tagGroup SexThe Challenge

The Challenge


Note: I thought about putting this in the Gay Male category, but the characters aren't really gay, just drunken frat boys. I also thought about putting it in Anal, but it's not totally anal. So it's in Group Sex, but I wanted to alert anyone who might have a problem with either of the above two topics. Also, this isn't a quick wank story. It develops, so stick with it.


The heat was almost unbearable. My fellow pledges and I had been hiking through the woods for what seemed like an eternity. It would have been pleasant had we not been loaded down like pack-mules.

“Let’s go, ladies!” Brother Greg, the Pledge Master shouted at us from the end of the line. “So far, none of you is worthy of being an Alpha Sigma Sigma brother! You’re bitching and moaning like a bunch of little girls!”

“Fuckhead,” Gary mumbled in front of me.

“Did someone have something to contribute?” Brother Greg shouted.

“No Sir!” we all chanted in unison.

Suddenly, there was a whoop from the front of the line. “We’re here!”

We quickened our pace, desperate to reach our destination and rest. We rounded a sharp turn in the path, and then carefully navigated a small slope, which would have been minor without our heavy loads. The trees thinned, and we reached a clearing at the edge of the lake. The water sparkled invitingly. I briefly imagined myself naked, plunging into the cool water.

I found a shady spot and dumped my rucksack and camping gear on the ground, then collapsed along with the rest of the pledge class. The heavy smell of pine was almost intoxicating. The fraternity brothers passed out bottles of water to us, and we drank gratefully. I wondered how they’d beaten us to the campsite?

Judging by the position of the sun, it was afternoon. The pledges had all set out early that morning, caravan-style, from the campus. The drive up to the mountains had taken around four hours. It had taken quite some time for all of us to get loaded up, and we’d been hiking for about an hour. We hadn’t been allowed to eat or drink or take a piss all day. It was all part of The Challenge.

“You have fifteen minutes to rest, then you will set up camp.” Brother Greg began. “When every last thing has been set up, then, and ONLY then, will you all have another chance to rest. You will then take a swim and freshen up for the rest of The Challenge. Are there any questions?”

“No, Sir,” we replied half-heartedly.

“I didn’t hear you!” Brother Greg shouted.

“NO SIR!” we shouted back in unison.

Fifteen minutes passed like fifteen seconds. Much too quickly, we were back on our feet, setting up camp. Between all of us, we managed the task in a surprisingly short period of time. I think we were all dying for a swim. The pledge class surrounded Gary and me as we worked to complete our final task. We had to start a campfire without benefit of matches. We’d arranged a tent of twigs and had found some dried grass and old newspaper to stuff underneath it. I looked at Gary.

“What now?” I asked him.

“Don’t you know?” he replied.

“I thought you knew,” I told him.

“Oh, fuck!” Marty said. “Come on, guys. I’m hot and sweaty and I need a swim!”

Marty was a wretchedly thin dweeb with coke-bottle glasses who routinely got on my nerves. I was about to tell him to fuck off, when I had a brilliant idea. “Give me your glasses,” I told him.

“My glasses?” he asked. “Why?”

“So I can start a fire, asshole.”

Marty handed me the specs, and I grabbed a piece of newspaper. I went to the edge of the lake, turned towards the sun, and held the lenses of Marty’s eyeglasses over the newspaper. The sun was getting low in the sky, but I prayed this would work. After a few minutes, the paper began to smoke. Suddenly, a small flame began to lick at the paper. I walked quickly, but carefully back to the campfire site, and gently eased the burning paper under the pyre of sticks. The dried grass and newspaper quickly caught, and we fed more into it until the twigs caught as well. We added more wood, and soon enough, had a roaring bonfire. The pledge class let up a cheer.

“Okay, pledges,” Brother Greg, said after inspecting everything. “Strip down and swim.”

We all ran towards the water, stripping down as we went. We were so hot and so tired that nobody cared about modesty. Except Marty. He stood on the shore in his briefs hesitantly. I wasn’t concerned about him, though. The water was clear and cool and invigorating. I dove underneath and swam until I reached deeper water. It was much colder out there, so I moved back to the shallows. When I finally resurfaced, I saw Marty standing on the shore, fully naked, hands clasping his ankles. Brother Greg was behind him, the pledge paddle firmly in his grasp, aiming for Marty’s butt. In one swift move, Brother Greg brought the paddle down with a sharp crack.

