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Upskirt of hot business woman in the street
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Upskirt of hot business woman in the street

Michael B. December 5, 2017

I was once again ready to utilize my original upskirt making method and I found the perfect candidate to do so. There was a hot business woman lighting up her cigarette and walking towards me, along with her goofy chubby looking colleague or friend, whatever. I’ll return to that bit later. Firstly, I need to say how blown away I was by this woman’s appearance. She looked like she walked out of some movie where she plays the main seductress that ends up with the main star.

Her dress was casual yet classy, and her stockings and high heel stilettos made her look like a million bucks. So anyway, as she was approaching, I started looking around and faking that I’m lost by this park and that I desperately need to find a specific street. I stopped them both when they were very walking by me.

Sexy business woman lights up a cigarette

“Hello, can you help me find a street? I’m a bit lost” – my punchline for stopping them

Turns out they were both pretty happy to help, with no hurry whatsoever. I should get some kind of an acting reward for this conversation. I managed to fake out like I’m a total stranger in this city, while in reality, I probably know it better than they do. Don’t call me crazy, I do it all just go get a good upskirt look.

Conversation that leads to upskirt

I’m writing from my memory, but conversation started with something like this:

  • Me: Hello! I think I’m lost, can you help me out please?
  • Business woman: Sure, what are you looking for?

I nearly blurted out – your pussy in upskirt, but I resisted saying it.

  • Me: I need to be on this street (and I shown them a map on my phone, like one block away, with several turns)
  • Funny looking guy: Oh that is easy, let me explain, you go left, right… (and so on)
  • Business woman: I think it is better if he goes right, right… (and so on)
  • Funny looking guy: I don’t think so… (and he starts explaining why)

You get the picture, they were almost arguing about where I need to go and which directions are better. I found it all funny and at the same time, I was adjusting my candid camera to take a peek into her upskirt. It didn’t take long before the angle was proper and I saw what I genuinely wanted to see – her sweet pussy bulging inside a thong and her thighs in stockings, all without her knowledge.

Finally upskirt of this hot business woman

I’m saying business woman, because she like she just walked out of the office, and considering her fancy short dress, I’d say he is a manager or something higher up for sure. So, to continue, I finally got to see her upskirt in full, without her ever being aware that I’m staring at her hot bulging pussy inside sexy lace panties. Funnily enough, she was dressed up like she is on her way to meet a lover, yet I saw a menstrual pad wrapped up around her thong. Not a turn off to be honest, considering this is already as sexy as it gets. Her stocking tops were revealing that her legs are smooth shaved, and it means when those days of the month pass, she’ll be rocking it, I’m positive. Before I continue, with photos, you can also check out first one I made during conversation with a hot blonde.

Photo gallery of upskirt encounter




I’ve took out a few photos from this and I even made a video, but I’ll return to that later when I figure out how to reduce video size to publish it here. Anyway, the reason why I took out these two photos is because I wanted to give them their own space, I think it is well deserved, to say the least.

Funny guy that struggled to explain directions

I just have to show off this guy. It was hilarious how much he bothered to help me out, while in reality I was making him look like a total cuck in my clever plot. He seems like a good guy, and she is obviously the bossy one in their duo. I kind of believe they are dating or something, or they are just too super duper close to each other. Never the less, here is the cuck.

Guy doesn't know he is filmed

Sorry dude, you’re the cuck of this story

And finally the moment you’ve all wanted to see (me included, during this whole encounter):

Upskirt closeup shows lace thong with menstrual pad and stockings

It is sort of fun that she wears such sexy fishnet stockings and even a half transparent lace thong, during her menstruation. I guess she wants to feel sexy at every day of the month, including these. I don’t know who is this sexiness intended for but it sure isn’t for me and I was happy to peep on it like a real voyeur, deep in her upskirt.

Sexy upskirt shows lace thong with menstural pad

I wouldn’t mind swimming in the red sea when it’s presented so nicely

Final thoughts about this upskirt method

I think I’ll be doing more upskirts in this manner, with candid camera and stopping people to ask for directions. I’ve perfected it and it does the trick so, yeah, I’ll be using it more and more, which means that xUpskirt.com will soon be nicely filled out with all kinds of hot girls and women. Next time I’ll try a more bold approach and I’ll try to find out more info about the girl as well. This time it was tricky because the funny guy was ruining the atmosphere. She would probably be flirty and such when alone. So anyway, next episode coming soon (I hope).

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About The Author

Michael B.

I'm the owner and operator of xupskirt.com and also a very big fan of upskirts and hot girls, as you've probably noticed. I'm doing upskirt videos for a very long time and I believe I'm good at it.

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