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Related article: Pledge Class - The Blow Job Task 5 Note: This story series includes depictions of gay sex, straight sex, bisexual sex, sex between college students and high school students (both male and female), and incest. If that's not your thing or if it is illegal for you to read this story, then stop. This story is made up and does no depict anything true. Comments, suggestions, and helpful feedback are welcome. - DerekGuy17gmail.com Recap: Five freshmen have a final pledge task to blow each of the other 4 pledges on successive nights. Austin got his High School sister to be his substitute on the first night. Chet got his older sister to do so, but in return was fucked by her boyfriend. Nick reluctantly got his longtime girlfriend, but she got to fuck two of the other pledges in return. Only an exclusive girlfriend or a sibling can sub for the pledge himself. Pledge Class  The Blow Job Task Part 5 - Dylan Sunday Night Dylan begged and begged Mia to do it. Despite being an all-star athlete with girls hounding him, Underage Anal since they began dating in the third week of college, Dylan had remained exclusive with Mia (if you didn't count the hags of last week). His fuck date with Skye was still four Underage Anal days away. Mia refused and told him he was a pig and if that's the kind of fraternity he was in, she wanted no part of it. He quickly told her he was joking the whole time and she dubiously believed him. But she wouldn't talk to him anymore. Monday Dylan loved his sister Desiree and had trouble thinking of his 17-year-old sister sucking his friends. She wasn't a sexual person and he didn't remember any longtime boyfriends. He called her Monday afternoon and tried to bring up the subject of sex. Two years apart in age, they really didn't know each other. Dylan had always been busy with sports and then sex. He didn't have time for younger siblings. Underage Anal The conversation got nowhere fast. It was pretty obvious she was a virgin, and after he somehow worked blowjobs into the conversation, he realized she had never blown anyone before. Was he going to have to Underage Anal suck his friends himself? His girlfriend had refused. And his sister likely couldn't do it even if he somehow convinced her to try. Wednesday After Tuesday's pleasuring by Austin's sister, Dylan tried one Underage Anal more time to convince Mia. Before he finished his first sentence she kicked him out of her dorm room and told him to fuck off. What the fuck do I do now? Thursday Dylan had convinced himself he'd have to get Desiree to do it. It was unfair and wrong, but he didn't have any other choice. With Jess and Sam already having fulfilled their brother's turns, he knew he needed his sister to do the same for him. Dylan skipped classes and borrowed a car to drive four hours home to see what he could say to her in person. Maybe he could get her to practice on a couple guys that day. And what he could he give her in return? What would she want to make this bargain? What the hell&how could he think of his sister this way  like a piece of meat. He was thinking irrationally - he had never considered Desi as a girl despite her good looks. Within 30 seconds of entering his home he discovered it couldn't work no matter what. Not only was Desiree incapable of blowing four strange guys, but she also had come down with the flu and was in bed with a high fever and frequent vomiting. "Fuck!" Dylan grimaced. "And fuck you too!" he heard. He turned around to see "Little Dylan." Dylan's younger brother Doug was a smaller version of the original. Having just turned 16, he had also finally reached 6' tall. Doug had the same piercing blue eyes as his brother and retained the soft, baby skin of youth. Not nearly in the same class of athlete as his brother, his body was well defined, but he hadn't added enough bulk on his muscles. The raw material was there, he just hadn't come into his own physically or spent as much time in the gym as Dylan had. Doug idolized his brother, but also resented his brother's athletic success somewhat. Dylan found Doug to often be a nuisance, but they generally got along. Dylan's opinion of his younger brother had improved somewhat just over a year ago. The night of Doug's 15th birthday, he found the high school freshman in bed with two sophomore girls. Dylan hadn't had two girls at once until he was a junior. Doug was clearly straight and Doug seemed to always be on the make. Wait a minute, Dylan thought as he greeted his brother. Am I now considering having Doug do the blowjobs? I'm losing my mind. And