My story has a classic start. I’ve always been into masterbating and touching myself to whatever excited me. but slowly over the years I started to get more and more curious about what cock would feel like and why it felt good. Looking back on it now, the porn that I started to watch more had some longer shots of the dick or I would find myself looking at the guy’s hard cock. After a while (right after I had a shower) I had the thought of touching my ass, not penetrating it yet but feeling it. I spit on my finger to make it wet and rubbed it around my hole while I jerked off. so many thoughts were running through my head but one that really put the nail in the coffin for my ass was when i had the idea of putting on some sissy caption porn. I had just recently heard about sissy porn and got curious. when I found something to my liking it made me fall even deeper into it. it was a joi cei video and at the time i only knew what joi was but when the video started playing and told me i would need to have my cum in my mouth for this video the naughtiness of it kept me going. At the time I only jerked off to it while rubbing my hole but eventually sissy videos and sometimes gay porn pushed me to try something more. After a bit of jerking off I wanted more than just feeling it on my hole, I stuck one of my fingers inside me just a tiny bit. I was clean thankfully and was able to take one finger. feeling it while jerking off made my head tilt back and jerk my dick even harder. I squeezed it, moved it, felt around my ass, you name it and I probably did it(at least everything you can do with one finger half way in your ass).after that it was only a matter of time before I kept going and filling myself up even more. At first it was two fingers then three and after a while I was able to get four inside me while I watched gay/sissy porn and came so much more. I found some things around my house that i could stick up my ass so i could rub my balls while jerking off. it all accumulated to the last thing i have experimented putting in my ass. i wanted deeper and was always thinking what if i had a dick in me that could fuck me so i could jerk off and have my ass played with. now before i saw what was the best thing i put in my ass that made me cum so much and wish i had i don’t feel any attraction to this person. one day when i was left alone for a week i couldn’t help myself and kind of looked around my brothers room and found that he had a big vibrating dildo. again i didn’t think of my brother at the time at all, the only thing that was going through my mind was how i could use this. that day after getting all cleaned up and putting down a towel just in case i loaded up some porn and started to jerk off. i put a condom on it so i wouldn’t make it as dirty, i used my mouth to put it on some of the way. there is no way i could have gone all the way down as the toy was probably 7 inches or more and very thick. after fingering my hole and making it a bit lose i teased my hole with the tip of the dildo. after i bit of the video and teasing i couldn’t wait anymore and stuck it in me. it was a bit much but i could take it, i got it half way in and turned it on. fuck me did it hit all the right spots making me fuck myself for a bit while i just let my dick harden. once i got used to it i put it even deeper, letting it reach the deepest parts of me all while my cock never went soft. i turned it up more and fucked myself while jerking off and had some sissy porn on. i couldnt take it anymore and fucking blew a giant load all over the place. it landed on my chest, stomach, bed, almost hit my face, near the end it dripped down my dick. i just sat there for a bit recovering from it thinking to myself how i wish i had this toy. if i did my ass would be destroyed all the time by it. after i gained my strength again i got up and cleaned everything up. never got another chance to take it so sadly have still yet to feel another vibrating dildo in my ass while i cum buckets.
