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I Won a Tickling Bet at the Office (M/F)

blur_5

TMF Novice
Joined
Apr 14, 2006
Messages
64
Points
18
So, about 18 years back, I was working at this marketing agency. There was this art director, Ortensia—she was around 5'4", always in sandals or heels, and had these really pronounced arches and nice toes. She was about 26. My approach at every job was always the same: keep a low profile, be friendly, seem harmless, act confident but never try to be the leader. That always worked for me, and it did here too. We got along really well. Ortensia was a total font nerd—she knew everything about the history and theory of fonts, and she was actually kind of proud of it. She kept her hair short, just to her jaw, had a pointy face, and dyed her hair this reddish color.

I also knew she was ticklish. People in the office, including me, had poked her before and she'd always jump and go into this defensive pose. I had this routine I’d used a few times with other women: I’d dig up some weird or obscure fact about something they liked, then make a bet about it. I’d throw out some random fact that sounded fake, she’d call me on it, and I’d insist it was true. After some back and forth, I’d go, 'Wanna bet?' She’d say, 'Yeah, what do you want to bet?' and I’d poke her side and say, 'If I’m right, I get to tickle you.' That’s exactly how it played out.

One day she was working on an ad, messing around with italics, and I told her, 'Did you know that in the 16th century, people wrote entire books in italics to save space?' She goes, 'Nah, you just made that up.' I hit her with, '¿Cuánto quieres apostar?' (which is basically 'How much do you want to bet?' in Mexico). She says, 'Buy me lunch.' I nodded, poked her, and said, 'But if I’m right, I get to tickle you.' She gave me this look like, 'What? Yeah, whatever.'

I’d done this routine enough times to know when it would work, but honestly, I never did it at work. This was the one time I broke that rule, just because I really wanted to tickle her. She immediately started searching on Yahoo (yeah, people still used Yahoo in 2008, believe it or not). Took her less than two minutes to see I was right. She gave me a look, I gave her one back. She said, 'Fine,' and lifted her arm, but I just raised an eyebrow and pointed at her feet.

It was almost noon. I wasn’t about to let this slide—I figured it had to happen right then, since I might not get another shot, and I was about to quit that job anyway, so whatever. She had her high heels on. Her feet were kind of wide and meaty at the base of her toes, but with this really pronounced arch. She just said, 'Whatever.' I pulled up a chair and sat next to her. She took off one shoe and put her foot on my lap. I made a face, and she took off the other shoe and put that foot on my lap too.

The office was always noisy—TVs blaring, people playing music out loud (it was 2008, after all), so I figured her laughing would probably go unnoticed. As soon as I touched her soles, she jerked and tried to pull her feet away. I looked at her and said, 'Don’t move.' I started drawing circles on her soles with my fingers, looking her right in the eyes. She made this hilarious face, trying not to laugh.

Then I scratched her arches with my nails and she squinted. When I went under her toes, that was it—she started laughing and kicked me away. She said, 'Okay, okay!' and I was like, 'What? That wasn’t even a minute.' She goes, 'We didn’t agree on a timer.' So I said, 'Alright, 30 seconds.' She put her feet back on my lap and this time I tickled the tops of her feet, just lightly. She giggled and scrunched up her soles. Then I went back to her soles, just soft touches. When I thought time was almost up, I went back under her toes with my nails and she tried to hold out but ended up laughing and pulling her feet away again. Then someone yelled from across the office, 'You both get back to work!' So we did. She was still smiling, a little embarrassed, but I tried not to make it weird. Nobody really noticed. I bought her lunch anyway.

I never brought it up again. I knew I’d gotten lucky and didn’t want to push it. I quit that job a month later and never saw her again. I was always the type to cut off contact with coworkers after leaving a job. As I said, at the time, I always tried to keep a low profile. Man, I sound like a total psycho, haha.

I never tried that again in such a public or risky way at work, but it was worth it.

1769980773625.png
Here’s how I remember Ortensia around 2008.
 
Great story! :feets: Thanks for sharing your experience here. 😀
Wonderful drawing to go with it, too. :feets:
 
Wow. She looked like a babe with sexy feet too. Thanks for sharing another tale.
 
When she said "fine" and lifted her arm, what was she wearing? Was it what's in the sketch?
 
When she said "fine" and lifted her arm, what was she wearing? Was it what's in the sketch?
She used to wear tank tops, t-shirts, and sleeveless blouses. That day, she was wearing one similar to the one in the sketch.
 
Great story! :feets: Thanks for sharing your experience here. 😀
Wonderful drawing to go with it, too. :feets:
Thanks, it’s incredible how we can now instruct a machine to create an accurate drawing of someone based on our memories.
 
Super cute tale. You are one lucky guy…and I envy you! 😁
 
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