Session with Jon

Have you ever wanted to hear from a tramplee that I have trampled? This is the post for you. Some time ago there was a request for this and we've finally got to it. We talk about the few times we have met up, what happened in each session and our thoughts about all of it! Also some plans for a future trample session, when travel is allowed.


Jon (joinjonjon) lives in Singapore and has visited Sydney a couple of times pre covid. If you're a trampler in Singapore, or visiting Singapore, I highly recommend him.



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We had been messaging a little bit before you first came to Sydney. I remember you were travelling with a family member, so we were limited on when we could meet up. The night we met I had had a really busy day and it crossed my mind not to come, but I couldn't pull out last minute. Because we hadn't met, I didn't know what you could handle and was unprepared. In hindsight, I should have brought more shoes. I thought you were going to be one of those guys who says they can handle a lot, but in reality can't. I was wrong. And it was a nice surprise!

What are your memories of this session?

Yeah it was definitely a very hot session for me. I felt totally crushed and flattened that night. I am so glad that we actually met up, though yes I was pretty unprepared too. I had tired myself out touring around Sydney and all. I should have known that it might be an intense session, I would have been more physically prepared. I was also very excited to meet you because prior to that, I had not really met anyone who is purely into trampling. I have been meeting people who are open to try it out but they all had very little to no experience. That night, there was no instruction or guidance needed from me, I just simply played my role of a carpet and was trampled all over. I was almost integrated into my Airbnb’s flooring!

Box 20. Nike Presto 85kg on 56kg

Either I didn't realise that it was your first proper session, or I had forgotten. You took a lot that night so that was impressive. With trampling it makes a big difference when the other person you are playing with knows what they are doing. That sort of opportunity doesn't come around a lot though, so playing with newbies is still good if only for practice.

It was an eye opening session for me as I was pushed against my own limits by taking an 85kg trampler jumping on me and without any reservation. Most 'tramplers' I had met would often hold back a little in order not to injure me. At that point in time it was my hardest session.


When you think back on that session, is there a moment or moments that stand out as favourites to you? I'll go first.

Because I hadn't realised how well you would handle my trampling, I hadn't anticipated having as much fun as I did. I haven't rewatched the videos before doing this chat, but I have some distinct favourite memories. I loved when I was trampling you and your legs and arms would flail about. It made you look like you were really struggling under me, but yet you weren't actively trying to push me off you. It was like some sort of coping mechanism for you. There were even a few moments where you started coughing as I was stomping and jumping on you. I didn't stop in these moments and the sadist in me totally got off on continually stomping as you were coughing and spluttering. The other thing I would say is, I think that session helped me solidify what my favourite type of tramplee is: a strong but small slave. It's common knowledge I will trample anyone and everyone who wants it, but seeing my big sneakers on your small frame and knowing how hard I was going on you, that was quite exciting for me. You took it well.

Wow! That’s pretty much similar to what I loved too! I loved the entire session mainly because of the intensity. I did not need to fantasise about more or imagine the worst that could happen to me because it was already happening. It was so intense, I had to keep up with it. Finding moments to grasp some air and relax my muscles. My lungs were constantly running out of air due to the stomping and jumping from an 85kg weight on my petite body. There were some moments when I started wheezing too. My legs were screaming for help under the weight. The pain is real but the pleasure overrides everything. As I recall, yes I really struggled but also I was very much in a state of 'high'. My body needed to shout mercy but my dick was telling me keep going.

Box 27. Presto Trample

The night we met was quite early in your Sydney trip, do you recall if it took you long to recover from this session?

Yes that was the start of my trip, I had a good rest after the session and over the next few days (about 2-3 days). I was actually quite breathless. I had to pull myself together to take deep breathes many moments throughout the following days.

I don't know why but that turns me on so much.

Every time I struggled to breathe, I was reminded of the session and the immense pain and pleasure. This would get me very aroused all over again.

Lets fast forward to your second visit to Sydney. This time you came on your own, and we were both much more prepared for the action. In fact, we had several hours of trampling over 3 of the 5 days you were here. When you were travelling to Sydney this time, were you scared or nervous at all, knowing what happened in our first session?

I was a lot more prepared this time round. I had ample sleep and water. No vigorous exercise before meeting, etc. I knew it was going to be x3 harder and more intense than the previous session, so I was a little nervous but much more excited for what was to come. I was looking forward to trying more different types of shoes on my body, and also to try two tramplers on me at once.

