TrampleTalks 18: PilotBoots

This TrampleTalk has been a while in the making, over several chats online and finished off with some in person questions when he visited Sydney late 2023 with his partner. We chatted while looking at his extensive collection of photos and video, and in a TrampleTalks first.. asked more interview questions while trampling his partner together at the same time!

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Many of us know of you, but don't know much about you. Perhaps you could tell us a bit about yourself to start with.

It's an important question. Thank you for having me on your blog. Hello everyone.

My parents were both officers in the military, so I was born into a military family. My father was a fighter pilot, and my mother was an air force academy professor. As a result, I grew up on an air force base. I had no idea it would have an effect on my sexual life when I reached puberty.  Until I came out with my own website in 1996, I thought I was the only one in the world having this kind of man to men trampling fetish.

I can see where the name 'Pilot Boots' comes from now. Was trampling something that you were interested in right from the beginning then? Or was it something you came across through boot play, or something similar?

I followed in my father's footsteps to become a pilot, but then I went my own way to become a military doctor. 

I recall a day when I was about six years old.  I usually saw a battalion of soldiers in training from my bedroom window. On that day they were training as usual, but my attention was drawn to a drill sergeant standing on the heads of two soldiers who were lying down on the hot paved grounds under his heavy combat boots. The drill sergeant continued briefing his battalion without looking beneath his combat boots. Ignoring those two poor soldiers. My heart was racing, and it was possible that this is what drew me into this fetish world.

You mentioned the website you started back in 1996. Was it something you did so that you could find other guys into it?

I always thought I was the only person in the world, but when I was in medical school in 1996, I found out that I wasn't. "PainterD" had a website where he crushed fruits and other things with his boots and sneakers. I think he was from Germany. Back then, people used dial-up modems to connect to the internet, which made it very slow. I couldn't believe I saw something like this. So, I went ahead and bought a PC so I could learn more about it. That's how I got started in the online world of M4M trampling.

PainterD

What was the name of your website?

PILOTBOOTS MASTER ORIGINAL.

I made my own website using HTML and most of the content was about M4M trampling. At that time, digital cameras were still expensive, so I had to use a regular camera, develop the pictures, and then scan them. Back then, there was a group on geocities, so I put my first website there by geocities/castro/pilotboots.html. 

There were later webrings that added more similar websites to it. As in, brothers in boots, from the Netherlands, and so on. It has long since disappeared, together with geocities.

That’s right. You have a very impressive archive of M4M trampling stories, pictures and video. How did that all begin?

Because I had my own website, I set the rules for those who wanted to join me to see my materials and exchange ideas. So, rather than charging them with a credit card, which was a very complicated procedure, I decided to exchange two trampling photos or two stories, and my collection began.

I know you had a good friendship with Smashman. Can you tell me more about him and your sessions with him?

I am going to take you back to the year 2000.  At that time, someone named "Protero" set up a M4M trampling forum on Delphi. There were lots of interesting trampling stories and photos submitted to this forum, one such person who contributed was 'Smashman'. He sent me a message about his plans to go on a trample tour in Europe, and yes, I did meet him back in 2002 and many times from then on.

Smashman started trampling a long time before we did, in the 1970s. He is an extremely smart mathematician who went to Harvard. A few years ago, he died of cancer. He gave me most if not all of his trampling archives. This also added to my digital collection, which is now about 5TB and photos album to be scanned.

Have you met any other well known people in the trampling community?

I've met Tom (tjfsf1) a few times also. One time when I was in the US Tom was on his way to Idaho I think. Smashman was texting him and Tom replied that he was out of town. When he found out I was there, he replied "I'm coming!" and he met us. It ended up being a very intense session. I also met him in Orlando, I made his face unrecognisable. It was so terrible, but he said he was happy.

Can you tell us about that last session on Smashman?

I was the last person to trample on Smashman before he passed away. He had a pacemaker by that stage, but still wanted to be trampled. He said if he died he wanted to die happily. I asked him why he wanted me to do it and he replied because I am a doctor. It took place at the end of August 2012 in his hometown of San Francisco.

It must have been quite sad for you, I imagine he would have become a good friend.

I have many good friends in the trampling world. But that's a problem. When you become friends, it's can be very difficult to get excited sexually.

