There is my story of how my inflatable fetish has started and growth bigger and bigger.
I am in my early 30’s but it all started at the same time that I start my discoveries of how you can play with your own body. I was probably around 11 and at the same time I was discovering masturbation: the first dry orgasms and the first not dry orgasm which happens the time that, I do not why, (probably just because it was filling good 😉

I decided to roll my dick between my palms kind of like when you try to start a fire with a stick.
But before that I believe my first experience of “OhWhatTheHellIsThatNiceSensationDownThereLetMeTry Again” has involved a large trash bag and a lot of that fake straw used for packaging. I was preparing a carnival costume the kind of which you put a large cardboard box on yourself that you then paint and make nice. The point is that it happens that the box in question was full of plastic straw used for the packaging of whatever was in the box and I was in need to dispose them. Then I take a large plastic trash bag and I half filled it with the material I got then the idea to use the half-filled plastic bag as a sit, kind of like a bean bag. To try to find the right balance between the air and the straw I started with the bag quite full of air. Close the bag with my hand, and sit with the opening between my legs controlling the release of air from the bag a then rapidly discovered that the pressing of the thin inflated plastic bag in my groin area while it was slowing deflating was giving me fun and nice sensation. At the time I was not able to name it but now is real clear in my mind that it was arousing me. After a few times of this deflate and eventually some small popping of the bag I felt the growth of a stronger sensation and I reached my first dry orgasm.
I have enjoyed the bag for few days while it was laying around my room before it eventually got trashed but the pandora vase was open. Fast forward few months, in which in the meanwhile I was stucking all sort of plastic bags in my undies, between my undies and my pants, and inflate them tight to recreate that nice feeling. At the time I was really discovering it and I was not sure of what was it happening, and I am still not sure, to this time how, I managed to do not get caught. But the summer was finally approaching and there happens my second biggest episode that definitely tied the knot of my fetishism with inflatables.
I went to the sea with my parents and the family of one of my friend of the same age. In the morning while we were going to the beach passing by a nice toy shop that being on a sea town in summer was full of nice inflated toys left under the sun in display. I managed to get from my parents a nice inflatable mattress, one of the normal kind with 4 or five tubes and a nice one camber cushion. Obviously it ended that also my friend got one similar to mine. The day went on with us playing in the water with our new inflatable toys at a certain point boys being boys the game became a fight game of us using our riding our mattress as noodles and randomly fighting essentially trying to tipping each other but also a strange game in which where were jumping out of the water and try to cover the other’s cushion with the one of our mattress. In any case the game was rough enough that there were a lot of leg movement and jumping that have this was leading to all sort nice sensation rising from all the movement of the vinyl in my crotch area and the friction of the inflated plastic with the thin fabric of my swimming suit. During the game my cock may have been became fully erected but I did not care as the inflatable was hiding what was going on between my leg. The weight of my body was pressing the mattress in a V shape with the vinyl bouncing on al the right point. In addition, I was bit by bit deflating the mattress to gain better stability until I reached a nice point where the mattress was half deflated and the part that was underwater was completely deflated and gently brushing the tip of my cock under the layer of fabric, but some time the mattress has the feeling of being nicely inflated as my weight was pushing the air tight in the part of the inflatable outside of the water. So while the innocent game outside of the water was going on under the water the pleasure sensation has continued to growth until I exploded in one of the most memorable orgasm of my masturbation life, but then taken by embarrassment I tipped myself off the mattress and swam away with the sea water that had clean the nice mess that I did in my swimsuit.
From that point I had take care of that mattress that has been for a long time my only inflatable toy that I have been using essentially every time that I was coming back from school where I was using anything (pajama pants, ropes, climbing gear) to bend the mattress between my legs and gently inflating and deflating by testing any kind of lotion to get my dick lubed and fuck the mattress at the best that was possible. For quite a long time my ability to get new inflatables was really limited. I remember once I used the excuse of a carnival party to dress as learning swimmer with swim trucks, mask and snorkel, fins but most important swim ring and arm band. It has been extremely difficult to find the two inflatables in a no summer season then at the party be February was probably at around 5 degrees outside and probably 15 inside and being me essentially naked has resulted in a really cold party but I had a couple of new inflatable that I was able to justify to be around.
For a long time I have been using the arm band (the classical orange one with two square cushion each): I was placing one into the other with one perpendicular to the other resting on the part the is not getting inflated, then I was proceeding to inflate all the different chamber to have my tightly inflated fucking toy with many different holes where to put my penis and holes from where the tip of my dick was also able to come out for wonderful oozing of my teenage cum. Then when I was able of drive on my own I have been able to have a little stack of inflatable with the classic intex whale. And many other toys in the time I have experimented many different way to ride toys tried out some balloon have some popping experience that has not been bad ( a particularly enjoy try to pump to pop some toys that I would like to get rid off) and most recently I have discovered the pleasure of naked ride a nice toy like the IW fox full dusted of baby powder in a slow and controlled manner until I climax in a wonderful orgasm.
Nowadays I live with my wife that know about my fetish and we have found a nice balance between me enjoying my fetishism and our non inflatable sex life with some rare blur of the border line. But to these days my preferred way is to bring inflatable to a body of water and enjoy a slow ride with an orgasm that can be build in hours by trying out any different kind of inflation of the toy until I am ready to cum at the gentle touch of vinyl trough the spandex of my speedos