Just Playing Around

Back in the days where flirting included a spanked bottom. My Wednesday classic this week,  number 64,  is an absolute doozy,  from the play ‘We Dude It‘. A girl is spanked on the seat of her skin tight daisy dukes. CLICK HERE to see this wonderful pic on my main blog.

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Sorority Spanking Sundays – 70

Number 70 in the series and this one takes us back to 1928. This resembles the very first spanking that I ever saw in America,  where a girl got a birthday spanking with a broom just like this one. Of course it was only symbolic,  but she stood on a chair in front of the entire camp.

As always,  this will be added to my WINDSORS SORORITY SPANKINGS folder,  which is the most popular feature on my main site by far.

silver spruce 1928

Dad’s Love Birthdays

Unfortunately though,  his 20 year old daughter doesn’t enjoy them as much 🙂 This was an Ebay find from a while ago of what is purported to be a Father giving his daughter 20 good smacks for her birthday. Whether that is the case or whether someone is taking literary licence we will never know,  but we do know that the girl is getting a spanking!!

This will be added to my WINDSOR’S BIRTHDAY SPANKINGS folder.



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Sorority Spanking Sundays – 69

It’s time for the weekly sorority spanking pic as part of my ongoing series. This is number 69,  but if you click on the link to the folder below you will see that I have many more in the sorority spanking folder.

One thing that I have considered doing is creating a weekly paddling pic as well. I also happen to have tons of them and I am looking for a place to put them. Hopefully I will work that out soon.

As usual,  this pic will be added to the WINDSOR’S SORORITY SPANKINGS folder and the pic is from Riverdale in 1949. Quite an unusual one as well as it seems that the girls are getting spanked with some type of gym shoe.

riverdale 1949

Sorority Spanking Sundays – 68

A double dip this week,  one spanking pic and one pic of girls painting their paddles. The spanking pic is from 1928 and the painting pic is from Iowa but I didn’t note the year,  but obviously it is from the 60’s.

The spanking pic will be added to me WINDSOR’S SORORITY SPANKINGS folder.


Sorority Spanking Sundays – 67

Now that I have a bit more time on my hands I should get back to posting this weekly feature every week. I’m sure that I still have enough material to share with you for another year or so,  if not longer.

This weeks sorority spanking is from 1949 and is from the University of Pennsylvania and features at least two girls hand spanking one pledge.

This will be added to my every growing WINDSOR’S SORORITY SPANKINGS folder.


Email me at:

Richardwindsor@ Richardwindsor.com