My first real actual trampling 26 min read

Continuing to write down my experiences, I’m going to jump past some times in my teenage years to my first real actual trampling. I’ve had my aunt walk on my back, and my older sister and her friend step on me in heels once as a dare, I’ve been crushed under furniture before and figured out candid car crushes down to a science, but for many years I fantasised (sometimes even daily) about trampling experiences, dreaming up fictional scenarios in which I could be unknowningly crushed or stood on by women but never really working out. I often imagined meeting a woman with a sadistic streak who would enjoy trampling.

Sorry to burst your bubble, but I have yet to ever meet a woman who enjoys that for their own pleasure, not one. The silver lining is that trampling is actually pretty mild compared to many fetishes and it doesn’t involve any sexual contact or nudity, so it’s pretty easy for them. All the women I’ve gotten to the stage of asking have been pretty happy to do so for cash. They’ve all been willing to do again too and the subsequent times are much better, they are acustomed to what I like, and jump straight in… Literally. I’ve discovered that women in that industry have a knack for very quickly identifying what a man desires, and moulding themselves to that image. For instance, one woman said on my 2nd visit when she saw me in the foyer ‘Oh my gosh, I was just thinking about you the other day when I was tying up these heels, I was frustrated and wanted to stomp on someone haha’ she said as she pointed to the sexy pair of sharp heels with straps that wrapped around her ankles and up her calves. Still, she wouldn’t do it for free of her own accord, but will happy do it in exchange for money. In a cruel twist of fate, many men have messaged me or replied to my ads explaining their sadistic desire to stomp on me, and would even offer me cash to let them. I have declined all these as I’m straight, although I was tempted by a couple M/F who wanted to both stand on me and make-out, him in dress shoes and her in heels).

Anyway, as part of my career I often travel internationally to visit business clients. Many of these countries have legal prostitution, and brothels are a regulated industry, completely legal, but with guidelines for worker safety, mandatory health checks, etc. Here’s how my first experience went once I finally built up enough courage to visit. I don’t remember everything word for word, but I remember the main gist and so re-created as true to memory as possible, but events 100%.

It was mid-afternoon and I had a break between two business appointments. I thought it would be less busy during the day. The address can be found online and it led to a non-descript plain warehouse-looking building in an industrial area. There is no advertising, just a small car park for customers, and past that a gated car park with a sliding door for the workers’ cars (I’m pretty sure that is for worker safety so stalkers don’t copy their number plate or follow them home etc.). I parked a fair way down the street and walked to avoid having my rental car seen in their carpark.
At the front door is a small note that reads ‘press the doorbell and wait to let in’. I do. Very obviously pointed at anyone standing at the door is a large camera. After a moment I hear someone adjusting the locks and an older woman appears. She invites me inside and I follow in, heart racing and hands literally shaking. Once inside, the best way to describe it is to imagine a mechanics’ waiting room, but replace the large car posters with naked women, that’s what it looked like, a business waiting room like any other. She did the usual small talk and then asks if I have been here before. I explain I have not. She walks me back to the shop counter and there is a price list for rooms and women. She explains the way it works is that I pay a fee to the establishment to hire the room, and then a separate fee to the woman for her time. Whatever I want to discuss with the ladies when they come out. I look over the menu and select a 30-minute room hire, there were options for 45 min, 1 hr etc. The room hire for 30 minutes was approx roughly $50 USD when converted back.

She then explained that there were currently three ladies on right now, and directed me to go take a seat on the lounge and the women would come out and introduce themselves one-by-one. (Wasn’t until months later during a conversation with one it was revealed that they see the cameras in their staffroom, and individually decide if they will come out and introduce themselves or not) I sat awkwardly on the lounge, twiddling my thumbs and after what felt like an eternity, really only a minute, I could hear that sexy click-click sound of heels along tiles. The door opened and I was a little stunned, she strode out in black lingerie and heels. She looked to be in her late-20s or early-30s, slim with an athletic build, long dark hair pulled back loosely, and a confident, slightly playful expression. She held out her hand for me to shake, She introduced herself with a smile as Elle (obviously a fake name, but I didn’t mind one bit) and sat down quite close beside me, almost touching.

I was almost expecting her to be trashy, covered in tattoos and piercings, but I was pleasantly suprised. She had beautiful big brown eyes and only simple ear piercings, if dressed she could pass as any number of typical professions. Put her in scrubs and you would not doubt she was a nurse. Put her in average clothes and you wouldn’t pick her as anything other than an attractive but typical woman at the local mall, which made this all the more thrilling.

