Fridays are for the bros

It started out like any regular Friday evening - for a while we - Miles and I - had this tradition that we'd meet up on Fridays and have a smoke and a drink, play games or watch some movies and talk about whatever was on our mind. It was a great way to keep in touch and relax amidst our busy lives that often got in the way.

"Hey! Have you ever played with your hole?" At some point, Miles asked me - quite casually.

"Nah", I chuckle, taking another hit, "I'm not gay, bro..."

"I mean - you don't have to be..." He paused for a bit, "Nora told me that she likes to use a strap and I think she wants me to do it with her..."

I looked at him, a bit shocked, "Careful, bro! She's gonna turn you into her bitch!"

We both chuckled at the idea and got back to watching the movie, chatting about random stuff from time to time.

"Do you think it feels good though?" Miles asked me after some time.

"What?"

"You know... getting... fucked..." he sounded slightly ashamed.

"Probably... if you're gay though..."

Miles chuckled, "You think they're built different?"

"No..." I thought for a bit, "But you wouldn't like kissing a dude... at least I assume that..." I ginned.

He was silent for a bit, "Yeah, but you would enjoy kissing a girl - it's the person you like or dislike, not the act..."

"Well, sounds like you really could like to try it, huh?" I nudged him lightly with my elbow, smirking.

"No," he sounded slightly defensive, "It's just that Nora is a great girl and I'd like to make her happy, but I'm scared... I think it would hurt..."

"It probably would... but it would also depend on how big the thing is..." I grinned, thinking about how big the dildo she'd use on you could be, "Think she'd get a massive one to destroy you?"

Miles blushed slightly, "I don't know... I just think I'd like to try it before we do it together..."

I looked at him and chuckled, "So what? You want me to fuck you, bro?"

"Fuck off, man!" He slapped my body with the back of his hand, "Bet you'd be into that, sick freak!"

"Me?" I laughed, "You're the one who brought it up!"

"Oh, come on! I'd never do it with a real cock! That would seriously be gay!"

We chuckled about it, but with that, our conversation died down for a while, yet the matter stayed in my mind.

"Have you tried anything already?" I asked after a while of silence between us.

"What do you mean?"

"You know, like fingers or something?"

"Oh... nah... nah... man... I'm too big of a chicken!" He chuckled.

"So you'd like me to help you somehow?" I asked, sensing that might be the reason why he brought it up.

He stayed silent for a bit, keeping his eyes on the TV screen, "I don't really, know... Maybe? You're just my closest friend, so I felt like you're the only one who I could talk to about this..."

"Ay, I get you, man... If you need anything, I'm here!" we shared a genuine smile and he thanked me before our minds went back to the movie again.

As the credits began rolling Miles put his legs up on the couch, turning towards me, "You know... I'd like to have my first try with you... I mean not like you - you, but... you know what I mean..."

I chuckled, "Of course, man! Do you have a toy or something?"

"Nah... I was thinking maybe you do?" he hung his head down.

"Nah... I don't have any toys either..." I began thinking, "But I do have a banana..."

"Wouldn't that be kind of large, though?" He looked back up and I could sense his nervousness increasing.

"Oh, come on, man - she's not gonna be fucking you with a toothpick!"

"Shit, yeah... you're right man..." he paused for a second, "Okay... okay... let's do this man... I'm gonna go to the bathroom quickly and you get everything ready, alright?" he sounded like he was trying to gather up the courage and convince himself into doing it.

I wanted to ask if he was sure, but didn't, not wanting to cause him worry and doubt,

"Alright, man!" I have a sympathetic smile.

We both got up from the couch and went our separate ways. I grabbed a banana - it was still quite green, bought just the day before and headed to my bedroom to grab a tube of lube. I also grabbed a towel and laid it on the couch.

Miles soon arrived and took in the view before him.

"Everything's gonna be okay!" I assured him.

He sat down on the towel and both of us fell silent, waiting for the other to initiate further talks.

"What position should I be in?" he finally asked.

"I don't know... Let's google!"

I opened up my phone and searched for "best positions for anal masturbation for men", opening up the first article I saw, I scrolled down.

"They say you can do it on your back or in doggy, or also squatting..." I looked back at him, it seemed that as we got closer to the thing, he was getting more worried about it.

"I guess on the back would be good... or maybe doggy - then I wouldn't have to look at your face..."

