The first pair of sneakers I ever got to indulge in were Converse, Chuck Taylor All Stars, just like the ones at this link, but dark blue instead of black:
https://www.nike.com/t/converse-chuck-t ... hoe-VyKzNO
At least, I think they were proper Chucks, but it's been a long time now that I reflect on it.
They belonged to my sister's friend, who we'll call Cybil. Cybil was skinny, long brown hair, hazel eyes, nice teeth, legs to die for, cute high-arched feet with long toes and healthy nails. She was kind of an attention-whore at parties and gatherings, willing to be loud and weird to get attention or feel special. She wasn't close to my family like some of my sister's friends, but she came over every once in a while.
I was in high school, a freshman. My sister would move out just a few months later after she got a good job. Cybil had just had a pretty ugly break-up (she really picked "winners" if you know what I mean: drug dealers and two-timers being her de riguer).
She'd had those cons for years as I remember. I vaguely recall their deterioration. The seams becoming more split and frayed with time, the laces getting dirtier, and they certainly seemed to get looser. I hadn't seen her do a lot of shoeplay up to this point so I was excited when I saw her and my sister chilling in the living room with my mom.
Cybil was sitting on the couch, one shoe off, her socked foot tucked under her thigh, while she idly played with her other shoe on the floor. I was hard in seconds. For the time being, I continued on my way to the kitchen, and I really took my time making a drink and sandwich so I could enjoy the show. She wasn't very frenetic, but she did periodically cock her ankle up, rake her leg back, and let that shoe slide down to her toes. Sometimes it'd fall off, other times she bent her toes up to keep it on.
I lingered as long as I could to watch the show, but my dad would be home from work soon (the master bedroom adjoined the kitchen and mom and dad kept the door open until they went to bed or watched something for the night), so I ate a bit of my sandwich, grabbed my drink, and slunk back to room. I left the door cracked, eager to listen in on them in the living room, my heart skipping and thudding. I hoped I might get a chance with those shoes.
Then I heard mom ask Cybil if she wanted to stay the night. Cybil said yes. I felt that youthful sort of exuberance at the mere possibility of something becoming more real, more tangible. I just might get my shot, I hoped. I killed another half an hour with homework, my TV volume down to eavesdrop. Cybil walked by my room to use the bathroom: in her socked feet. "Please stay that way," I muttered to myself, crossing my fingers.
Dad cooked dinner when he got home, just a ludicrous amount of spaghetti. I didn't eat and said I'd have some later. It wasn't the sandwich, just the butterflies in my stomach. Cybil and my sister sat in the living room while they ate. Mom and dad retired to their room for the night, and I dreamed of what those sneakers must smell like.
Not long after dinner, my sister and Cybil went to my sister's room. Again, as she passed by my door, Cybil was in her socks. My sister closed her bedroom door, and I was off! I walked from my room normally (though I wanted to run). There they were and the coast was clear. I couldn't risk anything too overt, but I did approach her shoes, my heart in my ears.
The insoles were super worn, with beautiful dark foot impressions. I picked one up reverently and smelled. Worn canvas and leather, her foot sweat, and from the scent and residue I could tell she wore them barefoot with well lotioned feet. I was quick to replace the converse just as I'd found it. There would be more time for this later, after everyone had gone to sleep. When I got back to my room, I came perilously close to jerking it, but I wanted to save my load for the main event.
It would be hours before everyone fell asleep, and that was the hardest part of the night. I played Twisted Metal on Playstation, read part of a book, did anything I could think to pass the time, but it drug on so slowly. Across the hall, my sister's door opened a couple of times as the girls went to the bathroom or my sister poured them drinks from the kitchen. Each time, I remember feeling the fear of something going awry, Cybil grabbing her shoes or having to leave early or somesuch.
Fortunately, oh so fortunately, the evening passed. My sister and Cybil went to bed. Dad would've already been asleep for an hour or more by then and mom would be tucked into bed reading drowsily if not passed out. I just couldn't contain myself anymore.
I crept into the living room, carefully studied how the shoes were positioned for their later replacement (I'm sure a lot of you know what I'm talking about), and with shaking hands, carried them back to my room. On my way out, I turned the light off in the living room, just in case someone glanced in there, it would be harder to tell the shoes were gone.
I closed my bedroom door and went to town smelling and worshiping the right shoe (the bitterness of the insole was surprising and exciting in ways I didn't expect) while I experimented with fucking the left shoe, greatly enjoying the way the broken in canvas of the heel-cup yielded to my cock as I began to grind against the insole.
I came in two stages, an initial burst and then this long, lingering series of pulses. I was as deep in the shoe as I could go when I climaxed, imagining her toes, socked and bare and hosed, sliding over those dirty impressions and imprints. It was, in a word, magnificent. The amount of cum was ludicrous compared to my usual mild loads.
Back then, I didn't know if it would stain, but I figured it would. I cleaned out the inside as best as I could with toilet paper and a sock that belonged to one of my cousins that had stayed with us the previous summer (I had the full pair and that was the one I came in of the two, and no, I didn't get a shot at any of her shoes sadly).
For a while, I just appreciated the sneaker I didn't cum in. I huffed the scent, licked the insole a few more times, almost masochistically. Still, my paranoia eating at me, I decided to put them back. In the dark of the living room, aided by a single shaft of light coming from the kitchen, I replaced and positioned the converse as well as I remembered them being and scurried back to my room, high and light-headed from the whole experience.
Unable to fall asleep, I considered going back out there to grab them for another round, but I heard my sister open her door and head to the bathroom. I realized how lucky I'd had it in the first place and didn't press my luck, but oh how I wanted to.
I didn't get to see Cybil put them on in the morning, but I never heard one word about it and, knowing my sister and the company she kept, I would have if they ever suspected anything.
Sadly, in the last stretch of years, I've only gotten to be intimate with one more pair of cons. But alas, that shall be a story for another day.
*Edited for a couple of typos I caught and other nitpickyness.
