The Brogues 16 min read

This is a retelling of an event that happened with my ex-partner some years ago. It stands out as one of the best tramplings I had with her. Some days before this trampling happened, my partner had bought herself a new pair of tan brogues, which were fashionable for girls at that time. They were practically flat, but their androgynous look and sexlessness made them very appealing to me, these were shoes for her to wear when she didn’t care about looking sexy, these weren’t shoes she had picked with my interests in mind, and that made them very attractive to me.

She showed them off to me while wearing thick navy tights and a dress she had also purchased that day. She looked absolutely stunning, and the dress and shoes both exaggerated her long and shapely legs.

It was autumn in the city at that time, and our road and street were both carpeted in a slimy mulch of leaves and dirt. While she was walking around showing them off for me she started sliding along the floor and looked troubled. “I think I’d better take these down to the cobbler’s before I wear them out, or I’ll end up on my arse!” “It’s OK, I’ll take them in tomorrow on my way to work,” I said, as quickly as I could. Like many of our trampling games, this one would begin with an act of service.

I had been trampled before by shoes she had had resoled from this particular cobbler, and it had always felt amazing. the soles they put on had a pattern of long, straight furrows made from hard, dense rubber. they felt amazing when paired with her slow, causal trampling style. So it was with no small amount of anticipation that, after I kissed her goodbye the next day, I walked to the cobbler’s shop halfway down the road. They smiled and said that I could pick them up that evening. As I stepped out into the cold air, I texted her:
Ready to pick up this evening. I was thinking you could make sure they’re not too slippery after dinner?

When I sat down at my desk, I felt the phone vibrate in my pocket. her message simply said “I will. can you help me make sure they won’t slip if I step on any disgusting rubbish?” I replied that I’d do whatever my queen commanded. I don’t mind telling you, it was a long day at work, and as soon as 17:00 hit, I bolted without saying goodbye, and also without my satchel. I arrived at the cobbler’s just as they were closing and I exchanged the yellow docket for the shoebox and walked home as fast as I move.

When I arrived, my partner was visiting a friend, so I had the house for myself, to begin preparing dinner. Before I got into the kitchen, I had to have a sneak peak and press my fingertips to those deep furrows of pain. However, when I opened the box, I found that the soles were not as inspected, but rather that the whole surface was filled with a surface of interlocking shapes, like a cross between pyramids and sharp little teeth. each one was a point and they all interlocked to ensure that, no matter which way the wearer slipped, they would bite in and take hold. Immediately, I got hard thinking about how much they might hurt with so little effort on her part. these were no skinny stilettos to balance in, so she could stride with confidence.

On the way home, she texted me “I love you”. Although we were always affectionate, I knew that this message meant that she would be ‘in character’ from the moment she got home, so I took the time to send her a text back saying that I loved her too and appreciated her for indulging me.
She arrived as I was finishing the dinner, and wordlessly removed her coat and sat at the table. I brought her her meal, and a glass of coke, and she ate slowly, watching me squirm with anticipation as she enjoyed every forkful. “I’m done. take these away.” she announced, and then got up and sat down on the couch, texting her friends. She knew I loved it when she treated me dismissively, and so I went and washed the dishes before coming back through into the main room. When I came back through, she simply said “bring my shoes”. When I brought the box to her, she rolled her eyes at me. “Put them on! for fucks sake, do I have to do everything?”.
I knelt by her feet and removed her ballet flats from her feet. she had extended her long, shapely legs onto the coffee table. I slowly removed the brogues from the box, and with my hands shaking, loosened each lace, the back of my hand releasing the smell of new leather as it brushed against the material. I held the left shoe in my hand as she placed her left foot into it, the pressure of it fitting on her foot driving those soles into the palm of my hand, feeling like the holes of a cheese grater. I could tell this was going to be very painful, but didn’t say anything for fear that she’d be discouraged. I laced up both shoes and she wiggled her feet in them. She said “I’m not ready yet” and pointed at me to lay down in front of the sofa while she went back to her phone.
Without another word, she swung her feet down from the table and rested them on me, with the back edge of her heels resting on my sternum and cheek. Because they were brand new, and the heel had not been altered, these burned intensely, even with just the pressure of her legs leaning against me. She was silent as she browsed the internet, with each move of the heel on my sternum aching like having the back of a knife dragged across my skin. I could feel the one on my cheek pressing the skin of my cheek down into my teeth and after a while, I could feel the skin going numb. It felt like I was down there for an eternity, but in truth, it was only ten or fifteen minutes.
Eventually, she moved her feet, her heel clipping my nose and making my eyes water as it swung past my face and came to rest on the floor. “Right,” she said “let’s see if you managed to do this properly. Hands.” This was her command meaning I should place my hands flat on the floor for her to step on. She had picked it up from one of her murder mystery programmes, and knew the brusqueness was an immense turn-on. I moved to the kneeling position with my hands flat on the floor and she stepped forward tie and she slowly stepped forward until the toes of her feet covered one of my hands. That sole was killer, t once grabbing my skin and biting into it. The sole of her brogues were hard, even without the brutal grip and I gasped as she crushed my fingernails. She slowly lifted her right foot and moved it to rest the heel over the nails of my other fingers before shifting her weight. “How do they feel?” she asked me. I was able to gasp “firm… hard!”
“Good” she replied, “They feel very comfortable from where I’m standing” and she started to rock backward and forward between her heels and toes, making me audibly gasp with every movement.
After a while, I tore my gaze away from her shoes and let my gaze carry all the way up to her beautiful green eyes. She was 6 feet tall. Taller than I was even when I wasn’t in this degraded position. she was looking down at me with a mixture of boredom and curiosity, not at the hurt she was inflicting on my hands, but on the paroxysms that crossed my face at the slightest shift of her weight. “Right,” she said, as she stepped off and reached for her ‘phone. “I’m bored of looking at you, so I’m going to check my phone. Sit up, with your back to the sofa. If I hear one word from you, or you make me slip, I’ll kick your fucking face in. Do you understand?” my heart was pounding in my throat as I nodded and sat up as requested. By now, I had stripped off my trousers and underwear so that my cock and balls were lying flat against the tile floor. I could see her face illuminated by the light of her ‘phone screen, but I knew she wouldn’t be able to see much of me. Once I was in place, she stood in front of me, and began to gradually and disinterestedly walk forward.

