Helping a Friend

I felt bad for him. I really did, but as his best friend, how on earth could I possibly miss out on the opportunity to terrorise him with incessant teasing about the one thing he trusted me enough to confide in me about?

He knew it was all jest, we'd been best friends for as long as either of us could remember, so teasing him about his broken dick was always going to be on the agenda, and he accepted that when he told me.

Evidently, his parents had decided against getting him and his brother snipped when they were babies, so Jason's dick had always looked a little different to mine. I never really paid any attention to it when we'd shower or go swimming, until I realised that I was gay, and then I began sneaking glances at him whenever I could.

As close as we were as friends, Jason was undeniably attractive, and I'd been secretly longing for him for longer than I cared to admit. He knew it, so I guess it wasn't that much of a secret, but he'd always been pretty cool about it, and teased me just as much as I had been teasing him in recent weeks.

"Do you think they'll let you keep your foreskin in a little bag or something?" I asked him as I sat next to his hospital bed whilst he scowled at me.

He'd gotten circumcised, and he'd asked me to come with him because both his parents were working, so what did he expect? He'd had a condition called phimosis, so he'd never actually seen the tip of his dick before.

The doctor came by after about an hour and gave him the all clear to go home, but not before laying down some cringe worthy ground rules that I'm sure Jason wished I wasn't privy to.

"No masturbation for at least six weeks" he said, and Jason's eyes widened. "Don't get it wet for the next few days, and make sure to keep the bandages clean".

With my help, Jason squirmed his way out of the bed and sheepishly stood up.

"And no sex" the doctor added, looking at each of us.

I sniggered, Jason swore under his breath, and a few minutes later we were leaving the hospital a foreskin lighter than we'd entered.

As the days turned to weeks, Jason seemed to be healing pretty well. Neither of us were particularly modest, especially around each other, so I'd gotten front row tickets to watch the healing process from start to finish.

He was quite well endowed, and I had to admit, seeing his glans so exposed after a lifetime of being hidden was quite exciting for me, and even more so for him.

"Bro, every time I touch it I feel like busting a nut!" He said, "it's like a million times more sensitive".

I could tell that after three weeks, my best friend was becoming painfully frustrated at the lack of orgasms he was having. Not only was it obvious in his absurd mood swings and miserable humour, but he told me.

"I wake up like five times a night" he groaned as he lay on my bed one evening, "all I can think about is jerking off!"

"It's been three weeks" I shrugged, "only another three to go".

I did feel terrible for him. He was an eighteen-year-old boy, and what guy that age had ever gone that amount of time without beating off? It was cruel, but there was nothing I could do to help. Or was there?

"It's a pity" I sighed, turning my attention back to the Playstation, "you wouldn't have this problem if you were gay".

"Oh yeah?" He asked mindlessly, as we played, "why is that?"

"Because you wouldn't have to jerk off to cum" I explained.

He paused the game and glared at me.

"What do you mean?" He almost barked, and I laughed. "Nathan! What do you mean I wouldn't have to jerk off?!"

"Well" I smirked, "guys have a thing up their ass called a prostate, and it's basically the equivalent of a G-spot".

"Bullshit" he said, though I could see the hope in his blue eyes.

"If it was bullshit, would I have these?" I asked, and pulled open my top drawer to reveal something I'd never showed him before.

We trusted each other with everything, so I had no issue showing him my collection. It was nothing crazy, but since my eighteenth birthday, I'd slowly been building it up, and now I was quite proud of my stash of dildos, butt plugs and vibrators.

"Holy shit" he laughed, as I threw them onto the bed and he recoiled in fear, "you really are gay!"

I grinned and the two of us stared at the handful of silicone sex toys.

"You can cum from that?" He asked, curiously.

"Yeah" I told him, "better than jerking off, that's for sure".

He didn't believe me. I knew by his expression that he didn't, but he continued to stare at the toys and couldn't help but ask questions.

"Why is it shaped like that?" He enquired, pointing to one of the vibrating prostate massagers.

"So it hits the right spot" I explained.

"And cum comes out your ass?" He asked seriously, and I snorted with laughter.

"It comes out your dick, you idiot" I grinned, and now he looked really perplexed.

The two of us sat in silence for a moment as Jason considered this bizarre news. It was quite funny to watch, but I was almost certain that he'd tell me to put away the toys. Instead, however, he reached for one.

"These don't have like... Butt juice on them, do they?" He grimaced, and I shook my head as he picked one up.

