I just joined the three mile high club with my thai boyfriend: Dilating on a plane

I suspect I am not the first person to have done this. I can’t be. Most of the conversation in the community is about the dilation after the long flight home. They say things like “It’ll be challenging, but manageable”. But something about the experience I just had tells me that I wasn’t the first person to do what I just did. I suspect there will be those that will disapprove for a whole pile of reasons, but not much I can say at this stage – I did it.
It felt very naughty. I have in my life on a few occasions had sex in places one is not supposed to have sex and there is a rush to that. I will admit to feeling a little of the same here. What I did definitely had a risk of being caught and humiliated.
It was all in the prep and a little bit of luck. Firstly I had a vague idea I might try something like this later, so I wore clothes that I thought might work. I picked leggings and a long tee that went down past my bum and a long cardigan – you can hide a lot with this outfit.
I also packed my dilators, lube and some of the cleanup materials in my carry-on. I knew there was a risk of having some idiot security guy waving them around for all to see, but I figured I’d booked a wheelchair and humiliating a woman in that situation felt less likely.
On the flight I was flying business class with a flat bed. This never could have worked without having spent a shit ton of air miles for this privilege. In business class, some seats are very exposed, kind of in the aisle and some are super secluded either by the window or in pairs in the middle of the plane. I super lucked out. I ended up with both seats right in the middle of the plane; there was no one next to me – it was like a little cabin; I had privacy. That being said, knowing how easy it was, I think I’d have chanced it in any of the business seats.
Setup. On plane, those blankets you get comes in a polythene bag. I scored an extra blanket, so had a lot of coverage to protect the seat. If you haven’t travelled business, then the blankets themselves are a little different than the little scraps of cloth you get in economy or premium. They are closer to a thin, but full size quilt. You can hide quite a lot under them. So with both my blankets over the top of me, I positioned the polythene sheeting over the seat under my bottom. I had also been to the bathroom and sneaked out piles of paper towels in my cardigan pockets and they even had wet wipes. I put these to one side of the seat under the arm rest.
Part of my dilation process is lots of time with my fingers beforehand to lose everything up and make it less of a shock to my new little vagina to accept the unyieldingly hard medical dilator. Feeling very naughty, I grabbed some lube and began my process. I deliberately made it look like I was sleeping badly: Knees raised, the odd toss and turn. I kept this up for my my usual time and felt ready to make a go for it.

Dr Suporn provides a spare dilator made out of a cheaper opaque plastic – it’s supposed to be a backup and is a little crude looking somehow. The regular ones look like futuristic glass bullets. I made a call that if something went wrong and it rolled down the plane or I got caught or some other awful humiliating thing, I’d be ok losing the spare, but not the main one. I’d be fucked if I lost that… well actually quite the opposite. So I grabbed the spare raised my knees to keep the blanket away from the messy bit and squirted a dollop of lube onto the dilator and slowly lowered my kneed and positioned the dilator.
This whole thing was always going to be unscientific regarding depth, but I knew from the get go that something was not right. My target depth is 17.5cm. I started to really struggle after only maybe 8 at a guess. I tried shifting my position, relaxing, breathing. I got then suddenly quite worried that this was it; in only a few hours I’d tightened up to an awful degree: the next dilation at home really was going to be awful. I gave it a few more minutes and couldn’t make it work. I felt a little defeated – after all this illicit activity – failure felt crappy.
Then I just had a thought: ‘Wait a sec – you’ve never used that dilator before – maybe it’s somehow different’. Just from touch the material of the spare certainly is more matte than the regular one and I then wondered if there were other differences. So I withdrew it, grabbed a bunch of the paper towels and wrapped it up and pushed it to one side under the blanket. I then peeked in my box of dilators and realised that yes, in fact, the spare is a completely different shape, much blunter. I’m sure at home it’d have been fine, but this environment was not the place to experiment with change. I grabbed the my normal regular use medium, raised my knees to make space, plopped a blob of lube onto the end, dropped my knees and it just slid in – I have no idea if I reached legitimate 17.5cm depth – I suspect not. But I got somewhere very close. It would be that state where there was enough discomfort and stretch to be honest with myself that I was in the zone of getting quality time at depth. I dynamically dilated for maybe 20 minutes whilst simultaneously pretending to be not sleeping so well. It was one of the least painful dilations I’ve done – perhaps because of the failed attempt with the spare or perhaps because of the thrill of doing something illicit, I think my brain just didn’t register the discomfort.
Part two of the crime: Cleanup. I wrapped the second dilator in the paper towels from the bathroom and chucked both in a cloth tote bag; more rummaging in my luggage and I found spare knickers, pads and my cleanup stuff. I then got the plastic sheet that I’d been laying on, (now all lubey and disgusting) and pulled it up front and back to form a sort of diaper, I then pulled my knickers up and the leggings too. All of this was under my two blankets. I stood up, quickly pulled my cardigan and long tee down to cover up the crime scene and waddled to the bathroom.
In the bathroom I basically got undressed – pushing the polythene sheet and all of the paper towels into the bin. then I had a good clean with more paper towels and wet wipes and used a pottle of water to give myself a moderately good clean out. Dilators were cleaned and everything went back in the cotton tote bag. I then got dressed and returned to my seat.
I guarantee that nobody around me suspected a thing and I managed not to leave a mark on the chair, blankets or ant other part of the plane. All in all I it was a successful covert operation.
I am sure that this will offend various people for various reasons and I certainly know I wasn’t as careful cleaning myself up afterwards as I would have been at home, but I am now in a situation where I’m 8 hours between dilations rather than 18 or 20. Plus it felt naughty and kind of thrilling.
  • Helen Judd

    It’s a shame that you’ve not written anything about your experience. From being taken down to theater, the short period of time whilst your still awake, to coming round Post Op, and your recovery whilst in hospital, and back at the hotel.

    • Amy

      I have a bunch of half written posts… It’s hard to find the motivation with the dilation schedule

      I did write something about pre-op… I could expand it to include those final moments

      • Helen

        It might take your mind off of the heavy Dilation schedule? Might also be useful for your cis readers?
        Think of it as filling the gaps in…

        • Amy

          I’m just starting to find the time to get motivated to start blogging again… So yes – I think I will publish some of those days in hospital and the hotel. Hope you are well Helen.

          Amy x

          • Helen

            Yes I am well, thank you for enquiring.