“So I hear it’s your first time here, what are you looking for?” she said with a warm smile. I had to remind myself she doesn’t give a fuck about me, she probably despises me behind that nice smile and she is only talking to me for the money. But that’s all right because at the same time I am reminding myself I don’t care about her at all either, I’m using her body to get off, then walking out and never seeing her again. It’s completely transactional and we are both playing our part. Anyhow, I rehearsed in my head lots how I would approach it this.

“Hi, nice to meet you Elle. I’m looking for something a bit different. I don’t want any sex, I literally want to lay down on the ground and have you walk on me.”

“Okay…” she said slowly, head tilting “like one of those back-walk massages?”

“Exactly, but then after a few minutes, I want you to roll over and have walk on my front.”

She seemed fine so far.

“And then I would love you to keep these heels on. I enjoy pain, and it leaves little red circle marks that I really like.”

I said it looking down at her shiny black stilettos. Her toe cleavage was just visible, entrancing, and I almost got lost there. I had to look back up and make eye contact again.

“Oh my gosh,” she said, shocked She reached down to her crossed legs, turned the heel out, and showed me the nib on the stiletto point.

“These would stab right through you!”

“Nope, done it many times before, just leaves little red marks that I love. Is that something you’d be interested in?”

“I mean, sure if that’s really what you want, I just have to walk on you,” she laughs. “I normally charge $150, but being first time and no sex, I could do that for $100… special price just for you.” She replies, leaning forward and using her arms to slightly compress her chest together, her push-up bra cradling them together to create deeper cleavage. She knew exactly what she was doing. Thinking back, I should’ve waited to meet the other two ladies, but I was too keen to get into it, finally a woman who would actually do it for me, zero judgement. Or at least zero repercussions on that judgement, as I walk out and never see her again.

“Let’s do it!” I say.

“Never done this before, it’s going to be fun!” she giggles. “Just go tell the manager, and I’ll come get you in a minute,” she tells me as she steps up and then struts away and disappears behind the door, fully aware I’m staring at her ass as she walks away, transfixed and almost drooling like a dog.

I tell the manger, before sitting back down to wait impatiently until I finally hear the heels coming back again. She gestures me in and says follow me. As we walk down the hallway past doors, I am again watching her. I’m 5’11”, and I’m still taller than her in the heels, I’d guess maybe 5’4″? She opens the door and gestures me in again. I wasn’t sure what I was expecting, but it looked like a motel room really, with an adjoining shower and bathroom, one wall almost entirely covered with a huge mirror.

“Now, we always do a health check first,” she says as she sits on the bed and puts on gloves. “Come over here. I usually play a ‘sexy nurse’ for this. I know you said no sex, but policy is policy.” Her demeanour had changed slightly, but after I dropped my pants in front of her, she pulled back the foreskin, looked under my balls etc. as I looked around the room. “All good,” she smiled, “and I always take payment upfront.”

“Yes,” I say, rummaging through my pockets and handing it over. I purposely have one note left, another 50, but I sit it visible to her under my wallet on the bedside table, part of my plan for later. She notices, but makes no comment. Now that the formalities were done, her tone changed back.
“Now tell me exactly what you’d like me to do?” she purred after putting the money away in her wallet on the far side. This was finally my chance: no judgement, no protecting myself from seeming weird, or having to repress what I want. Finally!

I started off: so I’ll lay down somewhere. We looked around and decided the wall with the mirror so that I could still see, and we pulled a chair over so that she could balance more easily. I stripped to my boxers and laid down. There was about three ft between the wall and the bed. She sat on the bed and was cross-legged again, dangling one foot near my head.

“Did you want to take my heels off for me?” she asked.

Of course! I roll over on my side for a moment to slip the first one off her foot, my hands shaking as they reached her first stiletto heel.

“Oh honey, no need to be nervous, this is all about you,” she reassured.
I slid it off her heel and pulled it forward to reveal the most beautiful light pink pedicure.

“Oh wow,” I stammered. “They’re gorgeous.”

I was referring to her whole foot, they were petite and soft, a size 6 I noticed on the insole of the heel I was holding. But, she must’ve thought I was referring only to the pedicure.

“I got it done yesterday,” she beamed. “I like it when guys notice my pedi.” Again, I know that probably isn’t really the case, but I didn’t care anymore, she had me hook, line and sinker.

I was beginning to almost think she liked me. I then explained I just wanted her to come over and walk on me wherever she wanted for a few minutes. She stood up and walked right over to my face, teasing me with both feet less than an inch from my face, so close I could’ve reached them with my tongue, before she tentatively placed one foot square in the middle of my back. The warmth of her sole pressed against my skin. “Tell me if it’s too much,” she said, giggling again as she wobbled slightly and adding weight until both feet were on me.