anyway, even if he could ask Doug and even if Doug agreed - what would the guys say if he brought his teenage brother as his substitute? This task was going to kill him. "Dylan, what the hell are you doing here?" Doug asked. "Why aren't you in school, Dougie?" Dylan barked. "Don't call me that, dickwad. I'm playing nurse, watching Desi. Dad is off in London and Mom had to run to Dallas on an emergency business trip. I volunteered to watch her. We don't need grad students to stay with us anymore 'cause you're not around to fuck them. But Desi's pretty self-reliant  she vomits without any help  so it's been a pretty free day." Dylan avoided explaining his presence as the two boys chatted about life, school, and girls. "Wanna smoke?" Doug asked. Dylan was safe from any drug tests for the baseball team for a while, so they went up to Doug's small bedroom and Doug loaded up his bong. Dylan had a much bigger room filled with trophies that he refused to vacate when heading to college despite a request from Doug. Dylan wasn't a big pot smoker. Doug seemed to be heading towards becoming one. The 16-year-old took huge hits off the bong, while his 19-year-old brother held back and remained a bit sharper, although the edge was gone from his voice. As they smoked more and more, the conversation got looser and freer. Having some shared embarrassing stories of their sexual adventures, Dylan turned the conversation in another direction. "Have you ever fooled around with guy?" Dylan asked "What&do&you&mean?" Doug choked out as he let out smoke from his lips with each word. "Have you and a buddy ever jacked each other off or something? Lots of guys do it. In sports they do it all the time." "Have you?" "Of course!" Dylan admitted trying to sound nonchalant. Actually, until the Underage Anal previous night, he had never touched a guy or been touched by one. His and Brandon's mutual jack-off was a new experience. But now was no time for the truth. "Happened with a some baseball buds in High School. We were all drunk and I jacked this guy off. Then another bud sucked me off." In truth, although Dylan had always checked out other guys, mostly confirming he had the biggest cock, he had never thought much about being sexual with a guy. "You were blown by a guy?" "Yeah. It felt the same as a girl. In some ways Underage Anal better&And I sucked him too," he hastily fibbed. If he was going to get results, he'd have to take risks. Doug was silent for a while. "Wow! I never imagined that you&I thought you&well, this one time I saw you and this girl together in the living room. And she was, well&" Doug was remarkably nervous. "She was giving you head. And it was really hot and looked so good. And Will was here too and we both went back to my room and then we&well, we were so turned on and so, we&we sucked each other. I never thought you had&I was worried it made me gay." "Was that it?" Dylan asked, trying to hide his excitement that he might have found a potential substitute. "Yes. I mean&no. Will and I kept doing that for a while and we tried some other stuff. But we were just kids then." Will Turner was Doug's long-time best friend. "And, I guess I've done stuff with some other guys too. But no one has ever fucked me. You know I'm not gay. I am with girls all the time. But sometimes, when there isn't a girl around or I just want to do something different, I mess around with a guy." Dylan found his cock began to twitch at his brother's revelations. "Doing stuff with a guy once in a Underage Anal while doesn't mean you're gay." Dylan had no idea what he was saying, but he had an opportunity he wasn't going to pass up. "Listen," Dylan tried to get his brother's hazy attention. "I need your help. The biggest favor ever. I need you to drive up to my college tomorrow night. And then, as part of my fraternity pledge task, I need you to suck off each of my four frat brothers." Doug said nothing and took another bong hit and let the smoke exhale from his lungs before responding. "Ha ha ha. You're shitting me, right?" He couldn't believe his brother's words. But the piercing blue eyed stare told him that this was the truth. Quickly Dylan recounted the nature of the task, the rules, Mia's refusal, and the real reason he came home. Doug sat quietly for almost two minutes before finally responding. "Okay. I'll do it. But it is going to cost you. For each guy I suck, I get one thing from you. Non-negotiable." Dylan knew his brother would relish having this power over him. But what choice did Dylan have. The favors couldn't be worse than Dylan having to do the sucking himself. "Tell me what I have to