Chris loved fucking Danny. He jerked off thinking about it regularly, in bed and in the shower, in the restroom between classes, etc. His dick was pretty much always hard whether he was fantasizing about the last girl he saw walking by or he was thinking about Danny's tight ass. But lately, a new fantasy had been creeping into Chris's mind. When he had first started fucking Danny, Danny didn't seem to like it much at all. But, after the first few times, Danny had started to get into it more and had moaned and gotten rock hard while Chris was fucking him.
Chris had tried pretty much everything imaginable with a girl. And now he had done quite a few things with a guy, but there was one thing he hadn't tried yet... and that was getting fucked. The thought of trying it was making him get hard more and more often.
The easiest way to try out this new fantasy of his would be just to ask Pat to fuck him, but somehow that didn't seem right. And besides, Pat had never shown much interest in doing anything with Chris when he and Danny had been together. And anyway, Pat and Danny had been pretty much MIA over the last few weeks. They both had seemed to have been avoiding Chris and even each other. So, Chris needed to figure out another alternative.
Fortunately, it didn't take Chris long to put together a plan. Chris was currently serving as the pledge master at his fraternity. As per his usual personality, he treated the pledges like complete crap whenever he could and enjoyed doing so a great deal. And it turns out, that may play to his advantage. None of the pledges were that particularly intimidating, with the exception of Derek. Derek had come to College to be a tight end on the football team. But, his freshman year he had hurt his knee and that was the end of his football career. He subsequently pledged the fraternity. Derek was about 6'4'' and muscular as shit. Chris was very confident that he could pretty much beat the crap out of almost every guy he knew, but he wouldn't ever want to test that theory with Derek. That made Derek the perfect co-conspirator for Chris' plan.
But, the first part of the plan required Chris to figure out which pledges to get involved. And in order for him to decide that, he needed to see what they were working with. There were 14 pledges and he knew right off the bat that three of them would not be participating in what he was planning because they were not remotely attractive. That left 11 of them he needed to check out.
Chris started the plan by demanded all 14 come over to his house on a Friday night he knew that none of his roommates would be around. He told them they were coming to a pledge event called "fuck all the other fraternities." Once they all arrived, he made sure they all had enough alcohol to get them relaxed. Then he told them what the purpose of the night was. One by one, they were going to go into his bedroom and jerk off until they jizzed all over a t-shirt of one of the other fraternities on campus. Granted, that did seem a bit odd, but it wasn't like he was asking them to get naked and jerk off together or see each other's dicks. So, after a few more drinks, they started the process and Chris sent the first pledge into his bedroom to complete the deed. Once the pledge was finished, he was to throw the soiled t-shirt into the clothes hamper in his bedroom and come out and keep drinking with the rest of them.
Waiting for 14 pledges to go up to his bedroom and finish jerking off took a lot longer than he anticipated, but he wasn't really in much of a hurry. He was enjoying hanging out, drinking and shooting the shit with the rest of the guys. After the last pledge had finished and blown his load over the last t-shirt, Chris told them all to get the fuck out and go back to their rooms. It was at that point, that the fun really began.
What the pledges hadn't realized, is that Chris had put a hidden camera in his room and had recorded the whole night's activities. So, once all the pledges had left, he made himself a strong drink and went upstairs to review the recording. Unexpectedly, just watching the tape had been a huge turn on in itself. But, the real purpose of doing this was to evaluate each of the pledges. In order to finalize his plan, he wanted to see which pledges were worthy enough of taking part. And by worthy enough, he meant he wanted to find out which pledges had dicks big enough to make him interested in having them fuck him.
Now, just by watching a video of them jerking off, he really couldn't tell the exact size of any of them, but he could get a pretty good feel of which ones were too short and which ones were too thin for him to be interested in. When he had first thought of this plan, he figured once he got to this point, he would probably be able to narrow the group down to 3-4 guys. But, it turned out that his fraternity was much better at picking new members than he though. There were three pledges that didn't look to be that long, but had cocks as thick as beer cans. Two other pledges looked to be have average width, but looked to have at least 8+ inches. Another pledge looked like he had close to 9 inches and was also pretty damn thick and then last, as he had planned, was Derek. Chris wasn't sure that Derek's cock would match the rest of him, but he was extremely happy that it did. When Derek first showed up on the cam and pulled his underwear down,
his soft dick hung down to his mid thigh. As he started jerking it, it just got bigger and bigger. He couldn't be sure from the video, but it looked to be over 10 inches and was the thickest cock of the bunch. When Derek exploded onto the t-shirt in the video, Chris exploded all over himself. He checked out the video to see which shirt was Derek's and then went and got it out of the hamper and enjoyed sniffing it for a while. Long enough to get hard again and cum another time. He then went to be thinking about the next part of his plan.
