The Contests

By Hymen Cleverpants

Published on Aug 30, 2016

Gay

The RenFair Kilt Contest

By Hymen Cleverpants

My buddies and I made plans to head to the RenFair upstate. It was Celtic Weekend, so of course I wore my kilt; I had a nice tan cargo shorts-styled one. I wore my Superman shirt with it, and I think I looked pretty good. I'm about six feet tall, with black hair and blue eyes, and I hit the gym pretty regularly, so I kind of looked like Superman in a kilt. When I got to the car with Jeff and Kyle and Margie, none of them were dressed up at all! I was annoyed, I mean, that's the point of RenFair, you gotta at least do something, but was too late to argue.

When we got there, we saw part of the special Celtic Weekend ceremonies was a "Best Knees in a Kilt" contest later in the day. Jeff and Kyle said I should enter, but it was really when Margie said it would be great to do it that I weakened and put my name in. Margie was super-cute and I hadn't slept with her yet. She was always very flirty with me and I knew it would happen soon.

So we spent the day watching a fire show, a human chess match, and some other stuff, always being sure to stay liquored up on mead (a honey wine you get at RenFair) and beer. I saw these two fratguy bros in a silly costume dressed as a dragon or something, it was pretty funny. It was lots of fun, and I always have a great time looking at all the titties on display; bodices are a great invention.

Finally, around 4pm, it came time for the "Best Knees in a Kilt" contest. It was at "The Blue Boar Inn", one of those fakey little buildings they have there; a place to buy more beer, but in the back is a secluded little stage, where they do some of the more naughty pg-13 shows. Jeff and Kyle each made me chug a cup of mead before I got up on stage.

It started out silly; The Lord Mayor of RenFair was in charge, and Grace O'Malley (a pirate queen) was the main judge. There were some 15 guys, all in kilts, and a small audience of friends (we all had our cheering section). We all had to get up onstage and prove our manliness. Some guys flexed their muscles, some guys just shouted.

The Lord Mayor called me up, "What is thy name, son?"

"Caleb", I said.

"Nay, I think it is Kal-El", he joked, looking at my t-shirt. It got a good laugh.

I brought out my secret weapon, a rose, which I gave to the Pirate Queen. Or, I was about to, when I "accidentally" dropped it, and bent over, showing off my rear to her. I picked it up off the floor and handed the flower to the blushing Pirate Queen. Margie did that to me all the time, when she was wearing a short skirt, she called it the "bend and snap". I figured I had it all sewn up. But then the last guy was this short chubby guy in really impressive hobbit-looking stuff.

He told the Lord Mayor his name was Everett, and said, "Behold! I can summon the Loch Ness Monster!", and those two guys from earlier, in what I thought was a dragon costume, turned out to be his friends.

The Queen picked the finalists, me, Everett, and a kind of nerdy guy named Jason, who had nice Celtic styling going on, aside from his glasses which kind of spoiled the look. He had hiked up his kilt to show his thighs to the ladies, so he made it into the finals as well. The rest of the guys were dismissed and joined the audience. The Lord Mayor told the three finalists to get on our knees.

"Now it's time to see if these boys are truly regimental!", he shouted, "Girls, do your thing!"

The Queen and her friend came up behind each of us, and with a stick, lifted up the back of our kilts. I suddenly realized they were checking to see if we were "True Scotsmen", and these strange girls were about to check if I was wearing underwear under my kilt. And worse, I was! I never thought it would go THIS far!

The drooling women checked out the bare butts of the other guys. They got to me, the last one, and upon seeing that I had tighty-whities on, they called out, "FOUL! He has on panties!"

"This will not stand!", shouted Lord Mayor, who came up behind me and pushed me over onto my face roughly, pulled up my kilt, and yanked off my underpants to the cheers of the crowd. I was pretty sure everyone saw a flash of my butt as he lifted my legs up off the ground and into the air. The offending panties were thrown to the crowd. Lord Mayor gave my butt a stinging spank and I yelped at the unexpected pain, as he said, "Thou'rt no real Scotsman, son. Thou lookst like a man, but methinks you're a little boy." The crowd laughed at that, and I looked out to see Jeff and Kyle cracking up. Margie just looked sad.

"On your feet, lads!", shouted The Pirate Queen, "and turn around!" We all jumped to our feet and faced the back wall. "Hands on heads!", she shouted, and we did as she requested. I could feel the Lord Mayor come up suddenly behind me as I heard her shout, "And UP!" All three of us had our kilts lifted up by someone behind us, our asses bared to the crowd, and what was worse, our dicks and balls out to this strange woman to judge. No one had said the contest would go this far. My face heated and I blushed all over as I was exposed, and I heard cameras clicking out in the audience. I heard whooping from the other two as well as their bare bottoms were shown to all, and their manhoods judged.

