The most exciting was my best friend's mom (Debbie) who I got to tickling on many occations. She was the neighborhood MILF and the nicest person in the whole world. The first experience was the best because I had been waiting literally years for an opportunity to tickle her feet. I mean, I dreamt about. I would see her swimming at the pool or at our house in sandles or heels or barefoot and would try and think of anyway I could get a chance to tickle her feet. Many times I came very close but just never got the nerve up. It happened at Christmas time while I was playing cards on the floor with my friend during a Christmas party. We laying down by the sofa when buddies mom on the sofa right between us. She had on heels and nylons and her legs were crossed and kicked backed. She was sort of pushing her feet out of her shoes with her toes, just exposing her feet. All this was happening while she was talking to a neighbor. My buddy caught me staring at her feet and dared me to tickle them. I was embarrased. I could feel my face getting flush. Being younger I was afraid I was going to get in trouble, but after much cojoling by my friend, I very nervously, but excitedly, tickled the instep of her left foot. My heart was pounding. My dream was comming true! She bolted up right and stopped in mid conversatom for a brief moment. But a second later she resumed and didn't say a word to us. My buddy was cracking up. All of sudden my friend's mom kicked up her leg and crossed them so that her left foot was dangling over her right, directly in front of my face. Her heel was slightly hanging down. My buddy then looked at me and dared me to take off her shoe and tickle her. NO FIGG'N way! I thought. Then HE grabbed her shoe and started to slide it off. It was to the point where the shoe was dangling off her toe when she finally said, "Hey, don't do that." So he stopped, but to my amazement she left her shoe hanging right there.
Well, I guess my buddy was afraid of getting into trouble or somethng, so he stopped daring me and we went back to playing cards. Several minutes went by, and I just couldn't concentrate on a game of cards as I kept thinking about what had just happened. With that foot sitting right in front of me, I was dying, I mean just dying to tickle her again. Ten minutes later, my buddy said he had to go to the bathroom and was left lying on the floor alone staring my friend's mom. I decided I was going to go for it. I sat up indian style and moved as close as I could to her dangling shoe and then fake a yawn and a strech, intentionally swinging my hand around to lightly touch the underside of her foot. While I did this I dragged my fingers across her sole. Oh it felt so good! Unintentionally, I acidentally knocked her shoe off. Whoops! Now I was really embarrased. "I'm sorry Debbie!" I said. "That's okay." She said. I reached down and grabbed her shoe to hand it to her, but before I did that I decided I needed to go for one more time. So looking up at Debbie and smiling I reached over to her now completely exposed sole and tickled saying "coochy coochy coo!" Debbie gave out a little laugh, but rolled her eyes and said sarcastically, "have you two been having fun tickling me all night?"
"Yes I said!" and tickled her one more time. Debbie rolled her eyes one more time, grabbing her shoe and stood up. "You boys are silly, go tease someone else."
My friend came back and unfortunately Debbie put her shoes on and this time kept them on for the rest of the night. Several times I'm sure she caught me staring at ther feet, so I think she knew that if I had another opportunity to, I would tickle her.
