My most embarrassing riding experience happened two years ago, when I bought my 4th pony. I was helping a friend to look for a pony for her young daughter. At one ranch I saw a beautiful chestnut Welsh pony gelding with a flaxen mane and tail, but the price asked was $ 5000. I did not want to spend that much, but I really wanted that pony. I went to look at the pony again, but I was still reluctant to spend that much.
It was a hot August weekend when I went to town to visit a friend who has a swimming pool. I put on my bikini, and a very short summer dress. When I left my friends house, I did not want to drive wearing the wet bikini. I took of my wet bikini and put it in the trunk of my car. I put on my dress, and I was naked under my dress. I had intended to drive straight home, but decided to stop on the way to have another look at that wonderful pony. When I arrived at the ranch, I asked the owner if I could look at the pony again. She guessed that I wanted the pony for myself, and asked if I use an English, or Western saddle, and if I do show riding. I told her it was pleasure riding, and I normally ride bareback. She smiled at me in a way that made me self-conscious, and I'm pretty sure I blushed. I asked her if she could ride the pony bareback so I could see how well trained he is. She put a bridle on the pony with a bit and reins, and led it into a riding arena. Then she said, "I want you to ride the pony to see how you like him." I told her I don't have any riding clothes along. I was really embarrassed when she said that I can ride like I am. She made me feel even worse when I told her that I was naked under my dress, and she started laughing. When I said I was afraid someone might see me, she said her family was gone for the day, and would only be back at night. Then she urged me to mount the pony. she cupped her hands for me to place my left foot, so I could swing my right foot across the pony's back. She looked directly between my legs as I mounted the pony. Then to my relief, she said she will wait in the house while I ride the pony. The pony was really wonderful, reacting to all my commands, and was just the right size to really feel comfortably between my legs, and under my buttocks. The owner said that she could see I would love that pony, and treat it well. She lowered the price by $500. That was my most embarrassing riding moment, and how I acquired my 4th pony.
erikarider erikarider
36-40, F
4 Responses Aug 16, 2014

I bet she was watching from the house

I wish you could of ridden my Welshies I would of dropped the price as well, 😉.

I'm glad you overcame your embarrassment and went through with it - turned out well any way. hope sometime both you and a pony will be bareback riding in front of others!

I don't understand why you got embarrassed. Maybe she understood your nude and bareback riding preference because she also enjoyed it that way?