The next morning he called Derek and told him to report to his house. Derek was physically intimidating, but mentally, he was pretty dull. He seemed to just do what he was told. So, Chris didn't think he would run into a big problem with recruiting him to help him out with his plan. Once Derek got there, Chris fed him a few stiff drinks, which he drank down without much of a problem. Once he got the nerve up, he started asking him some questions.
"Derek, as you know, we have a reputation to uphold in the fraternity. We need to make sure that all our pledges can fuck the girls good and long."
Derek just grunted his response, "Sure."
"How do you think we can make sure we got the right pledges?" Chris asked.
"Don't know, pick out a slut to fuck them all?" Derek responded.
"Well, you'd think we could do that, but unfortunately, the types of girls we like to hang out with aren't the type who would fuck an entire pledge class." Chris said.
"Hanging out with the wrong bitches then." Derek mumbled.
"Derek, don't get fucking smart with me." Chris ordered. "Now look, it's my job as the pledge master to make sure we have the right pledges. And I need your help."
Chris went on to explain his plan. Derek listened and didn't seem surprised or grossed out, or even very interested in it at all. After Chris was done explaining what he wanted, Derek simply said "OK" and left it at that.
Chris let Derek go back to his dorm room and told him he would call him back later that night. At about 10pm, Chris called Derek and the other six pledges he had decided he was interested in and ordered them to report back to his house. He didn't give them a theme for the night, just told them to get their asses over there.
Once they arrived, he again started feeding them alcohol. The night started out as being pretty laid back. But, then Chris brought out two bottles of tequila. All during the night, Chris had also been drinking heavily to get prepared for what was about to happen. Once the tequila come out, Chris started peppering the pledges with trivia questions. Questions about the school, questions about the fraternity and questions about the fraternity brothers. All the questions were ridiculously difficult and Chris didn't expect any of the pledges to be able to answer any of them. But, he played it off like they should all know the answers to each and every question.
Every time a pledge got a question wrong, he made them take a shot of tequila. He also berated them for being stupid and a horrible pledge and swore that none of them would every make it as a brother in his fraternity. After about 45 minutes of this, and Chris making sure that each of the pledges had taken several shots of tequila, he turned to Derek and put his hand on his shoulder, which was the cue they had discussed, and asked him another impossible question to answer. When Derek, as expected, responded with the wrong answer, Chris again started yelling at him for being a piece of shit. But, this time, Derek didn't just take the abuse and the shot of tequila.
Instead, suddenly Derek showed some emotion and stood tall to tower over Chris and yelled, "Fuck this shit and fuck you, you piece of shit! I'm not taking it any more!" At that, Derek shoved Chris half way across the room and face down onto the couch. Chris stumbled more than he meant to and almost face planted onto the coffee table. But, he ended up on the couch. Derek quickly lumbered over and moved Chris so his whole body was on the couch face down with him on top of him holding his head down. He then started looking around at the other pledges.
"Aren't you guys fucking tired of this piece of shit?"
None of the pledges said anything. None of them even moved. They all looked terrified.
"Come on you pussies! This jackass has been treating us like shit from day one. None of the other brothers treat us like this. He just gets off on being an ass. He wants to humiliate us and make us feel like crap. And I'm fucking tired of it and you should be too!"
The other pledges started looking around at each other and a few started nodding in approval.
"Well, I think it's time we show him that we are men and not just a bunch of bitch as pledges!"
At that, Derek grabbed Chris's pants and forcibly yanked them down so he was there in just his white tightie whities.
"Damn, this punk as bitch even wears little boy underwear!" Derek yelled at the other pledges. He then grabbed Chris' underwear right in the middle of his ass crack and torn them open exposing Chris's hairy ass.
"Now, we're going teach this fucker a lessen he won't forget. Who is going first?"
The other pledges looked completed confused and a bit afraid. But, Derek wasn't about to quit now. So, he went to the nearest pledge and stood right in front of him.
"Dave, Chris has treated you like a little bitch for months. It's time to return the favor." As he said this, Derek grabbed Dave's jeans and unbuttoned them and then pulled them down. Dave looked shocked to be standing there in his white boxers. Derek didn't care. He then pulled Dave's boxers down exposing his cock.
Derek then grabbed Dave's cock. "Dave, take this little pecker and show him that you're a fucking man". Derek then shoved Dave so that he fell on top of Chris. It was Chris' naked hairy ass right against Dave's semi-hard cock.
Dave started to push himself up and get off of Chris, but Derek stopped that by ordering him to stay where he was. Derek realized he was going to have to start this off properly. So, he went around to Chris' face, pulled out his cock and ordered Chris to open up and start sucking him.
