My Best Mistake - Part 1

All characters are 18+

I'd never actually 'come out' as bisexual, but the majority of people in school and even at home, knew that I had a certain interest in men. I wasn't feminine and I played football too, so I never got a hard time from anybody about it.

It was a Friday night and my parents had gone to my aunts house for the weekend. I decided to stay home, mostly to enjoy a weekend of nudity and porn, because as an active eighteen-year-old, I was constantly horny.

I was still a virgin, and too nervous to try any of those random hookup apps, so the likely outcome was going to be lots and lots and lots of jacking off. By the time my parents had gotten into the car, my shorts and boxer briefs were already down to my ankles and I was coaxing my long, smooth cock to erection.

I found a video of a very handsome jock-type guy, his muscular legs were spread wide and his abnormally large cock was pulsing against his stomach, and then, without laying a single finger on it, an explosion of thick, white cum burst from his large cock head and sprayed across his chest.

I was in awe. How had he managed to cum without even touching himself? Was it just another 'porn trick'? I continued watching as the muscled young man orgasmed and moaned, and then finally he reached between his legs and pulled a large glass dildo from his hole.

I hadn't noticed it at first, but I realised that the man had orgasmed just from the dildo. My mind raced. I found the idea of it so hot that I nearly came myself. I'd never put anything inside myself before, not for any reason in particular, I just simply hadn't had the urge to, until now.

I began searching the internet, trying to work out how the man had reached orgasm through his ass and finally found the answer.

The elusive prostate orgasm.

I'd never heard of it before, but the more I read, the more I wanted one. The idea was relatively simple, I just needed to find something with a curved shape, lay down on my back and go to town.

I scoured the house, searching for something to slide into my asshole. I routed through drawers and presses, cupboards and cabinets and finally had a selection to choose from. I felt rather embarrassed at the idea of using my families items to butt fuck myself to oblivion, but my horny urges had well and truly taken over.

The end of my moms hairbrush looked too uncomfortable, not to mention it was straight, not curved. The torch handle looked more inviting, though that too was straight. The banana ticked the boxes, but I knew that my virgin hole would be far too tight to take the width without smashing it to mush.

My eyes fell on the last item on the table. I wasn't exactly sure what it was, but it was about the width of two fingers and quite long. It looked like it was made of steel and was heavy enough too. The best part? The end curved upwards, just like the dildo from the video. The worst part? It was my brother's.

The latter bothered me, but not enough to abandon my mission. I grabbed it, raced back into the living room, my excited cock jumping and slapping off my legs as I did, and began to set the stage.

The article was quite detailed, and explained how to position myself for maximum pleasure. I stuffed a cushion under my lower back, spread my legs and pushed the head of the object against my pink ring. Instantly I knew it wouldn't work.

"Lube!" I spat, reading further down the article "lots of lube!"

I went on another search through the house, strings of pre-cum flying from my excited cock as I imagined how awesome this would be. I found what I was looking for rather quickly, and deleted the idea from my head that explained why a tub of KY Jelly was sitting on my dad's locker.

Back in the living room I positioned myself again. I lathered the dildo-esque object with lube and squirted some down my smooth taint, shivering as it slid across my unexplored asshole. I decided to ease myself into it, pushing a finger in first.

I can't explain the feeling. It wasn't painful, it wasn't even uncomfortable, but it felt strange as my tight ring expanded and contracted against my fingertip. I slid it deeper before pulling it back out and applying more lube. I had a feeling that my dad would be needing to replenish his stock by the time I was finished.

I jammed my finger back inside myself again, awkwardly circling it in an attempt to loosen my painfully tight sphincter. It was warm and soft inside, and I found it quite entertaining to prod around in there.

After a few minutes of exploring, I reapplied the lube and entered with two fingers. Once again, it didn't exactly hurt, but it was now beginning to burn. My sphincter muscle was starting to tire, I could feel it loosen against my fingers and after at least ten minutes of constant fingering, I pulled my sticky, wet fingers from my asshole and I was ready.

My cock had strangely become soft, even though the entire situation was rather stimulating. I was however, producing vast amounts of clear fluid which was pooling in my bellybutton.

I read the next steps in the article.

Angle the object so that the curve is pointing up, think of it like you're trying to touch your penis from the inside.

I did the calculations in my head, trying to work out exactly how to do this. I pushed the bulbous tip against my sensitive hole and gasped as it slipped inside. It did hurt this time.

I breathed deeply, allowing my pained ring to acclimatise to the intruder and as the pain began to wear off, I slid it deeper.

"Angle the curve up" I repeated to myself, trying to now figure out which way was up in my own asshole.