“I’m not too heavy, am I?” she enquired, looking down.

“Not at all, very light actually,” I told her. She walked around for a few minutes, initially very tentatively, but slowly getting more and more relaxed. As she grew more confident the pressure changed — her steps became steadier and more rhythmic, the weight shifting smoothly across my back with each deliberate placement of her foot. Her soles were soft and warm, and I could feel the slight dig of her toes each time she transferred her weight. She really was actually quite light, so even with both feet above my lungs, I could still breathe in quite easily. We had really good chemistry and just chatted away the whole time. I was trying to treat her like any other woman I would meet, not just a piece of meat.

“How’s your day been?” I asked.

“Pretty quiet so far, actually. You’re only my second today,” she replied.

“How do you like this work?”

She gave a small shrug. “It pays the bills and the hours are flexible. Some days are better than others.”

“How many clients a day usually?”

“Depends. Sometimes four or five, sometimes only a couple.”

In between all of this chat, she was shifting between holding the wall and the chair back, to walking over me, placing a foot down and then transferring her weight. I would let out a soft moan or a “that’s good” as both reassurance and encouragement for her. In the mirror I could see her looking down at me with a focused but relaxed expression, the whole scene looking completely surreal… She was literally standing there on my back in lingerie casually chatting. It was like talking to that one girl from the office you only ever occasionally talk to in the lift, that same chill, semi-informal, relaxed feeling, just another day small-talk. I was rock hard the entire time, thoroughly enjoying every moment under her. It was amazing.

I then asked if I could roll over. “Absolutely,” she said. She stepped off for a moment and I lay on my back looking up at her. I explained I wanted her to step wherever she wanted again, just not on my neck, and to have fun with it, forget I was even a person. I told her that if it was too much I would tap her ankle, and if she could hop off for a moment if I did that. She readily agreed.

“Did you want me to be naked too?” she asked nonchalantly.

“If you’re comfortable to?” I asked giddily.

“Wouldn’t last long here if I wasn’t,” she laughed, before unclasping her bra and seductively dropping it onto the bed, reavealling her breasts. She went to take off her panties, then stopped for a second, instead asking

“Ready?”, raising her foot over my chest.

“Absolutely.”

She then stood both feet up onto my chest. The sudden weight of her settled across me as I looked straight up at her body, her ass right above my face. She began to shimmy out of her panties. They dropped to her feet on my chest and she used one foot to rub her warm panties across my chest for a moment, before sliding them down my stomach and letting them sit over my boxers. She could clearly see my raging erection fighting against the fabric of my pants.

“Someone’s excited,” she teased as she ran her foot along my member from base to tip through my boxers, before taking a few steps to turn around. Even once she was fully naked and walking on my front, the conversation kept flowing easily between us, the same good chemistry carrying on as if nothing unusual was happening at all. As she walked down onto my stomach carefully, I flexed my abs to keep her from sinking much, it was a strain, but not too much.

She again just dropped into the conversation, “Do you have a foot fetish too?” as if we were discussing a menu at a restaurant or something equally average. I answered with a sheepish “Yeah,” looking at this beautiful woman standing naked on my stomach.

“Great!” she beamed, making her way back to my chest. She leaned forward and held onto the chair above my head, lifting one foot off my chest and stroking the side of my face. She started up near my eyes, her beautiful toes tracing the outline of my face before arriving at my mouth. She knew. I knew. I opened my mouth and she guided just her toes in one by one, allowing me a moment to indulge each one as she too moaned above me. It was absolute bliss. I closed my eyes and revelled in the moment, caressing her foot in my hands and gliding my hands further up her smooth ankles and flexing calves as we continued. They were perfectly soft and moisturised, she must’ve literally shaved or waxed that morning, it was amazing.

I wished the moment could’ve gone on forever as she alternated feet allowing me time with each. but I was smashed back to reality with the realisation that I only booked and had money for 30 minutes, and I had no idea how long it had been already. I opened my eyes and gently guided her foot back out of my mouth.

“Time for heels?” I asked. She stood off and walked over to her heels, stepping into them and adjusting before sauntering back over to me.
“Are you sure? It’s gotta hurt,” she said lifting one leg and inspecting the stiletto heel.

I reassured again and then laid my hand out on the carpet. “Here, let me show you, can you put a heel in the middle of my hand here?” She kinda nervously lifted one foot and the heel rested right in the middle of my palm.
“When you’re ready you can stand on it.” She transferred some weight, and it was instantly painful but she was holding back still.