"So let me get this straight" he continued, feeling the soft, velvety texture of one of my vibrators, "you stick this up your ass and you can cum?"

"You don't just cum" I told him, pressing the button on it so he could feel the powerful vibrations, "you explode, and it's the best damn feeling you'll ever have".

His eyes widened as he held the toy. It was the strongest one I had, and watching my best friend hold something that had been in my ass on more than one occasion was making me rather horny.

"Could I... I mean... Can I borrow one of these?" He asked nervously.

"Sure" I shrugged, "but it will probably take you another three weeks to work out how to do it" I added with a laugh, and Jason sighed.

"Isn't it simple?" He groaned, and I shook my head.

"It took me ages before I could finally do it" I said, "you'll be able to jerk off by that stage, anyway".

Jason's shoulders dropped and he turned off the toy. He looked miserable, and as funny as it was to see how much of an impact not jerking off could have on a guy, I was sympathetic.

"Just think about how good it will feel when you can finally do it" I smiled, taking the toys into my arms, "it'll be worth it".

As I dropped my stash back into the drawer, Jason said something that I never thought I'd hear from my best friend.

"Will you do it for me?"

Internally, I began to freak out. The idea of helping Jason cum was already making my dick swell in my pants, but I had to play it cool. If he saw how into it I was, he would surely change his mind.

"Um... Yeah, I guess" I shrugged, and took out my favourite toy.

It was pretty thick, even by my standards, but it was my go-to when I wanted to feel the tremendous pleasure of a prostate orgasm. I hadn't lied when I told him that it had taken me quite a while to learn the tricks, and even then, I usually had to finish myself off with my hand. This was going to be difficult, but I was certainly willing to give it a try.

"Go and have a shower" I told him, "don't get dressed when you're done".

There was nothing unusual about Jason showering at my place, but he'd never returned from the bathroom naked before, and when I watched him leave the room, I couldn't help but fist pump the air.

Finally, after countless nights fantasising about him, I was going to get my best friend naked on my bed. Sure, it wasn't in the way that I'd imagined, but perhaps this was even better! All I needed to do now was not fuck it up.

Fifteen minutes later Jason walked back into my room with a towel wrapped around his waist. He looked around and sniggered.

"This is romantic" he said, noticing the pulled curtains and candle flickering.

"You have to be relaxed" I told him, "or else it won't work".

"I feel like you're about to but a spell on me or something" he laughed, "a gay spell".

"You're the one that's naked" I reminded him, and without thinking too much, I unhooked his towel and pulled it away from his body.

His cock looked exceptional. Don't get me wrong, it looked great before his operation, too, but there was something so exposed about it now. I felt a pang of misery when I remembered that I couldn't touch it.

"Alright" I nodded, my eyes unable to be pulled from his perfect pole, "lay on your back and spread your legs".

"Yes sir" Jason joked, and walked pretty casually toward my bed.

God, he was hot. He wasn't your typical jock or gym bunny, but he did have a good body. He was just one of those people who was blessed with everything, and I stared at his plump, flawless butt as he crawled onto the bed and lay down.

"I hope your mom doesn't walk in" he joked, but the idea made me gag so I locked the door and returned to him.

"Are you relaxed?" I asked him, taking the bottle of lube in my hand.

"You're about to shove something up my ass, bro" he said, "I wouldn't exactly say I'm relaxed".

"Well you need to be" I told him, "lie on your tummy".

"My tummy?" He chuckled, "what are you, six?"

"Just shut up and do it" I said, and lathered my hands in lube.

Perhaps it wasn't the right stuff for the job, but it was all I had, and I was determined to make Jason enjoy this so much that even when his dick was better, he'd want to return.

When my naked best friend lay on his stomach with his cheek buried in my pillow, I straddled his back and he grunted.

"Your fucking zipper is shredding my ass you moron" he spat, and I realised he was correct as I stared at the faint red line caused by the sharp metal.

"Shit, sorry" I said, and got to my feet.

"Um... Do you... I mean, should I..."

"Just take them off, bro" he sighed, "I don't really care at this point".

I felt another flurry of butterflies in my stomach, but I wasn't going to argue with him. I pulled down my pants until I stood in only my boxer briefs and t-shirt, and crawled back on top of him.

"If you put your dick in my ass I'll beat the fuck out of you" he warned me, and I sniggered as I imagined it.

"Alright, now try to relax" I told him, adding more lube to the crease between his shoulder blades.