The other pledges were all in shock. It wasn't clear if they were in shock over what was happening or at the size of Derek's cock. But, Chris did what Derek told him and start attempting to suck on his huge cock. Chris kept chocking and gagging on it but Derek didn't care. He went a little slow at first, but then just grabbed hold of Chris face and started pounding his mouth with his cock. Chris was gagging and crying, but Derek didn't stop.
Dave was still laying on top of Chris and hadn't started doing anything yet. After a few minutes of getting lost in having Chris' mouth on his cock, Derek looked back up and ordered Dave to join in.
This time, it didn't take much to convince Dave to participate. Dave pushed himself up from Chris and exposed his rock hard dick, which was slender, but about 8 inches. This time, he didn't look around or pay any attention to the other pledges. Instead, he grabbed his cock, and directed it right into Chris' tight asshole.
Chris was already having a hard enough time dealing with the uncomfort of having Derek's massive member assaulting his mouth. He had realized that doing this was probably going to hurt, at least at first, but he was willing to deal with that. He was drunk enough that it was going to dull some of the pain, but when Dave shoved his long cock into his ass, he was immediately rethinking this entire plan. But, Derek didn't give his mind much time to focus on the pain in his ass because he kept fucking his mouth so hard. Chris couldn't figure out which to focus on.
Once Dave's dick got all the way in his ass, he didn't take long to follow Derek's lead and start going hard and fast. No mercy for Chris. Dave had never had his cock in such a tight and warm hole before and he was enjoying it a great deal. This wasn't making love to his girlfriend, this was pure, animal fucking and all he could think of was taking that hole as hard as he could.
Neither Dave nor Derek were remotely interested at that moment in the other pledges and Chris wouldn't even begin to think about looking to see what they were doing as all his holes were being raped. But, they were all enjoying the show. All but one of them had already pulled their pants down and where jerking their cocks. Two of them were helping each other out by jerking each other off.
After a few more minutes of enjoying Chris' mouth, Derek remembered what he was supposed to be doing and he started looking around the room. He smiled by what he saw. All the guys were certainly having a good time. But one of them, still looked nervous as shit and had his pants on.
Derek grabbed Jeremy, who was the nearest pledge next to him and quit his assault on Chris' mouth so that Jeremy could start enjoying it. He then walked over to Steven, the pledge that was looking nervous. As he did, he saw Dave pull his dick out of Chris' ass and cum all over his back. He laughed at that and then saw Dave get up and Neal quickly take Dave's place over him and start thrusting hard into Chris' ass.
Derek went up to Steven and asked him what the problem was. Steven just stared blankly at Derek and eventually said, "Man, I don't know."
For some reason, that pissed Derek off. And, a pissed off Derek in general was not a good thing. But, a pissed off Derek with a ragging hard on was definitely not a good thing.
Derek definitely wasn't anticipating doing this, but he grabbed Steven in a pretty much a bear hug and walked him over to the other couch in the room and threw him down. As he was face down on the couch, Derek grabbed under him to undo his pants and ripped them down around his ankles. He did the same to his underwear. And then hovered over Steven's naked bottom half. He didn't think, he just stuck three fingers into his mouth, got them wet and shoved them all into Steven's ass, which was surprisingly hairless. Steven yelled out, but it didn't bother Derek. He just started fucking his ass hard with his fingers and with his arm, he took his forearm and put it on Steven's shoulder's so he couldn't move. After a couple minutes of loosening Steven up with his fingers, he pulled them out, and got all the way on top of Steven and forced his huge cock right against his hole. His fingers had definitely not prepared Steven for what was about to
happen to him, but Derek didn't care. He had a hard time at first forcing his cock into Steven's ass, but once it was in, he used it just like he had used Chris' mouth. Steven kept trying to get up and crying and yelling. Derek called over James and told him to put something into Steven's mouth to stop him from making noise. James had no issue complying and immediately starting fucking Steven's mouth.
Derek looked over and saw that Neal had finished fucking Chris' ass and had also cum all over his back and Jeremy had switched from fucking Chris' mouth to fucking his ass.
Chris had gotten over the initial pain of getting fucked much quicker than he thought it took Danny to get over it. He was already really enjoying the pounding he was getting. Each cock that entered his hole was a little different. Some were long, some were thick, but the all felt amazing. And each time one of the pledges cam on his back it made his own dick drip a little more precum onto the couch. He was even able to be remotely aware of the other people in the room at this point, mainly because there wasn't anyone currently fucking his face. He was pretty surprised that Derek was fucking one of the other pledges, but it just made the whole scene that much hotter.
