New Town, New Friend, New Me

Dear Readers:  My sincere thanks to all of you who have reached out via email to share your thoughts and feelings as this journey has commenced. It’s been a pleasure to finally get to this chapter in Jared and Rae’s story. 

Appreciate all your patience and hope you continue to enjoy it.

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FROM CHAPTER 11

Then Jared positioned a larger finger at my entrance (had to be his thumb) and pressed it in. Felt way bigger actually in me but at least it was nice and wet with my spit.

“Enjoying yourself?” Jared said, pulling his mouth against my ear and softly blowing into it.

“Yes.” I groaned, my voice almost breaking from how this felt.

Sean and Jared chatted for what felt like an eternity while I remained in this position. Every now and then, I’d relax a bit but Jared would reignite my fire by stabbing my insides with his thumb.

In fairness to me, when I looked at the wall clock, it was 12:46am. So Jared had been inside me for over 35 minutes. Talk about a finger fuck fest.

I also appreciate that he asked for my spit because usually he just goes in dry. I was enjoying the moist feeling of him in my ass – much better than the rough, dry fingers I usually got.

Of course, Jared had never put his thumb in me before and I have to say its size made it far more uncomfortable than the two I’m used to. Even more than the three fingers for some reason. 

Fortunately, the time had allowed me to really stretch out for him - by the end of their phone play by play, I was no longer in any pain. Which was also good because everytime I thought I’d relaxed enough Jared would wiggle it around and practically explode from the simulation.

Finally, Jared turned to his phone. “Alright, Sean. Nice chatting but I’ve got to get Rae here to bed.”

“No worries, mate.” Sean replied.

Jared watched the call disappear from his phone screen. Then turned his attention back to me.

“Rae, it means the world to me that you like this. You’re better than any girl I’ve ever dated and the best bro a guy can ask for.”

I let my guard down in my reply, “Jared, it means the world to me that we’re friends.”

“Hell yeah, Rae Rae.”

I smiled, happier than I’ve ever been. His finger twitched inside of me. Except it wasn’t his thumb in my ass, it was the head of his cock.

Jared’s dick was in my ass.

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CHAPTER 12

Virgin Ass – 2

Jared’s DICK was in my ass!

… Well, the tip anyway.

I cannot believe how dumb I am when I’m this horny. How the fuck did I not notice it was his dick?! 

The truth is I know the answer: Somewhere deep inside me, I’ve been hoping for this moment. 

Until Jared, I was strictly straight and would never have thought about gay sex. Now, all I can think about is this giant cock and whether Jared will take my virginity with it. My horny monster merged with my psyche and offered but one statement. A phrase that kept reverberating in my brain – I want to get fucked.

Bye, bye virginity. I felt like I’d been waiting my whole life to find a friend like Jared. The best bro – the one who would take my cherry and show me what men are for.

I felt ecstasy race through my body like tiny creatures were running up and down the surface of my skin. The call with Sean ended; Jared placed his left hand on my shoulder softly holding the side of my neck. Firmly but gently putting himself in control of my body.

I felt the tip of his cock pulse in my ass and felt wetness in my hole. HIS wetness.

It felt so good being this close to Jared. To feel the heat of him behind me, his rough, manly hands on me and part of him (now my favorite part) slipped inside of me. It was as if my whole life was leading to the moments that followed.

Despite the heat of this moment, it also occurred to me that Jared’s cock was inside of me without a condom. You know that thing they say in porn…

Raw.

Unprotected.

“Hey Jared. Do you think we should be wearing a condom?”

“You mean me?”

“Oh. Yeah, I guess, I mean you. Cause you're the one…” I couldn’t say what was happening out loud so I just stopped talking.

“What’s the matter, Rae Rae? Not a fan of bareback?”

There was that word. The one that made me feel naughty when I clicked on that category on Pornhub. The one that seemed to mean you were a slut.

“No, it’s nice. Feels good - I just thought we’re supposed to be safe.” Oops, just told him I liked his dick in me. I’m going to assume Jared already knew that.

“Oh, sure. You got one, then?” he said, whispering into my ear while moving his dick around a bit inside of me.

“Uhhh. I don’t know.” My mind raced trying to remember, “I might have kept the one they gave out in health class.”

“Better go find it then. And hurry up; I’ve got blue balls.”

I tried to pull away from Jared but he held me there another moment, savoring the feeling my hole was giving him. Then he slowly removed his cock.

I suddenly felt more relaxed but also this other feeling of emptiness that crept up in the back of mind.

I raced around my room, rifling through drawers and looking through my school bag. Jared seemed to enjoy my franticness as he sat down on the edge of my bed, slowly stroking himself, while I darted around half naked.

“Lose the rest of your clothes,” he said.

I paused briefly to rip off my shirt and pull off my trucks. Now naked, I continued my search in my desk drawers. 

A moment later - eureka! I found it. And proudly held it above my head.

Jared seemed disinterested as I ran over and showed it to him. “Stroke me, buddy.” he said as I handed the condom to him.

I grabbed his cock moving the precum at the tip around to keep it nice and moist.

Jared tore open the packaging. I kept squeezing and slowly jerking his shaft as he placed the tip on his dick, then flipped it over and tried the other side.

Jared rolled the condom down covering his head. I withdrew my hands in anticipation of the rest getting covered. 

I should’ve realized that something I’d been keeping for 2 years and likely sat in my school bag for far too long, wouldn’t be in the best shape. Because as Jared got it down past his beautiful mushroom tip and properly onto his shaft – the condom gave up.

Maybe it was how rough Jared was being with it, or just that it was old, but the whole side of it ripped open; leaving giant tears down the side.

“Got another, Rae Rae?” he said nonchalantly.

I was panicked: “Sorry. That’s my only one.”

Jared leaned his face in, closer to mine. His eyes sparkled as he stared into me and said, “Well, dude. We are both bros, so not too worried about getting you pregnant.”

I laughed. “That’s true.” I said. 

Jared pulled it off his cock, tossed it onto the floor and went back to slowly playing with himself. I stared at it, realizing how much I wanted it. How much I’d wanted it for a while, probably since that first night Jared stayed over and dreamed about fucking somebody while using my ass crack for stimulation.

“Gonna need lube.” he said, interrupting my thoughts.

Oh right! How could I not think of that. “Sorry, Jared. Don’t think I have any of that either.”

“We can use spit but given that it’s our first time and you’re tight as Hell, we need a bit more than that.”

“What about something from the kitchen?” I offered, now desperate to get Jared back inside of me.

“Nah. I have another idea though.”

Jared stood up from my bed. He brought me to him and used his large arms to spin me around. Then he pressed on my back, making me bend over a little.

I heard him spit into his hand. Then I felt Jared push his digits (definitely fingers this time) into my ass. He grabbed my arm with his free hand and put my hand, palm up in front of my cock.

Oh no - I see where this is going.

Jared jabbed into that button inside of me. I yelped in pleasure. Two more sharp jabs and my brain swam with ecstasy as my cock swelled. Rockets of cum burst from my cock into my hand, filling my palm with spunk.

Jared pulled his fingers out of me. I was still amidst my orgasm as he pulled my arm to spin me around towards him. He pulled my hand forward and dropped his big cock right into it, covering the bottom park of his dick in my spunk.

I needn't remind you how grossed out I am about my own cum. I’ve had to taste and eat my own cum too many times already since meeting Jared. 

  Coming down off my orgasm I became very aware that Jared was using my hand to smear my load all over his cock. Lubing it up for – oh god – my ass.

Jared was about to fuck my own cum into my hole. 

This was the worse, most demeaning thing I could think of, and yet, seeing his big dick there and the smirk on Jared’s face as he looked at me watching my cum prep his dick to fuck me, I knew I was at the point of no return.