"And down! I've seen enough," she said, and our kilts were lowered again. Though not entirely, they tucked them into our belts in the back to keep our rears exposed.

The Pirate Queen conferred with Lord Mayor, who announced, in his booming voice, "We Have a Winner! The Man with the best Loch Ness Monster, Everett!" The crowd went wild for the short hairy guy, who took some bows. "Kneel! Kneel to your master!" They let down Everett's kilt and forced me and Jason to one knee, which almost exposed us to the audience.

"Everett, milord, you win these coupons for free drinks, which you can probably share with your Loch Ness Monster. And second place goes to Jason! You get one drink coupon for being such a good sport." His kilt was also lowered, minimizing his exposure.

And then the Lord Mayor turned to me, still on my knee. "And poor Caleb. Poor Kal-El. You're the loser of the day. Not even bringing into account you wearing panties to a kilt contest, you didn't measure up to the other men, little boy. And as such, you have to worship the winners. Here, you don't deserve this `Super-Man' shirt, as you are clearly lacking." I was shocked by his words, but he and The Pirate Queen pulled my shirt off as I drunkenly tried to resist. I was left only in my kilt and boots, my impressive physique on display. I heard cheers, laughter, and wolf-whistles from the crowd as I was stripped.

The Pirate Queen leered at me, "You have two choices, big boy. You can either go under the kilts of the other two and lick and worship their bigger dicks and balls, or you can show the whole crowd the little thing you're packing under your kilt.

"No, but I'm straight!" I whimpered.

"Exposure, then?", she pulled at my kilt, slowly lifting it up my knee.

I started to cry. "No no, I'll do it. I'll lick them. I'll worship them." Nothing could be worse than for this whole crowd to see me fully nude, and especially Margie, to see my dick and be told it was smaller than these guys. At least I'd be under the kilts of the other Men, no one would see my face as I was abjectly humiliated before them.

First I was brought back down to both knees in the middle of the stage, and Jason was brought to me. He lifted his kilt and threw it over my head. I was enveloped in the Celtic plaid and the manly musk. I assumed this was as far as the joke could go, and waited for someone to call a halt, but no one did. Jason rubbed his dick on my face, it certainly seemed very large. "Well, start licking, boy!", the nerdy fellow said. I did as I was told.

"You see," the Lord Mayor addressed the crowd as I began, "the loser acknowledges the primacy of the true Scottish man. Beneath his tartan, Jason has a mighty staff and pendulous balls, which Caleb must demean himself before. Here, let us spread him out a little".

I felt Lord Mayor behind me kick my legs a little farther apart, showing off my ass to the audience again, as my kilt was still hooked into my belt. I gagged and wept a little more as I licked Jason's shaft. He was erect now, and wiped some pre-cum on my face, under my nose. I smelled his manliness before me.

"Now the balls, bitch," Jason husked, getting bolder as another man slavered before him. Indeed he had heavy balls which would barely fit in my mouth one at a time.

And then, a miracle! "All right, that's enough," said Jason, "I'm straight, I don't want to waste this on some dude". He whipped away his kilt from my sweaty, reddened face. "You sure can lick a nutsack though, Caleb", he smirked manfully, as the crowd laughed at my humiliation.

The Lord Mayor boomed, "All right Everett, bring your Loch Ness Monster up here!"

Everett came downstage to me, and I guess there was some confusion because his bros dressed as Nessie came up to the stage again too. Everett lowered his kilt over my head and I was confronted with the fattest dick I'd ever seen, with a set of heavy hairy balls.

"Go ahead Caleb, you're gonna take it all!" Everett whooped, and I began licking. Jason had been bold, but Everett was bolder, I don't know if he was gay, but he was happy to grab my head and guide me where he wanted me to go. I licked his swiftly hardening dick, which got unbelievably larger and thicker.

He guided me to his nuts, those hairy globes. I could feel his dick dripping pre-cum on my head as I did. He guided me up and I wasn't sure what he was trying to get me to do, he pulled me down onto his dick and I had my mouth closed till one of his Nessie Bros smacked my ass, I shouted and his dick went in my mouth. I couldn't escape as he pushed me up and down his mighty shaft, stretching my mouth out and making me gag.

"Should I?" I heard Everett say, and there was a roar from the crowd.

The Pirate Queen laughed, "Go on with ye Man, you've nothing to be ashamed of!"

Suddenly his kilt was lifted up, and instead of the promised privacy, I was revealed to all sucking Everett's huge cock. There was a cheer and the cameras flashed again. This was too far, and I tried to pull away, but he held me fast before him, the huge dick pistoning my mouth and throat. I screamed as much as I could, around it but to no avail; I could only gurgle and gargle around the meat in my mouth.