Box 110: Roshe 85kg on 56kg
Box 110 B: Roshe 85kg on 56kg (Alt View)

You definitely took a lot more second time around! My memory of the first day was that it was more of a warm up day with just me on you. We did three rounds of trampling, with Nike Roshe, Nike 270s and Nike Airmax90s, starting with the Roshe because they are a nice and soft sneaker sole.


I remember wondering if I was going too hard on you, knowing that we had a lot of sessions lined up. I didn't want to damage you so that we couldn't do all the rest. In the end I went hard on you anyway and you took it really well. One of my favourite parts was when you would roll over, and I decided I would just walk all over your arms and legs. I think it was the first time I had ever trampled a tramplee's foot before.

It was a warm up session but every stomp reminded me of the previous time we met. And seemed to be as intense if not more intense than the first time. Yeah I loved that every part of my body was crushed. My feeble limbs were all trampled like a cockroach. And when you trampled on my feet, it was like drawing a comparison between the mighty feet who crush and destroy versus the feeble useless feet which were a hindrance, meant to be crushed and kicked out of the way.

I remember we basically moved the whole room around so we could have space to film in that small room.


That room was nice and bright for filming. Every now and then I actually faced the camera and couldn't help but to flirt with the camera lens with my teary eyes shouting for help.

Box 143: Nike 270 Trample
Box 143 B: Nike 270 Trample (Alt View)

Actually I forgot about this part. I remember watching the videos later and really enjoying the look of despair in your eyes. But I knew you were enjoying it, because there was no effort to stop me at all!

I think I would rather get myself trampled until I pass out, than to actually stop the process.

You should be careful saying that to me...

While being trampled I remember thinking to myself if only we could somehow record the experience with both the face of the trampler and the tramplee, that will be a very nice video for future reference. But yes, discretion is important too, and I fully understand it. So I tried to remember and capture everything as much as possible in my memory!


I've definitely thought about this too, but I keep coming back to the fact: once it's on the internet, you have no control over it.

Yeah especially for such a hot video, it would spread like wild fire.

Box 118. Airmax90 85kg on 56kg
Box 118 B. Airmax90 85kg on 56kg (Alt View)

Day 1 was great and a lot of fun. Day 2 was even better for me, with my friend joining. How did you enjoy two tramplers on you at once? What do you remember of the session?


Day 2 was very very very hot, two tramplers taking turns to torment me. Both of you were merciless and throughout the session I was making weird noises almost non-stop. I guess your friend was quite well trained by you. He had this smirk and indifferent look on his face when he trampled and jumped so hard on my chest. I remember both of you took turns to stomp on my chest, I secretly wished that you guys would never stop! My whole body had so many shoe prints after that session.

I remember when you guys were wearing the white socks, it was a really painful experience. Both of you (160kg in total) were just grinding and standing on a small spot on the upper part of my chest. I was literally dying below as a foot rug while both of you were enjoying in the high heavens, making out with each other while carelessly grinding your feet on me. I was kicking my legs on the floor and grasping for air and suffocating but looking up, you guys were having a great time. It was really hot, I will never forget what I saw.


Box 119. 160kg on 56kg in Socks
Box 119 B. 160kg on 56kg in Socks (Alt View)

Well actually that was never the plan, and also, we had trampled together before but we had never made out with each other. It was definitely my favourite memory from that day because it was so unplanned and very hot. I remember being so turned on in that moment hearing you struggle underneath, we were both full weight on you.. and my eyes locked with him and we just started kissing. I remember thinking we are crushing you underneath our weight, and neither of us cared at all. That would have to be in my top three trampling moments I think. I've done something similar since, but I loved how impromptu that was.

Your friend was much lighter so I was fearing more for myself when you were on my body. But not long into the session I realised you were both on par in terms of pressure and pain inflicted on me. Your friend just didn't care about me and used great force on me. I was quite glad to be trampled by the both of you that day!

Box 109. 160kg on 56kg
Box 109 B. 160kg on 56kg (Alt View)

This is something I have joked with him about a few times.. he is lighter than me but he goes hard to make up for the weight difference. He is not into trampling like we are, but sees it as fun anyway. In our early sessions I actually had to tell him to pull back, don't go so hard. He was eager to be brutal right from the start. You would never know it, he's a really nice guy actually. I was very surprised when he easily turned into this aggressive trampler in front of me.

I am glad he is so open about this and willing to give it a go and not to worry much about me on the floor. Thanks so much for arranging such a session!

