iiinova — where your digital self keeps evolving

Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 08/10/2026

I got my septum piercing sized up to 10 gauge this week. I think it looks good!

Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 05/10/2026

[adult: chastity cage on a naked cis male genitals] A little glimpse into how Locktober is going for someone who has been secured for almost two years now:

close up of a flat metal chastity cage secured to a white cis male with a chunky pair of testicles and a hafada piercing

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 07/09/2026

I feel as though this is an excellent example of what is likely artificial intelligence. It is basically all hot garbage, only tangentially related to actual reality.

Henry VIII is also memorable for his chronic wife addiction. He had six wives, all called Catherine. He was a Catherine-aholic. Or Catholic for short.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 25/08/2026

A friend of mine suggested that I should share these because he thought they were really good. Yes, I took these. No, I'm not talented; I just happenef to be at the right place at the right time and caught the moment, so to speak. I really do live in a beautiful place.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 25/08/2026

Well, I clearly seem to be an East Coast kind of guy.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 04/08/2026

So ... I'm supposed to take one of these at bedtime ... but I'm not supposed to lie down.

Take one capsule by mouth in the morning and one capsule before bedtime. Do all this for 10 days. Take with at least 8 oz (large glass) of water. Do not lie down for 30 minutes after.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 31/07/2026

Oh look ... the Nazi mobile is back. This time I got to see the driver and his pal as they exited the vehicle and walked down the sidewalk, both old white-haired boomers. Is anyone surprised by this?

an ugly gray cyber vehicle made by Elon Musk's company Tesla parked on the street where I live in the residential parking where it doesn't belong.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 09/07/2026

Just in case you were not sure if I was neurodivergent, I have to share that I just started saving pictures of really beautiful Victorian doorknobs and other door fixtures in a unique folder on my phone. They are just so pretty !

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 08/07/2026

I am having a dreadful morning, but a dear friend sent me a picture from that pride festival a few years ago when I had my beard styled with rainbow glitter. She successfully brightened my day considerably. What do you think? Is the T-shirt accurate?

a cheerful bear boy in grey shorts, black polished boots, black socks with yellow stripes, a T-shirt that reads BEARDED, TATTOOED, GAY & THICC, and a leather club vest with more than a few pins.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 20/06/2026

[bare chested nearly naked man] As I bask in the warm glow of my reading lamp, I am amazed by what a great job my stylist always does when trimming my beard.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 13/06/2026

Anyone else have a decorative platter of personal lubricants in their bedroom for ... ahem ... guests? No? Just me? Okay, I'll own this. 😊

an oval white porcelain platter with a lovely transfer printed border of flowers holding an assortment of individual packets of intimate lubricant

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 07/06/2026

Does that look like the mail room, you morons! You left my package on the sidewalk in front of the delivery location!

An Amazon notification advising that my package was left in the mailroom. The photo shown in the notification is a package sitting on a sidewalk outside of a building.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 01/06/2026

I tried to share this from #PixelFed but it definitely didn't work. All I got was a text post full of code, not an image. 🎺 Anyway, since it is the first day of pride month, I was remembering that one time at Pride when I had my beard decorated with rainbow […] [Original post on woof.group]

an adorable guy showing off his beard which has been decorated with bands of rainbow glitter.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 25/05/2026

Time to consecrate, and then I can begin opening some doors and closing some others. It may not be a professional job, but it's handmade by my hands so I love it.

an old brass skeleton key hung on a brown braided leather rope with three faux brass beads above each knot

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 07/05/2026

[adult, male, naked, chastity] @Frank_NL @bootblackcub My little buddy is feeling pretty smol

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 01/05/2026

@Frank_NL For example, I felt like some color this week. Sometimes I think it's just stubbornness on my part; an insistence on being me regardless of the opinion of others. This is not to imply that it's always as simple as that. I have to navigate the same […] [Original post on woof.group]

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 25/04/2026

Goodbye, Coyote 💔 All of your club brothers loved you

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 18/04/2026

Yes, it was time for another beard trim this afternoon. I clean up pretty well, eh?

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 04/04/2026

[Alcohol] For anyone who is interested, this is what we are enjoying tonight:

a nicely chilled bottle of Robert Mondavi Private Selection Buttery Chardonnay, California 2024

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 15/03/2026

Oh, I also came home with a tote of wine! Don't judge me, we live in interesting times.

A black canvas foldable tote bag with six compartments, each just large enough for a bottle of wine. In this picture, all six compartments are filled.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 27/02/2026

[lewd pic of genitals in chastity] I think I'm going to start referring to my favorite day of the week as Flat Cage Friday. If you appreciate this pic, say thank you to @Frank_NL who is the source of the horny feelings that led to me posting this pic of my little […] [Original post on woof.group]

two chubby testicles with a hafata piercing sit gently under a flat steel cock cage between relaxed thighs. date and time stamps indicate that the wearer has been locked up for 58 days

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 03/02/2026

I finally got the lamps that I picked up at a consignment shop hung over the kitchen island today. I think they're marvelous. They make me happy every time I look at them. They are a massive improvement over the dreadful big box store fixtures that were there when I moved in.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 02/02/2026

All calendar months should look like this, with a holiday week at the end of the year to sync up the solar and lunar calendars.

February 1st is on the first Sunday of the month and February 28th is on the final Saturday of the month. Perfection!

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 23/01/2026

A friend of mine on the lgbtqia.space server reached out to me on Recon because he can't access his Fediverse account due to the message in the screenshot below. He is in Europe, not in the UK. He is not using a VPN. Does anyone know how to contact an admin at the lgbtqia.space server?

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 21/01/2026

Oh my heart ... there were 10, now there are 6. I have no rational explanation for how the tray suddenly fell off the table for no reason. I was sitting quietly on the sofa scrolling on my phone when suddenly <CRASH>.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 06/01/2026

So happy that I have been dragged into an office during this miserable season. This is the thoroughly uninspiring view gazing out of the door of my office at the grey skies.

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Midtown Masochist 🐻 (RB-050) 🐷 @richboy50.woof.group.ap.brid.gy · 04/01/2026

Events over the last year or two have isolated me to an extent. Being rather unhappy with this state of affairs, I put some effort into going out to the first bar night of 2026 hosted by my home leather club. It was the right choice, I think.