"I don't know man... do whatever you think is best..."

"Fuck... this is so stupid... Okay, I'll just do it on my back..."

He laid down on the towel, with his ass towards me and lifted up his legs. It was weird seeing my best mate in such a position, but I was a bit too high to really care.

"Maybe take another hit - it will help you relax..." I suggested and he did.

"Fuck... I can't believe we're actually gonna do this.

Once again, I wanted to offer a way out but thought that it would be better to get this over with for his sake. I figured it would be on his mind all the time if he didn't find out how it feels.

I squeezed some lube onto the banana and rubbed it around.

"Alright, man, you're gonna have to let me see your ass now..." I said, now getting a bit nervous myself.

He pulled down his sweatshorts and boxer briefs, just enough to reveal his hole. His crack was hairy with a soft pink hole in the middle. I had never seen a man like that before, and the fact that it was my best mate, made it even weirder. I squeezed some more lube onto my fingers and put them against his ass, starting to slowly rub it. My heart was beating so loud and fast you'd think I was the one about to get fucked; I can only imagine how hard Miles's heart was beating.

"Oh, fuck, oh, fuck, oh fuck..." he quickly whispered as my fingers rubbed against his virgin hole.

Once he was lubed up enough, I placed the tip of the banana against his hole.

"Okay, you ready, man?"

"Yeah..." he didn't sound sure of it, but I didn't question him and began to slowly press the banana against his hole.

"Fuck, fuck, fuck..." he whispered.

I continued pushing, slowly applying more pressure, but his hole didn't want to give in.

"You're real tight!" I chuckled, trying to lighten the mood.

"Uh-huh..." he replied faintly, not finding the humour in my comment.

I tried pushing a bit harder, but it clearly wasn't working, "Look you just have to let your hole relax, or else we won't get anywhere..."

"Maybe we could try something smaller for the start though..." He looked up at me pleadingly.

My mind immediately went through the contents of my kitchen, thinking of phallic objects that could do the job.

"I mean... I have sausages, but I don't think they'll be firm enough... a carrot?" I looked at him inquisitively.

"Okay..." he replied, unconvinced.

I got up and soon returned with a washed carrot.

"You know, this could work better since the tip is so narrow..." I said, showing him the carrot, before applying lube to it.

I put it up against his hole and began pushing it in. I had to hold the tip as it was a bit flimsy. With how much lube we were using and how skinny it was, it went in very easily, slowly beginning to stretch him out. At first, he didn't react in any way, just staring at me, but when the vegetable began getting thicker and putting slight pressure on his hole, he became vocal.

"Oh, fuck, oh, fuck, oh, fuck, oh, fuck..." he mumbled.

"Does it hurt?"

"No, no... it's just really weird and... yeah, like really weird..."

He lit up another joint and smoked it frantically.

"Oh, fuck, man! Fuck, fuck, fuck!" his quiet mumblings didn't increase in volume, as I pushed further, but he began talking faster.

The carrot was quite long, but not very thick, so soon I reached the maximum girth of it and began to slowly fuck him with it.

"Alright, this is as thick as it's going to get... how do you feel?"

"Everything is fine, man... everything is fine..." he replied, seemingly trying to convince himself about it rather than me.

"Okay..." I kept moving the carrot back and forth slowly, "Let's keep going for this for a bit and then move on to the banana, alright?"

"Yeah... okay..." He still didn't seem sure of the plan.

The whole thing was rather mechanical, other than his nervous ramblings, there seemed to be no indication that either of us was gaining any pleasure from this - it just seemed like a coincidence that the act had sexual implications.

"It probably needs to be bigger to feel good..." I spoke to avoid silence.

"Don't you think it would only cause more pain?" he asked more calmly; I guess he had gotten more used to the size and movement, plus, the weed probably helped quite a bit too.

"At first... but look, you've already gotten used to the size of the carrot, I'm sure you can get used to other sizes as well... it's just a matter of stretching yourself..." I thought out loud.

"Shit, man! I don't want a loose fucking hole!" we both chuckled.

We began talking about other things, leaving the movement of my hand in the background as if it were nothing.

"Okay, I think I'm ready!" he finally announced and I was pleased that he had been the one to suggest switching to the banana.

I pulled out the carrot and set it down on the coffee table. His hole still looked very tight, but I hoped that it would at least be more relaxed. I grabbed the banana and reapplied lube to its greenish-yellow skin.

