Every year I go to a relatives house where the whole family gets together for a party. A relative of my aunt is an absolute MILF. 40's, blonde, small and tight body. Every year she wears a pair of high heel leather boots to the party. It's torture enough having to look at her boots all day knowing I will never be able to pump a load in them or on them. To make matters worse, every year after dinner everyone gathers in the living room and talks. At this point, she always TAKES HER BOOTS OFF and says "my feet get really hot in these." She then always places the boots next to her, in a room full of people, so I have no chance of sneaking a quick cum on them. However, this year was different.
After dinner when everyone was in the living room, I sat in my seat and watched (as subtly as I could) her take her boots off. Once they were off, she stood up, walked around the corner and down the hallway. She returned just a few seconds later. My mind began racing as the only things down that hallway are the door to the garage and a bathroom. I shot up out of my seat and went to "go to the bathroom." Right by the door to the garage is where the family keeps their shoes (everyone at the party kept their shoes on, she was the only one wearing heels though). I get to the end of the hall and see that she had placed her boots with the other shoes! I finally had my chance after years of only dreaming about this happening!
I was only going to grab one of the boots, but I said screw it and took both into the bathroom and shut the door. I was already rock hard when I dropped my pants. I'll admit they weren't the hottest pair of boots, but they had heels, were leather and worn by a MILF and that's enough for me. Precum was oozing from the end of my cock so I used that as lube and began rubbing the soft, smooth leather on my cock and balls. I even wrapped the ankle part of the boot around my cock and jacked off, it felt so good. As I was doing this, I made a shocking discovery. I saw what appeared to be a dried yellow cum stain on the front of the right boot! Is it possible that her husband cums on her shoes?
Figuring the outside of the boot had already had the "treatment," I folded down the ankle part of the boot so I could clearly see the inside of it. I kept jacking off with the other boot wrapped around my cock until I pumped my entire load into the inside of the right boot! The foot bed was made of leather, but the sides of the inside were made of fabric. I tilted the boot so my cum would go to the end of the toe. Then I used the outside of the boot to wipe the rest of the cum off of my cock. I collected myself, placed the boots back in the hall and sat back down.
She had quite a bit to drink and obviously she likes cum on her shoes so I don't think she will mind what I did to her boots. I had to leave before she did so I didn't get a chance to see her put them on. However, I did take some pictures which I will upload later.
Last edited by SneakyCreamer
on Thu Dec 20, 2012 6:19 pm, edited 1 time in total.