Windsor Wednesday Classic – 253

And so it begins, year number 17 of this spanking blog. To be honest, over the Christmas period I wasn’t sure how long I would keep blogging, but thankfully for you guys I love to provide new material for you all to enjoy.

Shoot, there are some blogs out there that might not survive if I didn’t have globs and globs of rare spanking pics for them to lift 🙂

So look, there might be an increase in playful spanking pics, I mean, spanking is supposed to be fun after all, but I know that there are still hundreds of spanking pics out there yet to find. Don’t worry, I’ve got your back, I will find them eventually 😉

This image will be added to my SUPERLATIVES spanking folder. There are some really excellent spanking pics in that folder that got their first run on the Internet on this blog.

6 thoughts on “Windsor Wednesday Classic – 253

  1. 17 years of perseverance. Congratulations. I wondered how long OBB had been around, so I scrolled down to the first post and found it was Aug 15, 2007. Now in year 16.

    I have not noticed your pictures on other blogs, but I don’t read many blogs. I copied one of your pictures the other day and plan to post it with credit.


  2. Richard, your journey to today is like a modern-day adventurer. I so envy the things you have done, the places you have seen, the bottoms you have spanked or seen spanked. You are the Indiana Jones of the spanking world, never really getting the acclaim you deserve. You start new business adventures and travel the world. You are a man among men! Keep doing what you do! Go bravely, and may the sun warm your back as you go!

  3. A lovely natural picture, and the superlative indicates they’re both pests, I guess!

    Well done, Rich!

  4. Bogey,

    Likewise, I rarely, if ever, visit spanking blogs anymore. There was this one blog which I don’t even know if it exists anymore, and the owner once said that he was searching for spanking pictures and found this awesome collection of “Playful” spanking pictures and then shared them all. He shared every picture from MY “Playful spankings” folder and didn’t once offer up any love in return, lol 🙂 Another blog once asked for extra details on some pics, so I asked which ones and he basically listed every pic that I had posted 🙂 Once again, not even a sniff of common courtesy by sharing a link back to my blog. After that I gave up, want the details for pics moving forward? Good luck with finding them 😉 Like I said, I barely even notice anymore because I rarely visit spanking blogs anymore.



  5. Fatherjim,

    The journey isn’t over yet, even though it might not currently be my number one outlet. Sometimes by taking it slow and not forcing things I tend to keep my enjoyment from the lifestyle. While I will no longer attend spanking parties, it doesn’t mean that my spanking days are over. One time in the future I will organize a weekend cabin where I expect to make a few films. It will cost me a few thousand dollars but one can dream, can’t they? That’s why I hope that my Youtube channel takes off so that I can fund it. Either a cabin in the woods or perhaps even a beach house.


  6. Theo,

    Yes, there have been numerous pics found under the “Pests” title, but sometimes you have to look under “Pets” as well 😉 These are the type of pictures that require a lot of patience to find, mostly by grinding a page flipping session 🙂


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