Shoesession

Every day on my lunch break and commutes for work, I hunt for candid feet, boots, heels, legs, ass, face shots, milfs, teens, etc. Two days ago on my break, I was already headed back to the office when I stumbled upon a beautiful milf in boots. She was the quintessential NYC rich bitch blonde milf type.

When I got close to her, I noticed her stockings were a little ripped and I instantly got hard, while snapping some videos and photos. I followed her for about a block, taking slo-mo videos to capture each of her delicious steps from every angle. I got even harder thinking about how much her feet must have been sweating in those tights, marinating inside the leather boots and building that intoxicating stench.

She entered a restaurant that was a bit like a food hall, so I followed her in and waited in line right behind her. Luckily, the line wasn't moving much. I "reached into my pocket" and started pleasuring myself very inconspicuously, all the while fixated on her ripped tights, sexy skirt, and leather boots. I couldn't hold it in any longer and exploded in my pants, while nobody suspected a thing. On my way out, I grabbed some napkins to wipe my cum in a nearby bathroom. Wish I could have also flicked a little cum on her boots to leave my mark, but the post-nut clarity told me I should just be on my way

Great boot pictures - thanks for sharing!
I think I would have asked the lady if she would sell me the boots or let me borrow them

I love them, could you upload more photos like this, like photographing people on the street.

Love these pics! Perfect angles! I love it when chick wear boots with big gaps around the tops like that…..I’d pay her to let me pour custard down the shafts of her boots & watch her strut around in them

Those are incredible boots! I’d be following her like a horny dog filling my camera roll up too

Those boots are sexy

Thanks guys! They were some truly sexy boots and a delicious woman for sure. It has been an incredible boots season here in NYC and I will update this thread soon with all my best catches

WOW, that skirt, boots and sexy legs, really nice milf, great pics!!

Thanks, really appreciate the support on this post! I always thought I was gonna take my catches to the grave but they’re just too good not to share. I'm going to start regularly posting the best candid boots that i've had the pleasure of catching here on this thread. Also, here is a link to what I do with my wife's boots:
https://shoesession.com/forum/viewtopic ... 18&t=95823

This next set of photos was of a very sexy and mature blonde office lady in the park. On my lunch break, my eyes lit up when I noticed this beautiful milf sitting with a colleague (who wasn't nearly as attractive). As I approached, I got my camera ready and ended up making 4-5 loops around the bench they were sitting at. I love when they are with someone and engaged in conversation, because they usually don't notice anything suspicious or even see you. I tried getting all different angles of her beautiful, mature legs and boots. I also got a face shot (not the clearest, sorry bout that) which usually makes the candids so much better when you can match a pretty face to the sexy boots.

Something about the shoes and boots of office ladies gets me going crazy. Just knowing that they're sitting in a cubicle for 8 hours a day, moving around, their feet squirming and marinating in the leather-infused sweat with no escape, is the hottest thing in the world. I imagined I was this lady's personal boot licker and worm under her desk, being stomped on and abused, and at her command, when her feet get too hot, being allowed to unzip her divine boots and absorbing all the scent and flavor of her feet into my greedy nose and tongue. And if I do a good job servicing her feet, she rewards me with being able to hump and cum on her legs/boots. What a life that would be

Also very sexy boots, something about blondes and black leather boots makes me weak. My trip to NYC has been magical, almost convinced me to move here if it wasn’t so expensive. She definitely has that sexy managerial aura that makes me want to listen to her every command while she stomps around in those boots. Can’t wait to see what else you’ve spotted! NYC is a goldmine!