“On one foot please.” I could hear her giggle nervously as she leaned over to grasp the chair and lifted the other foot out behind her. Still not much pain, and looking at her calf flexing almost like she was on tippy-toes, I realised most of her weight was still on the ball of her foot. No matter. I continued gently, “And now lean back on the heel with all your weight.”

I heard her mutter “Oh my god” before committing. I felt the tendons in my hand all get pushed aside out of place as her full weight came bearing down through the heel tip. The sharp point dug in hard, the pressure intense and concentrated into a tiny circle that felt like it was about to punch straight through. I winced in pain, but did my absolute best to hide the searing pain and let out a loud fake moan of pleasure. “Wow That’s so good,” I said. It only lasted a fleeting moment before she stepped off entirely.

She looked quizzical, almost examining me in a way. I guess sex work is her career and she’d discovered something. It would be like a mechanic examining a brand new model car, or a chemist with a new compound.
“You must really be a masochist! You’re getting legit sexual pleasure from pain,” she asked again with a furrowed brow. I showed her my hand. For those who’ve been trampled in heels you will know exactly what I mean, but it leaves sexy little red imprints, the shape depending on her heel type. She left little square prints, though the heel nib was worn and so slightly rectangular. “I absolutely love these marks, they’re like hickeys!” I explained enthusiastically in an attempt to encourage more of that behaviour from her.

She leaned in a little closer, eyebrows raised. “Wow… they really are perfect little squares,” she said, sounding genuinely curious.

“Could you walk on me now and leave lots of those all over me? I want them still there in a few days to jerk off to and remember this,” I explained. I figured we probably only had ten or fifteen minutes left at most, and I wanted to make every remaining second count.

“Alright then… You’re definitely going to remember this,” she said with a small smile. My demonstration must have worked, or maybe it was her thinking she had a genuine masochist under her. Either way, the shift in her behaviour was immediate. She seemed to have no qualms about it at all.
She stepped back onto my chest and began treading deliberately across me. At first she still placed each heel carefully, slowly adding pressure and watching my reaction, but within moments she was standing fully on the sharp points, shifting her weight from one foot to the other, then slowly walking up and down my torso. She stomped lightly in places, ground her heels in small circles, and purposely pressed down hard to dig deep into my skin. The pain was actually excruciating, sharp, concentrated, and constant, but I did everything I could to hide it. I kept my breathing steady, forced soft moans instead of gasps, and only let the occasional tight wince cross my face. Every time she dug deeper, I purposely re-assured by dropping little ‘wow’ or ‘that’s so good’ comments among the moans of pleasure. For a few solid minutes she worked over me like that, leaving a trail of those perfect little red squares wherever her heels landed.

It was working, she continued to become more bold and aggressive, the extent of my suffering hidden from her. Finally, she lifted one heel out behind her againlike a ballerina, and settled her full weight onto a single stiletto driven straight into the centre of my chest.

From below the view was almost unfair. Her smooth, tight stomach and her breasts hanging above me, the curve of her ass as she held the pose, the whole image was overwhelming. And every bit of it, all the weight of her, travelling straight down through one tiny fraction of an inch of heel. The entire mass of this gorgeous woman, channelled into a single unrelenting point.

That point trapped a small circle of skin and nerve between the hard tip of the shoe and the unyielding bone. It felt like a hydraulic press: a burning, concentrated pressure that forced the air from my lungs and made the rest of my chest seize. The skin around the heel stretched tight and white before it flushed deep red. I lasted five or six seconds, each one worse than the last, before the agony peaked. I tapped her ankle hard, just short of crying out.
She hopped off immediately.

A clear, deep red square was etched into my sternum, the edges slightly raised and still warm. She bent over me, still completely naked. Her breasts hanging close enough that I could have reached them if I’d lifted my hands as she leaned in to inspect the mark she’d just left.

A perfectly manicured French-tip fingernail traced the rim of the imprint with almost lazy curiosity. It caught on the dented skin and she made a small, interested sound.

“Wow. I can actually feel the dent. That’s crazy.”

“The worst of the pain is gone in a few minutes,” I explained, still trying to keep my breathing even while she stayed bent over me like that. “The marks usually last a week. They turn into little bruises after a day or two, then they fade.”

“How long left?” I asked.

“About four minutes,” she said.

“Perfect, give me one minute to recoup,” I said, standing up. She laughed at me saying it looked like I had chicken pox or something with all those red marks and that she couldn’t believe she did it.

