Yes, on quite a few occasions.
Briefly: I worked as a delivery/service person for a company. Sometimes in making small talk during deliveries or servicing appliances the subject of tickling would come up. Now to be honest it was not always me who brought it up! LOL! You would be surprised how often someone asks if you are ticklish when you have a heavy item you are carrying into their house! Fortunately none of them ever tickled me then! LOL!
But I digress: Some of our regular customers I got to know quite well. A few in particular were always barefoot whether they were inside or outside and I used to tease them they must have pretty tough feet and they probably weren't even ticklish. To a person they said they were still ticklish despite being barefoot all the time.
Now we are talking about various age ranges and levels of attractiveness. This was always done in the spirit of fun and never had any sexual overtones!
A couple stories: One lady, who in the end disappeared with our merchandise before it was paid for

, while doing the delivery we sat at her kitchen table and as she crossed her leg her barefoot hit my knee. Her sole was almost black from being bare outside. I made comment that she must be the barefooted type with a foot that dirty and she said she never wore shoes if she didn't have to. I asked if that made her less-ticklish and she said she hadn't been tickled in a long time so she didn't know and extended her foot toward me, so I tickled it and we found, to both of our delight, that she was indeed still ticklish.
Second one: This was with a regular customer. It was a Saturday afternoon and all our delivery trucks were out. She called our shop to have her VCR repaired and a loaner borught to her, so I took my vehicle to make the delivery and then go home. She had a daughter who was in her teens at the time and while I was talking to her the daughter kept getting between us and fussing around in front of me. I was slightly confused until her mother told me that she probably wanted me to tickle her. Still slightly confused I gave her a little rib tickle and she kept coming back for more. Her mother proceded to tell me that the daughter just loved to be tickled. So while we were talking I kept tickling. Eventually I was sitting down and going over the agreement for the loaner and I asked the mother if she was ticklish and she said "Nope" and raised her arms for me to tickle her sides and ribs! LOL! Her daughter said that her mom wasn't ticklish anywhere...not even her feet and then asked if I was ticklish. I lied and said no! LOL! Every time after that the daughter expected to get tickled when she saw me! LOL!
Last one: I was delivering to a long time customer and had just finished going over paprerwork. Their daughter, again around 18-20, was sitting with her leg propped up on an ottoman, complaining that her ankle hurt. I told her I had a good cure for that I started tickling her barefoot. She never moved, but started laughing and yelling "Dad! He's tickling me!" He replied that she should have had her barefoot out there like that and it was too bad for her!
😛
There was one lady I would have paid to tickle! LOL! She was an exoctic dancer, maybe 5' tall and she HAD to have size 12 feet! They were HUGE and always bare! Tickling never came up with her though so I had to pass that up.
~ toyou