“Thank you, Sir. May I have another?” Marty asked through gritted teeth.

The pledges all stood silently in the water, watching Marty take four more blows, while the Alpha Sigma Sigma brothers stood on the shore chanting “Give him another one, better than the other one!”

After the final blow, Brother Greg looked at all of us and said, “If I tell you to strip down, you strip down!”

“Yes, Sir!” we shouted from the water.

“This is The Challenge,” he continued. “Your last opportunity to prove yourselves worthy of being Alpha Sigma Sigma brothers. Tonight may push you past your point of endurance. Some of you will triumph and some of you will falter. If anyone wants out, now is the time to say so.”

I thought for sure that Marty would chicken out, but he just stood there, his legs shaking slightly. I looked around at the pledges standing in the lake. No one wanted to leave.

“All right, then.” Brother Greg said. “You have fifteen minutes to swim.” Then he turned and headed towards his tent.

Marty eased himself into the lake along with the rest of us. Much too soon, Brother Greg blew a whistle to signal the end of our swim. As we reluctantly left the cool water, we all came to realize that our clothes were missing. The brothers eyed us with amusement. The pledges all stood there, dripping and naked, waiting for someone to tell us what was going on.

“Gentlemen,” Brother Greg said. “No need to go looking for your clothes. You won’t be needing them for The Challenge.” We all looked at one another in confusion. “Once again,” Brother Greg continued. “This will be your last chance to opt out of The Challenge. Does anyone want to leave?”

I was apprehensive. I couldn’t fathom what The Challenge involved which required us to be naked. But I had endured a long, frequently humiliating pledge season, and I wasn’t going to quit now. I looked around. No one chose to go.

“All right, then, pledges. Time to eat.”

We all made our way to the campfire. It was twilight and starting to get a bit chilly, so the warmth was welcome. Long sticks had been peeled and laid out for us, along with packages of hot dogs. Brother Mark had tapped a keg, and handed each pledge a plastic cup of beer as we lined up for a stick and a dog. It was amusing in a way to watch a group of naked guys try to roast hot dogs in front of an open fire. If you’re too far away your food is raw, if you’re too close, your dick feels like it’s on fire.

We ate and drank and drank and drank. And when the food ran out, we drank some more. I looked out at the lake as the sun was setting, and realized that what I’d thought were buoys were actually beer kegs keeping cool in the water. Maybe The Challenge wouldn’t be so bad after all.

The sun finally sank below the water line, and it was dark. Although it had grown cool, the Alpha Sigma Sigma brothers began to strip down and swim in the darkened lake. It struck me as odd, but a pledge doesn’t question a brother.

Brother Greg stood atop a large, flat rock and addressed us. “And so it begins,” he said with a sly grin. “For your information, pledges, this property is owned by an Alpha Sigma Sigma brother, an alumnus who graduated thirty years ago. He has offered it up to the fraternity for The Challenge every year since he inherited it twenty-five years ago. Before that, Alpha Sigma Sigma had to choose a new location each year. But every Alpha Sigma Sigma brother has experienced what you will experience tonight since the fraternity’s establishment more than fifty years ago. It is never spoken of, even by those pledges who are blackballed.”

I glanced around. Most of the brothers had emerged from the lake and joined us around the fire. They grinned knowingly. I was starting to get nervous.

“You,” Brother Greg continued, “Will also not speak of this, even if you are blackballed. Do you understand?”

“Yes, Sir!” we all shouted, although a few nervous glances were exchanged.

“Alright, then. As you may have realized, there are twelve of you pledges, and twenty-four brothers. We will divide up into two groups. The brothers have already drawn numbers, now it’s your turn. Form a line in front of the rock.”

We did as we were told, then Brother Greg held out a paper bag. “Choose a number. That will be the group you’re in. When you have your number, go stand with your group.”

One by one we filed past Brother Greg and reached into the bag. Gary was in group one. So was I. Marty was in group two. I looked around at this group of naked college guys and couldn’t help but think what a surreal scene this was. As an added bonus, the brothers had all donned Lone Ranger-style masks. In the firelight, it was almost impossible to tell who was who.

“Let the games begin!” Brother Greg shouted.

“Form a circle,” I recognized Brother Mark’s voice barking the orders to group one. We did as we were told. “Okay,” he continued. “Grab your ankles.” Gary and Todd groaned. “Two extra for these two!” Brother Mark ordered the other brothers.

