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Related article: Pledge Class - The Blow Job Task 3 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: With a final pledge task to blow each of the other 4 pledges, Austin got his High School sister to be his substitute on the first night. Only an exclusive girlfriend or a sibling can sub for the pledge himself. Surprisingly, Austin also got blown by his sister. Pledge Class - The Blow Job Task Part 3 - Chet Monday Night Chet's sisters Erica and Samantha were 28 and 24. Chet had been a welcome unexpected pregnancy in the family and, as the only boy, was doted on by everyone. Because of the ten and six-year age gaps, Chet wasn't Underage Tits that close to his sisters. Sam had been on her way to college just as Chet was hitting puberty. Erica was married and had two kids, so Chet decided Sam was the better choice. She also lived only an hour from the school. On Monday, after his last class and soccer practice, he borrowed a brother's car and drove to meet his sister for dinner. They met in a crowded sushi bar and swapped school and job stories over a big boat of raw fish. Sam worked in advertising and had been a success from the start. Already she was earning big bucks and she never hesitated to spend them on herself or her family. Sam was taller than Chet, about 5'7". She had curly brown hair that stretched down to the middle of her back. While her breasts were average in size, her figure was exceptional. Every part of her body seemed to be designed to fit her perfectly. Sam's green eyes accentuated her perky nose and easy smile. Putting down her chopsticks, Sam looked turned those eyes directly to her brother. "Chet, we've had our edamame and rainbow roll. Now, did you drive up here for a free meal or something more?" Chet smiled and dove right into the matter, never one to mince around with words. Sam laughed repeatedly when she heard his predicament and his proposed solution: Sam should substitute for him in the blowjob task. "So if I do this - suck your 4 friends - and I'm not saying I will even consider it - you'd have to do something for me. Something big." "Like what?" Chet said with his big grin on his face. He knew his charms weren't nearly as effective on his sisters as they were on everyone else, but it was always worth a try. "Well&it'd have to be something similar." Her mind was racing in a way Chet didn't like. "I'll blow four guys&if you blow one." "What the hell are you talking about?" Chet demanded, his smile immediately disappearing. "Trevor's birthday is coming up. We have been exploring our fantasies. He revealed that he has always wondered what it feels like to be with a boy. And I have Underage Tits always wondered what my little brother would like having sex. Now we can both get our wish." Trevor had been Sam's serious boyfriend for 2 years. He was also in advertising with a youthful face and firm physique. Chet had sometimes imagined sex between Trevor and Sam  and it was always really hot. "You want me to blow Trevor?" "And maybe more than that. Basically, I want to you to spend a night with Trevor, Underage Tits doing whatever he wants. And I get to watch. You do that and I'll suck your little friends. If you won't or if refuse Trevor, you'll have to suck all four yourself." Chet and Sam returned to her apartment. She had called Trevor on the cell phone and told him to meet her there for a fantasy surprise. On the way over, Sam shared a few of their previous fantasies they had fulfilled: Sam with another girl, Trevor with two girls, dressing up like Underage Tits a French maid, a cowboy, and even a little SM. It all turned Chet on. Trevor arrived at the apartment about 20 minutes after Sam and Chet. He was greeted with wet, sloppy kiss from his girlfriend as she whispered, "Your birthday present fantasy is in my bedroom. You can do whatever you want between now and midnight." It was 8:52pm according to the bedroom clock. Trevor entered the bedroom to discover Chet. The 18-year-old sitting on the bed with his arms crossed across his bent legs, almost fetal like. He was only wearing his boxer-briefs. Trevor's initial confusion transformed into a wide grin as he realized the opportunity in front of him. Without a word, Trevor began to disrobe, tossing his clothes onto the floor. At 26, Trevor worked out regularly and had tuffs of dark hair on his shapely chest and a trimmed treasure trail leading into his grey silk briefs. "Lay back," he ordered and Chet dropped his head onto the pillow and stretched out his legs. He was terrified, uncomfortable, and a little excited too. Trevor sat on the edge of the bed and picked up the boy's foot. He began to lick his toes. Chet had never had his toes sucked and discovered the power of this erogenous zone. He made a note to try it with an appropriate girl soon. Despite himself, Chet felt his dick begin to harden. Trevor removed Chet's boxer-briefs and