Pup Milo
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Pup Milo
@pupmilo.com
Your friendly service/beta pup and serial replier. Witty online, bumbling IRL, and struggling to keep the @tailwags.dog pups in line.

📍Washington DC

#dcpup #dmvpup #pupplay #pupkink
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It’s not where you go. It’s the pups you meet along the way. ❤️❤️❤️

@puptunder.bsky.social
@pupsaki.bsky.social
@apuprex.bsky.social
@puphawks.bsky.social
Reposted by Pup Milo
What about those of us who can't get erect? 😖
November 5, 2025 at 12:31 PM
Pups stan for public transit! 🚌🚇🚋🚎

#Pupride2025 #pupkink #pupsridetrains
🚇 Doors Opening — This is a Bark Line Train to Dogtown! 🐾

Join your fellow pups and handlers as we take over @wmata.com for our very first PUP RIDE!

Meet at 1PM outside Smithsonian Station then ride to Metrobar for Sit, Stay, Sip.

More info👉 partiful.com/e/7uugY3fR0Z...

#dcpups #pupplay
November 5, 2025 at 12:25 PM
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If you voted today, you’re exponentially a hotter person. Just saying
November 4, 2025 at 2:32 PM
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Who’s a Good Boy?! I’m a Good Boy.

Thank you @pupmilo.com for working hard to provide fun daily challenges and to all the participating pups @tailwags.dog for helping make a wonderful #locktober.

Looking forward to defending my title next year!
🏆 🐕
#pupplay #trophydog
November 3, 2025 at 1:57 PM
A few pups were ready to watch the 17th Street High Heel Race when a couple of women squeezed in front of us and blocked our view.

Milo was not happy.

#pupplay #dcpups #getoutofoursafespaces

📸 Pup Reddy
October 29, 2025 at 4:00 PM
Reposted by Pup Milo
TailWags Got a Glow Up 💅

As TailWags hits its one year anniversary, we have a new, fresh logo and website. Check it out and share with your pup friends: www.TailWags.dog
TailWags
CHECK OUT OUR CALENDER FOR UPCOMING EVENTS!
www.TailWags.dog
October 26, 2025 at 2:14 PM
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Privet Paw-mrades! You can call me a pawmunist, if you must. It's high time the pawletariat siezes the means of pawduction and we shall do Karl Barx proud. Pups of DC, unite! You have nothing to lose but your chains!

No gods, no masters. Eat the rich ... or at least dinner at La Cosecha.

#dcpups
October 14, 2025 at 4:16 PM
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Made a new freind and gave him a gift!
I promise I didn't stick my bone in this one... 🤮.

#Halloween #pumpkin #jack-o-lantern #pupplay
October 14, 2025 at 4:32 PM
Look at these cute dogs!!! 😍
The TailWags pack ended our monthly Pup Bar Crawl at Revolt.

Follow us to see where the pack heads to next month!

📸: @pupmilo.com

#dcpups #pupplay #dcgays
October 11, 2025 at 4:32 PM
@apuprex.bsky.social says this is the laziest crawl I’ve ever made.

In this economy, who can afford to do a lot of walking between bars?
🍻 Pup Crawl this Friday, Oct. 10 🍻

We always hang out on the gay side of U and 14th. Let's be adventurous and explore the straight side, then scurry back to our side.

➡️ RSVP at partiful.com/e/bpmy0z9yUr...

#dcpups #dcgays #pupplay #pupkink
October 9, 2025 at 3:36 PM
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guys @pupmilo.com is making me do wicked things
October 8, 2025 at 1:11 AM
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October 1, 2025 at 1:02 AM
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@puparpi.bsky.social took this adorable pic of me and @pupdryx.bsky.social at @tailwags.dog’s last unleashed 🥺
September 30, 2025 at 2:02 PM
Helpz!!! I'm drowning in balls!!!
September 26, 2025 at 12:42 AM
I come up with the craziest ideas sometimes. I should get a medal. 🏅
@pupmilo.com has a crazy idea. What if we did a pup crawl but like stayed in one bar instead -- for real this time. Let's do that at Uproar this Saturday!

Come Sit, Stay, and Sip with us! It's going to be one paw-some night out! 🐾

#pupkink #pupplay #dcgays #dmvgays #dcpups #dmvpups
September 23, 2025 at 1:27 AM
Baarrrk!!! I is here to have my booty plundered. 🏴‍☠️
September 20, 2025 at 12:56 PM
Just because I’m locked doesn’t mean my little guy can’t enjoy some fresh air.

#fcf #caged #locked #chastity
September 19, 2025 at 6:49 PM
Reposted by Pup Milo
Is it a park? Kinda. Is there water? Probably not. Is it a cute all outdoor space that we have limited time left to enjoy while daylight dwindles and the weather still cooperates, mostly? Absolutely.

Pup dinner is at National Landing Water Park this week.

#pupplay #pupkink #dcgays
September 16, 2025 at 11:12 AM
The weather is going to be perfect for this pup crawl!!!
🍻 PUP CRAWL THIS FRIDAY, SEPT. 12

The dog days of summer are over, and Shaw’s outdoor beer gardens are calling! We’ll catch the perfect weather before it’s gone.

➡️ More info & to RSVP: partiful.com/e/AxADFhIY6N...

#dcgays #pupkink #pupplay #dcpups #dmvpups
September 9, 2025 at 6:47 PM
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The pups are taking over As You Are for dinner again this week! Join the DMV's goodest boys for a lowkey dinner.

#pupkink #pupplay #dcgays #dcpups #dmvpups
September 9, 2025 at 5:34 PM
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September 6, 2025 at 9:22 PM
San Francisco Pups!!! I’m in your town. Any pup events happening tonight?

#sfpups #pupplay #pupkink
September 5, 2025 at 9:09 PM
Had a good time getting sized for my new pink @kink3d.com cage at @mrsleather.bsky.social

Cage is so comfortable. No reason to take it off. 😈

#pupplay #pupkink #chastity #publicnudity #exhib
September 5, 2025 at 2:07 PM
Follow this “anxious bean”.

Totally not true when they are around me. 😊
Bark Bark! I’m Ace! We’re gonna try this Bluesky thing out. 😌 Don’t Expect a ton of spicy content cause I identify as an anxious bean.
August 24, 2025 at 2:00 AM
Reposted by Pup Milo
Looking for an early start to your Saturday night? Join a bunch of good boys at Shakers and then at Revolt.

🍻🐶🐾
🍸 Join other dogs at this month's "Sit, Stay, Sip," a new TailWags social where we crash a local queer bar. This Saturday, we head to Shakers at 5PM, Aug 23.

Then, let's show some love for DC's newest queer bar, Revolt, for their soft opening at 7PM.

#dcgays #dmvgays #pupkink #dcpups #pupplay
August 23, 2025 at 12:57 PM