Sassy Cassy
- 2 years ago
- 47
- 0
Learning To Toy My Ass As A Boy free porn video
One of the first things I tried, ill-advised, was the toilet paper roll holder without lube. I lay on my side on the bathroom floor, with the shower running in the background, and reached back with the cylinder in my hand, trying to part my butt cheeks with my fingers while still holding on to it, and pushed against my ass hole, trying to make it go in. Wasn't happening. My asshole seemed like it would never budge, and I gave up after a few minutes.
The next thing I tried was a toothbrush. There were a bunch of old toothbrushes still in the bathroom closet that no one used, so I tried putting the hand lotion I used to masturbate on it, and seeing if it would go in. It did. It felt...weird. Fun because it was naughty, but so thin there was no pleasure, just the strange feeling like having your temperature taken that way as a kid. I tried pumping it in and out, and it was OK, but I wasn't super into it, and I don't think I ever jerked off while doing it.
Eventually, I found small bottles of shampoo and lotion in the closet, which had rounded tops to them, and thought that might be something better and more dick-like to try. There was a couple of smaller ones of the same size, probably 3 1/2 inches in length and 3/4 of an inch thick, and a larger one, which was around 5 inches long, and probably the diameter of a thin penis. As always, I excitedly took the excuse of shower time to lock myself in the bathroom and experiment with my newfound toys. Kneeling on the bathroom floor, I squirted some hand lotion on my fingers, and reached back to cover my asshole with it, slightly sticking a finger in to start to lube the inside. I then covered the 'head' of the small bottle with lotion as well.
With a little trial and error, the smaller bottle started to go in. There was a little pain and resistance, but not too much. Eventually I started to feel the small bottle glide away from the finger pushing against the bottom of it, and into my ass. The first time I tried this, I think I only tried putting it in an inch or two, and then taking it out against a few times, but soon after, I was experimenting with things like how far I could put it in - I was super careful at the time not to push it in too far, because I didn't know if it went all the way in, if I'd be unable to get it back out again, but I really liked the feeling of having it go in far enough that I could feel my asshole start to encompass it, and it was especially nice to glide my finger around the rim of my asshole while that was the case - and also experimenting with pumping it into my ass quickly in succession. I found, in general, putting the bottle into my ass was intense enough that I was never going to last very long doing it before cumming, if I was jerking myself off at the same time. Basically 10 seconds of the pumping motion was all it would ever take to send my young body into orgasm, and shooting cum across the bathroom tile floor.
The larger bottle was more of a challenge. It had a top that went to full thickness very quickly, so it was very hard to get it in initially. I would only save trying to get it in for when I was really horny about the idea of something big in my ass, and at first there were many times where the stretching would just be too painful, and I would stop. Other times, I managed to get it in, and with my asshole finally open enough, feel it slowly start to move forward into my ass. Unlike the smaller bottle, this one was large enough to feel almost like I really needed to take a dump when it was inside. It was an intense feeling, but certainly helped to bring me to orgasm very quickly, like the smaller bottle did.
Over time, the small bottle became just the prelude, and the larger one the main event, and every time I would bring my jerkoff session to a close by pushing it nearly all the way in to my ass. I found when it got in far enough, there was another pain deeper in that I started to feel. I didn't know what this was, or if it was a bad thing, so I didn't dare to mess with it too much, but often just a little of that feeling helped bring me over the edge to orgasm.
I also tried lots of other experiments with the bottle. I borrowed some thick tape to take into the bathroom with me, and tried to find a way to tape the bottle to the top of the toilet seat, so that it would stick straight up, and I could sit on it. I found the weight of my body forcing it into me was more prone to create a little bit of bleeding, so I was wary of too much of that.
I tried putting a few towels on the floor, and sitting on them in a way that would give the bottle a soft cushion to push into, and so not go all the way into my ass. This didn't always work. One time, I was nearing orgasm, and suddenly I was greeted with a very intense feeling. I came, because it felt so intense, but then I got up to find the bottle, and what I feared was true: It was nowhere to be found. It had gone all the way into my ass, and my ass had closed up behind it. In a bit of a panic, I knelt down on the floor and started pushing. I was so goddamn scared I was about to be a kid who had to tell his mom that he had put one of her shampoo bottles up his ass and now it was stuck there. What a nightmare! But thankfully, it came out without too much difficulty.