Derek was still pounding Steven, but soon realized that if he kept going, he was going to cum and he didn't want to do that yet. So, with a deep stroke, he thrused the entire girth of his cock into Steven's ass and laid completely on top of him. He looked up at James and he immediately stopped fucking Steven's face and he whispered to Steven, "Are you going to stop being a little bitch and join in the fun, or do you want me to keep fucking you?"
Steven could barely talk, but he managed to mutter out that he would join in. At that, Derek pulled out of Steven's ass and pulled him up. He stood being him and waited for Jeremy to finish fucking Chris. Once Jeremy had finished and cum on his back, Derek forced Steven towards Chris' ass and forced him on top of him.
"No fuck him like I fucked you." Derek growled.
Steven didn't take long to comply. It was actually Steven who had the second biggest dick in the group next to Derek. And although Chris' hole was pretty stretched out by the various cocks that had been fucking him, Steven's hard cock in his ass immediately took his breath away. Steven didn't fuck him as hard as the other guys, but the size of his cock was hard to take. Chris, for the first time since that first cock had entered his virgin hole, had to focus on pushing out and accepting Steven's cock into his ass.
Derek apparently didn't like how slow Steven was fucking Chris, so he decided to help the process along. While Steven was sliding his big cock in and out of Chris' ass, Derek got on top of Steven and thrust his dick back into Steven's hole. This way, Derek was able to fuck Steven hard and thus make Steven fuck Chris hard.
Both Steven and Chris started moaning loudly and squirming in pain. It didn't matter to Derek, he just kept plowing Steven.
the other pledges were all either spent from fucking Chris or jerking each other off. Derek ignored them. He focused on Steven's ass and forcing Steven to pound Chris.
Suddenly, Steven started moaning and squirming more and more and Derek felt his ass tighten around his cock so tight that it almost made him cum. Then Steven went completely limp.
It took Derek a few seconds to realize what had happened, but then he caught on that Steven had cum inside of Chris' ass. That made Derek smile. He pulled up and withdrew his cock from Steven's ass and ordered Steven to "eat it."
Steven apparently didn't understand the order, so Derek yanked him off of Chris and then grabbed him by the hair and forced his head directly towards Chris' asshole. He then made Steven lick all of his own cum out of Chris' ass. After a close to a minute of forcing him to do that, he then forced him to move up to Chris' back and eat the cum that had been shot there by all of the other pledges that had fucked Chris.
Once Chris' back was clean of cum, Derek got up and allowed Steven to do the same. Derek stood there looking around the room at all the other pledges. They all stopped and stared at him. His dick was still rock hard and sticking well over 10 inches out. Steven stumbled over to hide behind the other pledges. Derek smiled and said, "We're done here, everyone get the fuck out."
Chris was completely satisfied and sore as shit. He had gotten everything out of the night that he had ever imagined. He know understood why Danny seemed to enjoy it when he fucked him.
But, as all the other pledges left, Chris tried to start to get up and he immediately felt an elbow in the center of his back.
"We're not fucking done yet boy." He heard as he was forced back down on the couch.
Chris couldn't help but smile. But, that smile was quickly erased by the feeling of Derek's massive cock pushing against his hole. The first cock in his ass had hurt, the next several had felt pretty good, Steven's had hurt again, but Derek's was a whole different story. He felt like someone was sticking their forearm up his ass. He tried to push out to make it hurt less, but it didn't help. Nothing helped. It just fucking hurt. He kept waiting for it to get better, but it just wasn't happening. And Derek wasn't showing any mercy. He was fucking him as hard as he could. Chris could feel Derek's sweat dripping all over his back and neck.
Chris couldn't imagine anything hurting worse than what this was hurting, but then Derek abruptly pulled his entire dick out of his ass and that hurt ten times worse than having his cock fucking him. Derek grabbed Chris and forced his whole body around so that he was laying on his back with Derek on top of him. Derek then started his assault on his hole again.
Chris was in so much pain that he didn't realize how hard his cock was. He definitely didn't' realize that his cock was gushing precum and he didn't realize, until it happened, that he was cumming all over his own chest and cumming so hard that he hit his own face with his cum. But, once he did, he felt fucking amazing and seeing Chris cum all over himself, pushed Derek over the edge. He pulled out of Chris' ass again and jerked off with his cum also landing all over Chris' chest and face.
Derek moaned and looked down at Chris for a few seconds. He then leaned down and started licking the cum off Chris' chest and face. Once he got a good mouthful, he pulled Chris' face towards him and kissed him and forced Chris to take all of the cum in his mouth into his.
Once Chris had swallowed all of his own cum mixed with Derek's cum, he laid his head back down on the couch.
"Thank's pledge master. I had fun tonight." Derek said, then he got dressed and left.