Anyway, it was difficult for me to say no to his session request. I was accompanied by a well-built biker buddy. With his Sidi racing boots and leather biker suit. Tom (tjfsf1) was also there too.

Could he still handle the trampling well or was he limited?

Yes, he surprised me. I had to jump really high and hard. To a man of this age, and this stage of cancer. He was an amazing tramplee to the end

His partner was also a doctor, who took good care of him but was not involved with trampling. So I decided we better do it in my hotel room and not in their house, that we went back to later after the trampling session.

I was going to do a short session, maybe 10-15 minutes, just to please him in lieu of his health. However, the session lasted about 3 hours. I warmed him up and gave him a belly stand for three minutes to see if he could breathe properly, which he could. My biker buddy was initially more afraid of breaking him than I was. But after seeing me on him he was fine, and had no problem trampling him with me. We got some good photos and video. The last 10 minutes of the session we spent on quite high jumps, off the bed onto his belly. When I say it was hard, believe me it was very hard and only a few tramplees in my experience can handle it, Smashman being one of them.

Tom arrived at Smashman's invitation part way through the session. It was a good thing he came because I was getting much more intense with him. He usually didn't want his face or head trampled, but I obviously enjoyed that. So Tom fit right in because he enjoys that.

Those who knew Smashman would know that my weight was no problem for him. He could easily withstand trucks weighing 3 tons. He enjoyed seeing stars from the weight that was on top of him. So the only option was to actively jump extremely high and powerfully.

Prior to this session, Smashman visited me in France in 2004. He was not afraid to request that skiers trample him with their ski boots / snowboard boots. I was amazed by him.

You have a partner into trampling also is that right?

Yes I met my life partner "Boutadict" back in 1999. Boutadict is a French guy who likes to have his cock crushed by combat boots. He helped me put together my library of content.

We've talked about sexuality before, what do you consider your sexuality?

I have never had sexual intercourse with men, and it has never pleased me, but I do love oral sex regardless. So trampling is how I imagine myself getting erected; even when I have sex with a woman, my mind wanders to M4M trampling. I'm not sure what my sexual orientation is. I trample both men and women. I obtained several dominatrix slaves who were willing to pay any price to serve me.  And they like it when I'm on top, like in cuckold stories. So I kind of get used to feeling on top of the world when I have a slave suffering under my heavy boots while I enjoy doing whatever I want to him or her with my boots. 

I didn't realise you trample women, does this happen often? How do you like to trample a woman?

Well, don't you think you can too? Gender equality no?

I have never trampled a woman, but when I imagine it I think I would step differently. I'd definitely be open to trampling a woman for the experience but I'm not sure it would excite me like trampling a guy.

My girlfriend used to adore my feet when I was in the Air Force Academy. When I returned home early one day, she was licking the soles of my Corcoran Jump Boots while masturbating herself. So it continued from there. She adored the fact that I trampled with one boot on her stomach and another on her head/neck area. Particularly when I am completely ignoring her while doing something else, such as talking on the phone or writing my note. It got me excited when she moaned from my weight under my hard boot soles. I wanked myself while standing full weight on her head, just like you did. It took me a while like 5 minutes before I cum. She had trouble explaining to her parents why her forehead had my boot print on it.

Would you say you are bisexual then?

Yes, in terms of sexual intercourse, you could say so. But I enjoy getting a long good blow job while standing full-weight on the heads of poor slaves. Have you ever tried this?

A label is not necessary then, you like what you like.

Exactly! It's annoying somehow that we have to label ourselves as "Gay Trampling" despite not all of us being exactly that. But if we don't you will land on another side of the trampling world which is not for us.

No, I haven't tried that position before. I find when I am standing full weight on a head I prefer to jerk off than have oral sex.

I have not had sexual intercourse with either sexes in a long time. My partner began as my human carpet, and the relationship grew from there. We've been together since 1999, and I'd say I've trampled him less and less, until I didn't trample him at all five years ago. I don't mind seeing him trampled by a good friend who understands what it means to be trampled. Trample is the way into my sexual arousal; without it, there is no sex for me.

Are you saying you haven't trampled your partner for the past 5 years?

Yes, he has been complaining ever since. But, as a doctor who takes care of his health, it's difficult for me to see bruises on the bodies I've cared for. With slaves, it's a different story; if they ask nicely, I can go really hard on them.

