Bets
#1 of Bets
I'm not a gambling man. But sometimes, a bet is the best way to solve an issue. Like who has the bigger dick.
Me. Obviously.
But Jesse, a cocksure- pun intended- wolf that was only a half-inch shorter than me, thought otherwise.
"No way, dude. Emma said I was huge." His voice cracked with an odd mix of anger and hurt when he said his most recent ex-girlfriend's name.
"So? She's far from being an expert on cock." Thank God we were alone in the locker room, as this is, by far, one of the weirdest conversations I've ever had. It was after school. I had stayed after for one of my classes, and had decided to catch a hot shower since the water heater at home was broken. He was part of the baseball team and had stayed after for a bit of extra practice. Read: whacking off. Apparently, he couldn't do that at home.
But I digress.
"And you are?" Fair enough. For all that I'm gay, I'd never seen another guy hard outside of porn, and I hardly think that counts. "Besides, you know what a slut she is." I had to stop myself from laughing. A week ago he was the perfect love-struck puppy, following her around like she owned him. It was pathetic. Really. I'm not jealous of her. I'm not.
"At least I have one. Unless you want to tell me something about her?" We weren't friends. Not even close. But God I wish we were.
He made a face. And made it attractive. "Ew." He laughed for a second, before turning serious. "You started this, let's get it over with." I didn't. I turned one of the many corners in the locker room to see him sitting on one of the benches with his almost-hard cock in hand. I may or may not have not been unable to stop staring. He may or may not have asked me if I saw something I liked. I most certainly did not say that I would have if he wasn't so tiny.
Maybe it is my fault.
"Wait, a second." I held up a paw to stop him from grabbing his sheath. "I distinctly remember you saying 'I bet I'm bigger than you.' Or something to that effect. So what's the bet gonna be?"
I hoped he wouldn't say something stupid.
My gayness is no secret; in fact, I'd probably faint with surprise if he didn't know. What is a secret is how much of a crush I had on Jesse. So I was kind of torn.
There was a part of me that wanted him to win and have his way with me, but I knew he wouldn't be able to resist telling everyone how he had fucked the cocksucker. With that, any hope of even having a friendship with him would be out of the window. So no.
Another part of me wanted to win and have my way with him, but I knew he would hate me for it. We might be friends if I promised to keep it secret, but any hope of something more would also be out the window. Still no.
The last part of me wanted to forget this whole mess. I crumpled that piece of me into a ball and threw it into the darkest corner of my mind.
No way was I going to miss the chance to see Jesse in his entirety. Read: I really wanted to see him hard.
So I pretty much got screwed no matter what. And not in the way I liked, either.
"Loser gets fucked."
Damn. He said something stupid.
He had this smirk on his face that told me he was sure he was going to win. Of course, he was sure. Unless Emma freaked him into being gay. I couldn't decide whether I'd like her for doing that or hate her for hurting him.
Before I get into nitty-gritty details, I suppose I should describe my self. I'm a tall, thin, quite intelligent, far from athletic, mostly black wolf. And, at the moment, naked.
We both were. Under normal circumstances, nudity wouldn't be a problem as the school required showers for P.E. students whose class was before lunch. I'd had such a class last year. But these were far from normal circumstances. During the year since that class, I'd realized I was gay and formed a crush on the guy in front of me. And said guy had a bit of pink still showing. To say not getting hard was hard is an understatement.
I reached up to finger one of my piercings in thought.
Win or lose and worst come to worst, I'd have the best night of my life, he'd never talk to me again, and the entire school would talk about me and how gay I am. Which wouldn't be much different from now.
Win or lose and best come to best, I'd have the best night of my life and get a boyfriend.
"Deal."
He scooted over on the bench to give us each some room to "work." I sat down, perhaps a little closer than I should have, and he looked up and frowned. I smiled and winked in return and he looked back down at his sheath. He had one hand cupped around his balls while the other danced lightly over his tip.
I looked away and down at my own sheath. Just from being so close to him and the little show I'd seen, I was already a quarter of the way out.
I grabbed my slowly stiffening length and began to rub it as I watched Jesse do the same out of the corner of my eye. Soon both of us were panting and moaning. I don't know about him, but his moans turned me on. A lot.
