Penny Loafers Part 1 2 min read

This entry is part 1 of 2 in the series Penny Loafers

written by Obiwan
original source of the story was Mistress Destiny's Femdom Forums

4.7
(10)

Ever since I was in my last year at college I have had a thing for this type of footwear. The cause was a girl who was in my year, tall, blond, and with a bad attitude. In the summer of ’92, I was sunbathing at the back of my collage in an outdoor theatre, when this girl showed up. We couldn’t stand each other and as I was a little immature at the time I made some derogatory comments to her. I don’t remember the comment but I remember what happened next.

One of my mates shouted at me to “LOOK OUT!” and as I opened my eyes, there was this girl, standing over me with her foot raised over my groin. For detail purposes, she was wearing a red turtle neck jumper, knee-length skirt, black tights, and penny loafers, one of which suddenly found itself being pressed down into my groin. Had she stamped down I would only have felt pain, but she lowered her foot slowly, pressed it onto my genitals, and proceeded to attempt to crush my dick like a cigarette.

This was, as you can imagine, not the worst thing that has ever happened to me, but it was in public and people were starting to stare, so I thought I’d better get out of there, so I attempted to sit up. The right move for a tramplee, wrong move to avoid being embarrassed. “DOWN!!” came the voice from above, and she put all her weight onto the sole of her left shoe which made my dick feel like a pancake, and brought her right loafer-clad foot up onto my chest, where she stood on me for about five minutes. In private not long enough but there were other people around and I felt everyone looking at me.

I couldn’t move, as she was about 6’2″ with at least size 8 feet. and I am 5’10” with, thankfully, a fairly strong torso. Anyway, in the end, she got bored with, as she called it, boy-squashing, and decided to step off, but before she did, one of her friends said she wanted a go, so the loafer on my chest was placed on my abdomen, leaving my chest exposed. Her friend walked up to the side of my body, which was still painfully, but enjoyably pinned to the ground. Her friend was about 5’6″ wearing a blouse, blue jeans, and black knee-high street boots over her jeans, with smooth soles and low heels, like riding boots.

These boots were certainly made for walking as far as she was concerned, and my chest was used as a doormat for a few minutes, being walked over, trodden on, and having the boots wiped all over it. By that time I was in a lot of pain, and the only thing that saved me was the fact that it was time for the afternoon lectures.

Series NavigationPenny Loafers Part 2 >>

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