Experiences with boots

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MonkeyDLaw
Posts: 79
Joined: Sun Feb 13, 2022 6:14 am
Location: Valencia, Spain

Experiences with boots

Post by MonkeyDLaw »

guys, what is the most exciting/risky story with leather boots. be it sister, friend...
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c-w
Posts: 47
Joined: Wed Mar 23, 2011 11:50 pm

Re: Experiences with boots

Post by c-w »

Working colleague of my Lady, see here (in German): Hot boots of GF's coworker
(German Original here: Stiefel einer Kollegin meiner Freundin)

Cheers
cw
My tumblr about boot streetshots: Boot Streetshots
My tumblr about chastity, ballstretching, bootworship, discipline and obedience:Stretch these balls and lick those boots!
MonkeyDLaw
Posts: 79
Joined: Sun Feb 13, 2022 6:14 am
Location: Valencia, Spain

Re: Experiences with boots

Post by MonkeyDLaw »

Nice job mate 😊
I have some story in reference to the first post, but first I want to see some other people's stories
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qazwsxedcrfv
Posts: 281
Joined: Fri Jun 07, 2013 9:33 pm

Re: Experiences with boots

Post by qazwsxedcrfv »

Don't know why I can't upload pictures anymore, so hopefully just the stories will do. I've taken a lot of risks over the years, mostly in my teens and 20s. Never got caught, but have slowed down since then. Sometimes I'd be at someone's house and have access to their shoe closet or I'd be at a party where women left their boots by the door and I'd take a chance at quickly pleasuring myself with them. It's hard to pick just one story, but I'll try to limit myself. The first big risk I took was with my mom's brown leather boots. They were the pair that started my boot fetish and my favorite to cum on for a long time. By the time I was in high school she never really left the house except once a week to go grocery shopping. That was my opportunity every week to get to her boots (and her heels too). Her boots and shoes were behind a bunch of junk in her closet and it was a pain to get to them and then put everything back the way it was before she got home, so eventually I started keeping some of her shoes in my room for constant access. She never noticed, but it was risky in case she found them or decided to clean out her closet and saw her shoes were gone.

I now have a friend with a pair of black, low-heeled, knee-high leather boots that are currently my favorites. We met in the military years ago. I got out and she stayed in, so we don't see each other as much anymore and that's the main reason we never got together. Once when I was visiting her in Europe I got a bootjob from her in a cathedral. There was nobody else around and she got down on a low chair for kneeling while praying. I knelt down on the floor behind her and had a big shopping bag next to me to block the view in case anybody came by. Looking back we had plenty of time so I wish she'd taken her time to give me a really good bootjob and let me blow a massive load all over her boots, but since we were in public and didn't know how long we had we were both trying to hurry. A few years later she was briefly stationed near me, so one time that she spent the night she wore her boots over. In the morning I jizzed and pissed all over her boots, then she wore them to church while they were still wet. My cum dried while she was wearing them so she wore her boots out in public all day with visible cum stains on them. Those were my most exciting experiences with leather boots.

The riskiest experiences I had were the few times I got bootjobs from women without them knowing. I did it a couple times with girls wearing cowgirl boots too, but I'll just talk about the women wearing knee-high leather boots here. One time was at a party at a friend's house. She had all the lights off and we were just using glowsticks as lighting. Since it was dark and we were sitting on the floor I was able to position myself behind her with her boots in my crotch. She was wearing low-heeled, knee-high leather boots, which are my favorite style and similar to the pair my other friend has, except these were brown instead of black. I whipped my dick out in the dark and she was unknowingly giving me a bootjob. The hottest part was that she was talking to me while she was doing it. The other time was at a bar with a stranger. She actually knew what she was doing though. She was wearing a similar pair of brown leather boots and crawled up on the stool next to me. I was sitting and she was kneeling with her booted feet stuck right into my crotch. She glanced over her shoulder, said "sorry," smiled at me, and continued pressing her boots into my crotch. I immediately got a huge erection which I know she had to feel with her boots because I was wearing fairly thin pants. She moved around and sometimes had one foot on my thigh, other times one foot right on my dick, and sometimes my dick squeezed between both her boots. We were there for at least a couple hours and she stayed on her knees the whole time with her boots in constant contact with my crotch and thighs at all times. I also regret not trying to get her number because she probably would have given fantastic bootjobs. She's the only total stranger who's ever given me an unsolicited bootjob.
Last edited by qazwsxedcrfv on Tue Jul 04, 2023 5:16 am, edited 1 time in total.
chrisw22
Posts: 24
Joined: Thu Jan 20, 2011 9:07 pm

Re: Experiences with boots

Post by chrisw22 »

My closest call came as a young teen (in the 1970s). My mom had a pair of knee high lace up crinkly dark brown boots with a 3" chunky heel. Unlike modern lace ups, these did not have any zipper. They laced all the way up. They took a couple minutes to put on and the same to take off.
One night my parents went to a party and I took the opportunity to wear them. Well, they came much earlier than I expected. I heard the garaged door opening and I freaked. In a mad rush I unlace hook after hook as sweat drops were forming on my forehead. My mom opened my bedroom door to say good night no more than two seconds after I shoved them under my bed and closed up my robe to hide my erection. "good night" I sqeaked back. She asked if I was ok and just said I was tired. It took half an hour before my heart stopped pounding
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boot.perv.2
Posts: 381
Joined: Tue Oct 25, 2022 1:27 pm

Re: Experiences with boots

Post by boot.perv.2 »

qazwsxedcrfv wrote: Wed Mar 01, 2023 7:03 am Don't know why I can't upload pictures anymore, so hopefully just the stories will do...
We no longer host images on Shoesession, and it's been that way for several months. We got a DMCA takedown legal notice from Southern Charms, mostly likely due to all the ChristinaUK pics that had been uploaded.

The way around this is to host your images on a free image hosting service. I use imgbb.com, because it doesn't have the spammy BS most sites have, but there are other ones out there you can use.
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