Have you ever been trampled yourself? Or are you strictly trampler only?

It happened once a long time ago. When the chemistry kicked in, I was turned on.

Do you trample many other guys often?

About two or three times a year these days. Finding a good doormat is not easy. I'd rather have a few really good sessions than a lot of bad ones.

What do you look for in tramplee? What are your preferences?

I enjoy humiliating slaves by having them fully naked while I am fully clothed. Slaves have limits as well, but I tried to add to their fantasies about why they were here and what they were looking for.

I dislike talking doormats. The doormat should not speak. Moaning is acceptable, but it is the most they can do. Then I dislike doormats who brush up against my boots. If I'm sitting down and they want to lick the sole of my boots, they should turn around on their own without touching my boots.

I also dislike slaves that smell. Bad smell, bad body odours turn me off. I always ask the slave to come to me presentable, showered and fresh. They will get dirty after that due to my boots, I don't care.

I don't mind how slaves look, size, fat, slim, large, small. What I mind is the attitude, stupidity turned me off. My time is as well precious, I don't like to waste it with a bad session.

What style of trampling are you into? Do you get into hard action with jumps and rough shoes, or do you prefer gentle more endurance type of style?

Jumping is exhausting, so I'm a lazy trampler. I enjoy walking on my doormat and standing on its face to watch them struggle to support my weight. Normally, I like to see my slave naked, and an erection is an indication of how excited they are and whether or not I am a good trampler.

So how did your first trample experience come about? Who was it with, what happened, etc.

That was when I was 9 years old. I crushed a fellow classmate's hand with my football cleats, and as a result of this incident, he became addicted to me and became my first slave.

Did he keep finding ways to get trampled by you? I wonder if he turned into a big tramplee as an adult..

He was looking for any opportunity to be trampled by me. Then puberty set in, and I discovered how to please myself, as did he. You'll be surprised to learn how similar the worlds of trampler and tramplee are. I later have him trampling another kid for me. It was nice to have a slave who was willing to take on the role of alpha whenever his master desired.

What was your first proper session like?

My very first session was probably when I was learning how to wank while I was standing full weight with my boots on my slave's face, outdoors. That slave was also a classmate, but he was also destined to be my slave. He is now married and has a happy family.

I know you have some pretty amazing trampling stories, what is one of your favourites? 

One of the sessions that I recall was in Northern Europe during the dead of winter. I'm dressed warmly and comfortably in my heavy hiking boots with small metal spikes. My slave paid for a ticket from where I went to his home, a large mansion with a private garden. He was a very important person, polite and well-dressed, but one of his fantasies was to have a trampler like me stand full weight on his head while he lay naked on the ground, with his partner sucking my cock until I cum. He begs me not to leave until I really cum. Well, it took his partner about 8 minutes. The partner was trying his best to make me cum quickly and I was trying my best to resist, to stay standing on his head for longer. But with all of the excitement, everything was so perfect outside. He had my Lowa Boots print with trademark as a hematoma on his forehead for a week. He had to put a plaster on his brow during a press conference. Very intense and fascinating. He cum right after me, with the strongest sperm jet I've ever seen for a man his age. He was overjoyed, as was I.

Can you tell me some more of your favourite sessions?

I remember one session, which took place in Germany. It was an old prison that had been closed down and is now available to rent. A group of slaves were able to get it for the weekend, and they asked me and other masters to join them there for a session.

One of the slaves managed to bring these wood pieces into one of the rooms and place them on the floor. I can't remember if it was a slave's or a master's idea. So there was that wood on the floor, triangular in shape. We had some introductions, then we had the slaves bring us our drinks. They were naked while the masters were fully dressed in uniforms, leather boots, tall boots, and so on. You can imagine how painful it was for slaves to walk barefoot on this triangular-shaped wood. Later, when one of the slaves was punished, it was handcuffed and pushed down on the ground on top of those triangle-shaped pieces of wood.

Did you stay somewhere close to the prison for the weekend?

No, both masters and slaves were accommodated inside the prison. I was assigned to be a commander for a day. I don't like flogging, fisting, or anything else that has to do with ass/asshole. So I got the trampling punishment method. Trampling is my preferred method of sexually energising myself and my slaves.