When the tip of the first toe started to crush my foreskin, I knew this going to be agonising. there wasn’t much weight on it yet, but those interlocking teeth on the sole immediately smeared the skin and pressed in flat into the floor, especially as she moved her other foot forward and the weight shifted from the front of her foot to the ball, dragging the skin backwards and twisting slightly. the next foot came to land next to the shaft of my cock, with the tip of her toecap touching my left testicle. she paused for a moment to type a message then lifted her first foot again. My cock swelled as the pressure was lifted, but only for a while as her foot moved further forward. when she next stepped down, my cockhead was trapped behind the ball of her foot, while the shaft was pinned under the length of that fearsome sole.
The pain was excruciating, like hundreds of tiny pinpoint burns flaring as she added more and more of her weight, until eventually her foot squeezed my cock and she could stand more or less flat. by now I was breathing heavily. But it was only when she lifted her second foot that the agony really begun as her weight slipped slowly backwards to accommodate the motion of her walk. each of the backwards-printing treads grabbed a tiny part of my skin and dragged them away from my body and under ever more weight. If my cock had been a leaf or another piece of rubbish, it would surely have disintegrated under the pressure. my cock started to flatten under the pressure, but as her other foot moved forward, my testicle was caught under the toe as she added more weight to that foot.

The pinpricks of the tread hurt this time as well, but they were nothing compared to the unyielding hardness of that hard sole on my delicate testicle, pressing down until eventually, it was forced out of the side of her shoe and the soft, sensitive skin felt the full pressure of those jagged treads as she got comfortable.

Over the next few minutes, she continued the pattern of moving forward, millimetre by millimetre one foot at a time. each shift in her weight and slight movement making me open my mouth to gasp, but not making a sound. eventually, the tip of her toes were pressing into my pubic mound, my shaft was trapped between both feet, and my balls each had a little pressure on them. I looked all the way up her denim-clad legs, over her hips and her waist, to see if she had deigned to notice me, or if the phone was more interesting. No prizes for guessing which one it was. Eventually, I felt her slowly rock backwards onto her heels and off my cock. as the pressure eased off, the sensation returned fully to the thousand screaming wounds over the surface of my cock and balls and I gasped. In many places, the skin was stuck into her treads, and her raised toes lifted my cock with them for a distance.

She had barely lifted up for a few seconds before her weight swung forward again and her toes once again flattened my cock and balls. each testicle had moved back into place when her feet had lifted, so when she rocked back forward they were trapped in place under the treads of her toes for agonising moments before they slipped backwards, away from the agonising weight. The shifting of position made those sharp jagged teeth chew the skin and flesh of my genitals as they scraped in both directions, forward and back, each movement smearing my agonised and broken skin further and further into her tread pattern.