do." Doug thought quietly again for few minutes as he continued to smoke, mulling various possibilities, rejecting others. Finally, he was ready. "Here they are. Non-negotiable! Number 1: Get me laid with a hot sorority chick while I am up at your college. Number 2: I want you to trade bedrooms with me. Number 3: I want you to suck me right now. Number 4: When we are all done tomorrow night, I get to go back to your dorm room and fuck you." His brother was gay  or least bi! Dylan observed in shock. And what kind of twisted requests were those? "Fuck you!" Dylan said to his brother, trying to remain strong and negotiate some options. "What are your choices, LynLyn? Doug used their parents baby nickname for Dylan. Dylan hated it. You can suck four cocks or one. Desi isn't in any condition to help out - and she's a lesbian anyway." Dylan blinked as things began to make more sense. He was learning a whole lot about his siblings this visit. "Your girlfriend won't help you out either. Is it the fourth condition? We can wait and see about that one - I might want something different by tomorrow night." Without waiting for a response, Doug unzipped his pants and pulled out his already hard 16-year-old 8" cock. Clearly he was going to resemble his brother in one other way. It was skinny and long, but the head was large and oversized. Unlike his brother, Doug was circumcised, an unexpected change of heart by his parents in the 3 years between them. Dylan nodded in appreciation of his brother's well-formed cock. He looked into his brother's face and saw his own piercing blue eyes staring back at Underage Anal him. He had to admit, his brother was cute. Dylan took in a deep breath and realized that sometimes you had to do crazy things to find success. One was better than four. He leaned over and tried to take his teenage brother's cock in his mouth. The position was Underage Anal awkward and he couldn't get a good approach from where he was sitting. Dylan hopped off the bed and onto his knees in front of his brother. There he had better access. He took the oversized head in his mouth and began to move up and down on his brother's staff. It was so smooth and the skin was so soft. But the rod was iron hard and seemed to be getting even harder as Dylan worked on it. "Watch the teeth," warned Doug as Dylan had done so many times to other girls. Dylan Underage Anal thought about the expert suckings he had gotten from Jess and Sam the past two nights. He tried to copy their actions. He knew he was unprepared to swallow more than a couple inches of his brother's skinny tool, but he could still do a bit with the head, shaft, and balls. With the bong hits having removed most of his anxieties, Dylan dove into his task with surprising enthusiasm. He had never thought about being with a guy - let alone his brother - but there was something primal and fulfilling about making Doug write and moan. He understood the power one had over a boy when you took his cock in your mouth. "I'm going to cum!" Doug cried. Dylan pulled off and used his hand to jack his brother. "Oooooo&Oooooo&.Oooooo&" Doug moaned and then with great force jerked his hips as he shot right into his brother's face. "Fuck, Doug!" Dylan muttered as the semen poured out in gushes continuing to make a mess on Dylan, Doug's legs, the bedspread, the floor - everywhere. "That was fucking awesome!" Doug shouted as he dropped backwards onto the bed. "And I knew you were lying before. You've never sucked a dick before. I'm not stoned enough to know when you are talking crap. If you had done it, you wouldn't need me to do it for you. Dylan wiped the cum out of his eyes and lips. The taste wasn't so bad, but he wasn't planning on developing an affection for it. Was that what he had done to so many girls? "Be at my dorm by 7pm on Friday and we'll finish the rest of the deal. And go check up on our sister. I think I hear Underage Anal her throwing up." Friday Night "Get the fuck out of here!" Austin shouted. "The rules say that I can provide a substitute. A girlfriend&" "So where's Mia?" Chet asked. "Or it can be a sibling." Dylan continued. "So, here is my substitute." Wearing a high school baseball jersey and jeans, Doug looked like a tall typical suburban teenager. His moppy brown hair was uncombed and his cheeks were devoid of any stubble or growth. The four freshmen in front of him stared in disbelief. "This is my brother Doug. He's straight, but has agreed to be my substitute." "No fucking way," Austin voiced. "The rules clearly say a sister or a brother. If you don't like it, you can drop out of the pledging." Dylan was getting