I got to work on my plan. I placed the chair beside me and grabbed another two pillows off the bed, and the last $50 note. I lay back down again, pulling my boxers down and my dick shot straight up. I then placed the first pillow over my thighs, moving the chair over to beside my stomach and sitting the $50 on it.

“Elle, you’ve been fantastic, here’s my idea to finish. I want you to turn into a cold-hearted bitch. I’ll put a pillow over my face and thighs so you can’t see my face or eyes (No human connection to help her be vicious). I want you to be as brutal as you can on my abs. Jumping, stomping, twist the heels etc., and I’ll jerk off as you do to finish. If you can really brutal, that extra 50 is all yours too.”

“hmm… I can be a bitch.” she said with a raised eyebrow and sly smile.
The moment the pillow covered my face, she said “Ready?” I let out a muffled reply, but nothing. A few seconds still nothing, then suddenly the first stomp landed square in the centre of my abs and knocked the air out of me. Then she really started. Full stomps, then actual jumps, coming down hard on the stiletto points. Sometimes she balanced against the chair on one foot only, driving her entire weight through a single heel. She twisted the heels deliberately, gathering up folds of skin like a Chinese burn. Every impact was literally 10/10 pain. It felt like she was trying to punch holes straight through my stomach. I kept stroking myself as best I could through the onslaught, the pain and the pressure pushing me closer with every brutal landing, I used my other hand to push a handful of pillow into my mouth and bit down to avoid screaming out.

She slipped once during a jump. The heel dragged viciously across my stomach and left a long, deep, burning scratch that immediately started to sting. She half-stepped off, voice rising with concern, but I was already right on the edge.

“Keep going!” I yelled through the muffled pillow, voice desperate.
She only hesitated a fraction of a second before she came back even harder. More stomps. More jumps. One-footed full-weight presses while she braced against the chair, twisting and ripping skin. I thought I heard a buzzer of some sort sound, and the pain was so intense that I genuinely thought, if this continues much longer she could actually kill me. I was gasping, cock throbbing in my hand, every savage impact driving me closer.

A few more brutal jumps and I lost it. I came so hard, it sprayed several long ropes across her legs, heels, my chest and even up her thighs. The orgasm hit in the middle of her jumping full weight on my abs.

She finally stepped off. I ripped the pillow away, chest heaving, stomach a mess of deep red squares, a mix-match of scratches, cuts and outer layers of skin ripped off, and that long angry scratch bleeding. The fifty was still sitting on the chair.

She looked down at the mess on her legs, then at the state of my stomach, and let out a short, almost shocked laugh. “…Are you OK?”

“You deserve this” I said catching my breath, slapping the $50 off the chair and passing it up to her. I laid there for a moment to recoup, then I stood up and began collecting my things and redressing, using some toilet paper from the bathroom to dab the scratches that were bleeding. I quickly realised that bending, moving or breathing was painful in several spots, It looked dramatic but was all just superficial. The bleeding stopped quickly and it didn’t need anything more than a dab.

“Sorry about that one, I slipped,” she explained, she said walking over still naked and holding a palm over my cut, resting her hand there for a moment, her brown eyes looking up into mine.

“All good,” I smiled. “It’ll remind me of you. I’ll be thinking about you for days.”

I started getting dressed. Singlet first, then the shirt, then the slacks and the tie, ordinary work clothes covering a torso that was still a checkerboard of red squares, marks, and that long scratch. Bending to do up the trousers hurt. Tucking the shirt in hurt. It looked dramatic, but it was all superficial.
After that she came over and adjusted my tie slightly, then wrapped her arms around my neck and rose up on her toes before leading me out the door and back down the hallway. She took me to a separate door on the right which opened into the car park again. She stroked my arm and said another goodbye.

I quickly walked back to the car, feeling incredibly anxious that the entire world around just saw me leaving a brothel. I got into my car, and sat down in pain. I sat in stunned silence for a moment, the world around me looked like a normal average day. Yet 5 minutes ago I lied naked on a floor with a beatiful woman was stomping my stomach in heels, did that even happen?
I unbuttoned a button, and pulled aside the singlet… Yep, I have the proof.
The rest of the afternoon the marks throbbed under my shirt. Every time I moved or breathed I could feel them. It was a adrenaline rush all over again sitting in a meeting with the financial officer for a mid-size comapny, going over a multi-million dolllar deal, without the other suit having any idea that under a few layers of clothes, lied those marks and than 2 hours earlier I was naked on the floor doing that. I have been hooked ever since, and will write up more experiences when I get the time.