When her feet were fully flat again, I felt her wiggle in the way that she did as a prelude to standing on tiptoes. I knew this would be unbearable, I wasn’t ready for the amount of pain that I knew was coming, but I didn’t dare say anything in case she stopped. She rocked forward with both her heels in the air and every ounce of her gorgeous 6 foot frame on my cock and balls. It was every bit as bad as I expected, and worse, and better and more glorious and agonising. Her eyes had not left the screen of her phone, she neither knew nor cared how much worse this was than her doing it in Dr Martens or Vans.

As a reflex, my arms wrapped around her shins to hold her in place and stop the agony of her moving around, and this was what finally got her attention. She locked the screen of her phone and looked down at me. “Did I say you could touch my legs?” she asked.

“No” I stammered.

“Then you should let go, shouldn’t you?” Her voice hadn’t raised above her normal conversational tone. I lowered my hands to my side sheepishly. And placed my fingers flat on the floor. Before I could breathe, she twisted with both tiptoes, right, then left, then right again. Her movements were so quick that the hard wood of her heels clacked together with each movement. She was looking disinterestedly down at my gasping face. “Don’t make me remember that you exist again” she said, then stepped off while checking her phone. I could feel the air burn on my broken skin and I briefly touched my cock and felt dampness that had nothing to do with precum. Thankfully, the evening had drawn in and the room had become quite dark, so neither of us could see the full extent of the damage. I laid my cock and balls back down on the floor, and she once again began the process of taking tiny steps towards my genitals. The heels on these shoes hadn’t been altered, by they were short wooden heels with a very sharp plastic edge to them, completely unyielding. The first heel landed on my foreskin and immediately flattened it, but unlike her toes which had pinned and pricked, this was like the blade of a dull knife, and the pressure was just as relentless as she started to move her way backwards. Eventually, she was standing with both heels on the base of my shaft, and started to slowly march in place, altering which heel was crushing it and which was crushing a testicle. The most agonising part of this was that my testicles kept trying to escape directly away from my body, meaning that they got trapped you the sharp front edges of her heel. After a while of this, she eventually let both of her feet rest still, which was agony because the front side of each of her heels ended in a sharp triangular point, and one of them sank very deeply into my cockflesh and (as I later learned) was raising a deep black bruise.

When she stepped off, she recorded a voice clip to send to her friend. She stepped over my leg and was standing beside me. She was talking about how her day had been, and then raised her foot to step over my thigh. “Oh, and John in work was being an absolute flirt again,” she said into the phone as her left foot stepped down perpendicular to my cock, the width of the ball of her foot completely covering my shaft, but this time with the spiked treads digging in a completely different direction. As the stepped forward to bring her other foot beside it, she continued her message “It would be annoying if he wasn’t so hot. Maybe I should take him up on it? You know how I need a good fuck to keep me sweet”. She didn’t let her other footrest on the ground, but instead stepped straight over my other thigh so that my cock was crushed and rolled under the sole of those merciless shoes. By now she was looking back down at me as she had finished her message. “If you weren’t so pathetic, maybe I’d be telling my friends about the good sex we were having, instead of me using your worthless cock to test how it feels to step on shit.”

With these words, she stepped backwards so that her foot once again landed on my cock and she stepped back, this time rolling and grinding my cock in the opposite direction to her last step, but this time, she brought her other foot to hover over my cockhead and started to slowly switch which foot her weight was on so that either my shaft or head was being crushed down under those sharp sawtooth treads. The rocking motion, coupled with her cruel words and the sheer agonising pain got me close and closer to cumming under those brutal shoes but she was back to looking at her phone and fidgeting. The lifted the foot that was over my glans and I gasped as a limp puddle of cum came squirting out! My body was squirming involuntarily as she looked at me and wrinkled her nose “fucking disgusting” she said, but unexpectedly slammed her foot back down on my cockhead and pirouetted on the foreskin and glans.

The pain was unbearable in my post-orgasmic sensitivity and I tried in vain to lift her shoe off my mangled cock. She reached over to turn the lights on and audibly gasped at the scene on the floor as dozens of bloody footprints covered the area where she had been walking, and last of all, a thick smear of fresh blood looked like it had been painted on with a thick brush. She squatted down in front of me and looked at me with concern to ask if I was OK. I’m sure I must have said something back, but through the hazy cloud of adrenaline and subspace I can’t remember what it was. Once she had gotten over the shock, she sat back down and told me I should get in the shower as soon as her shoes and the floor were licked clean. It took a while, but I did as instructed, with the soles of her shoes especially rasping against my tongue as I licked up the coppery blood and flinty cum.

I examined myself in the long mirror, my cock was covered in scratches and bruises, there were two deep furrows on my face and my foreskin was swollen almost shut. I remember thinking as the hot water scalded my ruined cock that I was never more in love with her than in those few moments after a bit of brutality, and I don’t think we had a more brutal session than that one.