🥵🤤😵‍💫

1015 Days 🔒 — Yesterday was nothing short of wild. Spent 5 hours getting worked over by two wonderful ffriends. By far the loosest pup’s hole has ever been. Double Punches and nearly a triple.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

1014 Days 🔒 — Keep Em Swingin. Wild that this has become boy’s normal. When boy doesn’t feel the steel between his legs he feels incomplete.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

1004 Days 🔒 — Weight, Weight, Don’t Tell Me!! Pup wanted to impress Sir @allthingspossible0.bsky.social so he got himself a new 2lb 1.4oz ball weight. It’s super comfy and will become part of pup’s daily wear. #sk8erboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

I will say this, anyone who thinks it’s a good idea to deploying poorly trained military cosplay enthusiasts who the majority of the nation spent the last six months railing against due to their unconstitutional methods, is a either an idiot or fully aware of how petty and vindictive they are being

So apparently they are going to be filling “non-critical” positions like guarding exits and helping keep lines moving. The TSA’s union has already told management they don’t think this is a good idea and will be a distraction for agents who haven’t been paid in three weeks.

1001 Days 🔒 — Things don’t always go as planned. Was supposed to celebrate with a ffriend yesterday but they had to cancel. Thankfully pup was still able to have some serious ffun.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

1000 Days 🔒 — Pup made it!! Locked is the only way this pup ever wants to be. Not planning to unlock anytime soon, if ever.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

999 Days 🔒 — Last Three Digit Day!! Tomorrow brings another big milestone. Excited to celebrate with some ffun.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

Cage = CherryKeeper Micro
Belt = Mr S Neo Waist Strap

995 Days 🔒 — It’s pup last five days in three digit numbers. Pup no longer enjoys the feel of being unlocked. Locked is life. Locked is right. Locked makes a good boy.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

🙋🏼‍♂️ Please

983 Days 🔒 — Better late than never!! Here a clip from a couple weeks ago. @thatpupdaxter.bsky.social spent some serious time opening my hole. That pup knows how to make this pup feel hole.
#sk8erboy #sneakerboy #chastity #fisting #latex #puplife #gaypup #fistpup #gearpup #permalocked #gayfist

983 Days 🔒 — Pup’s been working hard on wrecking his hole lately. This one is from yesterday’s double solo play session. Was so horny pup did two hour-long sessions.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

Just push the skin down and away from the pinch point as you slide the cage into the base ring. It’s definitely a two handed operation but shouldn’t difficult.

975 Days 🔒 — This means in 25 days, on March 21st, pup will have been locked for 1000 days. Shall we see if we can do another 1000?
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

968 Days 🔒 — Pup got really cold yesterday afternoon so it decided to suit up,
All The Way Up!! Went full drone for about ten hours.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

This one has been missed. Let’s all please welcum him back.

967 Days 🔒 — Pup’s still Ryder but suddenly he’s not in black. Absolutely loving my new light grey chest zip suit from Untitled Rubber.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

965 Days 🔒 — Nothing new to report butt we still here
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

961 Days 🔒 — Sir said they needed to hang lower so he bought pup another weight to add to the stack. This is pup default mode now.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

Such a good boy

956 Days 🔒 — Did another hour long training session last night. Spent some real time working my hole with the Maremaker 100, Wreckoner 110, and eventually my fist. The gape is so good!!
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

950 Days 🔒 — Shout out to @makoandtiger.bsky.social for their fantastic working modding two of my wetsuits and adding zipper. They do great work if you’re in the market.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

Oh. Man. I have discovered a beautiful new fetish. I was given an opportunity to unlock and worship my new shoes. I went feral. I crave more. Do you need your shoes/boots cleaned/worshipped? Thank you @rubber-sir77.bsky.social for the opportunity.

Another satisfied and satisfying nub!! Always happy to help.

950 Days 🔒 — Ever Smaller, Ever Longer
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

945 Days 🔒 — Just taking doubles again…
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

937 Days 🔒 — Post Pump Plump…
Excited to spend this evening being tortured and used by Sir @allthingspossible0.bsky.social
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

935 Days 🔒 — Pup realizes it’s been a minute since he last posted. 2026 is off to be busy start but pup is still locked and stretching on the regular…both balls and hole.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked