Jacking Off With My Best Friend - Cover

Jacking Off With My Best Friend

by Arkham

Copyright© 2024 by Arkham

Coming of Age Sex Story: Troy and I were best friends. When puberty hit all we could talk about was sex with girls, pussy and blowjobs. We watched porn in my room after school. It got to the point when we noticed our large bulges in our jeans, and how it would feel great to jack off. So....we did.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/mt   Teenagers   BiSexual   Heterosexual   Fiction   Incest   Brother   Sister   Anal Sex   Masturbation   Oral Sex   Voyeurism   .

When I was a teenager, I was incredibly horny. Surprised? Of course I was. Any dude is at fourteen. And fourteen was my big year. Puberty transformed me from a chubby boy to a lean, taller “young man”. And my cock got huge! I know how it happened and why, but when it is so personal, it seems like you are the only one going through it. I imagine the same goes for girls.

Yes, girls! I was into girls at a young age. Girls liked my looks. Having a hot, older sister meant I had a girl in the house, a real female other than my mom, to observe. My relationship with Leah, is a whole other story. (You can find that in my story collection.)

After puberty hit, I had my first big orgasm at fourteen. I think every boy has their own “first time”. And it is usually an accidental discovery. Well, for me it was. I was on my bed, on my stomach, semi-asleep, thinking about my sister’s best friend, Sadie, who was just on the other side of the wall that divided our bedrooms. She slept over. She had a hot body and was a bit of a tease to me. She was two years older than me--sixteen--like Leah.

I have a theory that sexual activity and success has a lot to do with proximity and geography. In other words, as the line in Stephen Stills song, “Love the One You’re With” goes, “If you can’t be with the one you love, love the one you’re with.” In my case, it’s the last part of that lyric that illustrates what I’m saying.

I was the only teen boy in the house. My sister and her friend were the only teen girls in the house. So, we could relate on that level. And sexual attraction would be part of the connection we three had, especially between Sadie and me. She tried out her flirting and teasing on me. In her mind I was representing all boys.

So, she’d flash her panties at me when she wore a short skirt. And she assessed my reactions. Now, at the time I didn’t realize this. It’s only now that I do. Seeing her panties gave me a huge bulge and she noticed it. Leah, too. I liked them noticing it. I didn’t cover it up out of embarrassment. Maybe I should have, but our family environment allowed such indulgences. It turned me on to let them see my bulge. My mom saw my bulge, too. (And THAT is another story you can read!)

I was on my bed, thinking about her and had a big, hard on. I started to grind my cock against the mattress as if I was fucking it. It felt good doing that, so why stop? I kept at it and a feeling of bliss and pleasure kept building and building. And then I squirted my first cum load. It was that fast. I was shocked. So, this was an orgasm? I knew what it was, but never knew how it would feel. I liked it. I made quite a mess. I cum heavy. I always have.

From that point on I began stroking my cock several times a day, and the rest is masturbatory history! I’m sure all males have their version of this. Maybe it happened to you--dear male reader--in the shower while washing your hard on. It’s the perfect place to shoot a load in privacy. And there is no mess to clean up. No evidence. Nothing for your mom to discover.

Let me introduce you to Troy. He was my best friend. He was my age, and he also had a sister, as well. Tammy was about Leah’s age, sixteen, but not as hot as her. Nonetheless, she had what any young teen boy wants: breasts and a pussy, if I can be blunt about it. And that was of interest to both of us. We’d share naughty things about our sisters with each other. Quite the boy gossips we were. We’d both had stories of catching them topless or nude and shared those juicy details. It got us very horny.

“Bulge” is another word for a hard on, an erection. Seeing Troy’s bulge triggered some changes in my relationship with him. During our sex talks I noticed his bulge. He noticed mine. I was as curious about his cock as he was mine. “Curiosity” is another word that triggers behavior and certainly triggered ours.

Puberty is a bitch. Let’s face it. You got the pimples, pubic hair and growing pains. Awkwardness, self-consciousness. All normal side effects. But one good thing most males will agree on is “The Transformation of the Cock”. Or, in my case--my cock. It was like one day I woke up, all pimply and weird and had this thing between my legs that wasn’t there before. I mean, it was like I had a hormone injection directly into my penis. It was so much thicker for one thing, and when I got a hard on, well, it was massive. Like a lot of boys, I got out the ruler and measured it from base to cock tip. Nine inches and change. More like nine and a fourth inches! (Damn right I’m bragging!) It was clear to both of us that my bulge was much bigger than his. Troy’s eyes never lied. I always knew how he felt. He became fixated on my bulge.

Whenever we talked about girls at school--seeing their panties under their skirts when they sat spread legged--or about our sisters, we would get hard ons. We’d casually comment, making wisecracks. “I’m bigger than you are!” I’d say in a trash talking tone.

“I wouldn’t want one THAT big. No girl will ever let you to stretch her pussy out!” he said, as if he knew what he was talking about. It made me wonder if that was true. Could that be true? How would he know?

Troy had a mad crush on my sister. I admit that I did, too. Yes, I was conflicted and confused about it. Leah was fucking sexy, had big breasts (38DD) and a killer body. She was captain of the cheer team! Cheerleaders are fucking hot and horny! I knew it was supposed to perverted to want to fuck your own sister. Just tell my cock that! I did whatever my cock told me to do back then. (It still advises me!)

We watched porn. His older brother had some videos we’d look at in his room, or he’d take it over to my house and we’d enjoy all it had to offer! What it offered got us hard. Fucking, blowjobs, lesbian sex, etc ... I caught him staring at my erection. He remarked, “Man, you are as big as those dudes in the videos!”