In what now seems like an amazing amount of effort, I also even a few times brought a screwdriver into the bathroom with me, and unscrewed the hinges of the vanity mirror, so I could then place the mirror on the floor to watch myself jerk off. Usually this would also include seeing if I could position it so I could see my asshole, and what it looked like to put the bottle in. Trying to lay down, and put my knees to my chest, while simultaneously lifting my head AND reaching to put something in my ass, proved too ungainly, so I usually resorted to watching myself jerk off (being able to see myself fuck my ass was going to have to wait until the smart phone came along).
I would also conjure up fantasy scenarios to go along with my play. Because I didn't have anyone to share my experimenting with (or could imagine daring to share it with), I would imagine having my own doppelganger appear to me in the bathroom, so we could play with each other. I imagined the two of us sitting on the floor together, jerking each others cocks. I imagined he would suddenly lean down and begin to suck me. I imagined him standing up and putting his own cock in my face, expecting me to return the favor. I especially got off to imagining him bending me over the sink, and preparing to fuck my ass - the feeling of the lube being applied to my helpless asshole, knowing he was then going to shove his dick in me, stretching out my hole, and pounding me until my ass made him cum, while I stood there, bent over, head down into the sink, feeling it happen.
I don't remember at what age I first created my own dildo. I used a rigid base, wrapped lots of toilet paper around it, and then wrapped the whole thing in electrical tape. The first one was probably slightly smaller than the average penis, but soon after I experimented with making it larger. As I did, I discovered the fact that that secondary resistance point located a few inches up your ass could be pushed beyond. Usually, as in the past, I would just use a gentle push against that sphincter as a trigger for orgasm, but other times I would dare to go really deep. As I did, I discovered the need to clean my asshole first if I was going to go that deep, and I found an old rubber water bulb in the closet that I would use to give myself a basic enema.
It's interesting that I will sometimes forget just how good the enema water could feel. If you made it super cold, it was an amazingly intense feeling. But for whatever reason I didn't wind up doing that all that much, and instead just used the enema for practical purposes of keeping clean.
With the enema doing it's job, as well as some upgraded lube, I found I could start shoving dildos into my ass fast and hard, and the spasms would sometimes get intense enough to nearly make me cum on their own, with no touching of my penis required. I really had to go hard to get a hands-free orgasm going, but I did a few times. After a year or two of getting myself off like this regularly, further experiments with materials, etc., the dildo was now probably the size of a big black porn dick (and I liked imagining that's what it was): About 10 inches long, and almost two inches in diameter. At first, it was one hell of a painful ordeal getting that thing in, so much so that I would usually have to forget how much, and then one day in the future get so turned on by the idea of a giant dick in my ass that I wanted to try again. But eventually, using the aforementioned water-based lube upgrade, I found I could get my asshole stretched to accommodate it pretty quickly. It's interesting to have watched porn for years, where it seemed unimaginable how painful and stretched the assholes of people had to be to be taking the dicks and dildos and strap-ons that I saw, but now I was at the point myself where I could have taken a big dick without too much of a problem.
Although all this got me off plenty, there was one thing I always realized that could probably make it better - not being in control of it. Echos of the fantasies I had had of being fucked without control, combined with the fact that the pulses and the pounding of the dildo always suffered from being expected, because I was the one doing it to myself. It seemed clear that either a fucking machine, or an actual other person, was required to reach that next level of intensity.
But that never happened. I wasn't physically attracted to most men, and I certainly wasn't open enough with my sexuality to be talking about my doing this with other people, so it's remained my own secret thing for my entire adult life. No woman I've ever been with was the type to do pegging or anything like that, and I never dared seek out a prostitute, transsexual or otherwise, to try it out. However, with COVID ending, and new sense that life is short, perhaps that will change in the future!
In the meantime, I frankly hope you get off to imagining the cute blonde boy I used to be, with his blue-green eyes and slightly chubby butt. Imagining me kneeling in that bathroom with the shower running, shooting ropes of cum across the floor as I plunge toys into my asshole. Or being bent over in front of you, feeling you spread his cheeks and lube him up, ready to pound his tight little asshole. You have permission to imagine doing whatever dirty pervy fucking thing you want to me, and I wouldn't mind hearing about it, provided it's not way out there. Thanks for reading. -->
Oceana
- 19.08.2021
- 18
- 0
