Double or Nothing

There was a pause. He didn't answer why he had that bulge in his pants. I took that to mean that I had guessed right -- that he was getting hard right now because he had been imagining himself walking naked in the woods, and more specifically lying down in the soft undergrowth and masturbating himself here, outside, in the middle of nowhere.

"You owe me a pack of smokes, and a soda, remember?" was all he said.

There was thus an unanswered question between us as to why, after we both watched this unknown guy stroke his cock to orgasm, my little brother suddenly had an obvious erection.

A wicked thought entered my mind. I thought about the fact that I had convinced my little brother to come and watch the streaker do whatever he was going to do by promising to buy him a pack of cigarettes and a soda. Now, presumably for the price of the cigarettes and the soda, we had watched, or at least I had watched, while the guy shot his cum on his own bare chest in the afternoon sun.

But there was still the matter of my little brother's embarrassing erection.

"You want to go double or nothing?" I teased him.

"What do you mean?"

"Well, I have a joint in my purse back in the car," I explained. "If you whip out your thing right here and stroke it for me, I'll let you have the joint, plus the cigarettes and a Coke. If not, I'm going to smoke it by myself."

"What? No way!" he exclaimed. "Forget it. Don't be ridiculous." I immediately wondered if I had gone way, way too far. We were brother and sister, after all. But I wasn't asking him to touch me or to, you know, do things with me. This was really just like the show-and-tell games that I was sure all brothers and sisters do, right?

Oh, what the hell did I know about what all brothers and sisters do?

But I was insistent. "Come on," I wheedled him, "it's really good shit, you're going to get so high, and besides, I already know you do it. What's the harm in showing me?"

He was still shaking his head. I went on, "come on, I promise I won't tell anyone, ever. Come on, you can do it for me. Please?"

Silence. I smiled at him with my best big sister smile. "Please? If you don't, I'll tell Sara that you got a stiffy watching a naked man get himself off in the woods while I was there." I was pulling out all the stops.

Again, silence. Then, my little brother surprised me.

"Fine," he said.

"But you have to show me yours."

Whoa, little brother! Wants to see my girlie bits, does he? Now it was my turn to blush. At first, I thought, that this wasn't going to happen. But then I thought that I not only was going to get to see his, but I was going to get to watch him doing the most private act with himself. For my part, I could just pull my pants down a little and keep my legs together and it's not like he was going to see much down there, anyway. Just my wispy little blonde pubes and those were practically invisible, as I knew from standing in front of the mirror in my room, waiting in vain for them to get full and thick like Mom's. He, on the other hand, was going to show me his engorged penis, and how his own hand rubbing it could give him sexual pleasure, and that was an unspeakably hot idea.

I screwed up my courage and made up my mind. Or maybe more honestly, I let my desire, sparked by secretly watching the streaker masturbate and further stoked by discovering that my brother had an erection right here and right now, take control of me.

"It's a deal," I blurted, before I could have second thoughts. Oh boy did I feel the blood rushing to my cheeks when I said that.

We just sat there for a moment without moving. "Well, come on, you go first," I insisted.

"No way," he said again. "We do it together." He paused. "On three. One..." Sitting there in the woods, his hands went to his belt, but stopped without undoing it. "Two..." he stretched out the word ridiculously as he unbuckled his belt. I wasn't wearing one, so I made a show of popping the button of my jeans, following his lead by remaining seated. He opened his own button, too.

"Three!" he exclaimed, and at at the same instant we thrust down our zippers, stuck our butts in the air and pushed our pants and underwear to our knees. As I remember that day so long ago, I think, thank God they've since invented boxer briefs, because, of course, my baby brother was wearing the universal tighty whities of 1974 under his jeans. Not that my powder blue panties were anything special, but at least they had some color.

Struck by a sudden rush of modesty, I drew my knees together and slightly to the side to shield my private place from my little brother's eyes. In the meantime, there was no hiding the fact that he now had a full-blown erection, as his stiff penis bounced free from his retreating clothes. I had been a little surprised that he agreed to put on this little private show for me, but judging by the way the veins stood out on his thick and rigid penis, he must have been in serious need of relief himself, and fast.

I cleared my throat and tore my eyes away from his bobbing member and looked him in the eye. He looked away, blushing.

"Go ahead," I whispered, trying to sound as matter-of-fact as I could. "Show me how you make yourself come."

He said nothing, and still looking off into nowhere he hesitatingly moved his right hand toward his stiff penis and held it for a moment at its base. "Oh, yeah," I encouraged him, "stroke it."

I guess I shouldn't have been surprised to find that my brother had a different way of masturbating than the streaker did. Unlike the different ways of stroking that the naked stranger had done, Jordan just gripped it up near the head between his thumb and one finger, sort of like the way you hold a pencil, and massaged it up and down, always staying close to that spot underneath near the tip, where it looked like a lot of nerve endings must come together.

I sat there mesmerized, watching my brother touch his own erect penis, and a question popped into my head and I blurted it out. "What do you call it?"

"What do I call what? Doing this?" he asked.

"No, what do you call your... you know, your penis?"

He kept stroking it, not seeming to vary the touch or the speed. "Well, I don't have a name for it, like 'Raymond' or anything, if that's what you mean," he replied. This got a giggle out of me.

"No, what's the word you use for it? Nobody calls them 'penises,' do they?"

"Oh, well, yeah, I mean no." He paused, still looking at my bare legs. "It's a 'dick,' ... and when it's hard like this, it's a 'boner.'" He continued to stroke it while I watched.

