TRUE FIRST TIME TALES
Wallace's First Time Tale
Not to brag, but my dad owned a pretty big company. He wasn't the CEO, he owned it. It had stores in almost every state, and more than one in most. He insisted on spending time at every store every year. Pretty much a week at every one. Stores close enough together would split a week. So he was away almost all the time. We'd see him once a month for a weekend, and for less than a week around holidays.
I had an older sister and two younger ones. I was the only boy. Sis was barely a year older than me, but both my other sisters were more than ten years younger than me. So dad was always gone, and mom had Sis and her two sisters. I pretty much spent my time alone.
We were rich enough that we all went to a very exclusive private school, and since we lived in a major city, it was within walking distance. And the tower we lived in was tall enough that walking down it was almost as far as walking to school. If we lived on the other side of the tower, we could have looked down on the school. But instead we had views to the north and west. Secure building, all that. So what friends I had lived in the building and went to my school. That wasn't many. Five. Two my age and in my grade, two older, one younger. There were other kids too, but I wasn't so much friends with them. Neither were most of my five friends. One of the older ones was a girl, the rest were guys. Liddy was more boy than Mike, who was one of the younger of us. He was kind of a wimp, and the most nerdy. She could kick most of our asses.
We pretty much lived with each other. Schooldays outside of school were spent at home with either tutors or 'a family' if we had one. Liddy, Case, and Tate did, but Mike, Daniel and I were latchkey kids of various flavors who were still expected at home for dinner anyway. So it was mostly Mike, Daniel and me after school on schooldays. Our weekends were mostly all six of us in the same bedroom from Friday night to Sunday night. And part of holiday breaks, and some of summer break. Around four to six times a year differing vacations split us up for varying amounts of time into various groups. Naturally, summer break meant all kinds of break time from each other in all kinds of ways.
When I was twelve, I had seen porn on the internet and been playing with myself for a while. Like all my friends. Well, Liddy didn't talk with us boys about that stuff. She said we were gross when the topic came up. So I knew all the guys were doing it. Even dorky little ten-tear-old Mike. And the stuff on the internet back then was mostly just images of women or couples. Video was still pay-walled and slow. Though you could find snippets of videos for free in certain places.
My sex drive was probably still on idle, if you know what I mean. I'd seen porn and learned how to jerk off, but it wasn't something I actually thought about doing. If I was bored and it was late or I was alone, I'd look at some porn and play with it. A few times a week? It was just a fun thing to do. I wondered what blow-jobs felt like, sure. Us guys had even talked about what it must be like, and how we'd heard it felt great, and the guys on the videos sure looked like it felt good. But it was just a curiosity, there wasn't much sex drive involved.
I did know that Daniel had pubes. He was older than me by a year. He'd told me in secret, but I was pretty sure he'd told the other guys too. He'd even pulled his pants down far enough to show them off. Just a few hairs around the very base, but he did have hairs. And I could just see enough of the base of his dick to tell he was growing down there. He'd told me that a few months before. He said he was over five inches, but I didn't believe him. He also claimed he shot sperm, but I wasn't so sure. He said it made it feel way better when you jerked off. I didn't think that was possible either.
So I was twelve, about to start seventh grade, and back from a month vacation in paradise with my entire family. The other guys and Liddy were all away on family vacations, except Daniel, who was back from his. They had left at different times for different lengths, and this was the first week of several that it was just Daniel and me. He was a year older at thirteen. He was over at my place one day, and he came up with this idea. We were playing a game against each other on my XBox in my room. When I say my XBox, I mean, my XBox. Not an X, not a One. An XBox. The 360 wasn't even out yet.
"You want to play the next game for a blow-job?"
Just like that, right out of nowhere.
I was like, "What the fuck?"
"Looser sucks the winner's dick," he propositioned, looking at me.
Serious, too. Not joking around.
"You'd really suck my dick if you lose?" I asked, knowing he wouldn't.
He nodded and said, "Yeah," at the same time.
"No you wouldn't."
He looked at the door. I didn't know why. Mom was mostly pregnant and almost never came up around my bedroom or my older sister's room. The maid wasn't here today, and the morning assistant had already left after making breakfast and clearing up and them making lunch. Besides, now that my little sister was walking around and opening doors, I kept my bedroom door closed and locked all the time.
He looked back at me. He looked so serious.
"When I was staying with my cousin in Chicago, we did it."
"What?"
Suck dicks? No way. Wait. Boy or girl cousin? Sex? With a cousin?
"We sucked each other off."
That answered most of my questions, and left me stunned.
"You sucked your cousin's dick?"
I was shocked.
"Yeah. It was awesome!"
Holy shit! No fucking way!
"I mean, getting sucked was! Sucking it wasn't all that great, but it wasn't all that bad. Honest."
He was smiling like crazy. He kind of looked crazy.
Then he said, "So if I lose, I'll suck your dick. Will you suck mine if I win?"
He was making it like a dare.
But I didn't dare. Suck a dick? And his was getting bigger. And he had pubes. And he said he shot cum.
"No."
And I meant it.
"Okay. But I really want you to see what it feels like. So can I?"
"Suck my dick?"
"Yeah."
I thought about it. I figured it wasn't too gay. It was just a friend. And it was just to see what it felt like. And I really wanted to see how good it felt. And it was only Dan.
"Well, okay."
"Cool!"
He looked really happy. He dropped his controller and reached for my pants. I sort of jumped back a bit in surprise. I mean, geeze. I'd thought he meant after I'd won the game.
He said, "Like my cousin told me, if you don't want to say so."
"No, it's cool. I just, though you meant, if I won."
He sort of laughed, then said, "We can wait until I kick your ass if you want. Or just skip your humiliation."
"Ha-ha. I win almost half the time."
"Yeah. So, you wanna wait until I win first?"
No, I didn't. I wanted to see what a blow-job felt like.
"No, that's okay."
I put my controller down, and he was already getting my pants open. By the time I had my hands at my sides again, he was pulling my pants and underwear down to my knees. Then he was over my lap. I felt his mouth wrap around my dick!