I was beginning to sweat now. Not because of the physicality of the task, but because of the awkwardness of it. What way was up?

I winced as I twisted the object, it nicked something inside me and it appeared that even the slightest pinch in there was painful. I could feel the angle of it rubbing against my soft insides, but no matter what way I twisted it, I had yet to feel the pleasure that was mentioned in the article.

"WHAT WAY IS FUCKING UP!" I shouted at the screen, yanking the tool out with an audible pop.

I studied it, even positioned it again so that I could work out what way I needed to do this damn thing, and finally decided that I needed a better view.

I grabbed my phone, opened my front-facing Snap camera and positioned it between my legs. I had to admit, I was quite handsome and looked good with my legs spread and my smooth, pink asshole glistening with lube.

I watched myself in the camera as I pushed the object back inside my hole. It opened without hesitation this time, and I could see my ring expanding and tightening around the width. I went deeper, carefully waiting for the moment that I found my prostate.

By the time I'd gotten deep enough that it began to hurt, I realised I'd gone to far. Where the fuck was it?

I pulled it out slightly, waiting for the burst of pleasure again.

Nothing.

"Fuck!" I hissed, and my back was now aching from the position I was laying in.

I pulled the thing out and threw it aside. I'd just need to jerk off for now, and perhaps I'd come back to the challenge at another time. I fumbled with my phone, my lubed hands slipping and sliding as I eventually managed to lock the screen and left it on the coffee table.

I grabbed my heavy cock, pumping it to full erection and began searching for another video to get me off. The second I clicked back onto my favourite porn site, the screen went black, the battery icon flashing in the centre of the screen.

The sexual frustration made me want to punch a hole through the fucking laptop, but I grabbed my phone instead. As I did, my brows lowered.

Chase Daniels is typing...

I read it again. Surely it was a mistake. The only reason I even had Chase Daniels on Snapchat was because he needed to borrow my football boots one time, and despite the fact that we actually got on quite well when he wasn't being the schools biggest douchebag, I knew better than to decline his request.

I assumed that it was indeed a mistake, but a moment later I received a second notification.

Chase Daniels sent you a message.

Curiously, I opened it up. Perhaps he needed to borrow something else, but it had been quite a while since the last time, and I don't think we'd even spoken since. I began to read, and instantly the blood drained from my body and my eyes widened.

Nice story bro. Was that a mistake or??

My fingers moved so fast that I could hardly see them.

"No, no, no, no" I frantically mumbled to myself as I tapped onto my profile and a sickening feeling came over me.

There it was, posted 2 minutes ago. I wanted to throw up as I looked down at the screen and watched myself, completely naked, my face and asshole visible as I stuffed a steel object inside myself. Two people had viewed it already, and my heart felt as though it would explode in my chest.

I checked it quickly, needing to work out who I'd have to apologise to before deleting it. Chase was the first person, the second was thankfully a guy I barely knew. He lived hours from me, and it was unlikely that I'd ever actually see him again.

I deleted the story, furious with myself for having made such a stupid fucking mistake. Disgusted that two people, one of whom was in my school and knew me well, had seen it and on the verge of tears as I now had to explain myself to one of the most popular, cocky, and admittedly best looking guys in the school.

I double checked that the thing had been deleted and opened Chase's message again.

Sorry! It was a mistake. Please keep this between us, dude. Feeling pretty shit after that.

He opened it instantly. My mouth was dry and a cold sweat was covering my naked body. I was no longer horny, not even remotely, and my cock had shrivelled up to the size of a mushroom.

He didn't type, and I wondered if he'd simply ignore my message and proceed to tell every single person in school that I, Jason Harris, had uploaded a public story of myself fucking my own asshole. I felt like vomiting.

Chase Daniels sent you a snap.

What was it going to be? Most likely, him laughing. Maybe he'd managed to save it, and he was showing me all of the places he was going to upload it. My hands trembled as I tapped the red square.

He was indeed smiling. His perfect white teeth shining, and not because of any dumb filter. His beautiful dimples made his smile infectious, but I wasn't smiling today. Beside him, a young man who I knew as Max Harley. He was Chase's best friend, and another giant douchebag, but as handsome as his friend.

They'd both seen it, and now my life was sure to be over, until my eyes fell to the text line below the two painfully good looking jocks.

Why don't you take that pretty ass over to my place. Beers, pizza and maybe we can help you find that spot.

I couldn't believe my eyes. Was it a joke? Were they just teasing me? What if it was just a setup and they wanted to beat me up? My mind raced faster than it ever had before as I questioned their intentions, but there was only one way to find out.