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TRUE FIRST TIME TALES

Ashton's First Time Tale

 

This one was sent in fully written and ready. I edited it, with their permission, so that its style and format match all the other stories in the First Time Tales section.

 


 

I knew I was going to be gay about the same time as I hit puberty. I never had any doubts once I started getting erections and an interest in sex. By fourteen boys were all I thought about. Girls were kind of gross and about as sexy as that cardboard tube in the middle of a roll of toilet paper. Tits were as sexy as a pile of warm pudding. Dicks, now, they were fucking amazing. Balls were lusciously soft and wiggly. Boys' butts were so firm and round and alluring.

I had friends and ran around with them like any other boy, until puberty came along and I couldn't keep my eyes off my friends' packages and butts and legs and mouths and... well, I just couldn't risk them finding out I was such a raging homo, so I spent less and less time with my friends and more and more time alone.

By fifteen I really only had one good friend, and two other friends left. Connor was the kind of guy who didn't make fun of guys or act like an asshole. He was decent and kind, and always nice to anyone who was nice to him. I didn't mind spending time with him because I doubted he'd even care if he found out my secret. Jess and Terrence were also pretty cool, and didn't join in making fun of others or acting like assholes. I had illusions that Connor or Jess or Ter were gay, but they liked looking at girls and talking about them, so I was pretty sure they were straight.

The only real thing to do when we stayed over at each other's houses was to stay up late and jerk off to porn, so I'd seen their dicks all hard and red and juicy and squiring so many times I lost count by the time this happened when we were fifteen. I think we started when we were eleven or twelve. Before any of us had pubes or our dicks had grown any. I can remember our little sacks, all smooth and tight, and our little boners. We hid them behind our shirts or coats or a blanket at first, but after a year or so we didn't bother hiding anymore.

Connor was really tall and skinny, with red hair and gray-blue eyes. He's got these amazingly long fingers, and long arms and legs. Long nose, too. He was in my gym class in eighth grade, so I knew he had a long dick before I saw it in private. At fifteen, he had a good six inches that was growing fast, and would end up just over eight inches of lean dick with a round head. Pretty nice balls as well. Not much of an ass, though. It's almost flat and sits kind of high. He's too skinny to call sexy, but he's got a nice face. Connor shot in fast squirts, little shots, but plenty of them. It was always thin and shot pretty far.

Ter was a little short and lifts weights, with dark brown hair and brown eyes. He's got a pretty nice ass. He's compact, with strong hands with short fingers. Nice ass. Decent balls, but a pretty short dick that's nice and fat. Really muscular arms and legs. Ter came kind of odd - just sort of oozing it out in several gushes like two seconds apart. Really thick stuff. Not very much either.

Jess was sort of slim and average, with sandy-blond hair, blue eyes, awesome lips, a really nice ass, and a pretty average face. Jess would fit into any crowd, really, but he's a brainiac, so he's in with us dorky dudes. He had a pretty average dick and balls, but he could shoot more cum than the three of us together. Well, I could blast a nice wad, too. But I was always so turned on when we jacked off together that I couldn't help but blow a big wad no matter who I was jerking off with.

My high school has about four-hundred kids in it. It's a very small town in a mountain valley surrounded by even smaller towns, all surrounded by farms in the valley. There was nothing but forested hills and mountains around all of that. If there were other gay dudes at my high school they were keeping it as well hidden as I was, and I had no idea how to search them out. Being gay is supposed to be so open and free in 2014. Hah. Not in the little shit-hole where I lived until last year. To make it even worse, almost everyone was very religious.

So, the summer after freshman year in high school, ninth grade that is, one of my friends, Jess, went to this summer camp for science and tech. He's a brain, what can I say. He's kind of cute, too. Anyway, he comes back and a few days later he comes over to hang out. There's not a lot to do in that shitty little town, so hanging out at a friend's place is pretty much it. Connor is downstate with his family for the weekend, and Ter is home babysitting his two little sisters while his folks are over in the city for a wedding weekend. That left Jess and me with just each other.

Now, Jess had been telling us these stories about things that went on at that science camp. Seems that nerdy girls are freaky girls, when they're around a bunch of nerdy boys. Jess claimed he lost his virginity the first week, and got blow-jobs and pussy almost every day for the rest of the two months. We didn't believe him at first, but he sure had a lot of details.

One of those details was that a guy could get off without the chick even touching his dick. He claimed that this one girl used her finger up his butt and got him off that way. Well, first she was blowing him for like the fourth or fifth time that week, and using her finger up there, but this one time she sucked him for a couple minutes, then put her finger up there, and stopped sucking him. He said he lasted forever, and it felt fantastic, and after a very long time, he had one of the best orgasms he'd ever had.

Well, we didn't exactly believe him, of course.

So, he was over on this Saturday a week after he'd been back, and we weren't expecting any of the guys to be around, and my little bro was staying over at a friend's for the night. My folks went to bed about eleven, normal for them. We had internet in our little shit-hole of course, but it was pretty high in latency and made gaming pretty impossible. There was only one cable company that served us, so that was our only choice other than satellite internet, which was even more laggy but had higher bandwidth.

Still, watching porn was no problem. You just had to wait a second or two for it to start streaming. Of course, we were watching porn that night. Jerking off with a friend was no big deal. I'd beat the meat with Ter, Connor, and Jess more times than I can count. At first we would have a blanket or coat over our shoulder to hide our dicks, but after a while we stopped bothering with that and just went at it. I was more than fine with that. I enjoyed seeing the guys jack off at least as much as watching the videos. Well, probably more. Seeing my friends dicks, their balls, watching them jack it, and seeing them cum was fucking hot!

We had been watching porn for a while and were getting good and worked up. We'd found out a long time ago that taking some time to 'warm up' first made the finish a lot better. We were watching this one video where the chick was sucking a guy's dick, and she slid a finger up his ass.

Jess goes, "See?"

"What? Oh, the finger thing?"

"Yeah. I told ya."

"Yeah, no shit. I've seen chicks do that in other videos."

"Yeah, but I'm tellin' ya, you can get off from just that."

"There's no fucking way," I laughed. "You gotta do something to a guy's dick or he isn't gonna shoot off. Unless he's a total virgin or something."

"No. I'm tellin' ya, that finger thing can make ya cum."

I was interested, to say the least. I mean, anything having to do with making me cum was interesting at fifteen. I was trying to think of a way to get him to show me.

"You're good and boned, right?" he asked.

"Yeah," I said, feeling my hard dick in my pants.

He was massaging his too. We had been for at least half-an-hour by then.

"I'll bet you your IPad that I can make you cum and not even touch your dick. Just by doing that," he said, nodding at the screen.

I was like, Oh shit! I wasn't sure, but he seemed to just have offered to stick his finger up my ass! And get me off. Or try to, anyway.

Hell, I didn't care if he was right or wrong about it getting me off, I was willing to let him stick his finger up my ass anyway! I was pretty sure I'd cum just from his finger in my hole.

I was going to take his bet, but I had to make it look like I was hesitant and unsure.

"Well, what if you can't make me shoot?" I asked.

"What do I have you want?"

 


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