Slaves voted on which Master would be in charge each day/night, to which they submitted. Slave sessions in Germany are very interesting. Very orderly and well disciplined.

Did you spend the whole day trampling?

I spent a total of three days and two nights there but many activities occurred. Initially we broke the ice and got to know the slaves. Slaves were not required to know who their masters were. It affected them.

There are bad masters just like there are bad slaves. Surprisingly, I was chosen to be in charge for the final night that weekend. Not all the Masters had experience with trampling.

I'm not a big master, 176cm and 76 kgs, but there were those who were 200cm and 100kg with much smaller slaves. They were unsure if their slaves would survive if they put their full body weight on it. But after some tests, it was fine.

At one point I decided to have the slaves lay down on the floor to be the carpet for us Masters. The room was dark and only lit with few candles on the table, so as we trampled and walked on the slaves we couldn't always tell where we were standing. I was approached by another master who asked if I wanted a drink. We did not know each other well so we kept talking for a while, ignoring whichever slave was underneath us. The session was over after 30 minutes when I decided it was enough. We turned the lights on, a few of the slaves were unconscious after struggling to handle the body weight of the Masters, but no serious health accidents. Some of the slaves had cum all over their body. I had been standing on one of the slave's heads for a long time while twisting my boot soles, I almost teared off its earlobe. The slave was happy that I hadn't.

Another scene was in the toilet, can you piss when you stand on slave?

Yes I have pissed on many slaves .. not always while trampling them though.

There were few slaves who loved that idea. I told them to go to the bathroom if they wanted more.

There was an alpha slave who became a Master during the session. He came to thank me for exposing his dark(er) side. He stated that he never imagined that he could orgasm while pissing. When he approached one of the urinals, he noticed slaves laying nearby. He wore heavy Fox motocross boots and went to the urinal where two slaves were lying with their heads next to each other. He stood with his right boot on the head of one slave and his left boot on the head of another. Under his boots soles are deep dark piss mud. It was intense for him while unzipped his cock from his biker suit and imagining how painful it would have been for him if he had been the one lying down bearing 100kg of his Master's body mass. When it came to pissing, he was very erect and had difficulty pissing. So he was trying to stroke his cock instead, and by attempting both, it was out for both of them. He said it was the best orgasm he'd ever had. He was still in contact with me for a while afterwards, but our last exchange was many years ago. If he reads this interview, he will most likely appear to explain what happened to him that day.

You're obviously a big fan of boots, do you like sneakers as well?

In the M4M world, I'm mostly (99.99%) into boots and manly sneakers. I like how heavy it is, how well it protects my feet, and how I can use it to inflict pain on my human carpet. I don't like sock tramples, I don't like barefeet, and I don't like sandels. My preference is for manly footwear, such as heavy boots, hiking boots, and biker boots, with vibram soles; flat soles do not appeal to me. As a result, my doormat is suffering more than usual.

How would you describe your trampling style?

My general trampling style is not rough, but I like my doormat to suffer in ways that please me back. If the trampler is never satisfied, it is also the tramplee's fault. Trampling is reciprocal.

What was an unusual session you had?

It was a UK slave, with his Land Rover vehicle. His dream was to have his face replaced with the brake pedals, and have his hands on the clutch and accelerator pedals. He managed to do it successfully because he was a mechanical technician. I spent the weekend driving through the countryside while he was constantly under my boots, eating dirt from my boots tread.

He also enjoyed it when I crushed things under the tires while he suffered as a result of my treads. He eventually asked me to crush his grandmother's mementos, which I agreed to do, but I noticed he was crying as he heard the crack under the tire.

I'm surprised he managed to get that to work, must have been a good amount of space for him to fit.

You have no idea how enormous our tramplees fantasies are. I was once asked to crush a tramplee's eyeball with the heel of my boot, but I refused.

Ah yes, the old fantasy versus reality.. that's not going to be good in reality.

I had another memorable session in Montreal (Canada). My trampling pal was a Canadian firefighter, very muscular, handsome, big boots, everything was perfect. We did a lot of trampling together on a doormat together, who was from Quebec. He was a doctor, much senior (professionally) than me. In this regard, it was a lot of fun.

Sounds like you enjoyed the power imbalance.

