The boys quickly and efficiently formed a circle. Obviously they weren’t newbies at this.
“Shawn and Austin. You’re both confined here by a circle of your peers, and if you try to escape, you’ll forfeit the match. If you forfeit, you’ll become community property. Not the sole property of the winner, but the fuck toy for life for all of us. The loser will lose all his friends, his status, and his manhood.”
“Understood,” I said.
Austin just nodded, obviously not at all worried about the prospect of losing. His smug confidence only enhanced my determination to win, and to humiliate him thoroughly. To show not just him, but this whole school, the consequences of bullying.
“Both of you strip,” he ordered.
As we did, he continued speaking. “Shawn chose kickboxing, and I’ve added a stipulation that you’ll both be covered in oil to make it a little more interesting. And the goal, simply put, is whichever of you lodges his dick in his opponent’s pussy is the winner. Is that clear?”
“Yeah,” I said, already naked.
Someone handed Andy a bottle of baby oil, and he poured a torrent of it onto me. I rubbed it all over myself, while my cock quickly grew.
“Shit, he’s already hard!” someone cried out.
“Easier to slide into Austin’s pussy that way,” I replied.
“You’re so fucked,” Austin growled, not appreciating my humour, even as he startled when he glanced at my much larger cock.
“I win in that department too,” I smirked.
“Too bad you’ll never get to use it,” he said.
“All right,” Jeremiah said. “Face each other.”
We did.
“To be clear, if I blow the whistle, you both freeze.
We both nodded… while glaring at each other.
“I won’t ask you two for a good, clean fight, since I’m certain this won’t be one,” he added.
We nodded again…not breaking eye contact.
“All right, begin on three. One two, three,” he said.
We immediately began circling around each other. He was looking for an advantage, but I was just allowing him a few moments of self-confidence before I pounced. The boys were all cheering and calling out the grotesque things they thought were about to happen to me. “Get ready for the train,” and “Your backdoor’s about to get fucked,” and “You’re about to really be a pussy, you pussy,” and “He’s going to break you in two.” Everyone except Andy was cheering against me. Although I did glimpse out of the corner of my eye a late arrival… Brian had shown up.
After about thirty seconds of a useless circle jerk, I surprised him with a sudden kick to the face. As in my short body leaped into the air like a high jumper, and I kicked him right in the nose!
There were gasps from the crowd.
“Lucky shot, faggot,” Austin said, shaking his head, clearly caught off guard by my sudden attack.
“Get him!” someone called.
He tried to kick me, but I easily slapped it away.
He tried again, and I blocked him again.
Knowing he’d try again, I was ready. And when he did, I blocked him, and then immediately leaped up, spun around and kicked him right in the face, using what’s called a roundhouse kick for obvious reasons. Then, before he could recover from that first kick, I landed and spun like a tiger in the other direction, and kicked him again with my other foot.
He fell flat onto the mat, not unconscious, but obviously stunned.
As the crowd gasped in shocked silence, I went for the win by picking him up and pinning his back against my chest, one arm around his neck, and my hard cock knocking at his backdoor.
“That was too easy,” I whispered in his ear, as I held him in a lock I knew he’d never be able to break. I’d immobilized much larger men, and brought them to their knees with this hold.
I held him there, savouring my inevitable victory, allowing him to try to break free, allowing him… briefly… to think he still had a chance. I wanted to savour his emerging panic as he shifted from confident asshole to cringing victim pleading for mercy.
He fought against me with all his might, but I held him where I wanted him easily… this hold sapping very little energy from me, but usurping all of his.
For the first time, someone cheered me on… it was Brian, calling out. “Take him out, man.”
A second voice agreed, “Yeah, Shawn, break him.” Maybe Andy. Which used up my entire collection of friends around here.
Then a third voice, “Go for it, Shawn!” Whoever this guy was, he sure hadn’t been rooting for me until now. He’d switched sides!
As Austin kept struggling to break free, my dick rubbed against his asshole.
He whispered to me, “Please let me win. I’ll pay you.”
“I don’t think so,” I whispered back, loving to watch his growing realization that he was about to lose everything.
“I’ll come to your room and you can fuck me every day in private,” he offered.
“I don’t think so,” I said, keeping him securely locked in my hold as he continued trying to break free, although he was already getting exhausted.
“I’ll do anything,” he pleaded, almost loud enough for other people to hear.
“Yes, you certainly will,” I said, “as will your sister, your mother and your father.”
I started applying more pressure, feeling him gradually collapsing in my arms.
He really went crazy trying to break free from my hold, and for a moment I loosened my grip a little, just to give him some false hope. I was being a bit of a sadistic asshole, since I was enjoying this dominance thing a little too much. He was a symbol of all the bullies in the world, and I was David taking down Goliath.
As my dick flexed against his asshole, he fought harder… while the tip of my dick teased his asshole.
Realizing his loss was inevitable, he pleaded, “I’ll give you $25,000 to stop!”
“I don’t want your money,” I whispered, “I want your cherry. I want you to come on my cock… my little faggot begging for more.”
“Never,” he said, as my cock head was now poking against his asshole.
“But it’s inevitable,” I insisted, “in fact, it’s playtime right now, bottom bitch!”
“Fuck you! No, no, please no,” he pleaded, no longer quietly at all, even though various other guys were listening to his pathetic begging. “I’ll do anything, you asshole, I’ll pay you, I’ll pay you, I’ll pay yooooooou,” he screamed, as my dick slid inside his tight virginal ass, and he passed out.
“Shit!” someone gasped.
“He lost,” someone else said.
“We’re free!” someone else exclaimed.
“Yay, Shawn!” someone else celebrated.
Heat enveloped my cock inch by inch. When I was a few inches in, I slapped him awake, and his ass clenched around my dick. He locked me inside his no longer virginal hole, and he let out a pitiful moan.
“Nooooo,” he pleaded with a whimper, as my dick rested halfway inside him.
“You lost, Austin,” Jeremiah announced unnecessarily.
“No,” he protested, still doing his best to break free, but his struggles only assisted my dick in going deeper into his ass, until I was balls deep inside him.
“The king is dead, long live King Shawn!” someone cheered.
“You’re mine now, faggot. I’ve taken your cherry, your manhood,” I gloated, feeling so powerful, as the entire senior class watched me usurping his throne. Well… so to speak.
“Take your dick out of me!” he demanded in a thunderous voice… but even though he was thundering, it still sounded pitiful.