Looks like someone got caught doing something they shouldn't. From the interviews that I did with Dana Specht and Ophelia De Havilland, it seems like this is a popular fantasy for their clients.
Monday, September 29, 2025
Sunday, September 28, 2025
Saturday, September 27, 2025
Friday, September 26, 2025
Read All About It
Every month, on the last Friday of each month, I will share my current list of spanking eBooks. If you click on any cover below that takes your fancy, and it will take you right to that spanking eBook. Keep in mind that the eBooks below direct to the USA Kindle site. If you want to view my eBooks on your own country's Amazon site, simply go there and put Richard Windsor into the search bar, you can't miss my books. All eBooks are $2.99 or free if you have Kindle Unlimited.
Click on each book cover to view the details
Thursday, September 25, 2025
A Rare One
This pic comes from a private spanking collection that I own. The image below is the only one that I have shared from this collection. The reason for that is simple; it is because I believe the owner of the pics passed away, and someone sold their private collection. So I keep them safe as I hope someone will do for me when my time is up. ;)
Wednesday, September 24, 2025
Sheer Black
Seems like nobody thought to move the table. It could have been an even better OTK spanking pic if they had.
Tuesday, September 23, 2025
Richard and Sarah
Here I am spanking Sarah Gregory during a vending party. If business is slow, start a spanking. You will get an audience in no time. ;)
Monday, September 22, 2025
Dear Brat
Always loved this movie spanking still. That big old hand and the look on her face. I wonder if he did, in fact, spank her during the photo shoot?
Sunday, September 21, 2025
Saturday, September 20, 2025
Silky Satin
Be still my beating heart. Nothing beats a good spanking over a pair of silky panties. Satin, in this instance.
Friday, September 19, 2025
Thursday, September 18, 2025
Almost Perfect
The aesthetics are just about perfect, a wonderful picture with lots to study. The only thing preventing it from being a ten, the stick in his hand. It should either be his hand or a small paddle. Still, a great looking image.
Wednesday, September 17, 2025
She's a Rookie
Nobody told her! You NEVER wear red panties for a spanking. It is way too easy to try and match the color!
Tuesday, September 16, 2025
Monday, September 15, 2025
Polka dot Dress
I've always had this think for polka dots, and I'm not sure why. Even more so in this picture because it is the spanker wearing them. For some reason it really adds to the picture for me.
Sunday, September 14, 2025
Camp Spank
I always loved the idea of a spanking on a campsite. In fact, I'm sure that I wrote a story along those lines once upon a time.
Saturday, September 13, 2025
Mr. Windsor Spanks Again
It is so dark that you can barely see you sideburns! Assuming, of course, that you have nothing better to look at! :) My own handiwork.
Friday, September 12, 2025
Thursday, September 11, 2025
New Coffee Ad?
I'm sure that the idea for this spanking image came from the old coffee ad. This was from a series of pics as well if I remember correctly.
Wednesday, September 10, 2025
Back in 1936
Spanking was still as popular as it is today. Only back then they didn't mind spanking out in the outdoors.
Tuesday, September 9, 2025
A Proper Workout
No slacking off when it comes to physical fitness, otherwise, a good sound panty spanking will be on the horizon.
Monday, September 8, 2025
Meanwhile, in Texas
College life is still the same now as it always was. Who needs a sorority or fraternity for some spanking action? The dorm rooms are just as good.
Sunday, September 7, 2025
Self Service
You may find this strange, but I have always loved this photo. It dates back many years, and yet I still enjoy it even to this day. Desperate times call for desperate measures.
Saturday, September 6, 2025
Richard Windsor Himself
Look at how happy I am looking! A pair of dropseat jeans, not something that you see every day. This spanking scene was lengthy and produced many great pics.
Friday, September 5, 2025
Thursday, September 4, 2025
A Modern Day Woodshed
Look around, it definitely looks like a woodshed to me with all of those logs lying around. The perfect place for a good old-fashioned birthday spanking.
Wednesday, September 3, 2025
Tuesday, September 2, 2025
Single Leg Lock
And a half-slip to boot. Despite the unusual position, a good spanking hairbrush to sort out any wrinkles in the system.
Monday, September 1, 2025
Still Your Father
I'm not sure if the young lady was late for curfew following her date, or if this was a warning spanking before she left for that date.