not seen in a minute. He gets off when I talk about how other guys will use his cum as lube. So as to not be a liar, I took 2 other loads tonight. #feralfall 050
ChiTownHole @chitownhole.bsky.social · 07/10/2026static.klipy.comLion King: Mufasa & Simba at SunsetALT: Lion King: Mufasa & Simba at Sunset 050
ChiTownHole @chitownhole.bsky.social · 07/10/2026What if we fell in love getting a facial from the same cock? 050
ChiTownHole @chitownhole.bsky.social · 05/10/2026Nothing like a morning romp to put a smile on my face for this Monday morning. 040
ChiTownHole @chitownhole.bsky.social · 05/10/2026I looked up “smoldering look” in the dictionary and I found this hottie staring at me through my phone. 060