Before I had left school I had a Saturday job working in the local carpet shop/warehouse as a general hand. This is a true story I thought might interest you.
One of the secretaries (Debbie was here name) always wore high heel shoes or boots and thought nothing of walking or climbing all over the rolls of carpet. I got into work a little early one morning and while no body was looking I piled up some carpet off cut in the door way of the office and hid behind some rolls of carpet and waited until Debbie came in. I heard the clip clop of her heels on the wooden piece of the floor just down the corridor, as she came to the door of her office she walked straight on to the carpet then went into the office.
Debbie would come and go a lot in and out of the office a lot during the day and I thought if I put something under the carpet she would crush it and not realise it was there. My lunch was the ideal subject so I waited until she had left her office and lay my sandwiches out under the carpet still in the bag.
She came back and walked on my lunch as I heard the bag give a small pop sound. My lunch stayed there until lunch time, I don't know how many times she trod on them as I was working in the shop for some time, I saw her go out to lunch so I went back to get my lunch what I saw was a gooey mess in the bag some places had been a heavily squashed so this must have been where the heel had landed on them as you can guess I enjoyed eating my lunch that day.

After having Debbie totally crush my lunch into a gooey mess I thought there must be a way I could get her to trample me with out knowing.
We had a new delivery of rolls of carpet delivered and they were laid out in the corridor. As I was listing down the code numbers Debbie came in and walked full length of one the rolls of carpet digging here heels in as she walked. I watched and thought there was my answer lay under some carpet and she would walk on me. I pushed the rolls apart just enough for me to lay in between and pulled an end over me covering me completely. It was not long before Debbie came out of the office and walked on one of the rolls of carpet I felt it squash a little as she walked pass me and hoped that I would be luckier next time she came back. I could here Debbie talking to a lady and there voices were getting louder.
All of a sudden I felt a tremdous pressure as Debbie stepped on to my chest and stopped there. I could feel the heels digging into my chest through the carpet. As she spoke to the customer I heard her say one of the code numbers that was on a roll just here. She started to move around looking for the roll she wanted. Here it is she said and I heard her say come have a look just stand on the rolls you wont do any damage. The lady stepped on and stood right on my face before I could turn it to one side, she must have had stillettos on as the heel was digging hard into my forehead. The other heel was very light im glad to say as it was directly on my left eye.
I had a very big hard on and Debbie moved and stood right on top of my dick with here full weight. This hurt like hell and the customer moved forwards and stood on my chest. Debbie was rocking her foot in such a way to make me cum and I let little squirts out a little at a time.
They stayed there for what seemed an eternity but in real life about ten minutes both moving and digging there heels in to my chest and groin areas. Both then walked up my body and one at a time stepped on to my face and left for the showroom. I was able to slide out in time to see that the customer she did have three inch stillettoes on she must have been around the 170lbs so no wonder she hurt like hell, Debbie was very small about 120lbs or less and had white ankle boots with a thin high heel. I had several cut and burns on my face so I had to make the excuse a roll of carpet fell on me. Debbie walked back to the rolls and saw the dip in between where I was laying, she stopped turned and looked at me grinned and smiled then walked back to her office.
I never did find out if she felt me or knew it was me under the carpet but I enjoyed every minute of it.