I think most little boys whose mothers ride side saddle have probably at least once, had a sit on their mum's side saddles. My son, who loves anything about the military and history, has had a try on my side saddle especially after I told him about the soldiers from both World Wars (and even some men today), that lost their legs and who still wanted to ride and go hunting, rode in side saddles. He wanted to see how those brave soldiers rode afterwards.
I have two photos in my collection showing boys on side saddles and thought that I would share these unusual photos with you all. Both date from the early part of the 20th century, probably about 1910's.
I love this first one as the expression on the boy is priceless, he looks like he would rather be doing anything else but sitting on a horse. Look at the stirrup iron, it's a jointed "Groom's Stirrup"!
The second photo was taken at the seaside somewhere here in England and shows a toddler aged boy sitting in an even-by-this-date, old fashioned side saddle without a leaping head. I've always noticed in photo postcards and photos from the early 1900's and 1920's that that show seaside donkeys, that they are always laden with these REALLY old fashioned side saddles. I guess by the Edwardian era and the 1920's, there were tons of these relic side saddles around that no one wanted so the seaside donkey ride people picked them up cheap for the kids and ladies to ride in. There are still donkey rides at the beaches over here but adults aren't allowed to ride them any more.