defensive, worried they would somehow challenge his plan. "He's right," Brandon noted. Brandon had re-read the task rules so many times that he knew them word-for-word. "Who's first?" Doug spoke for the first time, bored of the standing around. It was Nick's turn to go first. He undid his belt and dropped his pants. He cock was flaccid and he had a pained look on his face. Nick hadn't spoken to anyone since last night's event. They wondered if he even could get hard. Doug pulled off his baseball jersey revealing a "Do You Know Where Your Girlfriend Underage Anal Was Last Night? I Do?" t-shirt - perhaps the worst possible outfit he could have chosen. "Take off your shirt," Nick ordered. Misinterpreting the motivation of Nick's request, Doug smiled and removed his shirt showing his hairless, trim body. He moved closer to Nick and pulled off his shirt. The high school student leaned in and started to suck on Nick's left nipple. The other boys were shocked by the sight of the two beautiful boys together. After a few moments of nipple rubbing, Nick pushed Doug onto the floor and repeated the position of Wednesday with Sam. His still limp dick was forced into Doug's mouth and Nick began to move back and forth, speeding up with each stroke. His dick started growing to full size. Doug was totally turned on to have a cock harden in his mouth and tried to relax his throat Underage Anal to take in more of Nick's 7 inches. But Nick was angry and was taking it out on the poor boy. He grabbed Doug's head and forced his cock all the way in his mouth. Doug was having trouble breathing and started to gag when Nick shot into his throat. He dumped his load of resentment and anger into Doug's mouth and then as quickly pulled out, walked away, and pulled up his pants. "I'm sorry," he mumbled to the coughing boy as Brandon gave him something to drink. Austin was next. The violence of Nick's face-fucking had kept the other boys from getting excited. Doug pushed him onto the couch and kneeled between his legs  the same position Dylan had sucked Doug the previous day. Taking out Austin's limp dick, Doug began to rub it gently with his hands. Soon he was covering the head with little kisses and then took his balls into his mouth. Austin had never been with a guy in any capacity until Nick Underage Anal jacked him on Wednesday. The boy was cute, but Austin simply didn't swing that way. Austin leaned back and closed his eyes. He tried to pretend it was a famous hot girl blowing him and settled on Natalie Portman. Doug had talent and it wasn't long that fantasy, tension, and his efforts had Austin shooting into the boy's mouth as Austin cried out, "Natalie!" to much embarrassment. "Your bro'z got skills!" Chet remarked as he beckoned Doug towards him. With their height difference and his own sexual confusion earlier in the week, Chet wanted to be blown standing up. Doug crawled on his knees over to the older teen as Chet removed his pants. Doug helped with the his underwear, shoes, and socks, leaving only a college football t-shirt. Chet was already hard and Doug dove right in. Dylan was surprised as to his brother's skills. Cleary he had done quite a bit of that "messing around" with other guys. Chet was already grunting and pushing his pelvis forward. Chet asked Doug to slow down and make it last longer, but the boy knew he had another guy to go and kept up the speed. Doug's in charge, he thought, Underage Anal not Underage Anal Chet. Unhappy as being made to cum so quickly, Chet decided to pull out and shoot directly in Doug's smooth face and chest whooping like a rodeo cowboy as he sprayed onto the boy. Doug much preferred swallowing than having all this cum on his body and raced off to the bathroom to clean up a little pissed off. Brandon was last. He was still fully clothed. Doug immediately thought this was another Austin - reluctant and needing help. But as he began to undress Brandon, he felt the boy's ample cock pushing at the fabric. Brandon had been incredibly turned on by the sight of the two hairless teens, Chet and Doug, going at it. He worried if he even touched his own clothes, he'd have already shot multiple times now. Doug was a perfect "little Dylan," but with a better sense of humor, a bigger risk taker, and a zest for life. Doug looked directly into Brandon's face. He recognized passion and hunger. Brandon wanted him so badly. He stared into Brandon's hazel eyes. The baby blues of Doug's corneas was captivating to Brandon and the boys suddenly were kissing, tongues slipping past each other's lips with powerful desire. Chet and Dylan, who usually made gay cracks