ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 21mWell summer vacation is officially over. I got a job. ❤️❤️❤️😭😭😭 1110
Reposted by ChicagoDomDaddy™️Z. @ztafterdark.bsky.social · 30/09/2026You couldn’t tell me shiiiit today 🖤 11322
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 30/09/2026Husband: Do you want ice cream? Me: No. I feel like popcorn. I’m gonna make popcorn. Want popcorn? H: No I want ice cream. M: Ok <makes popcorn> H: <Eats half my popcorn. Still has ice cream> I’m not gonna be the chubby one in this relationship much longer. 0220
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 29/09/2026I admittedly look at the world thru rose colored glasses. I’m not Pollyanna by any regard, but I look at things objectively and honestly and figure out how to be successful within the confines of our capitalistic oligarchy to not just survive but thrive and then enact change as much as I can. 1110
Reposted by ChicagoDomDaddy™️Pup Paimon @puppaimon.bsky.social · 28/09/2026This message reached me a week before I turn 27 and the timing could not have been more needed 2151
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 28/09/2026Watching many of my boys hit their 30s the past few years and several more who will be. It’s so stupid that gays focus on the importance of being in thier 20s and feel like they’re expired after 30. Lemme tell ya, from experience; my 30s were 100x better than my 20s, my 40s were 100x better 1392
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 27/09/2026Cousin girlfriend: Can I smell your crotch? No! Hmmm. Must be your feet. 010
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 25/09/2026I have absolutely zero FOMO for Folsom this weekend. And to cement my retirement from events and parties I attended a drag contest to support a friend, who won by one vote so my attendance mattered, and had to decompress on the couch for an hour after. I never expected to be a homebody but here I am 2280
Reposted by ChicagoDomDaddy™️Colt Spence @coltspence.bsky.social · 25/09/2026When I tell you to worship me this is what I expect 🤤 @lancewoodsxxx.bsky.social 836048
Reposted by ChicagoDomDaddy™️Zachary✨ @zachias.bsky.social · 25/09/2026My contribution to the gray sweats discourse 0131
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 24/09/2026It’s a Chicago thing. We have our own beer. 0200
Reposted by ChicagoDomDaddy™️ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 22/09/2026I did a long form video podcast about coming of age at the start of the beginning of the AIDS crisis. youtu.be/w8hrkGbigRkyoutu.beDark times growing up as Gay in the 90s: HIV epidemics, nightlife and moreYouTube video by Art Bezrukavenko 0503
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 22/09/2026I did a long form video podcast about coming of age at the start of the beginning of the AIDS crisis. youtu.be/w8hrkGbigRkyoutu.beDark times growing up as Gay in the 90s: HIV epidemics, nightlife and moreYouTube video by Art Bezrukavenko 0503
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 20/09/2026My primary Chicago boy is taking his mom to Europe for her birthday and their plane got delayed by a day. He was taking her back to his place for the night (she lives in another city) and decided to bring her by to meet me. I, of course, was genteel and polite but when I hugged him goodbye ….. 1322
Reposted by ChicagoDomDaddy™️Cell Block Chicago @cellblockchi.bsky.social · 19/09/2026LET'S GO! BEAR UNION TODAY. 3PM-8PM. TONIGHT: CHUNK is BACK in CHICAGO AT THE LEGENDARY CELL BLOCK for a BEEF-FEST like no other! CHUNK Chicago presents NYC LEGEND DJ DICAP & CHICAGO WIZARDS AMAN STER & DJ ANDY w/ THCKRTANKER HOT GOGO BEARS TREMAINE & CASH // HOSTED BY COACH MIKEY. #GETINHERE 0112
Reposted by ChicagoDomDaddy™️Chicago Eagle @chicagoeagle.bsky.social · 17/09/2026Two rooms. Four DJs. One very late Saturday night. 🦅 GORP + VERY SOMETHING take over the Main Stage while JUAN AKA GRIZZLY + TITO BARBOSA go underground in The Bunker. $10. Cover After 9:00pm 021
Reposted by ChicagoDomDaddy™️The Kennel Chicago @thekennelchicago.bsky.social · 11/09/2026Two years of The Kennel, and the pack keeps growing! 🐶🐾 Jackhammer celebrates 2 years of pup play. Music by Vanquish, JasperHoney420, Ryan Cezanne, Arthrotica. Hosted by Ruby, Rubber Excel, Wilde, Photon, Tracer, Grayson. Fri Oct 2, 9PM-4AM 0143
Reposted by ChicagoDomDaddy™️Jackhammer Chicago @jackhammerchicago.bsky.social · 18/09/2026GOLDILOXX is back at Jackhammer in just two days! Handsome hosts and beefy gogos are here to keep the big boys moving all night. Find a bear to take down to The Hole this Saturday September 19th from 9PM-5AM at Jackhammer. 6406 N Clark St 072
Reposted by ChicagoDomDaddy™️MAFIA Chicago @mafiachicago.bsky.social · 19/09/2026🎃 HOLE-A-WEEN at @jackhammerchicago.bsky.social 🎃 Get ready for a spooktacular night! Costumes are strongly encouraged Sunday, October 25, 4-8 PM Ticket drops: • MAFIA Members ($30): On sale Mon, 9/21 • General Public ($40): On sale Thu, 9/24 #FF #MAFIA 1101
Reposted by ChicagoDomDaddy™️Jackson Howell 🎥 @jacksonhowell.bsky.social · 19/09/2026Need someone to crawl into bed with after these long horny bar shifts 🥵🥰 956333
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 18/09/2026My 46 year old straight cousin is kinky af. He told us he fists his gf with both hands. One in the front hole one in the back at the same time. Last week he asked about cock rings. I’m going to visit them next weekend so I had to ask him a question in our family group chat. 🤦🏽♂️🤦🏽♂️🤦🏽♂️ 0261
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 17/09/2026Part of my journey has been learning about, embracing and intentionally employing compersion. I rarely experience jealousy these days. Rather I experience compersion. Makes for a much more joyful life. What is Compersion? Link in thread. 2180
