I apologize for the length of this but I felt it necessary to come to a natural break in the story...
When I was in high school, I worked at a gas station where all of the dayshift women (all in late 20s, early 30s) wore either flats or low heels all day long. I usually worked the afternoon closing shift, so I had many occasions to cum in their shoes. Their shift would overlap one hour with mine, so I got lots of sights to get horny as hell to. One of the girls, Michelle, wore a pair of black flats that were severely worn and stunk heavily of her gorgeous little size 6 feet. She mostly wore them barefoot but, on occasion, she'd wear them with pantyhose when she wore a skirt.
One particular week I had a lot of shifts and I noticed Michelle wore the same pantyhose and skirt 4 days in a row. I loved working with her because she dangled her shoes when she sat and dipped like crazy when she was standing serving customers or straightening up. Towards the end of her shift she would tell me how tired and hot her feet were from wearing on them all day. I would try to get as close as possible to her so that I could smell her feet when she popped out of her flats. I almost always had a bulge in my pants and I displayed it proudly in front of her. She never said anything but she'd steal glances and smile at me. She must have enjoyed knowing she had this effect on her 18 year old coworker.
On the fourth day of that week, her husband came in and asked her to hurry up or they'd be late for a dinner reservation. Michelle ran to the bathroom with her bag and came out dressed in a killer "going out" outfit. She came back into the store and set her bag on the counter asking me if I'd be a dear and put it somewhere for her. I did as she requested. As soon as she was gone, I went straight for her bag.
Jackpot! Everything she was wearing was in the bag and it was damp from her pussy and feet. I'm glad it was a slow evening as I spent most of it smelling her panties, pantyhose and flats. I wanted so badly to slip her pantyhose over my cock and fuck her stinky flats but I had to wait until closing time. Towards the end of my shift, I slipped her pantyhose on my cock and put one of her dirty flats on my cock and zipped up my pants. I untucked my shirt to cover the giant bulge in my pants and enjoyed the feeling of my cock pulsating inside her damp hose and shoe.
As soon as I closed up, I took her bag to the bathroom. I put her panties over my head so the damp crotch was right over my nose and started fucking the flat that was on my cock already. I raised her other flat to my nose and sniffed hard to filter the smell of her sweaty flat through the crust of her pussy secretions. I was overwhelmed by the combined smell of her pussy and her shoe. With fresh memories of Michelle dangling in these flats and driving my crazy, I came so hard I thought it would never end. I completely filled her flat and soaked the foot of her pantyhose. There was a deep lake of cum in the shoe. I knew she didn't have a shift until next Tuesday, so I left her flat as is. I had another shift on the weekend and I repeated this wonderful session with her other flat. Those were probably the most intense orgasms I've ever had with a shoe. I was scheduled to work with Michelle on Tuesday and could hardly wait to see her.
When I went to work on the next Tuesday, Michelle was wearing a shorter than usual skirt and had her flats on barefoot. My cock started to grow right away. I got even harder when I noticed some new stains on the toe of one of her flats. It wasn't a cum stain but something I had never seen before. We talked and, as we did, she was dangling but I could see her shoes sticking to her feet and required her to flex harder to pop out her heel. She casually mentioned to me that she might need to get rid of the flats as they were getting disgusting. I couldn't resist, so I told her I thought they were perfect for her and it would be a shame if she got rid of them. She looked at me a bit oddly and asked me why I thought that. I walked over closer to her with a very visible bulge in my pants and mustered up the boldness to tell her that I thought they were the only thing stylish enough to cover up her gorgeous feet. Michelle floored me when she slipped her one foot right out and held it towards me. She asked if I really thought her feet were gorgeous. All the blood had left my head and went straight to my cock but I managed to tell her that she had the most beautiful feet I'd ever seen. Besides seeing her sweaty footprint in the crust of moist cum inside her flat I noticed the pointed toes of both of her flats were stained. My cock pulsed heavily in my pants right as she looked down at it. She giggled a bit and said something about having an effect on boys.
When her shift was over, she popped off her flats and kicked them under the counter as she switched to socks/running shoes. As soon as I had a chance, I picked up her flats and discovered the new stains on the pointed toes of her flats were pussy juice! My head swirled. Who's pussy juice was it? I worked out a plan to find out.
As soon as I closed up that Tuesday, I sucked on the toe of Michelle's flat with the dried pussy juice as I dropped a massive load in the her other flat. As always, I left her flats back in their place. I licked and sucked the dried pussy juice off until her flats were clean, so I'd know if fresh ones appeared. I didn't have another shift until Friday and one of the other women, Rhonda, would be closing Wednesday and Thursday nights. It was time to find out if Rhonda was using Michelle's flats on her pussy. I dropped by the gas station to buy something to have a look behind the counter. Michelle's flats were sitting in the usual spot so I knew she hadn't taken them home. I also noticed that one of the other women, Karen, had left her pair of navy blue heels and brown flats there. Normally Karen took her shoes home....hmmm, strange.