"Do you ever call it a 'cock'?" I asked.

"No, that's pretty crude. I don't think I've ever used that word." He looked down at himself as he continued to give himself pleasure down there. Then he looked up at me. "You know, this isn't fair," he said, "you have to open up your legs at least a little. Right now I can't see anything."

I didn't want to do it, but I had to admit that he had a point, so I decided to grant his dirty little wish. I wiggled my jeans down a little further to make it easier, and keeping my feet together, I pulled them up closer to me so that I could bend my knees and open my legs a little for him. I found that, in this position, I had to stretch one arm out behind me to keep my balance, and I'm sure that stretching back this way made my half-naked pose look more dirty and seductive for him, not to mention anybody else who might happen to be near and see me exposing myself like this to my own kid brother.

I tingled, knowing that he was looking straight at my crotch (only fair, as I had been looking straight at his, after I had bribed and teased him into masturbating for me). "Lift up your shirt a little bit," he said. I wondered if he was going to ask me to flash my chest at him, which wasn't going to happen, but I just tugged it up across my belly for him a little bit, to give him a better view of what lay below.

As I parted my thighs for him, I was sure he could see the unmistakeable signs of my own arousal, which at this point I would have to describe as "extreme." I could smell my own scent and I wondered if he did, too. What would he think, smelling his own sister's wet desire? I desperately needed to get to my room alone and take care of my own little problem. But, damn it, that would have to wait all the way home. I can assure you there was no way I would ever, ever touch myself down there with someone watching me. I simply could not imagine doing that while any man was watching it, and especially not my own brother. I nearly moaned in frustration as I willed myself to wait.

I could tell that he, meanwhile, was very close to his climax. I remembered how the streaker had squirted his cum on his own chest and then, as far as I knew, left it there when he got up and walked away. That in itself was one of the most nasty, dirty things about what we had secretly watched. But my brother still had a shirt on, and it wouldn't be a good thing for him to walk into the house in front of Mom and Dad with semen stains stretched along the front of it. He needed to do something to keep that little mess from happening, and I had an idea.

"When you're ready to, you know, finish, you should stand up and point it away from us and, you know, let it go on the ground," I suggested.

I don't know if it was the better view of me that I had just given him, or if it was his big sister talking frankly to him about ejaculating onto the open ground, but one of the two or both seemed to have pushed him to the brink of orgasm. He struggled to get to his feet in time, made harder by the fact that his jeans were still around his ankles and one hand continued without interruption to caress his stiff penis -- his dick. He held the bottom of his shirt up out of the way and arched his back and groaned "oh God, oh!" His whole body seemed to spasm once, and then I watched as stream after long stream of white milky fluid shot out from his dick and painted the low green underbrush before him as his hand continued its gentle rhythm on himself. The first long ropes of his orgasm must have gone three or four feet in the air before arcing downward and splashing with a quiet "splut" sound onto the underbrush there by the side of the stream. Once he started to climax, he didn't swear out loud like the streaker had. He was obviously trying hard to keep quiet, and the result was that he gasped a few ragged breaths while he finished.

When he was done, I noticed that he had succeeded in keeping from making a mess except that one thin string of semen stretched from the tip of his penis to the inside of his underpants, and there was a little shiny wetness on his finger, which he wiped against his softening penis before letting his hand fall down do his side. There was no way to clean up the strand of cum in his underwear now; he was just going to have to pull them up and put up with a little stickiness on the way home until it dried. I wondered if there was any way that Mom would be able to tell what it was when she did his laundry, but I figured I would never know.

Once he had finished, my brother quickly pulled up his clothing and started adjusting his belt, all the while appearing to make a very intent study of his own shoes. I could see that his downturned face was a bright red. I knew how he must be feeling right then. I wanted to ease that feeling for him, out of gratitude for the terribly naughty thing I had just made him do. "Wow," I said, "that was incredible. And that was a lot of stuff you had in there. You probably could have hurt somebody." We both laughed. "Thank you, Jordan," I continued, putting my hand on his arm. "Now, let's get back to the car and get you that joint."

On the rest of the way home, we didn't talk about it again. In fact we were both quiet, apparently lost each in our own thoughts. It was an incredible thing he had just done for me, and I thought that overall, the whole afternoon had given me some ideas to try in bed with a lover someday. But I just assumed quite naturally that nothing like this would ever happen again. I smiled the rest of the way home.

My brother and I gradually relaxed around each other as the days went by, letting our little game, as I thought of it, fade into the past.

That was, until the next time that we both happened to have days off from our summer jobs.

I woke up after our parents had already left for work. I went into the kitchen for a glass of water and saw that they had left a list of chores for us to do before they got back.

I scanned the list and then took the glass of water back to my room to get ready for the day. I quickly noticed there was something on my dresser that didn't seem right. Focusing my sleepy eyes, I saw that it was an unopened bottle of Coke, just starting to show beads of condensation in the already-warm summer air. Next to it was an unopened pack of Newports -- my brand, as opposed to my brother's favorite Marlboro reds -- and there was something under the green box of Newports.

It was a folded piece of paper. Inside the folded paper there was a joint, rolled in my little brother's usual ridiculously careful style. I remembered that these basic items represented the "bribe" I had paid my brother to get him to masturbate in the woods that day while I pulled down my own pants and watched him. And then I noticed that, on the folded paper itself were these words, written in my brother's distinct handwriting:

"Want to go double or nothing?"