BigJim said:So when did you outdo yourself in the tickling department? How long did you do it for? How did you do it? What did you do? Who was it you did it to?
Fess up and share all, so your sins may be forgiven! 😀

Ticklish Damsel said:So, Big Jim, are you ever going to answer your own evil question?
I'm positive I'm not the only one dying to know![]()
Ticklish Damsel said:Ya Big Jim, it's naughty to keep us in suspense...
all the way yanno.
There were two evil parts to that. The first was during what I called the "tickle quiz". This girl you must understand, was more ticklish on her feet than she was anywhere else. Her feet were so awfully ticklish that even having them massaged was agony for her. I've never seen anyone gyrate, squirm and squeal so much through what was supposed to be relaxing and pleasureable. And if you actually sucked her toes or licked her soles.... Houston we have lift-off!!!
During this quiz, I laid down with her feet resting on my chest. I locked my legs across the top of her knees and gripped each ankle in one hand. I'd then ask her a question and if she got it right we'd progress to the next one, but if she got it wrong, the tickling started and didn't stop till she got it right. Now how I hear you ask, did you tickle her feet when both hands were holding her ankles?
Need I really explain? Her feet were on my chest remember, nearly right in my face. To tickle I just licked each sole in turn continuously. I couldn't have put her through an acuter agony if I'd hit her with a snooker cue! lol To top it all I was asking absoloute bastards of questions too, that she didn't have a hope of getting right. Things like "at what latitude and longitude did the wreck of The Hesperus occur?" Or "What deity in Roman mythology was the king of the gods?" Till then we'd been playing with safe-words, but we'd dropped them for that. There was a really sadistic side to this sort of play, because she knew that she couldn't stop the tickling unless she found the right answer, but the questions were really obscure. She was shrieking with laughter and howling "I doon't knooooooooo!!!" at the top of her lungs in this adoreable Scottish accent of hers. In the end I was feeling guilty so started giving her clues. (Apart from anything else my neck was aching and I needed a break too. lol) When the tickling stopped she'd be just lying there, gulping deep breaths and giggling in aftershock. Then I'd ask another question and you could sense her apprehension that it was about to begin again, but I'd make it an easier one. Then I'd go and ask another evil git of a question and the cycle of torture would start all over again.
She later told me that she'd never felt so desperate in her life, knowing it wasn't going to end, but not being able to think clearly, even when she wasn't being tickled, because of the apprehension of the penalty that awaited her.
)I locked her ankles in a leg scissors and started threading my leather gun-belt out of the loops of my jeans. I can still remember now the slight whimper of apprehension she gave, as we'd talked about bastinado before we ever met up, and she knew what was coming. This was the first time I'd ever used bastinado, although I knew I liked it from the clips I'd seen, and I was probably more het-up than she was. I folded it in half and snapped it briskly against the soles of her feet. I repeated this several times and each time she gave this tiny little squeak that just about broke the "adoreableness scale". then dropping the belt, I hooked her ankles in one elbow crook and started tickling her soles again. She gave this agonised gasp of amazement and started shrieking with hysteria instantly. The bastinado had made the soles of her feet literally glow, and they were now twice as sensitive as they had been before. I had never believed someone could have as ticklish feet as she did normally, but now it was on another planet. She struggled so hard that her knees nearly knocked a couple of my teeth out, and he lower legs bruised my forearms too. (I told her this on Yahoo the next day, and she laughed and said "Oh, poor YOU!"
)
She struck me as really confident and touchy-feely, and I knew I liked her a lot right then.
I asked a really simple question that I knew she knew the answer to, but all she could do was open her mouth and gulp like a gaffed fish. This one didn't need difficult questions to torture. The dread and anticipation of me going anywhere near her hips was enough to totally deprive her of any rational thought. True to form I tickled her so severely that she nearly passed out, not neglecting the "tickle button", on the top rib, right under the armpit and breast, that seems to be so agonising for some reason. Another memorable moment that night, was picking her up and holding her chest height with my right arm in front of the room's dresser mirror. While she could see herself in the mirror, I tickled the bejaysus out of her ribs with my left hand. She was snorting and chortling her way through the whole thing, gasping out comments like "Oh God, my hair's a mess!" Bless her little heart.
Ticklish Damsel said:BigJim,
Not surprisingly, you most positively do not disappoint. Love your tickling appetite! 😀
Docsoul said:She then I got up wiped away her tears and went for her inhaler. I was like damn...I didn't know she had asthma. Whew...it's a good thing I stopped. Unforgettable. To this day...I wonder if the opportunity to tickle her nightly would make up for her subpar conversation.
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