My First Time Under Heels 4 min read

Hot stepsister punishes her sibling by stepping on him with her spike heel

written by Jerry_from_Brooklyn
original source of the story was Unknown source

4.1
(34)

When I was 14 my father remarried and we moved into the bigger home belonging to his new wife. The hardest part of moving in with them was my new stepsister. She was a gorgeous 5’9″ blonde with a D-cup and legs then seemed to never end. She knew she was hot and she and her mom were always talking about who she might “get her hooks into” for which read “marry.”

Her beauty made me nuts and I could think of no one but her. She had this one pair of red high heels she liked to wear out to parties and the like, size 8 1/2. She called them her “six-footers” and would thump about in them getting ready announcing proudly, “Hey look, everybody, I’m 6 feet tall! I’m 6 feet tall!”

I think she just did that to make me h—- because I had once confessed to her that I thought tall women were cool, But that was back when we first moved in and I was trying to make friends with her. Of course, I soon discovered that she wouldn’t give me the time of day and resented my even being in the house.

One Friday night when she was out late I sneaked into her room and got her red heels. I took them to my bed and sucked the heels and licked the soles, dreaming that I was her slave. I pressed the heel-tips to my chest and imagined her stepping on me. The heels felt like cold, hard little points. I f—ed the inside of her shoe and dreamed about her sexy stocking foot being in there. Then, before I could keep it from happening, I came all over the inside of her shoe. I panicked and tried my best to clean it all out, but the strong odor remained. I was cleaning it more when I heard a car in the driveway and knew she was home. I only had time enough to quickly toss the shoes into her closet and run back to bed and pray that she wouldn’t notice.

The next night she was dressing for a party and put on the red heels. I was in the living room lying on my stomach in front of the TV. when she walked over and stood in front of me, modeling the shoes. She said, “You like these shoes, don’t you?” I knew right away she wasn’t being friendly. Her voice was cold and she never talked to me, anyway, unless it was to say something unpleasant. My heart was pounding. Did she know, or was she guessing? Had she smelled the shoes, or just noticed that they had been moved? My stomach began to shiver. Maybe this had something to do with something else. I could hope, couldn’t I?. I felt my face turning red. “Yeah,” I said, “I like `em okay.” She went around and stood at my side. Then she placed her spike heel firmly in the center of my right butt-cheek and stepped down with all her weight.

Those sorts of heels are named “spike” for a good reason. It was just like someone had nailed me to the floor by driving a spike into my body. I had dreamed about being stepped on with heels and even thought I knew what it would be like, but I had had no idea of the un-f—ing-believable crush they put down. I gasped, my eyes filled with involuntary tears, and I groaned out in real agony. The crush seemed to be lasting forever; I began to beg. When she stepped over and off of me I felt her heel stick to my skin a bit as it pulled out, like it had left a hole in me. As she thumped heavily away she tossed a glance back at me, flipping her blonde curls, “Still like these shoes, shithead?” she asked triumphantly.

As it turned out, I did have a hole in my butt-cheek from her heel, but it hadn’t broken the skin. But I could still put the very tip of my little finger in it. A huge bruise formed soon after and I had to lean to one side when I sat. The pain didn’t end for a full 3 weeks and was still sore some for months after. I am sure that she thought she had punished me severely, but I have to say that even with the terrible pain I would lie in her path again – god, what a rush that was to feel her spike-heeled foot come down on me like that.

Being crushed by a woman in heels is so much more wonderful when you are not expecting it and if it is done in real anger. It is still my best experiences and I have had quite a few of them. But I suppose you always have a fondness for your first

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