Jason shivered and groaned as I pushed my hands deep into his flesh, and suddenly I was getting hard again. Thankfully, my boner didn't seem to alert him, and so I continued with the massage as his breathing deepened.

"That actually feels good" he mumbled, his eyes closed as I worked his lower back.

On and on it went until I'd rubbed and pressed every inch of him above his waist. I was acutely aware that I was now sitting on his butt, and I was sure now that he was ready.

"This will feel a little cold" I whispered, and squirted another glob of lube just above the crease of his ass.

"Mmm" he breathed.

I considered using the toy to apply the lube to his special area, but he hadn't expressly forbidden me from doing it myself, so gently and slowly, I pulled his ass cheek aside and then my eyes fell on the most perfect asshole I'd ever seen.

Even without knowing who owned it, I could tell that he was a virgin. It was hairless and pink, and I began to wonder if my very straight best friend actually shaved his own butt hole. It was a question for another time however, so I ran my finger down his ring and he shivered.

"Fuck" he gasped quietly, and said it again when I did it again.

It only took a few seconds for his hole to shine from the lube. The toy was certainly too big to go right in with, so I decided to take things up a notch.

"I'm putting my finger in first" I told him, and I expected him to protest, but he didn't.

I pushed my fingertip against his soft, velvety butt hole, and with just a little bit of pressure, he began to open.

I'd never fingered anybody other than myself before, and there was something extremely arousing about it. A wet patch was already beginning to form in my underwear, but it was Jason who I was concentrating on now.

Deeper I went until my entire finger was inside my best friend. I left it there for a moment, allowing him to get comfortable, and slowly I moved it in and out.

He didn't moan, not yet, but I could tell that he was enjoying it.

I twisted it around, feeling for his prostate, until finally I danced over it and he gasped.

"Fuck!" He moaned, his body jerking a little.

"Just relax" I whispered, giving his bottom a reassuring squeeze.

It seemed to do the trick, and he lay back down once more.

Fingering a straight guy was amazing. Fingering Jason was beyond my wildest dreams, but here we were, and now it was time for the second finger.

"I'm going in with two" I told him, and he groaned. "Just breathe".

It was quite difficult to get my second finger into him, but after a copious amount of lube and some pushing and squeezing, eventually I managed it, and now he was breathing quite heavily.

"That fucking hurts!" He growled, but with each passing second, his sphincter began to relax.

I must have spent about fifteen minutes sliding my two fingers in and out of Jason's wet hole. It was extraordinary, and the only thing that could make it better was if it was my cock inside him instead of my fingers.

Regardless, it was now time to make my best friend feel something he'd never felt before.

"Alright, turn around and spread your legs again" I told him, and almost reluctantly, pulled my fingers from his butt.

Jason's cheeks were flush, but I doubted it was from embarrassment. He didn't really get embarrassed, which I guess was evident in the fact that he had just been finger fucked by me.

When he got into position, his eyes stayed on the toy in my hand as I doused it with more lube.

"That's going in there?" He gawped, and I smirked.

"It's not as bad as it looks" I assured him, and parted his legs a little wider so I had perfect access to his lubed up hole.

His cock had grown to a semi-erection, but that was fine. He didn't need to stay soft, he just needed to avoid jerking it.

I pushed the vibrator against his pink opening and watched him close his eyes and wince as it began to squeeze inside him.

"Ouch!" He groaned as his ring spread apart.

I pressed the button on it, sending shockwaves of vibrations through his most sensitive area, and Jason almost purred with pleasure.

"Feels good, huh?" I grinned, and he nodded as he became lost in it.

Further and further I slid it until I knew it was at just the right spot. I twisted it around to get the edge against his prostate, and when I did, his eyes shot open.

"I'm gonna piss!" He gasped, and tried to move until I grabbed him.

"You're not gonna piss" I laughed, "it just feels like that, now just relax".

Nervously, Jason lay back down and I pushed the vibrator against his special spot once more. Almost instantly, his cock began to leak pre-cum onto his smooth groin, and my best friend started to moan.

"Shh!" I sniggered, knowing that my parents were in the room below.

I kept the toy in place as Jason squeezed the bedsheets and began to sweat. He was doing his best to stay quiet, but every so often he'd let out a low moan of arousal.

His large cock remained semi-erect, which is usually what my own one did, too, so I wasn't too concerned. I slid the vibrator back and forth inside him, which made his slender body arch and his mouth hang open.

