Windsor Wednesday Classic – 270

Today we have a senior superlatives triple header. As you all know by now, I try to keep my posts with a maximum of three spanking images, that way I feel that the viewers can appreciate each one. Just a personal choice and opinion of mine. Though of course I will throw out a six pack every now and then of images that would rarely see the time of day otherwise.

All pics will be added to my SUPERLATIVES folder.

The first image is one that I have sat on for four years now and I really love this one. While it is obviously much older, to me it has this ‘American Pie’ feel to it, mostly I guess because the guy looks like Jason Biggs. It would be a stretch to say that the woman looks like Alyson Hannigan, but you can see where I’m going with this, right?

The second image this week is one that it would have been likely to have made its own post, it is certainly good enough, but I will throw it in with this three spot this week. What is it that he is holding do you think?

And lastly, not a very good picture, but I am sure some of you out there will love it.

4 thoughts on “Windsor Wednesday Classic – 270

  1. Yes you are quite correct it does look like them.great find.I always enjoy otk finds and this was outstanding. Great finds.thanks for sharing and enjoy your day.

  2. There’s always something so wholesome and innocent about these sort of pictures.

    In the middle one, it looks like he’s about to swat her with a piece of scaffolding board!

  3. Jim, the moment that I found the image I saw the likeness to Jason Biggs immediately. Now it isn’t a classic spanking photo, but for some reason I absolutely love this picture.


  4. Theo,

    For me, some of these spanking photos are pure gold. They don’t have to be classics in the pure sense, just enough to allow ones mind to imagine what is happening.


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