Dude, I never get sick of hearing about this ex of yours. I don't usually post reponses, but I've read them all, and I figure I better tell you to keep them coming.
I live in the city too, and I used to work as a temp in offices all the time, and I've got a bunch of tickling stories. I love office tickles because the women are usually wearing business suits and stockings. I worked at one place where there was this busty Italian girl, barely five feet tall, with tiny feet, who always wore way-too-tight clothing. From Queens or Brooklyn, no doubt. She was engaged to an Italian guy who owned his own chain of pizzerias, and the guys last name was actually "Pizza" too! So I had to be VERY careful with her. But one time we were in the stock room, where people rarely go, so just having the privacy there was enough to make me get a bit dizzy. There was something on a high shelf she needed, and I offered to get it for her, but she said something about being an independent woman and went to get the step ladder. She had to climb to the top shelf (being so short), and she found what she was looking for. But it was something she needed to read, not take all the way down, so she just stayed up there reading it. After a minute she got tired of standing, so she sort of sat down, but couldn't; so she knelt on the top step of the ladder, leaving her feet sticking out behind her gorgeous ass. She wore dark blue pumps with nude stockings, and the pumps were brand new. I told her she'd better be careful not to scuff them, with her feet sticking out behind her like that. And then I couldn't believe my luck -- she said "oh, I should have taken them off first." My head spun, thinking of what I could do -- this was one of those times I dared to go ahead and do it. "I can get them for you," I said, and before she could object, I'd pulled one of her shoes off. That's when she got nervous, and said "no no, that's ok, I'll just be careful." But I had her shoe off, and her gorgeous tiny little bare sole was right there, so I thought fuck it, it's only a temp job...I won't be back. I practically held my breath; it was like jumping off a cliff into water; I made myself jump. "But if I don't take your shoe off, how can I do THIS?" and with that I ran a finger down her sole from toes to heel. The reaction was awesome! She jumped and let out a little squeak, and I was afraid someone would hear, but she got embarrassed and spoke in a whisper, saying something like "oh my god don't!" but I had her. She couldn't easily get up, and she was embarrassed about calling out; I just hoped no one would come in! "Don't what?" I said, looking up at her and grinning. I tickled her again, and it was perfect. I couldn't tickle her too extremely; she'd have fallen off the ladder. But I could lightly tickle her foot, and there was nothing she could do but squirm around and try to get her feet out from under her. I grabbed and held her ankle, and it must have taken her a full minute or two before she finally got free enough so that I had to let her go. She practically jumped down off the ladder before I could tickle her again, and I had that post-tickle moment (so many of us have been there) when I suddenly regretted what I'd done and grew afraid. She stared at me with this angry expression, but still smiling, and then she said "I'm never letting you do THAT again!" But unbelieveably, When she said "that" she reached out and tried to poke me in the ribs!
I jumped back instinctively, and then said "you'll have to try harder than that!" but she didn't take the bait, unfortunately. But she never had her mafia fiancee take me out, either, so all's well that ends well.