The Lord Mayor came up behind me with the Nessie Bros and he held my torso as the Bros unbuckled my kilt and exposed my lower half, leaving me sucking a dick onstage in nothing but my boots. Tears and sweat were streaming down my face as the Nessie Bros began spanking me. My smaller dick, shrunken in humiliation, bobbed as smack after smack landed on my tender butt-cheeks. I stole a glance at the audience and saw Jeff with his iPhone videoing my complete surrender to this short hairy man in a kilt. And Kyle snapping photos, as Margie sat, jaws agape at my debasement.

Suddenly Everett pulled me off his dick and cradled my tear-streaked face in his hands, "You don't like this, do you? You don't like my big dick in your mouth, do you? "

"No! Please, no more, no", I sobbed like a baby, not caring how silly I sounded, "no, I'm not gay".

He slapped my face firmly, "You do what I say. Now, you really don't want my big dick in your mouth any more? You're not even man enough to take this. Isn't that right? You're just a big pussy-boy with a little dick, aren't you?"

I nodded, chastened and weeping.

"Say it. Say it to all these people," he stood me up so I was naked on display for the audience. I saw even more people had crowded in to the little back area to witness my fully naked shaming.

I choked and tried to whisper the words, "I'm... I'm..." but I couldn't make them come out. The Nessie Bros came over to me and gave a huge slap to my ass, and I shouted "I'm a big pussy! I'm a big pussy boy!"

"Louder!" Everett said. My ass was slapped again, my little dick bouncing for the entertainment of strangers and my laughing friends.

"I'M A BIG PUSSY-BOY! I'M A BIG PUSSY BOY!"

"With what, now?", Everett prompted.

I broke down in tears again as I shouted "I HAVE A LITTLE DICK! I'M JUST A BIG PUSSY BOY WITH A LITTLE DICK!"

"And you suck big cocks."

"AND I SUCK BIG COCKS! I'M A LITTLE DICK PUSSY BOY AND AND AND I SUCK BIG COCKS!"

"And you take it in the ass."

"No!" I gasped, "I've never!"

Everett smiled wickedly, "Well, you're about to, Caleb. Guys?" The two Nessie Bros grabbed me and pulled me down to my hands and knees, to the delight of the cheering crowd. They stood on my hands and both of them pulled out their cocks (still bigger than mine), and rubbed their erections on my face as I felt Everett come up behind me, "Here we go, `Superman'."

My voice went unnaturally high and I squealed as Everett's huge monster invaded my virgin hole, I started shouting "No no no", until the two Nessie Bros got their dicks in my mouth to gag me and shut me up.

I had never felt less sexy in my life as I was double—no, triple-teamed by the young men, but maybe from all the alcohol, maybe from the rubbing of my prostate, I started to get an erection, myself. Everett's insistent pounding of my hole began to feel good, and I shuddered with unnamable pleasure as I was lost in sensation. I became the Big Pussy-Boy with a Little Dick that they said I was, and I sucked dick and took cock in my ass like a champion, hoping to make these superior men proud of me. The Lord Mayor pointed out my little erection to the audience, and heat throbbed in my head as I swooned. The Nessie Bros came on my face, one after the other, one blinding me with his spunk, and the other a straight shot all over my lips and in my mouth. I gagged on the taste as the audience shouted "Huzzah!"

Suddenly my body tensed up and I knew the shameful feeling – I was going to cum! I was going to jizz right in front of all these people as Everett was riding me. Everett must have felt me tighten up, because he grabbed my hair and said, "Here we go". Without even touching my dick, I had one of the hugest orgasms of my life. Pump after pump of spooge covered the stage as Everett came in my ass.

There wasn't much more after that. The Lord Mayor gave me my kilt back, to hide my shame, but said my shirt and underwear got lost, so I had to go barechested and freeballing the rest of the day. I tried to get the guys to drive me home immediately, but they wanted the last couple hours at the Fair.

That was humiliating, since everywhere we went I could hear people whispering about me, telling the story of the big hunky man who'd been reduced to a cocksucking mess. I got propositioned by several other guys throughout the day, with several of the bigger ones lifting my kilt to check out my shortcomings and to display them to others.

It was an awkward ride home. Margie sat up front, while I had to deal with Kyle in the back showing me photos and video of my perverse humiliations. I knew I'd never have a chance with Margie now, and Kyle and Jeff would always think of me as a Big Pussy-Boy with a Little Dick. I made them promise not to post their pics and videos online, but they were not the only ones to have recorded. By the next day, my debasement was all over the Internet, on Vimeo, on LiveLeak, on Flickr. Every moment of it online for everyone's consumption. One guy even found me on Facebook and posted my full name with the video of me getting railed by Everett and his Nessie Bros. I knew I could never live this down.

Next: Chapter 2: The Halloween Contest


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