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The oldest woman you tickled

I'd have to check my records, but I think it was Julia. She was in her mid-sixties at the time of our shoot.
 
I’ve tickled a couple of masseuses that were probably in their early 50s. Both were ticklish.
 
I guess 45. That was my last girlfriend.

I also remember years ago I went out with a 37 year old.
 
A Latina in her 40s. Who was extremely ticklish everywhere, and had a great, deep, belly laugh.
 
I worked with a woman who had just turned 66. She was about 5’2 and likely weighed under 105#. She basically ran the place (an adult day program) and we spent a lot of time together, especially before and after our open hours. She was exceptionally fit and had implants, which she was not afraid to expose. She was also very tan and had short blonde hair, typically wearing glasses. She was nonstop active (as was I) and she enjoyed being a constant flirt. I honestly bet she poked or tickled my sides or back at least once a month. I was always scared to retaliate, she was quite a lovely woman. One day I was on the couch relaxing and she jumped on top of me, took off her sandals and said to rub her feet. I’m not as into feet, but I did not complain. She was always in sandals and like the rest of her, very attractive. They were tan, lovely, and softer than I imagined. I waited patiently for an opportunity, then the phone rang. I said I’ll get it and gave her a quick flutter tickle and she lost it. Huge laugh with a lot of thrash but never really pulled away. I’m sure I did it longer than I should have but she never mentioned anything. Weeks later she came down and jumped on my lap while I was typing something up for her. She was being sassy about it and she reached up to point something out and I went for it. I tickled her armpits, then ribs, then even some sides and stomach, joking I never would have thought she’d be so ticklish. She was literally in hysterics the whole time. She was bending over and turning but honestly kept leaning into me and never said stop or tried to get away. When I got one side she turn on e and I’d get the other. Her stomach was very firm yet soft. Her shirt popped up a bit and her stomach was flat, tan, and she had a deep innie that literally melted me. She could not form a word but kept trying. Her laughter was turning silent and I figured I’d pushed my luck enough so I stopped. She leaned into me hugging me tight and said “I’ll get you for that.” Then she got up, straightened her shirt, gave me a quick attack tickle and ran upstairs back to work. I seriously sat there for ten minutes, just replaying what had happened.
Was definitely one of my favorite tickle moments.
 
The oldest (at the time) woman I had ever tickled was when I was in my mid 20's and she had a kid that was a senior in HS. I figuring that she was around late 30's to early 40's. I would lay on my side next to her with her closest arm under me and the wrap my legs around hers in a scissor hold then hold her other arm above her head. That gave me full access to her armpits and sides. she would laugh like crazy! I did briefly get her feet and they were ticklish too! I tried to get her to let me tie her up, but she wouldn't. We did enjoy good sex after me playing with her! And the best part was that I never had to call her up to come over. She'd always call me up and ask me if I wanted some company!
 
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WHAT A GREAT QUESTION -- Someone about 20 years older than me at the time in a sensual way, someone about 20 years older who was a mum of a friend, but no clothes off, oldest person, maybe late 50s were friends on 3 occasions
 
When I was 31 I dated a 40 year old woman. She wasn’t very ticklish. She told me that she was much more ticklish when she was younger.
 
I don’t know her exact age but i was 18 or so and she was in her late 40’s early 50’s. She was my next door neighbour at the time, amazing feet.
 
If we are talking like, legit session tickling, then I think the oldest was probably in their 30s? If we are talking cheeky sneak tickles here or there and just giving a silly horsebite, 70 year old client of mine who has very ticklish knees and I couldn't resist but give her a little squeeze on the knees 😂
 
30s if memory serves correctly. I'm gonna feel awful if I got this wrong but of all the many seshes I've had, I don't recall a lee out of their 30s. Wouldnt bother me in the slighest if they were but don't think I've seshed with any older. All my lees have been 20-39 top of my head.
 
My ex wife was 50 at the time. Petite, brunette, completely flat tummy. The best frantic cackle, ever! Followed by lots of teasing and making her cum
 
58. And omg ticklish
 

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