for the slightest reason, restrained themselves. They had each jacked off Brandon in the past two days, and had each been with another guy this week, so they were in no position to judge. As Doug kissed Brandon's neck, he saw his older brother staring at them. He recognized desire there too  although it was more buried. He needed to make this particularly hot. He stripped Brandon completely, but left the remainder of his own clothes on. Brandon tried to head to the couch as he had the past three nights, but Doug wouldn't let him. Standing the 19-year-old in the center of the room, he proceeded to lick him from head to toe and then to head again. Dropping on his knees, Doug kissed everywhere around Brandon's throbbing tool. But he didn't touch his dick at all. "Suck it!" Brandon begged. Doug ignored him and moved to his rear. He spread the tight cheeks and used his tongue to moisten his fuckhole. Holy shit! Chet gasped in admiration, jealousy, and surprise. As Doug rimmed him, Brandon shuddered in sheer ecstasy. "Please&suck me!" Moving between his legs, Doug attacked his scrotum. Brandon clearly shaved his pubes and balls, so it was no problem to take each ball in his mouth and work it over. It was deadly silent in the room. All the other pledges were staring in amazement at the delayed pleasure this teenager could bestow. Finally, and without warning, he swallowed Brandon's cock. He knew he didn't have long, so he deep-throated it Underage Anal quickly and used his tongue to stimulate it to climax. "Aaaaaaaahhhhhhhaaaahhhhhhh! Ahhhhh! Ahhhh!" Brandon shouted at the top of his lungs as his sticky seed shot down the boy's throat. Doug let the cock settle in his mouth and then slowly pulled off. He gently licked the entire shaft to cleanliness. Standing up, he looked into Brandon's hazel eyes and the planted an open-mouth kiss returning some of the cum back to its owner via their tongues. Doug stepped back, smiled, and then grabbed the bottle of water to clear his mouth. Dylan nodded appreciatively at his brother for his efforts and for this incredible show. He had forgotten the three remaining promises. But Doug hadn't. Doug broke the continued silence and looked at his older brother. "I want to make a change in my conditions. I am dropping the claim on your bedroom for something else." Without waiting for a response, Doug dropped back to his knees and pulled down his brother's jeans. His hardon was amply evident through his briefs and Doug yanked them down as well. The huge cock began to come to full 10 inch strength and the teenager wrapped his mouth around the head and bathed it in saliva. He didn't want to give Dylan a chance to think too much about what was happening. As he got a clear physical response from his brother, Doug finally released his own 8 inches out and began stroking it hard. The boys had seen both Austin and Chet blown by their sisters. But watching this boy with his own hard large dick blow his brother was transfixing. Brandon and Chet moved towards each other and Underage Anal wordlessly began to repeat their actions of the previous night stroking with deliberate intent. Austin and Nick were sitting on the couch. They had both long ago recovered from their own blowjobs and Austin began to play with himself as he watched Dylan and Doug go at it. Nick was sitting, still tense, next to him, his cock hard despite himself. For the first time in his life, Austin reached over grabbed his friend's hard-on and began to rub it. "Let me make things up to you&" he whispered. Nick said nothing and let his roommate proceed. It was a lot like masturbation, Austin thought, but he's getting all the pleasure. Dylan was so confused. His brother was an amazing cocksucker. His friends were all fine with it. Each of them was hard. He saw Austin stroking Nick, and Chet and Brandon going at it. Brandon sure got it up quick. Two days ago, he would never have believed any of this scene. Dylan stopped Doug long enough for both to remove the rest of their clothing. Seeing these two boys, so similar in body and face, gain pleasure, one from the other surged electricity through the four pledges. Chet shot first under Brandon's guidance. Nick then exploded onto his own chest. After a brief pause, Chet put extra focus on Brandon's cock and he made an additional mess on the carpet. Austin, stroking himself, continued to gaze ahead. Dylan usually took a while to cum when being sucked. Tonight was no different. Doug used the technique he had also learned from the same grad student who taught it to Dylan  he stuck a finger up his brother's butt. Before he understood exactly