"Oh fuck, bro" he breathed, his toes curling, "you weren't lying".

"I told you" I grinned, toying with his young prostate again.

After a few more minutes of teasing him, Jason reached for his eager cock until I slapped his hand away.

"You can't" I reminded him, and he groaned with frustration as he grabbed the sheets again.

"It feels so good, man" he whimpered, and then I increased the vibrations and Jason yelped with pleasure.

"Fuck, bro" I laughed quietly, "you have to keep quiet!"

"It's your fault!" He snapped, his body tensing again as another wave of pleasure rippled through him.

I had pinpointed his prostate at the beginning, and I wasn't giving him a second to do anything but moan and tremble. At this point I knew I could make him cum, so now I was going to play with him.

"Oh fucking fuck!" He gasped, his eyes widening again, "bro! Bro! I'm gonna... I'm gonna cum!"

I let him believe that for a moment, bringing him right to the edge, and then I moved the plug and he almost screamed.

"What the fuck are you doing?!" He asked me, a look of shocked horror on his handsome face as I grinned.

"Edging you" I shrugged, "you'll thank me for it at the end".

"Listen to me, bro" he said, and I could hear the desperation in his voice, "I won't. I won't thank you for it, I'll fucking kill you. Don't you know how much I need this? I will literally strangle you to death if you don't make me cum right... fucking... now".

I laughed as I brought the plug back to his prostate and Jason forgot every problem he ever had. He crashed back onto the pillow, arching his back once more and began to whimper and moan as his cock poured milky pre-cum into his bellybutton.

"Yeah" he gasped, "yeah right there, keep it there, oh fuck, I'm... I'm cumming. I'm cumming!"

I moved it again, and ducked when his hand reached for me.

"Dude, I'm fucking warning you" he cried, though it wasn't an actual cry, more like a 'I'm going to kill you' cry. "If you don't make me cum, I'll... I'll... Just fucking make me cum, man! Please!"

I'd had my fun. I could tell that if I fucked with him anymore he'd likely make good on his threat. Plus, he'd been denied his pleasure for long enough.

"Alright, alright" I grinned, "are you ready?"

"Yes I'm fucking ready!" He hissed, breathless and sweaty as he lay back down.

I turned the vibrator onto its highest setting and could feel the vibrations through his leg as I held it apart. Jason sucked in air and almost squealed as I returned it to his eager prostate.

His cock was now twitching violently in its own mess, and his sphincter was clamping around the base of the wet toy. I would have given anything to put my mouth around his pink helmet for the next part, but alas, it was impossible.

"YES!" He moaned, and I didn't bother trying to keep him quiet anymore. "Oh my fucking shit! Oh yeah, oh fucking fucking fucking fuck!"

Sperm began to explode from his semi-erect cock, spurting up his body, pooling in the crease in his neck as his balls crawled upwards and shot more thick spunk from his swollen cock head.

Jason was biting down on his knuckle now in an attempt to quieten his shrieks of pleasure, and all the while, the largest explosion of cum I had ever seen continued to drench his naked body.

His butt hole was clamping down on the toy as his three week load soaked him, and at one point, I watched as a rope of jizz splashed against his lips, and he didn't even bother to remove it.

The orgasm continued burning through him, making his toes curl, his legs stiffen, and his body shake like a leaf. Prostate orgasms were indeed powerful, but I'd never experienced one like this.

After nearly three minutes of moaning, gasping, twitching and drooling, Jason's body went completely limp and for a moment I thought I'd killed him.

"Are you okay?" I asked, sliding the toy from his wet hole.

"Dude" he gasped, his cum soaked chest rising and falling rapidly, "that... That was fucking... Amazing".

Even now, five minutes after the orgasm had started, his balls continued to churn and produce slow, lazy spillages of cum from his cock.

"Good" I grinned, watching him.

Jason didn't bother moving. I guess the ordeal had zapped every last ounce of strength from his body, so he just lay there covered in his own sperm as I cleaned up and put everything away.

He watched me as I returned to the bed and an exhausted smile lit his face.

"You know what this means, right?" He asked, still breathless as I shrugged.

"You can't just give me a taste and never do it again" he said.

I looked up and down his naked body and grinned.

"Well" I said, and ran my finger down his stomach, collecting a sample, "I guess we'll have to compromise".

I sucked my finger into his mouth, finally getting a taste of my best friend.

"Deal" he grinned.