I placed it against his hole and pushed it towards him. With a swift movement, the tip entered him.

"Oh! Oh my God..." Miles moaned out instantly, raising his upper body a bit, "fuck, that's big..."

"Do you want me to stop?" this time I couldn't restrain myself, genuinely worried about my friend.

"No, no... keep going..." I could sense worry in his voice, but I followed his request, slowly pushing the fruit further into his hole.

I watched as he frowned and squeezed shut his eyes, grunting out "shit", "fuck" and "oh my god".

"Should I start like... fucking you or keep pushing?"

"Keep... pushing..." he whined, holding his breath.

When the banana was about a third in it seemed to press up against something inside, causing Miles to moan.

"Oh, fuck..."

"What? Does it hurt?"

"No..." he was breathing heavily, "it feels really good..."

Not really sure what to do, I began to move the banana in and out a bit, unbeknownst to me, stimulating his prostate.

"Oh, fuck... man... shit, that feels good..." he began groaning harder.

"Ay... you gay or something?" I joked, and this time he also chuckled.

"Nah, man... it's just really making me grow, bro..."

Hearing him say that and knowing that I was the one in charge of causing it turned me on a bit too.

"Try going a bit further, man..." he said.

I did, pushing a bit further and then back a little and then some further again, applying more lube as it was drying out.

"Fuck... it kind of hurt at first, like around my hole, but now it like feels kind of good... fucking shit!" Miles explained, as his hands dug into the couch under the towel, "Honestly, I feel like such a slut..."

Hearing him say that did something in me and I could feel my soft cock get a bit excited.

As he talked, I had pushed the banana into him almost to the other end.

"Do you want me to push it in fully?" I asked, half-jokingly.

"That would be so hot, man..." I could sense that the weed was making him act a bit more loose as well.

"Okay..." I replied and applied the last push, forcing the banana all the way in and watching as his hole tightened around the narrow tip, "Holy shit, man..." was all I could get over my lips.

"Fuck... Is it all in?" he asked seemingly quite excited.

He reached over and felt the tip with his own hand.

"Holy shit, man! I'm such a slut!" he laughed, "And I'm so fucking hard... I feel like I could start cumming any minute now."

I just watched him as I felt myself growing a bit too - the way he was acting and the fact he had a whole banana up his ass was quite hot.

"Holy fucking shit..." He groaned and began pushing the banana out, making it reappear, "Nora is gonna be so happy!"

I grabbed ahold of the banana and continued to fuck him with it, pulling out some more and then back in, almost to the other end again.

"Oh, fuck... I can already imagine her sexy little body ramming that dildo into me..." he mumbled with his eyes closed - this time from pleasure, not pain.

"Think you'll start cumming soon?" I asked, quite curious.

"I don't know man... it feels like I'm about to, but it's not coming... and I don't want it to either..."

"Fuck... now you're making me curious too!" I chuckled.

"I mean if you want to..." he opened his eyes and grinned at me, but I didn't reply - just kept fucking him.

Suddenly he grabbed the carrot from the coffee table and began sucking on it.

"God, I feel like a fucking slut, man..." he said as he worked on it, just like it was a cock, making me grow harder.

He began moaning harder as we continued going - me working on his hole and him on the carrot. I was a bit disgusted by the cat that it had been in his ass, but he didn't seem to mind it, so I began to wonder if he actually enjoyed it more because of that.

"Ah, fuck..." Miles groaned after a while and pulled the carrot out of his mouth, "I think it's gonna be enough for today, man..."

Following his request, I slowly removed the banana, leaving his hole gaping.

"Holy shit!" I laughed, seeing it, "It seriously stretched you out!"

"Really?" He reached down and felt around his hole as it slowly closed up again, "Fuck, that's hot!"

I grabbed the side of the towel and wiped off the remainder of the lube from his hole.

"Damn, that was crazy..." he said, pulling up his shorts and sitting back up.

I knew we both were hard, but I didn't bring it up - we had never jerked off together or done anything sexual altogether before this, so suggesting that out of the blue seemed too far.

Miles grabbed the sticky banana and opened it up, taking a big bite of it, "Oh, fuck..." it seemed it was hard for both of us to actually realize what had gone down just now.

We put on another movie and Miles finished the banana; we didn't mention the whole ordeal the rest evening.