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 17/09/2026I don’t care if someone is cheating on their partner with me, but don’t fucking tell me you are because then we won’t fuck. Not because you’re cheating because I think you’re a shit person. And especially don’t try it if I know who your partner is. I’m not going to tell them but I do think you’re 💩 2120
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 16/09/2026Last night two different people messaged me to tell me how I impacted their life simply by being nice and kind when they were struggling. Both of them I hadn’t thought of twice after the interaction that we had that they remembered. One as long as five years ago. The other one last month. 2130
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 13/09/2026Robyn concert at United Center last night in Chicago. 0220
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 13/09/2026Today was the first day since Arc weekend where I felt really good all day. Had energy, wasn’t dragging, didn’t feel like taking a nap all day. Of course I woke up at 8:30, made breakfast and napped until 11. And got hyper focused on a side quest for an hour until I got yelled at. Lazy boat day too 2120
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 11/09/2026After a slow start to summer because of the crappy weather in June and July I’ve been hitting it hard since market days, then my birthday then Arc. This week has been spent catching up on sleep and responsibilities. Taking an extended break from nightlife, probably until Halloween. Lordy. 0130
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 09/09/2026Big event happening for me today! Wish me luck! More out later l! 2220
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 08/09/2026This is you. Especially the younger queers. Broadcasting your life on socials is inspiring little yous. And you’ll never know it. ❤️❤️ 1354
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 08/09/2026What an amazing August and Labor Day weekend. It’s like summer sucked and didn’t even start happening until August. June and July weather sucked, rainy cold cloudy in June. Then smoke from Canada and storms all July. And then we went to hit and humid asf beginning of August. Fun started market days 190
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 06/09/2026Ok, so a close friend, my younger brain clone actually, one of them, sent me this; “Also we have a new game; Ask Chatgpt this prompt: Do you think im a top or bottom in gay subculture.” And it sent me down a rabbit hole of top/bottom, D/s, control, role, position questions where I am basically 260
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 06/09/2026Peak queer poly: Husband drags primary boy off to breed him surreptitiously. 1250
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 05/09/2026I just wrote a huge long thread, and it was almost done, and it was great. Then I set my phone down for a second, drank some water, my phone went dark, and when I woke it up, Bluesky restarted and it was all gone. No cache. I know it does this. I should have expected it. I did. And did it anyway 190
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 04/09/2026Today If I want to do something, and my friends don’t, I do it by myself. Wasn’t always like this tho. I wanted to go to Italy for years. My Ex-Bf kept saying “next year”. When we broke up I booked Italy for the following summer. Then I met my now husband. This was October. Nearly 20 years ago. 1200
Reposted by ChicagoDomDaddy™️Jackson Howell 🎥 @jacksonhowell.bsky.social · 03/09/2026So fucking horny after chest day, I just need someone to get me off or get off inside me while I relax and game 🥵 639610
Reposted by ChicagoDomDaddy™️ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 03/09/2026On Market Days 2026 I gifted my 42 year old leather boots to my mini me; Mario, “Its-a-meee-a-mario” (Rollerdiscogay on IG) Luna. Who then promptly wore them at the Eagle San Francisco with my Daddy friend Ed. Mario is the SECOND Mexican boy to wear a those boots at the Eagle. 0334
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 03/09/2026In September 1984 I bought my leather boots. Red Wing Loggers. I bought them for a job, I was a ranch hand at the Equestrian Center at UC Davis. Working horses, stalls, cows, shoveling shit, straw and hay. When I left school I put them to work in the trades; asphalt, paint, concrete. Then I was gay. 3211
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 03/09/2026A dozen people flew into Chicago for my milestone birthday party. Another 300+ attended. One man was at my 30th birthday party. Another I’ve known since he was 19, he’s 49 now. One I took to PV for his 30th, he’s 45. I am eternally grateful for the people in my life, my family. Create your community 0250
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 01/09/2026Saturday after the beach bash for my birthday we all cleaned up and ate and recharged for a while, then by about 12:30 seven (7!!) of the boys that wear my collars and who I mentor and love as my brothers and family came to my place for an intimate afters. There was of course some sexy time, 1220
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 31/08/2026So this is on the gram right now. No idea how long it will stay up. www.instagram.com/p/DcuAQqKqId... 1170
ChicagoDomDaddy™️ @chicagodomdaddy.bsky.social · 31/08/2026Fuckin 60. What the fuck. Dude. Seriously. What the fuck. 6520
Reposted by ChicagoDomDaddy™️Kinky Things I Like @kinkythingsilike.bsky.social · 29/08/2026Best I can do for today. 0111