Pup Ryder

🙋🏼‍♂️ 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

915 Days 🔒 — A Very Merry Fistmas. Here’s a clip from Christmas Day with one of my favorite fisters. Couldn’t ask for a better ffriend to spend the holiday with.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

914 Days 🔒 — Officially Locked 2.5 Years As-Of Today. It’s odd but being locked has been one of the most rewarding journeys of pup’s life. Honestly couldn’t imagine not being locked.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

910 Days 🔒 — It’s really cold this morning, can you tell? Pup need cuddles, send cuddles.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

The One, The Only, Thee Incomparable…
@96khz.bsky.social

909 Days 🔒 — Pup has been super focused on stretching & pumping on a daily basis. Sir has been helping boy hold that focus with the goal of making a nice big pair of bull balls.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

906 Days 🔒 — Short clip from last night’s ffun session with one of favorite ffriends.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

903 Days 🔒 — Moto Pup, Engage!!!
Pup couldn’t help himself and bought himself his first racing suit for Fistmas.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

900 Days 🔒 — Two big milestones this month, today is pup’s 900th day locked which Sir and pup will be celebrating tomorrow, and 12/26 marks 2.5 years locked.
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

897 Days 🔒 — The Stretch Continues
#sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

896 Days 🔒 — #MXMonday
Sir’s ordered pup to spend the week stretching his balls. Gonna try to stretch at least 8-10 hours each day. #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

My ffriends are cooler and ffunnier than your friends…