Minutes passed and we both had leaned back against the lockers at some point, with all of our heads pointing up to the ceiling. I could feel my orgasm building so I slowed my pumping and looked to him. His tongue was hanging out of his mouth and his left leg was twitching ever so slightly. He was damn hot.
He had stopped growing no matter how hard he pumped, so I mentally compared our two lengths. I smirked to myself. I win.
I coughed to get his attention. He jumped in surprise. He looked at me and turned his ears down in embarrassment, the gray of his fur growing ever so slightly darker. I grinned at him and stood up. I shook my erection at him and raised my brows. Still flushing slightly, though it was a mystery whether it was excitement or embarrassment, he stood up in front of me so that our cocks just barely brushed each other.
For a moment we both stood there, neither of us having a plan on how to actually measure anything. However, we didn't stand there long before a flash of insight crossed his face and he reached out and grabbed us both. I'd like to say I didn't gasp with something resembling pleasure and embarrassment, but that'd be lying.
He held his hand still as he inched closer to me. I had to reach out and put my hands on his shoulders to steady myself from the pleasure of our shafts sliding together. Suddenly he stopped and I looked down to see why.
My tip had reached his knot before his reached mine. Quite an ingenious plan. I'm almost embarrassed that I didn't think of it. I say almost because of what happened next.
Upon seeing he lost, if only by what appeared to be less than half an inch, a look of disappointment crossed Jesse's face, before determination replaced it. He twirled to look at the bench before plopping down on his knees and bending over.
My cock jumped in arousal at seeing that fine ass presented to me. Before I could get over my surprise at seeing my crush bent over in front of me my body had reacted. I was behind him with my tip pressed to his tailhole before I gained control of myself. I pulled myself away and was pressed against the opposite wall of lockers before little more than the slightest of contacts had been made.
"Sorry."
He turned to look at me, surprise plastered across his features. "What for? You won. A bet's a bet." And then he turned back to look at the lockers. From my position behind him I could see that his arousal had flagged.
I crawled back behind him. I pressed my own arousal into him and leaned down so that my stomach was flush with his back. I felt him tense below me. He drew a deep breath before quickly releasing it. "Ready when you are," he murmured. His voice trembled.
I pulled back again and shook my head. I was too nervous about hurting him and he was too scared, even if he wouldn't admit it.
"Get up." I tried to keep the waver out of my voice. I failed. "You don't have to do this. I mean, I don't think you'd have done it to me either." The brief look that passed across his face as he stood told me the lie. I felt a flash of anger before tamping it down.
The locker room was divided into three sections: a general locker room for P.E. classes, a sports locker room, and the showers. I left the sports section before he could say a word and headed back to the general area, passing by the showers as I did so.
I don't think I could describe what I was feeling. I'm not even sure I know. It was somewhere between pride and defeat, feeling like he used me and I used him. Now in the general area, I grabbed my clothes and quickly began getting dressed. I heard a noise and dismissed it as Jesse getting dressed in the other room. So I jumped when I felt a hand on my shoulder a few seconds later.
I turned and almost jumped at how close he stood. He held a phone out towards me. A shy smile played across his lips. "Put your number in and I'll call you later. To figure out when I can do my end of the bet." There was a hint of something in his voice that I couldn't place.
Numb with shock, I grabbed his phone and looked down at it. I almost dropped it when I realized that there was a picture of a cock on it. Fortunately, in catching myself short, I moved it and realized it was just in camera mode. I turned the phone around and waved it, showing him it was at the wrong spot.
He had the grace to be embarrassed before grabbing it and fiddling with it for a few seconds. When he held it out to me again, the screen showed an interface to add a new contact.
I filled it out as completely as I could, though I skipped over the home phone. After I was done I handed it back to him.
He just stood there for several seconds, staring at me with a look of indecision. I stared back. He started fidgeting and then, before I could do anything, he threw his arms around me in a quick hug and pressed his mouth to mine. After the quick kiss he leaned close enough that I could feel his breath on my pierced ear.
"I'll see you later, Ian." And he was out the door before I could regain composure.
I decided then that I liked Emma.