Windsor Wednesday Classic – 259

Spring is upon us, a wonderful time to take your loved one out on a picnic. You did what? You forgot the Grey Poupon? It probably wasn’t the wisest idea to wear such a short plaid skirt, was it? And no, I don’t really care much as to who is watching!!

The above is made up commentary, just in case anyone needs to write 27 pages explaining why it is so 🙂

This will be added to my PLAYFUL SPANKINGS folder.

P.S. The reason that the image appears twice is because I have set a featured image for this post. The reason for doing so is that this “Should” update my Mobile page to feature this post as the new main Mobile header.

6 thoughts on “Windsor Wednesday Classic – 259

  1. Richard, Today’s pic and Sunday’s 144, were absolutely fabulous and are perfect examples of the types of pics I would happen upon in my formative years and feel an unexplained rush of emotion and feelings I took years to understand.

    Thanks for reminding me of those times when a single pic like these would change my day and in ways change my formative life!

  2. fatherjim,

    I was rather lucky this week to find a couple of gems. In fact I have even more that I am saving for my birthday week where I will post 60 images in 20 days, there are some really good shots amongst the selections that I am making. Like yourself, these are the type of images that I would have died for 40 years ago, but thankfully due to the Internet we can share these long lost treasures.


  3. Glenmore,

    Considering this is the 1940s I would guess, the wearing of a skirt so short would really be a good reason for a spanking, eh? Of course they are likely shorts but I won’t let the details get in the way, lol. What I also like is the position of her left hand. One assumes that he has her right wrist locked in his hand, but he is so skilled that he was able to trap the left hand as well, leaving unfettered access to his target. I have a feeling that she was dancing for a while after this 🙂


  4. Absolutely delicious! What makes it extra-special is that she is in bare feet!
    In addition to being a spanko, I have a highly developed foot fetish.
    When a picture shows a girl getting spanked, and her feet are bare – – Total Bliss!!!

  5. Dale,

    Isn’t it a fabulous picture? I don’t knock anyone for what their fetish is, far be it for me to judge being that I have my own proclivities, and many of them. One thing that I have never done is look at the footwear of the spankee, unless they are wearing saddle shoes. Being barefoot in mainstream spanking images must be quite rare to see? I just looked at the folder that I am putting together for my birthday posting and there are only three barefoot picture amongst them, all of which will be posted in the “Beach spankings” themed post.


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