1073 Days 🔒 — Pup calls it Stretchmaxxing #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked #gaywetsuit #geargay

1068 Days 🔒 — Geared Up…for what? #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked #gaywetsuit #geargay

1061 Days 🔒 — Pup is slowly working towards taking bigger doubles. A ffriend came over last night and gave pup a good long stretch. #sk8erboy #sneakerboy #chastity #puplife #gaypup #fistpup

1059 Days 🔒 — A Well Deserved Soak #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

1055 Days 🔒 — BIG STRETCH = BIG BALLS!! Gotta love a big pair bull balls on a dickless pup. #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

1054 Days 🔒 — BIG STRETCH!! #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

1053 Days 🔒 — After four weeks of travel pup is finally home and getting back to his training routine. Spent all day doing a series of 30-40 minute workouts. Did five separate blocks and this was the result #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup #permalocked

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

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

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

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

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…

895 Days 🔒 — Here’s a clip from last nights session with @jmarkedx.bsky.social rearranging my guts with his thick paws. Pup didn’t realize how much of his 2nd paw he got inside my hole. #rubbergay #ff #lockedboy #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

895 Days 🔒 — Pup has been so feral as of late. @jmarkedx.bsky.social came over and opened me up last night yet somehow my hole is still hungry. #rubbergay #ff #lockedboy #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

891 Days 🔒 — Last night left my hole feeling so loose it was amazing. After we played I plugged with the Gapekeeper 108 for about 40 minutes and this was the end result. #rubbergay #ff #lockedboy #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

891 Days 🔒 — They asked me to unlock while we played so I obliged but didn’t allow myself to get hard. Also amazing session! Took lots of punches and they jerked off inside me. #rubbergay #ff #lockedboy #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

889 Days 🔒 — 29 more days till pup hits the official 2.5 year mark. #rubbergay #ff #lockedboy #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

881 Days 🔒 — Spent the early part of the evening doing some serious training. Love that my biggest from @toppedtoys.com have gotten easier and easier to ride. #nonutnovember #rubbergay #ff #lockedboy #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

880 Days 🔒 — Had a great time at Philly Rubber Club last night. Woke up this morning and was rather pleased with how things looked…judge for yourself. #nonutnovember #rubbergay #ff #lockedboy #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup

876 Days 🔒 — Pup finally braved the cold morning air and made it to the gym. It’s time to get back on our usual routine. #nonutnovember #rubbergay #ff #lockedboy #sk8erboy #sneakerboy #chastity #cherrykeeper #puplife #gaypup #fistpup #gearpup