Now that’s my kind of sommelier 🖤 🍷

Just because you can cum doesn’t mean it will be easy @jai-boi.bsky.social. Supervision is still required.

The best seat in the house…I mean dungeon.

Getting ready to celebrate the end of Locktober with @jai-boi.bsky.social.

#Locktober is almost over. It was a fun month. I enjoyed finding other ways to help @jai-boi.bsky.social#Locktoberrelieve a bit of the pressure, if not the frustration…

Missed last weeks #MuirCapMonday. But here is the last pic from my shoot with @robertsiegelman.bsky.social. Wearing my new colors and flagging for bondage subs. You know who you are. 😉

Monochrome Monday, chastity support edition. Helping @jai-boi.bsky.social through the last week of #Locktober #MCM

For maximum enjoyment, it’s important to properly secure subs like @jai-boi.bsky.social. The proper positioning ensures everything is accessible when needed…

I had so much fun with these last night. I’m glad @bondageheavy.bsky.social was able to provide me a target for batting practice…

Reposting to properly tag @bondageheavy.bsky.social

Decision paralysis: When you have @bondageheavy so nicely displayed in front of you, where do you start? (Hint: the answer is a 3 letter abbreviation starting with “C”)

In the mood to celebrate #FCF

Bound, helpless, and exposed. I wonder if the boy is enjoying it as much as I am…so hard to tell.

A good boy learning patience on the boiseat.

Glad my boy has been making good use of #Locktober

There’s a particular pleasure when you are able to force a boy’s rock hard cock into a chastity cage and he says “thank you Sir”.

One of the signs that it’s close to the end of October…

Every boy’s prostate is different. Some are exquisitely sensitive, others need intensity. For some, a gentle touch of the milking rod is enough to release a steady dribble of milk, and some need a lot of stimulation to yield a few drops. Until a boy opens his hole and lets you in, it’s a mystery.

We’ve passed the halfway point of #Locktober. Who needs a prostate milking?

It’s Monday again, so will be thinking of leather and good boys on their knees to get me through the start of the week.

Next Convergence will be on Saturday, 10/18 from 5 to 8 pm! It has been a year since our first event so this is our first anniversary!! @bothhandsbuck.bsky.social will be on boots this time. After taking a couple long breaks this summer we miss you and we're so excited to be back!

The highlight of my afternoon…

Happy #Locktober week 2! Some more thoughts on strategies for locked boys and subs to manage horniness and engagement as they gear up for the long haul.

It’s time to focus on your responsibilities this weekend…

Was a wonderful #MatesLeather25. Amazing weather and great leather, kink, and camaraderie.

Bonding in bondage: @jai-boi.bsky.social gets acquainted with another sub. I enjoyed watching him make a new friend.

Out and about at #MLW 📸 by Trypt (Recon)

An absolutely gorgeous weekend for #MatesLeather25. Was perfect for flogging @jai-boi.bsky.social#MatesLeather25 🎥: Griffin (Recon)

One of the pleasures of Locktober is having a locked boy suck your cock and swallow your load.

Happy #Locktober to all the chaste boys and subs. It’s day 3, so let me see if I can help you stop thinking about what’s between your legs and instead focus on other things that provide pleasure…

Such beautiful music.

Fall in Provincetown is the perfect time to be out and about in leather.

I love being able to appreciate @jai-boi.bsky.social from all angles…

Will be heading out to Provincetown with @jai-boi.bsky.social for #MatesLeather25. Like last year will be brining the cross, and a few implements to use with it…

Should be packing for #MatesLeather25, but instead decided to see how well I could pack @jai-boi.bsky.social#MatesLeather25into some bondage.

Curious chastity players you need these pro tips! Tag those newer who need it most or should wear a cage for their first time? 😈 Happy #locktober @mrsleather.bsky.social @kink3d.com

Happy #Locktober boys and subs 🔐. Thought I’d share a few thoughts on how to make it through the month feeling happy, healthy and of course, submissive.

Bondage and chastity are such a great combination!

It may be the equinox, but I think it’s better when there is a power imbalance…

What better way to appreciate a boy with a nice chest and abs?

Enjoying a chained @jai-boi.bsky.social

This was my view last night, courtesy of @jai-boi.bsky.social. I love seeing him bound and on display #bondage #BDSM

Its been a busy week, so it was nice to relax in some gear with a bourbon, and a bit of entertainment…

What are you thinking gimp? Or are you thinking? It doesn’t really matter. Since you’ve been transformed into an object with no free will, thoughts are irrelevant. Better to just let your thoughts drain away and accept the bliss of existing with no control. ⛓️: @jai-boi.bsky.social

Chains and straps are key elements of bondage, but the most important component is the ensnaring and restraint of your mind.

As requested by @dyger.bsky.social The hanged pup and the Hanged pup reversed #Shibari #gaypup #pupplay #gayfetish #bondage

As some of you surmised, when he saw the open door, @jai-boi.bsky.social crawled right in…Just had to attach the collar, and everything was set.

What do you think? Will I need to use the crop to get @jai-boi.bsky.social in the cage?

Is #SleepsackSunday a thing?

A long weekend is a good time for some relaxation, as @jai-boi.bsky.social demonstrates. I particularly enjoyed his restricted struggles as he adapted to his new reality. #Bondage #Sleepsack #BDSM