Anytime, we will have to organise him again for when you are back next. Do you remember how sore you felt by the time we got to day 3? Were you daunted by the fact I was bringing in another friend to do another double trample on you?


After the two sessions, I thought I was almost done because my whole body was sore. I thought maybe just 1 minute of trample and that's it. Little did I know that I could still take the third session. It was truly amazing. This new guy treated me as if it was my first trample of the trip! Despite being light, he actually jumped and trampled quite hard on my chest. I was feeling so helpless even under a small guy like him. Maybe because I was already quite sore.


Box 133. Double Shox Attack
Box 133 B. Double Shox Attack (Alt view)

So you think in future you could easily do three sessions again like that?

Yes, perhaps with 1-2 days break in between might really help.

Do you have any favourite moments from day three?

I remembered somehow you guys were grinding and twisting your feet on my body. He was turning clockwise on my chest and you were turning anti-clockwise, it felt like my body was tearing apart like a soft toy. Then you guys were rocking my body back and forth, twisting your feet up and down. My body followed the movement and I felt like I was mopping the floor. I had no control over my body except to make those weird noises again. Inevitably, I could not control myself when you were rocking on my dick, I cum! Spasm and squirm a little as I shot out my load in my pants under your sneakers.

After all that we had some foot fun on the balcony. You guys pressed my face against the wall with your feet, I had so little room to move myself. From that point I felt like perhaps I was born and destined to live under both of your feet.

The third day was really interesting for me. I remember thinking that it was supposed to be a lighter day, you would be sore and it was more of a wind down. My friend Nathan was joining who hadn't done much trampling so I was going to show him how I did it and give him some tips. It ended up being another rough session. I distinctly remember saying that I wouldn't do any jumps (maybe to make you feel at ease) but I ended up jumping! Once more, you didn't try stop us or use any of the safe words.


Box 158. Adidas 85kg on 56kg
Box 158 B. Adidas 85kg on 56kg (Alt View)

We only did two scenes, the first of which was just me on you in my Adidas basketball boots. That was fun, they are big sneakers and looked huge on your body. Then it was us two in Adidas NMDs on you. Towards the end we got rougher and rougher on you, he was following my lead and doing the same to you. Without lifting our feet, we were rocking your body back and forth, it was quite entertaining. I hadn't realised you were close to orgasm though. I had forgotten that you said you wouldn't cum the whole trip until the end, so you could still handle a lot of action. I think it was actually when we started jumping on you repeatedly and in sync that you shot your load. Nathan was on your chest and stomach and I was on your crotch and thighs. I heard noises from you that I hadn't heard before. I looked down wondering what was happening.. quickly realising what had happened.. and then seeing the wet patch appear in your shorts. I clearly remember being briefly disappointed, knowing the trampling was all over, but then I remembered how much you had handled on this trip and I was content with what we did. I was also quite impressed that I had helped make you cum by jumping on your crotch.


Box 152. Double NMD Trample
Box 152 B. Double NMD Trample (Alt View)

Yeah I was in so much pleasure! When I haven't cum it's like I have some sort of super ability to withstand a lot of pain, but once I cum it's all over and I am just a weakling. It was a good time and made me realise once more that I could take more than I imagined.

The balcony foot worship was a nice end to it all. Nathan wanted to make content for his instagram but I enjoyed this too.


Yeah it was chill and a form of relaxing post fun.




When you went home to Singapore after these sessions I know it took you a while to recover. Do you remember how long it was, and what were you thinking during this time? Did you regret anything?

I was actually thinking, perhaps if given the chance I would love to try three or four tramplers on my body at once. When I was on the plane heading back to Singapore my chest felt heavy and I had to breathe deeply to catch my breath. I was wondering if I needed any oxygen support halfway mid-air (just kidding). It turned out to be fine, the next few days I basically slept in and recovered within a week. But I had our sessions on my mind every now and then.


That was my next question, whenever you make it here next would you like to try three of us on you? The only problem I think would be space on top of you. Being a small guy, it will be hard to trample and move around on you when we are all on at once. It's a challenge I will happily accept though. I'm sure we can stand and step on you all at once, taking turns to trample you properly or doing walkovers up and down your body. You will become very resistant to some hard trampling under all of us!

Yes like taking turns to jump on and off my body or a multiple stomp thing! Lots of stuff to experience.

Can't wait. Watch this space for Round 3...



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To find the videos from these screenshots visit www.bentbox.co/shwtguy and look up the Box number to view.





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