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Voyeur flirts and jokes to see upskirt of sexy milf
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Voyeur flirts and jokes to see upskirt of sexy milf

Michael B. January 3, 2019

Oh yes, feels good to be on the prowl again. I’m walking around the city and looking for potential girls to have fun with and there she was, a very interesting tall milf, with a gorgeous face and slim figure in a tight pencil dress with black and white stripes. I just had to get to know her and of course, I really wanted to do an upskirt video of her along the way. I’m walking behind her like a real voyeur and filming her from all angles before the time is right to approach her.

Sexy milf walking down stairs

So tall and so sexy, impossible not to notice her

My idea, as always, is really simple, to chat her up and to let my candid camera do all the work while I stand close to her and talk. I bumped into her and said I want to ask her something but that I first simply must say how good she looks. I also asked how come she was smiling before I even approached her and she said she just finished a conversation with her best friend and it got her in pretty good mood.

Flirt and joke while spying on extra hot milf

She was really flattered when I complimented her appearance and she didn’t have a slightest clue that I’m recording every second of our encounter with my neatly hidden camera that is pointed right at her. I noticed she is eyeing me out while we talk so I got really bold and brave to ask her out. After all, it was all or nothing kind of thing, and I already got the voyeur video of her so why shouldn’t I try to get inside her panties as well?

Hot milf smiling and listening to a guy

Her face while I was telling my joke

We had a quick conversation and since she was already smiling and responding well to my advances, it was time to pull out the big guns and show her what I really want, but in a subtle, funny manner. I decided it was time for a very cheesy but awesome pickup line and I’m happy to report, it worked like magic (literally). This is how it went down:

  • Me: We should definitely go out sometime, what do you say?
  • Sexy milf: Oh really, you think you can amuse me?
  • Me: Sure thing, I will show you a magic trick
  • Sexy milf: Haha, what trick?
  • Me: It is an awesome trick, but I need your assistance to perform it
  • Sexy milf: Sure, what is the trick about?
  • Me: We make my cum disappear
  • Sexy milf: Hahahaha

She was barely able to stop laughing and she gave me her number as soon as she gathered her senses once again. You’ll soon see what I’ll hopefully see on my date night with her, once I finally call her up and fulfill my promise of showing her that magic trick. Honestly speaking, if all goes well, I’ll make my cum disappear in her tight pussy, in her sweet ass and in her charming mouth as well. She looks so good that I want to fuck and explore all of her sexy holes.

Beautiful milf laughing after she heard a joke

She bursts in laughter when I finished the joke

Her face before and after my joke will tell you just how much she liked me and my sense of humor. With that in mind, I’ll now show you what happened meanwhile, through the eyes of my secondary hidden camera that was in her upskirt during our entire conversation.

Voyeur points candid camera between her legs in upskirt

When I reviewed what my candid camera caught in her upskirt, I was even more sure I want to see her naked on my bed and that I want to fuck her for all she is worth. She wore a sexy lace thong that was more transparent than covering and it revealed how her crotch is smooth and almost completely hairless, with an exception of a tiny hairy patch on top of her pussy. Her ass cheeks are smooth, round and firm, just perfect for a good time.

Candid camera photo of hot milf's upskirt

It looks really cozy in her upskirt

You’ll see even more of her pussy and ass from upskirt point of view in the following voyeur picture gallery, as well as more pictures of her walking around the street. She is dressed so simply yet it looks very seductive on her and makes her body shape look so fine that you want to touch her, everywhere. I bet her pussy is milky to the taste and wonderfully wet for a hard dick. I hope I’ll soon know that for real.

More voyeur upskirt photos of milf’s hot pussy in lace thong

Here is even more pictures and screenshots from all the voyeur videos I made of her. You can check xUpskirt main page if you want to know where you can find that specific voyeur video, as well as all the voyeur and amateur videos that I ever made. Meanwhile, enjoy the awesome upskirt pictures that will tell you even more about this milf. We voyeurs like to say that a voyeur photo will tell you more than any voyeur’s words.



If you’re not convinced of this milf’s hotness by now, take another look. Her pussy is so delicately small and packed inside a lace thong that you’ll want to smell it, finger it and finally fuck it. Not to mention her amazing round ass and how nicely her butt cheeks look in upskirt. I’m really hoping I’ll get to do some anal sex with her along the way, if our date goes really well.

Few thoughts about this hot voyeur encounter

From her perspective, she just had a pleasant and fun encounter and she flirted with a total stranger and gave him her number. From my perspective, I did all that, with an extra benefit of making two voyeur videos of her with the help of my candid cameras. She doesn’t really know about my perverted voyeur side and I hope I’ll fuck her at least a couple of times before she ever finds out about what I did.

Sexy milf walking away on the street

Sexy milf walks away after she gave me her number

I’m still recording a video and some photos while she walks away from me and I’m once again looking at her sweet ass wiggling away, thinking how I’ll soon get to tap that butt in the privacy of my house. I’ll just make sure to prepare a bit and to make sure that everything goes smooth when we’re on a date. My hunch tells me that I’ll be balls deep inside of her in a matter of days.

No worries, I’ll brag about fucking this milf and I’ll give you all the details when the time comes.

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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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XUpskirt.com is my private website where I’ll be sharing my best upskirt photos and videos. I’m cooperating with some other voyeur sites as well and you can find my upskirt material there too. I hope you love what you see as much as I love creating it.

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