“Good job, dude. Now go lay on your back on the bed.”

I walked over the end of my bed and laid back. Then reached up and instinctively used my hand to spread my legs apart (getting some cum on my thighs). 

He crouched over and locked eyes with me. 

As slowly as Jared had instructed me in my striptease two weeks earlier, he removed the rest of his clothes. 

I laid there, taking him in – a prolonged, proper look at his physique. Jared was a great deal more muscular than I remembered and he even had a bit of a six-pack. The best look for a bro in my option.

“Breathe, dude. And enjoy the feeling I’m about to give you.” he said, moving towards me.

I nodded, letting him know I was ready to do this. Ready for my best bro to pop my ass cherry. 

He stood between my legs at the edge of the bed. Slowly he entered me, pressing his dick, inch by inch deep into me. And constantly reminding me to breathe. 

It started off okay given how much he’d fingered me of late. 

As he passed his usual point, it began to feel like I was getting ripped in half. Searing pain rushed through me and I struggled to take a breath.

“Breathe, dude. I got you.” he said, pressing himself past the quarter mark. “And don’t think too hard about how good a job your jizz is doing, keeping me slippery.”

Fuck. So humiliating. 

As his cock neared the halfway point, I became more and more thankful there was something besides spit on his dick. I felt stuffed and the most intense pain I can ever remember. Even with tears of pain streaming down my cheek and my insides being rearranged by the cum covered invader, I let him continue. 

Then a magical thing happened: the side of his cock brushed up against a special place in my ass and everything miraculously felt better. In fact, I was on cloud 9.

I was skipping through a field of cocks, blasting me with ropes of cum like a water park for cock lovers. I no longer cared that my own load was now inside of me or that more and more of Jared was burrowing its way into my intestines. 

No, all I could think about now was how horny for cock I was and how fucking great this felt.

A few minutes later, Jared was completely inside of me. Balls deep, as they say. 

I was in Heaven. I felt closer to Jared than I had ever felt to another person.

He was enjoying it too. I could feel his cock twitching a bit, releasing precum into me. Jared’s face told me how good it felt too. His usual cool-guy smirk had become a proper smile.

He continued to stare down into my eyes; as if watching what was dancing through my head.

He held his cock in that position, allowing my ass to stop resisting and relax a bit. 

A few moments later, Jared started pulling it back out - about halfway and then pressing it right back into me. I let go completely and accepted the immense pleasure rushing through me.

My ecstasy only increased as Jared fucked me. I made sounds I’ve never heard before and even Jared moaned despite himself. We even started breathing in sync with one another.

The better it felt. The harder and faster Jared fucked me. Never rough but intense and unwavering. The more intense, the more verbal I became with my pleasure.

Sweat poured off of him coating my chest, legs and cock in his manliness.

Pretty soon my ass was used to him enough that he could come almost all of the way out of me and then go all the way back in. This meant, his cock would strike my ass button on its transition back into my depths and you guessed it, caused me another orgasm.

Only seconds of build up, as Jared kept steadily fucking me, and my cock exploded cum all over my abs and chest. But Jared didn’t let up. 

He just kept going, enjoying himself as I teared up from the pleasure of cumming.

What seemed like hours later, but could honestly have only been 5 minutes. Who cares? Jared leaned in, and said, “I’m getting close.”

I nodded, knowing where this was going.

He put his hand behind my neck and held me. Our eyes locked, almost as if I was his girl. His stare was piercing - like he knew everything about me, even things I didn’t know about myself.

Jared whispered, “Ask me.”

I didn’t hesitate. “Please Jared.”

He shoved himself all the way into me and I felt his cock swell even larger in my ass. I squawked from the pressure inside of me. 

“Fuck yeah, feel your bro’s cum filling up your ass,” he called out as his own orgasm reached its peak.

Hot cum from Jared’s cock exploded deep inside of me. Shot after shot painted my insides with his dude batter. Unbelievable.

