Misadventures of a Horny Boy - Part 1: The Flashlight (gay/masturbation, teen)
I got my first dildo through an accident.
We used to have a big flashlight. Like, almost impractically big. Dad sometimes used it when fixing things in the house or in the rare case when we had a power outage. Most of the time it was just lying around in the garage.
When I was still in school, there was a time where I was home alone a lot. Dad worked until the evening so even when I came home late, there were usually a few hours where I was on my own.
And being in the heat of puberty, most of the time I was pretty horny.
I masturbated so much and so vigorously, my dick was actually sore or swollen more often than I could count. And after a while just jacking off didn't quite do it anymore.
I figured out that I liked playing with my butt pretty early. Fingers, pens, or vegetables all ended up inside my rear at some point. Among other things. But one day I wanted more.
From the countless times I searched the house for something new to shove up my butt, I already knew pretty much every object in the house that was even just remotely dick-shaped.
The flashlight had already crossed my mind many times but previously I was too intimidated to actually try it. Not that day though.
My horniness reduced intimidation to mere respect but let me tell you, the thing was huge. Basically as thick as my wrist and more than twice as long as my dick.
I took it up to my room and started the preparations to carry out the ill-advised plan to fuck myself with this flashlight. With the buttons and other parts breaking up the cylindrical shape I didn't want to shove it up my butt as it was but since I didn't have any condoms (let alone any that would fit that monster) I just wrapped it in a small plastic bag I took from the kitchen.
I didn't have any lube either and after quickly realizing that some kind of lubricant was necessary for this plan to work out, I got some body lotion from the bathroom.
Looking back, I didn't put nearly enough of it on the flashlight but once my dick was hard I was a stubborn (or maybe just dense) little hornball so I simply ignored the pain, thinking that it couldn't be avoided.
At that point I had a somewhat slippery, huge flashlight wrapped in kind of uncomfortable plastic, ready to go up my not technically virgin, but hardly experienced butt.
I undressed and stroked my dick in excited anticipation of what I was about to do.
Not knowing any better, I didn't prepare my butthole at all. Everything else I had shoved up my butt just went in without too much trouble, so I just didn't know better. And I was too horny to care anyway. I put the flashlight on a chair, spread my butt cheeks, and sat down on it. Nothing happened though.
My sphincter was barely even stretched so I just pressed on. It really hurt but I wanted this thing inside of me so I didn't consider stopping.
Eventually, I managed to force the first bit of the flashlight inside. The body lotion didn't seem to help all that much but it definitely would have been worse without it.
It stung like hell.
I needed a moment to breathe before I could continue. The hardest part was over, the flashlight wouldn't get drastically thicker beyond the point that was already inside of me.
With small breaks in between, I let myself sink down further and further. I still had to use my hands to spread my butt cheeks (and also my hole) but with gritted teeth and a little help from gravity, I pushed almost the whole flashlight into my back-entrance. It was a struggle though. I think I spent at least 10 minutes just getting to that point.
I pushed on, hoping to get it all inside, but judging from the discomfort inside my stomach when I pushed on further, I soon realized that this was as far as it would go.
Although I finally reached my goal, I was a little disillusioned.
More than anything, it just felt uncomfortable and I was afraid to let it slide out completely again because I wasn't sure I'd get it back inside.
For a few minutes, I slowly and carefully tried to ride on the flashlight in my butt, feeling my dick bob in arousal as it squeezed me from inside. But very soon my legs got tired. So I sat still and just wanked, but with my sphincter stretched as far as it was, not moving made it feel more and more like the flashlight wasn't supposed to be there.
All of this had seemed a lot better when I imagined it beforehand compared to how it actually turned out. But I wasn't ready to give up yet.
I wanted to change things up. And partly due to frustration, I wanted to know how it felt to be fucked. Hard. And furiously.
Pressing my butt cheeks together and putting a hand under the flashlight, I stood up and awkwardly shuffled over to my bed. I sat down, rolled on my back, and spread my legs. Feeling excited about the change of position I gripped the end of the flashlight and let my imagination run wild. I slowly pulled it out halfway and shoved it back inside faster than I probably should have. I flinched and let out a pained moan but I also kind of liked it.
The scenario that played out in my head was one I had imagined countless times in various variations: I was being fucked by a big-dicked man maybe twice my age. Who, how, and how relentlessly differed every time but this time I wanted it hard.
So while my hands were plowing my ass with an oversized household appliance I imagined being pinned down on my bed by the middle-aged man next door who mercilessly used me for his own pleasure.
It hurt and I could feel my butt getting sorer by the second, but I didn't care. I closed my eyes and gradually increased the tempo until the lack of proper lube made it too uncomfortable to go any faster.