what had happened, Dylan shot into his brother's mouth. The volume was too much and the boy pulled off receiving the rest of the gusher in his face, hair, shoulders, and chest. Austin immediately shot upon seeing this onto his own legs and the carpet. Although he had yet to orgasm himself, Doug stopped stroking his own dick, prepared to have more interesting action later that night. As the boys cleaned up the mess of their cum on their bodies and on the carpet, clothing, and couch, Doug broke the quiet by shouting to Dylan, "Where's my hot sorority girl to fuck?" Dylan had gotten Chet to find someone for his brother without explaining why. Mindy Simmons was an easy lay and had traditional slutty college girl looks  blond hair, pretty face, and big breasts. Chet and Austin had both been with her. She had a total thing for Dylan, but he had been off limits. Chet had told her that Doug was Dylan's fraternal twin and set up the date. Doug eagerly departed for his college girl action. While actual "date" events had been planned, within 15 minutes of meeting they were making out in the car. 10 minutes later, they were back in her dorm room having loud, sloppy sex. Late that night, Doug slipped into Dylan's dorm room. "How was it?" Dylan muttered from his sleep-like state. "Fantastic. My first undergraduate&girl." He had never told Doug about the grad student that had both experienced. "How many times did you do it?" "Twice. I came pretty quickly the first time, as you might guess. Then we did the second time slower doggie style." Dylan's roommate and former pledge brother Jared was spending the night with his girlfriend to give Doug a place to sleep. Dylan yawned and fell back asleep. Doug undressed completely but headed for Dylan's bed, lifting the covers and crawling into bed with him. He pushed his semi-hard cock up against Dylan's backside and rubbed it against the boxer-briefs. His right hand began to massage his brother's rock solid chest. His kissed his brother's neck and shoulders. "What the fuck are you doing?" Dylan barked. "Cashing in on the final part of my bet. Last part. Take off your underwear. I'll do everything else. You just need to relax" "I'll give you my bedroom at home and then we're done. You got everything else." "No. I get this. I know you are stronger than me and I can't force you  and I wouldn't want to. But I also know you never break a promise or a deal," Doug explained. "What if I blow you again?" Dylan offered. "You liked having my finger in your ass. You're going to love my cock, LynLyn." Doug reached and down and got some lube from his bag. He liberally spread it on and put his hand into his brother's briefs to spread it on is ass. "Make it quick." Dylan finally accepted as his brother massaged his fuckhole. Doug didn't listen to his brother. He knew he had to go slow at first. His brother was a big guy, but 8" couldn't just be rammed in. He had broken enough cherries to know what to do. Doug got his brother into a more accessible position and introduced him to the pleasures of guy-on-guy fucking. Under oath in court, Dylan never would have admitted how much he enjoyed that night. His brother was gentle and was damn good too. The forbidden qualities  he's a guy, he's my Underage Anal brother, he's too young, he probably should be wearing a condom  all set off huge warning bells that normally would have stressed Dylan to no end. Tonight, they seemed to only add to the pleasure. It didn't take Doug very Underage Anal long to finish. His grunting and moaning during the fuck, and especially as he shot up his older brothers ass probably woke half the dorm hall. They both collapsed in sweat and exhaustion onto the bed. As they spooned, Doug discovered one thing was still awake. "You got Underage Anal hard from my fucking you. That's awesome." Doug Underage Anal began to stroke his brother's long cock from behind, gently rubbing from top to bottom. He took his time as his brother unsuccessfully tried to fall asleep. Dylan would have to shoot to be able to sleep. "Faster. Harder." Dylan encouraged his brother. Doug kept his slow, deliberate pace. "Dougie, if you don't make me shoot soon, I will beat the living hell out of you." Doug laughed and complied, jacking his brother with such force that he nearly ripped the skin until Dylan shot all over the bed. Doug makes me feel so good, Dylan thought, as he accepted his brothers open mouth kiss. They both got up and slipped into Jared's bed, spending the night completely naked and comfortably wrapped tightly in each other's brotherly arms.
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