I bent over and grabbed my ankles and waited. It was the waiting that got me more than the paddling. The anxiety and anticipation was almost worse than the blow itself. I could see a pair of feet behind me. They took a step back and I knew it was coming. Using an unspoken cue, the brothers brought the paddles down on our backsides in unison. The brother behind me was strong. The blow almost knocked me off my feet. It took a moment for my brain to register, and then the pain came, spreading across my ass cheeks.

“Thank you, Sir. May I have another?” the pledges said together, a regular Greek chorus.

Gary and Todd received their bonus blows. “Thank you, Sir. May I have another?” they said.

The feet behind me moved behind Gary, who was next to me, and a new set appeared. Again, on an unspoken cue, the paddles came down in unison. This brother was not as strong as the previous one, but my ass was still stinging from the first blow. I gritted my teeth and fought not to flinch.

“Thank you, Sir. May I have another?”

Again, a new set of feet appeared behind me. I waited. The feet turned the opposite direction of the others. This brother was left-handed. He was also stronger than either of the first two. This blow sent me to my knees. I saw stars, and as I began to sit back on my heels, fiery tentacles of pain shot through my upper thighs and across my ass, but I still managed to keep silent.

“On your feet and assume the position, eyes down, pledge!” Brother Mark growled.

I struggled to my feet, found my spot again and bent over to grab my ankles.

“Thank you, Sir. May I have another?”

The left-handed brother moved behind Gary. This time when the blows rained down on our asses, Gary cried out and fell flat on his face.

“Another extra one for you, pledge!”

Gary slowly got to his hands and knees, and then stopped.

“Are you in or out?” Brother Mark asked him.

“I’m in, Sir,” Gary answered after a moment.

“Then assume the position.”

Gary found his spot, grabbed his ankles, and braced himself for the next blow. It came suddenly, and without mercy. Gary gritted his teeth and said, “Thank you, Sir. May I have another?”

The routine began again. The feet would move. The paddle would come down hard on my ass. “Thank you, Sir. May I have another?” Repeat. I was growing dizzy from being bent over, and my ass was so sore I thought I’d never be able to sit again, yet by the time the last brother had paddled me, I found myself semi-erect.

“Okay, ladies. You can straighten up,” Brother Mark said after the final blow had been delivered.

Several pledges wavered as they stood upright. The head-rush was incredible, mixed with the pain in my buttocks. For a reason I couldn’t comprehend, I was almost fully erect. Several of the others were, too. Two brothers passed out shot glasses, then filled each one with tequila. On the count of three, we each downed the shot, and then the process was repeated. The liquor was strong, and I knew in a few minutes I’d be blasted.

Two strong sets of hands grasped each of us by the arms and started us stumbling around to the other side of the campfire. There we saw the other group of pledges each tied to a tree, having his dick sucked by a brother. They had a direct view to what had been happening to us. I saw Marty with a stunned look on his face, an anonymous brother’s head bobbing at his crotch. The brothers led us to a huge tree, which appeared to have been uprooted for many years. Towels had been draped across the trunk.

“Hands out in front of you,” Brother Mark ordered.

We all complied, and our wrists were bound together with extraordinarily long pieces of white utility rope. Each of us had a brother lead us to the tree trunk, three on one side, three on the other. The other brothers were waiting there for us. Brother Mark had me. He positioned me in front of a towel, then pushed me down across the tree trunk. The brother on the other side took the ropes and pulled them down and under the tree trunk. Brother Mark spread my legs, reached under the tree and grabbed the ropes. He drew them up tautly, forcing my arms down against the trunk. Then he passed the ropes to the brother on the other side, who pulled them tightly, and passed them under the tree again. Brother Mark pulled them up again and passed them over to the other brother, who pulled with all his might, then wrapped the ends around my wrists and tied them tightly.

I could move slightly, but I was securely fastened to the tree with my legs spread and my feet not touching the ground. I turned to look at the other pledges, but on either side of me, all I could see was ass. I was number four on the tree, so the only faces I could see were two and six, Gary and Brad. They looked terrified. My dick had gone limp again.

I felt a pair of hands caressing my sore ass, making gentle circular motions on my cheeks. The hands on the ass next to me were doing the same. It was oddly arousing, even though I knew they were male hands and not female. I could see something being passed down the line, and when it reached the hands next to me I could make out the label. It was lubricant. Up to this point I’d been in denial about what was going to happen, but when I saw the hands pass the bottle behind me, and I felt the cold lube sliding into my ass crack, I couldn’t lie to myself anymore. I was about to be ass-fucked by another guy.

