all actors and depictions are fictional and over 18.
We were best friends. I'm pretty sure we were both straight but we've done a lot of experimenting with eachother over the years. It started out innocent, I watched my first porno at his house when I was 18. I was a late bloomer, I hit puberty later then most guys and I wasnt really interested in girls growing up.
My dad kept a much stricter watch on my internet use, at J's house we could do whatever we wanted.
We grew up together, we were comfortable talking about anything. I had never thought about anything we did before as gay, I assume girls do the same experimenting when they're alone. It wasn't until I was seriously considering fucking my best friend in the ass that I wondered if I could be. But I've done the regular stuff with girls and I really like that, but they don't want it in the butt and this was hot too.
It started about a week ago, we were texting about my girlfriend A, I wanted to stick my cock in her ass and she said no. I told J about it, he texted back "I bet it hurts, so I get it. I've always wondered what it feels like."
I jokingly said, "it can't be that bad, I've had some pretty big poops and that's not bad. I should try it just so I can tell A it's no big deal."
"Lol let's do it." He typed.
I replied with a thumbs up.
It was a joke. Obviously. But I started thinking back to all the things we did when we were discovering our bodies. He was the first person other than me to ever touch my hard dick. After ball we used to walk back to his house until my mom could pick me up, J lived by the school and I was out of town. We went into his room and logged onto his computer, he had left a porn page up.
"Your parents let you watch that?" I asked, trying to get a closer look.
He laughed, "ew no they don't know. I'm usually more careful."
"I mean my dad keeps a blocker on these websites, he knows if I even try to look at this stuff."
J moved out of the way so I could look through videos. I read out a bunch of titles and we laughed at the names, trying to guess at what things meant.
"What's a BBC?" "Why is there so much step mom stuff?" I clicked on one that said "double fisting her ass". it was too much. J took the keyboard and typed in blow jobs and we watched a video of a woman sucking and fucking a man while her husband watched and jacked off from a nearby chair. After probably three minutes of the video J looks at me and says, "man are you hard?" I looked at my crotch, I was so embarrassed. I tried to move it around in my shorts to hide it. "Don't worry dude, you can't watch porn without getting hard." I noticed he was holding his cock that was under his gym shorts. His hand covered it but I could see the outline of of his cock, he was clearly erect. He smirked and kept watching the video. After another few minutes I looked down and saw he was stroking his cock, still over his shorts. So I did it too.
Neither of us came that time, but this became a weekly ritual. I never really masterbated before watching that first video. I played with myself a little but I never came. I would get close and chicken out before the finish. But the night after we watched porn together I finished. I didn't know what to expect. I stroked my dick thinking of the video, thinking about the woman sucking a random dudes cock, how her husband hard as rock just watched as his wife got drilled by some guy. When I felt the tension starting to build I tightened my grip on my cock and pumped harder thinking of burying my cock in that whore, I felt like I had to pee, I let it happen, and I did pee. Or I thought I did. Cum shot out of my cock and covered my bed in front of me. "Fuck" a said as I ran to get Kleenex, a little disoriented and light headed.
I told J about it the next time we hung out. He laughed and said to keep tissues or a sock nearby. He said I could try spitting on it for something different. He pulled up the porn page again and let me look around. We found an anal video, there were two chicks, one with her head down and ass up, the other chick kept putting different sized toys in her ass.
I looked to J, he was rubbing his cock again, I did it too. He looked over at me and pulled his hard dick out of his shorts. It was my first time getting a real look at it. Mine was a bit bigger than his. I was uncircumcised, I think he'd been cut, his head was a lot more prominent than mine. I took mine out too. He looked at it, then looked back into the video, and we both jacked off. A few minutes later after the second girl had started using her fingers on the first girl, she started with one, then two, then three. It looked like she was working her way to getting her whole hand in but was taking her time (it wasn't as sudden and gaping as the first video I put on) J speeds up, he grabs some Kleenex on the desk and holds it to the tip of his dick as his body convulses and his hand slows.
"Dude did you just cum."
"Ya." He smiled but looked a little embarrassed, his face was red and a little sweaty. I didn't want to make him feel bad so I kept watching the video and jacking off. It was only another few minutes before I came. I started feeling the tension build so I grabbed onto the desk with my free hand. He handed me some tissues and I shot my load into it. It was intense, I felt so relieved but also a little ashamed and embarrassed. We looked at each other awkwardly and laughed again. Just a couple friends having a good time. This went on for awhile, sometimes we would race to see who would finish first. It was a few months before we touched each other.
We often talked about how good it would feel for a girl to finally touch us. I was starting to date A, and he was crushing on a girl who walked home with him after school. He told me they've kissed, he's felt her boobs over the shirt and she grinded on him a little. He said if she touched his dick he would probably cum right away and he didn't want to disappoint her.
"I'm more worried I'll be so nervous I won't get hard."
"A's so hot, there's no way you'd be soft when you see her boobs."
I blushed and looked away, "Sometimes I'm hard in class when we take notes and she's got her tits pushed up on top of the table, they're squished together and I really want to put my fingers in there."
"I've felt boob. I can't wait to feel pussy." J said longingly.
The next time we walked home after ball Js crush M walked with us. When we got to her house they kissed and J groped her boob. She went inside and he kept walking with me with a big goofy grin on his face. I looked down at his shorts and could tell he had a semi. When we got to the computer he typed in POV and we looked through videos of standing guys looking down as naked girls made them cum.
"Do you think it's better standing?" I asked part way through the first video.
"I don't know." He stood up. We usually sat in chairs at the computer (he had a swivelling office chair and I used a chair from the dining room) his cock was now a few inches from my face.
"Dude your dick is in my face." He laughed and said sorry. He didn't move though, he slowly strolled his cock, I could see it beside me out of the corner of my eye. It had never been this close to me, I turned slightly to try to get a subtle closer look, that's when he pulled it to the far side and swing his hips back so it slapped me in the face.
"Whoa!" I jumped back and yelled, but it was pretty funny, we both laughed and he sat back beside me. I didn't say anything but he got a bit of precum on my cheek.
"It won't be long now before M will be touching your cock. A wants to move slow. I hope I get to kiss her on the next date."