As the doormat was somewhat my senior, I didn't give a shit about him, which he was pleased about. The session was supposed to be for an hour but it ended up being 5 hours long. He brought a shopping bag with him, full of food, which we crushed all over him under our weight. Strawberry, fruits, you name it. It was a total mess. We ordered him to clean it all up while we were resting, and then we did it all over again.

I couldn't believe I would be getting blow job from such a senior doctor like him. I trampled him, walked on his face, wanking while I just trampled him. My trample buddy was heavier and appeared to enjoy seeing me have fun. We ended up putting boot prints all over his body. The slave came 3 times, he said it was the best session of his life. just before he was about to retire.

Many of my slaves always want to come back for more sessions, but I also need a good trampling buddy. Taking a picture while trampling is not easy, it will be ok if I do not record it. But it's a pity to not have a memory about it when you think about it.

Do you have a story from a hard or brutal session you remember?

Yes, quite a simple one. I stood on a tramplee's head for about half an hour while working on my PC. I almost forgot he was there under my boots.

Wow.. and was he struggling? Is this why you think it’s one of your hardest actions? Or just because the length of time.

Longer is better. I enjoy ignoring what is under my boots too. He kept asking for more. I think the dream of a tramplee is to be totally ignored by the trampler. He came without touching his cock, and still remained under my boots. Before too long he was erect again.

I know you like trampling the face and head, but do you enjoy trampling the rest of the body too?

I do, all over: fingers, hands, front is nice but back is also good. Why I love the head/face so much is because it's more humiliating.

Have you every crushed a slave's tongue?

Yes I have, but for me it wasn't very exciting. 

Till it bled?

No.. but bleeding would not have made me more excited either. 

I also like to crush a slave's cock while he is sucking my cock. I have done this many times.

These logger boots you have look very interesting. The spikes on the soles must look terrifying for any tramplee who sees them coming toward their body..

Yes, they are made for timber. I don't notice the spikes as I walk around in them but my tramplees certainly do.

Have you used them on many guys?

Yes, a few. You know, as a medical doctor, I'm very careful with what I'm doing, especially in boots like these. You have to think about where you're standing. The slaves kind of love it though, if you're doing it properly it's not that bad. 

And I suppose if you're not moving around too much it's easier.

Yes you have to stay more still in these. I had a guy who liked to be trampled with thumb tacks, you know them? 

Yes. You attached them onto your boot soles somehow?

No, onto his skin, pointy side down on him. Then trample all over him making sure to push them into his body. 

That's a new idea I never thought of. Must have hurt like hell!

Final question, what is some advice you would give to someone getting into the trampling scene?

Trampling sessions, for me, are a journey to please both the trampler and the tramplee. It's not like anyone can be a trampler; a dream trampler must understand how far a tramplee can go without asking if it's too much for them. 

As a trampler, the important part is not to hesitate. Once you hesitate, you need direction. Just keep going and trial it out, check out his dick and see if he is excited with what you're doing. That's always a great indication. Don't pretend either. Usually the tramplees they like to be ignored so enjoy it, push them to the maximum they can take. 

You'll develop skills after a few sessions. A good trampler understands trampling technique. If you want to be gentle with the tramplee, simply flex your knees upon landing. It will make the weight more smooth. But if you really want your doormat to suffer, don't flex the knee and keep your heels down. And the damage will occur as predicted.

Shwtguy (left) and PilotBoots (right) full weight on Boutadict.

Thank you for this talk. I can't believe your partner has held our weight under our boots for so long.

He is amazing, isn't he? You call these interviews by the name "TrampleTalks". I thought it would be fun to do some trampling while we are actually talking, no matter how long it takes.

It was a great idea, and great to meet you in person finally. We should do some more trampling together in future! Enjoy your vacation and welcome to Sydney.

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If you'd like to find PilotBoots on Instagram, click here. Once you have requested to follow him, be sure to send him a message "PilotBoots Shwtguy TT18" or risk being denied access to his private account.

You can also find him on X, click here.

You can also see a video of us trampling Boutadict in boots, it's out now on www.bentbox.co/shwtguy - Box 218.

Previews:

Box 218: PilotBoots & Boutadict

Box 218 D: PilotBoots & Boutadict (Side View)