A cold fear settled in my chest and I tensed up. I could hear Brother Mark working his dick behind me, lubing it up generously. “Ladies,” he said. “If you are tense and resist, it will hurt. If you relax and welcome it, you actually might enjoy it. Just remember, they don’t call us Greeks for nothing!”

The tequila had started to kick in and everything took on a dreamlike quality. I felt the tip of Brother Mark’s dick poised at my asshole, his hands gently holding my cheeks spread apart. I saw the same being done to the ass next to me. I felt Brother Mark slowly press into me as I watched the dick slide into the ass of the pledge next to me. I heard the pledge whimpering. It was Todd. Brother Mark’s dick was fully inside of me now, and he remained motionless as my sphincter adjusted itself to its new visitor. All the other brothers did the same to their pledges.

Brother Mark leaned over and whispered in my ear, “Just relax, Sean. If you relax, I’ll make you love it.”

There was something soothing in his raspy whisper, and something exciting, too. To my astonishment, I felt myself start to grow aroused. Brother Mark slowly withdrew from me, then gently pushed back in. The other brothers followed suit. Advance. Retreat. Advance. Retreat. Brother Mark was right. The more I relaxed, the better it felt. Advance. Retreat. Advance. Retreat. My dick grew rock hard as Brother Mark pumped my ass while I watched the other brother pistoning in and out of Todd. I glanced down the tree and saw Gary with a dreamy smile on his face.

Suddenly, the brother standing in front of me slipped a small pillow under my chin, and without warning stuck his dick in my mouth. He leaned over and whispered in my ear, “Suck it, bitch.”

I didn’t really have a choice. He put his hand behind my head and started pumping his dick back and forth into my mouth. At one point his dick struck the back of my throat and I started to gag. He pulled out and whispered again, “If you’d suck it like I told you to do, you wouldn’t gag.” Then he shoved his dick back in my mouth before I could reply. I struggled to suck on it as it moved in and out of my mouth. The brother slowed down and I had more success. I could still hear Todd whimpering next to me, but it was obvious that someone had shoved a dick in his mouth, too.

My dick was still hard as a rock and desperately uncomfortable, trapped between my body and the tree, rubbing against the terrycloth of the towel as the brothers developed an alternating rhythm, one fucking my ass, one fucking my mouth. Contrary to everything I believed about myself, I knew if this went on much longer I was going to shoot my load.

I didn’t have to worry, though. Brother Mark began to whisper, “Oh, fuck. Oh fuck. I’m gonna cum. I’m gonna cum. I’m gonna…”

Then he groaned loudly and I felt something hot and liquid in my ass. Brother Mark leaned heavily on me as he emptied himself into me. I felt his legs shaking.

The brother fucking my mouth began to moan. “Oh, yeah. That’s right, bitch. Suck me off. Suck me off.” Then without warning, he came in my mouth. A sticky, salty, thick mess. When I had completely drained him, he moved away and allowed me to spit.

Brother Mark slowly eased himself out of me, then smacked my ass. “Beautiful, baby. Just beautiful. I think we have a brother here.”

The brother who had had his dick in my mouth began to untie me. I was the first to be released from the tree, but my hands were still tied together. He and Brother Mark led me to the circle of trees from which group two had since been released. I could see them on the other side of the campfire, standing in a circle, grasping their ankles. The brother pushed my back up against the tree, and then bent my arms at the elbow so that my hands were at my waist. He passed the ropes to Brother Mark, who wrapped them behind the tree, then passed them back. The brothers repeated this pattern until I was firmly tied to the tree.

Brother Mark walked off into the darkness, but returned after a moment with a shot glass. He held it to my lips. “This should get the taste out of your mouth.” The other brother chuckled softly as I downed the tequila. Brother Mark took the glass and left. I heard a splash in the distance, and assumed he’d gone to the lake to wash off.

The brother in front of me took the small pillow he still had from before, and dropped it on the ground in front of me, then knelt on it. “Turnabout is fair play,” he said with a smile. Then he wrapped his lips around my dick and began to suck.

The sensation was intense. His tongue slid skillfully down my shaft and he nibbled the vein on the underside. He was better than Jennifer, my girlfriend. He sucked with gusto, taking the full length of my shaft over and over. I watched him for a bit, then turned my attention to group two.

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