We both froze for a moment. All I could feel and smell was Jared and me together. Our sweat, heat and his, you know, combined into one mass.

“Stay like this for a minute. You’re still getting used to me and I don’t want to pull out too quickly.”

I responded, “Smart. Thanks for caring.”

“Yeah, buddy. I always got you. You’re mine, remember?”

“Yeah, Jared, I am.”

“I mean it, dude. You’re mine and this is just the final step in a bro’s commitment.”

I nodded. 

I don’t know what to do with this information. I wasn’t afraid, I just didn’t know what this meant for my future. Ultimately, all that mattered in this moment of my life, is that Jared and I would stay bros.

We held this position, waiting for Jared’s cock to finally get soft. It took over 20 minutes. 

We didn’t really talk which gave me lots of time to reflect on Jared’s load in my ass. 

HIS LOAD WAS IN MY ASS!

What a day to be a teenager.

Coming down from it, I felt a little weird and not quite myself. But luckily, Jared seemed to sense this.

“You okay, dude?” Jared said, pulling his cock slowly out of me. 

I immediately felt empty and very sore. His cum was so deep in me I felt like it would never come out. It would just stay there forever reminding me of how Jared had taken my cherry and bathed my insides with his load.

“Yeah. I’m okay.” I said, my voice almost breaking from how I felt. 

He went and grabbed my new undies off the floor. He used them to wipe up my cum off of him and then tossed them on my stomach. 

He pulled me up, into him and nuzzled my neck a little. It felt warm and not as sexual, and made me feel better.

Then Jared moved away from me, leaving me to wipe myself off.

“Here, dude. You can wear these tonight.” he said, tossing me his discarded underwear from the floor. 

I eagerly put them on; my body reminding me of what I’d just put it through as I pulled them up my extremely sore legs and butt.

They were a bit baggy on me, but so comfortable and I couldn’t have been happier to be wearing Jared’s. The very boxer briefs he had worn all day, sweated in, and had held his cock. 

Fuck, am I still horny?

Jared pulled back the covers of my bed and plopped down beside me. I pulled myself up towards my headboard, crawling in the least painful position possible.

Up near my pillow, Jared pushed me onto my side and smacked my ass - a confident smack reminding the universe that he had taken it for himself.

I smiled to myself feeling my ass jiggle a little and Jared’s sticky load move around inside of me. 

Jared put his hands behind his head and said, “Night, Rae Rae.”

“Night, Jared.” I replied, now totally exhausted. Then immediately passed out.

* * *

I awoke around midday and found Jared staring back at me. Eye fucking my body with his gaze.

“Hey, not-virgin bro.” Jared said and reached behind me and squeezed my butt. 

It felt like his butt now. Not like he could take it with him but part of me felt like it would always belong to him now.

“Yeah, you too, not-a-virgin best bro.” I replied, smiling back at him.

“We better hit the showers. This whole room reeks of sex.”

“Okay,” I said, stretching myself out. 

Jared jumped out of bed. I rolled over, not yet ready to commit to standing.

Jared reached down for my legs and dragged me across the bed and off the end. I landed in a heap on the floor, laughing as I tried to stand. Boy was my ass hurting. 

I attempted to get up and failed. 

Jared took this to mean I was being lazy, so he reached down and grabbed me - one arm between my legs, grabbing my butt and the other behind my neck. Then he lifted my whole body off the ground and threw me over his left shoulder in a firefighter’s carry position.

He carried me across the house, despite my protests, smacking my ass continually and humming some random song. I felt like such a little bitch.

He carried me to my father’s bathroom - the one with the large shower and plopped me down near the shower.

Without a word, he reached into the large glass shower and turned on the faucet. Since he was still naked from the night before, he walked right in and let the water engulf him. 

I stood there admiring his form as the water ran down his jock body. Even soft, his cock was plump and brilliant looking. That cock that had been in my ass. The cock that had made me a proper man.