I took what he said at face value and didn’t give it much thought. I liked him looking at my bulge and him admiring my cock size. It aroused me. I started to have these concerns, though, that we were being “Gay” when we focused on our cocks like that. But, still, it aroused me.

On one occasion we were talking about hot girls we wanted to fuck--including my sister. I had some of her dirty panties to share with Troy. Leah’s pussy-moistened panties! We smelled them as we talked about her. Knowing she had worn these so tightly against her pussy was such a turn on. He shared that he recently jacked off into his sister’s panties! I was very curious about that! What a good idea!

He wanted to show me how he did it. He asked me if I minded that he jack off into Leah’s panties. I could watch. Why would I want to watch him jack off into my sister’s panties? That would mean I’d have to see his dick! And see it hard! (Was THAT a Gay thing? Was that okay?)

I had this feeling in my stomach, butterflies, and my hard on got harder! I liked what he was asking me. I just nodded, and he took that as permission.

He undid his pants and his hard on was barely concealed in his boxers. He looked at me for any last-minute change of mind I might have. (I had no change of mind.) He was sitting and raised his butt and pulled his underwear off from his waist and butt and then to his thighs and then off. His thick cock sprang up. There was ample pre-cum already dribbling down off his cockhead. I still had those butterflies. I liked how his cock looked. It had a nice structure. Even at that age, I could appreciate that. A good-sized cock head and thick shaft. His balls looked big, too.

Watching him stroke his hard cock with Leah’s pink panties and then squirting his load into them, for me, was off the charts hot! (I didn’t feel Gay about it, watching him. In no way am I putting down being Gay. But, in the context of that young age and in that era, it was the worst thing for any straight boy to be thought of as Gay! We were heading in that direction, though, no doubt about that.)

Seeing his hard cock, exposed for the first time was exciting. I like how it looked. But he quickly covered it with Leah’s panties. He stroked and jerked and soon orgasmed! He soaked Leah’s panties. Parts of it that were pink became a darker pink--drenched in cum. He tossed them to the floor.

“Your turn now,” Troy said as he kept his shrinking, but still thick, cock out. I looked at it and saw how it had changed from this steely rod to this softer, relaxed dick, drooling extra cum.

I felt nervous about pulling out my cock but was also turned on at that same time.

This was the first time I did this, exposing my cock to anyone. (Well, okay, it was around that same time that I exposed my new, “puberty cock” to my sister. I got my member out of my underwear, and it was rock hard and throbbing, and weeping pre-cum from its huge, mushroom head. I still marveled at it. It wasn’t that long ago that I had a boy’s small cock, and now this monstrous, man cock! Showing it off to Troy gave me even stronger butterflies in my gut--and balls!

Troy’s mouth was half open in awe as he looked at my erection. (What was he thinking?) I felt so powerful and sexy. I stroked slowly, giving him a show, to reach maximum erection.

“Man alive, Rog, I knew you were bigger than me, but, dude, your cock is so huge!”

He was enthusiastic about it. I liked that. I had mixed up feelings. I wanted him to jack me off. But I dare not say it, because it would be Gay right? He examined every thick, inch of my long cock with watery, lusty eyes. (Did he want to touch it? And should I let him? Hell, should I ask him?)

“Y-you, you, want to, uh,” I struggled to articulate.

“Can I touch it?” he talked over me.

I was surprised he said it like that, but then again, that is how he was. He was never one to beat around the bush. “Go ahead,” I said. I think my cock grew another quarter inch in response to how aroused I was.

I noticed he was hard again. His six incher was bold and arched upward. If he was touching my cock, I should be able to touch his. But for now, it was his turn to touch mine. He grasped my shaft first, firmly. It felt SO GOOD!!! He squeezed it and my cockhead swelled up to full capacity and leaked more pre-cum. He ran his fingers up and down the rest of my shaft and spread my pre-cum all over my cockhead. (Had he done this before with another boy? He was very confident.) “Feels good,” I mumbled, in a state of pleasant shock. He seemed to know how to handle my cock, how to jack it off firmly, to yank it hard and then ease up on it, with lighter strokes, and giving “it” time to respond with more throbbing and pre-cum. He had a look in his face, in his eyes of pure lust.

“Dude, it’s the biggest cock! Girls are gonna love it!”

I was thinking, yeah, girls will love it, even if I stretched their pussies. This was so cool. My best friend can be jacking me off and we can still talk about girls and pussy. (So, it’s NOT Gay, what we’re doing, I don’t think. I overthink.)

The way Troy handled my cock felt unlike anything I’d ever felt. Even touching my own cock and knowing how to jerk it, ease off, and then jerk it some more--didn’t feel as good as the way Troy handled it. This was surprising. This was something I wanted to happen again. I was nearing orgasm after about ten minutes of Troy teasing and taunting my cock! And then it happened. Man, did it happen!

I grimaced, growled and groaned as it blasted out from the depths of my heavy balls. He felt my cock swell as my orgasm was approaching. My cum load shot out powerfully into the air-- three or four feet in a white stream. I might’ve lost consciousness for a few seconds while he kept jerking it to get the last powerful pump out! I’ll never forget seeing my thick cum all over his hands. He had a mature look on his face. An expression I’d never seen before on him.

I noticed his neglected, hard cock and grabbed it. It only seemed fair. The way he made me feel, I just had to make him feel the same way. He was my best friend, and it was the right thing to do. So, I did it. I knew what to do, naturally. I had a cock, right? So, I jacked him off the way I jacked my cock off. He mumbled, moaned and groaned, liking what I was doing. His cock was thick and hard. Not as big as mine. I was clearly a good three inches longer than his six incher, and as thick as his cock was. (Leah and Troy were the first to say out loud that I was huge.)

 
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