Author's note: Thanks to Chief Hal for his proofreading assistance.
All characters in this story that are involved in any sexual encounter or scene are 18 years or older.
I couldn't believe I was doing this. Hell, the only reason I agreed to the dare, was because I knew there was no way Chris was ever going to manage his dare. Neither of us are anywhere close to being part of the "in" crowd. We were part of that typical group of high school students that were more concerned with grades than sports. As a result, we were not socially popular, but we were almost always in demand to be study partners for the girls that wanted to skate by without working any harder than they had to. It'd been that way since my sophomore year. Now as seniors, we're closing in on graduation, and just as in demand as before, this semester by those same girls, in chemistry class.
Chris was partners with Mandy Long. He had a crush on her, of course, but I doubt she had any interest in him at all, besides what he could do on homework for her, that is. I told him flat out that was the case, but he refused to believe me. Instead, pushing me into a bit of a bet. To prove she was interested in more than just his brain, all he had to do was to convince her to drop her pants for him and let him lick her pussy. If he could show me a picture of that, then I'd strip and jack off in the girls' locker room, in front of my chemistry partner, Becky Williams. I knew Becky had no interest in me other than my brain, but I wasn't worried; simply because, there was no way Mandy was EVER going to drop her panties for Chris, no matter how much he asked her.
So here I was, sneaking into the girls' locker room during the football game, one of the few times the locker rooms are unlocked at night, with little chance of anyone coming into the locker room. The cheerleaders would all be on the field until the end of the game. Becky wasn't a cheerleader, but she was still one of the hottest girls in school, or at least I thought so. The locker room was indeed empty when we slipped into it, we being me, with Becky following close behind.
"Now what?" She asked as we stood near one of the rows of Lockers. "I agreed to sneak in with you, so you going to tell me why now?"
I turned to look at her. "Would you believe me if I told you I had to get undressed and you've got to watch?"
"Say what? Are you serious?"
"I'm afraid so. I made a really lousy bet."
"And you lost?" She asked with a shocked look. "Oh Jesus Billy, I don't believe you. I'm risking getting suspended so you can pay off on a bet?"
"Well um, sorta. You see um, you're part of the bet."
"ME?! I'm not part of any stupid bet."
"No. You um, you don't have to do anything, you just have to watch and take a few pictures."
"Take pictures? Of what?"
"Me, undressed." I answered, feeling my face grow hot with embarrassment.
"Seriously? You got me to come in here with you so you could flash your junk in front of me?"
"Yeah, um, not hard, right?" I said quicky, blushing as I said it. "And um, on top of that, well, you sorta get to watch me jacking off."
"You're not serious!"
"Unfortunately, I am. The bet was to have you photograph me jacking off, naked, in the girls' shower."
She laughed. "Holy shit Billy. That's why you wanted me to sneak in with you? To watch you do that?"
"Yeah, 'fraid so."
"I don't believe this. I mean we can get suspended for this. I can't afford that! I only came as a favor because you spend so much time helping me. But this?"
"I know. But if we're quick..."
"Quick? How do you do that quick?"
"I'm not asking you to get undressed or anything. If we get caught it's only me without clothes. Trust me, it won't take long and I hate to welch on a bet."
"But this? You're assuming I actually want to see you do that!"
"All you have to do is take a picture with my phone. Come on. I've already offered to do your homework for two weeks."
"Okay. Make it four weeks and I'll stay!"
"Deal!"
"Better get to it then. I don't wanna get caught in here with you."
I walked to one of the benches and started undressing. I'd never actually been naked in front of a girl, except my sister. So, stripping in front of Becky, was more than a little awkward. Even more awkward to turn around and face her with a half hard dick, trying to cover it with one hand, my phone in the other.
"Well, um, yeah." She said, taking my phone, but not taking her eyes off my crotch. "Um, maybe we better get started?"
"Yeah. We better." I agreed, feeling horribly embarrassed. I turned and walked quickly to the showers and looked around. "Um one place is as good as another, I guess."
"It would seem," she said, following behind me. "Yeah." I said, taking a deep breath. "Never done this in front of anyone before."
"Never watched a guy do it either."
I nodded and moved my hands. I leaned my back against the wall and closed my eyes. I wrapped one hand around my dick and started stroking it, even though it was still pretty soft. "I usually do this to something to watch." I said, as I tried to picture Becky taking her shirt off.
"Yeah?"
"Don't girls do that?" I asked.
"You mean jerk off? Not exactly."
"No?" I asked as I stroked myself harder. "How do they do it?"
"Are you serious?"
"Yeah."
"We, um, we usually rub our clit with our fingers." She said sounding a little breathless. "What do you think about while you're doing that?"
"This?"
"Uh. Yeah."
"Honestly, I'm, uh, I'm imagining you undressing."
"You are?"