“Rae, stop stalling and get in here. You can check me out more later.” Jared said, interrupting my thoughts.

I went to remove Jared’s underwear and found myself hesitating. Though I definitely needed a shower,  I found I didn’t want to take them off.

“Dude, come on. I promise, I’ll let you keep them. Just get your ass in here.”

Satisfied with that answer, I shucked his boxer briefs and climbed into the large, glass enclosure with him.

For the first few moments, neither of us spoke and we avoided eye contact. I think the reality of what happened last night was processing. I know it was for me at least. Even my usually so collected mate struggled not to smirk and look away any time our eyes met. Nevertheless, we traded being in the water stream - sharing the shampoo and then the body wash.

Jared broke the silence: “Hey buddy, turn around and I’ll wash your back for you.”

I nodded and did as he said. I shivered a bit as his hands touched my shoulders - their touch acknowledging the connection between us somehow. I closed my eyes and allowed myself to be lost in the feeling of Jared’s hands as they moved from my shoulders to my back then down to my ass cheeks. He took his time and really made me feel like he was taking care of me; taking care of his best bro.

His voice in my right ear: “Rae, I hate to do this but gotta make sure you’re totally clean.”

I didn’t know what he meant, but I nodded once again - trusting whatever he was to do.

I heard the sound of the soap across Jared’s palm as he lathered up his cock. Then I felt his tip right at the entrance to my hole.

This time I didn’t run away or get scared. I was no longer afraid of this monster cock’s invasion of my body. After all, I think it’s quite clear that my ass belongs to him now.

Jared’s sudsy dick pushed against my still sore hole. Despite the aches in my midsection and the pain in my muscles, his 2nd cock invasion of my butt went much smoother. Not saying it wasn’t painful, especially given my soreness from last night, but way easier going. 

A good pressure and the fullness feeling returning as his soapy member stretched out my insides once more. A good stretching. And that wonderful sparkly feeling as he moved his shaft across my prostate. 

I moaned despite myself and heard Jared’s familiar cocky laugh behind me. He leaned in and whispered, “Got to make you extra clean,” and punctuated his statement by ramming himself balls deep into me. Then he pulled almost all the way out and slammed it back in.

My eyes rolled back. I turned my head and whispered, “Jared, I’m sorry to ask this.”

Pulling his cock out of me, he answered, “Ask me anything, Rae Rae?”

“Was that?” I hesitated and then said fuck it, “Was that the only time?”

“You worried I’m gonna fuck you again?” Jared whispered back confidently, and then pressured the head of his cock back into my ass. It was driving me crazy. I felt like I was gonna cum any second.

He moved in really close to my ear: “What’s on your mind, buddy? Just ask me.”

I swallowed. All of the last couple weeks came flooding back through my thoughts. Every moment that built to last night and there was only one question I wanted Jared to answer.

“Jared, could we-” 

Jared thrust his cock half into me.

“What?” he whispered intensely into my ear. I shivered from the eroticness of this moment.

“Could we fuck again? I mean other times. Maybe do more stuff?”

There I spilled it. My statements may have been driven by my edge of orgasm horniness but my desire was clear. If Jared was going to ditch me or beat me up for being gay, now was the time.

He laughed again behind me – a good sign, I hoped. Then ran his hands all over my lower back and felt up my ass again. He grabbed the base of his cock still in my ass and yanked it all the way out of me, then still slick, drove the whole thing back into me until he was balls deep.

I cried out in ecstasy and my cock exploded, covering the glass wall of the shower in spunk as my body convulsed.

Jared held me in place - my ass squeezing his cock. He slapped my ass a couple of times and ran his hands all over me as if taking me in.

“Yeah, dude,” he replied finally, my orgasm being to die down. “I think your ass is going to get a lot of attention from now on.”

“Brilliant.” I said, breathing so hard I thought I’d pass out.

“Starting now.”

To be continued