Pre-cum leaked out of my untouched dick more than usual, my toes curled and twitched with every thrust, and between my quickened breathing, I was making sounds that were right between pain and pleasure, but in the middle of it all, the two seemed almost the same.
I had seen pictures of super stretched buttholes online and the thought that mine might look the same now turned me on immensely.
By then I had gotten the hang of almost completely pulling out the flashlight before shoving it back in, and the deep thrusts going inside of me made me shiver.
I couldn't help but whimper.
Fully indulged in my fantasy I thought about what the imaginary man fucking me might want. What I could do to play a more active role than just providing a hole. I had read somewhere that bottoms could "massage" a dick by rhythmically contracting their sphincter to match the other's movements. It sounded exciting so I tried it. But since I now had to focus on both fucking myself with the flashlight and squeezing it with my butt, I screwed up the timing for both pretty often.
Almost every other thrust I accidentally contracted my sphincter and a few times it hurt bad enough that I had to pause for a moment. I tried it for a bit longer and was pretty turned on by the sounds I was making. I usually wasn't all that vocal while wanking but this time I didn't care. I was horny, I felt overwhelmed, and I wanted to let it out.
Besides, in my fantasy, the imaginary man fucking me was turned on by my gasps, moans, and the occasional pain-filled whimper and my still fully erect penis twitched in excitement at the thought.
I was playing along with this fantasy for a little longer but rather sooner than later I felt too spent and sore to drag it out much more. The pressure inside of me also made me want to cum really bad.
I wanted to beg the made up stud plowing my ass to fuck me into oblivion. To make me cum harder than I ever had before. I couldn't think clearly enough to get the words out of my mouth but I heard my voice rise as I entered the final stretch. The only things on my mind were the phallic object currently pushing my butt to its limit and the desire to feel my cum land on my aching and sweaty body after what I hoped would be my most intense orgasm to date.
And as I wondered how far I would shoot with a huge flashlight up my butt, I reached for my throbbing dick to finally push me over the edge.
Well, at least that was the plan. Until I heard the door.
Not the front door, my door.
Dad had come home from work earlier than usual and judging from the sounds I was making and the pleading tone in my voice apparently thought I hurt myself.
So there I was, naked, hard, and with a huge flashlight up my reddened butt, while my dad entered the room with a worried expression on his face that quickly turned into shock and confusion.
Needless to say that I panicked. I tensed up, trying to sit up straight and jerked away the hand that was holding the flashlight, violently pulling it halfway out of my suddenly far too tense butthole.
My dad probably barely managed to process the scene in front of him when I was already screaming in pain, as my repeatedly contracting anus slowly pushed out the flashlight until it fell to the floor with a thump.
Against all odds, I got away with only a mild injury and wasn't bleeding as much as I probably should have. Nonetheless, my butthole was bleeding and while I was still lightheaded from the stinging pain that caused it, I felt how dad carefully pressed a tissue against the wound between my butt cheeks.
Now, I've had my fair share of embarrassing experiences but this one is pretty damn far up top. I was too embarrassed to do or say anything and now that my libido wasn't obscuring my mind anymore I felt just how sore my body, and especially my butt was.
Not reaching climax after over an hour of wanking didn't even seem to matter compared to everything else.
Dad just looked worried and asked if I was okay between apologizing and getting new tissues until the bleeding stopped.
He left the room so I could get dressed again and I just stared at the once again closed door in disbelief.
I involuntarily touched the still stretched and sore hole between my butt cheeks and despite everything, my dick got a little hard again. Still intensely embarrassed by what just happened, I mechanically wanked my half-limp dick until I at least got rid of the pressure that hadn't gotten a chance to escape.
I cleaned myself, got dressed, and after calming down for a few more minutes, I timidly walked to the living room with a still pretty odd feeling in and around my butt.
Dad was waiting for me and we had a brief, awkward talk about what just happened. I promised not to do anything stupid or dangerous again while dad agreed to knock even when he thought I needed help. At least he didn't seem to mind that his son liked putting stuff up his butt.
Dinner was pretty silent as I was trying to avoid eye-contact and dad tried to avoid any topic that was even remotely close to butts, phallic objects, or anything entering something else.
I never touched that flashlight again. And I'm pretty sure it also took a while until the next time dad used it...
Even so, it didn't take long before things were pretty much normal again. But not without the occasional flashback or awkward silence.
A couple of days later I came home to find a bottle of lube and a dildo on my desk. Next to it a note reading "Let me know if you want a different size" and to this day the thought of my dad wondering how big a dick I want to be fucked with before going out to buy me a sex toy still haunts me. So even if the dildo he bought hadn't been perfectly fine, providing me with safe enjoyment for years, I probably wouldn't have had the guts to ask him for a bigger one. On that note though, thanks dad.