hesitantly began to rub the freshman's cock. Chet shivered in response to the touch. No guy had ever touched him before. He had never engaged in the homoerotic foreplay that other guys had  like Brandon, he was sure. He had always found another girl when he needed one. Trevor's hand felt different than a girl's. The strong, large fingers rubbed his dick until it was standing upright, stiff and eager for action. It was Trevor's first time with a guy too, but after years of quiet fantasy, he was quickly figuring out what to do. The hand came off and a new, wet, warm sensation replaced it. Trevor had begun to suck him with great desire. The older man gagged as he tried to take in too much, but persisted. Chet began to moan and move around until he heard a feminine laugh. To his left, his sister was standing in the doorway of the bedroom with a video camera in hand taping the whole sorry episode. Chet made a hostile face, but it quickly disappeared as Trevor's tongue bathed the teen's hard cock in delight. Then the mouth went away. "My turn," Trevor declared, kneeling upright on the bed. Chet closed his eyes and considered his options. One blowjob that no one will ever know abut  or four in front of everyone. This seemed like the best one out there, but he was extremely apprehensive. He pulled down his sister's boyfriend's red briefs and stared at the 6" cock in front of him. My sister's boyfriend is smaller than me, he thought with a sense of superiority. Chet opened his mouth and hovered over the pulsing prize. "Just do it!" his sister yelled. Chet took the cock's head in his mouth. It was a surprising sensation - salty, hot, and what he realized was pre-cum coming out of the slit. "Use your hands too," his sister helpfully directed. Chet moved his mouth up and down on the head worried about going any deeper. With his right hand, he stroked the shaft while his left played with the balls. He held back, unsure of what he was doing and unable to commit to the experience. While Sam shouted various suggestions, Chet struggled to comply. After about five minutes, Trevor pushed him off. "You are a crappy cocksucker, Chet." Trevor declared. "I am never going to get anywhere with that shit. And I want to blow my load." Chet gave a "What me, worry?" shrug in hopes that would somehow solve the problem. "Turn over," Trevor replied instead. With his eyes wide in disbelief, Chet turned to his sister. "I am not getting fucked." "You have two choices, Chet. You can get fucked right now. Or you can blow your friends yourself on Wednesday. Given the blowjob you just gave, it'll take hours for you to make them cum. If you can even do it." Chet sighed again, recognizing his dilemma, and rolled over onto his stomach. No one will ever know, he comforted himself. No one will ever know. And as soon as I can, I am going to fuck some girl hard. Trevor's large finger entered Chet's tight hole and massaged the insides. No girl had ever put her finger there before and the sensation with thrilling and intense. "Stop squirming, there's more to come," Trevor cautioned. The boyfriend added a second finger and then a third, slowly moving them in and out of Underage Tits the teen's butt. Sam moved in closer with the camera and caught a priceless close-up of Chet's straining face. She remembered her first ass-fucking by Trevor who had introduced her to the pleasures of back door sex. Trevor's cock was sufficiently lubed and he pulled his hand out. His dick glistened and throbbed as he pushed it into his girlfriend's sister's virgin Underage Tits hole. Chet screamed out in a mixture of pain and ecstasy, "Slow down!" Trevor reduced his pace and then increased it, repeating that rhythm over and over. Tears fell from the 18-year-old's eyes and he bit into the pillow to keep from Underage Tits shouting. Sam's camera continued to capture every moment. Trevor pushed, seemingly deeper and deeper with each thrust, until he suddenly pulled out and sprayed Chet's back and ass with his load. Trevor grunted in satisfaction and then lit up a cigarette. Sam kissed her brother on the cheek and told him that this was the Underage Tits incredible thing she Underage Tits had ever witnessed. Wile Sam and Trevor discussed the sensation of fucking a boy's ass, Chet pulled himself up and into the shower. "Be at school by 7pm on Wednesday, Samantha," he reminded her as he headed out the door. We start at 8pm sharp." He'd have to fuck some girl soon to get this sensation out of him. But, he had to admit to himself, being naked in front of his sister was kind of thrilling. And Trevor's cock did feel kind of good. Thursday Night "This is my sister, Samantha." Chet noted to the four, eager waiting pledges. "Call me Sam," she noted. The guys smiled at Sam's sexy body and sophisticated looks. Of the four, only Dylan had ever fucked a woman in her mid-twenties and that was back when he was 15 and slept with the grad student staying with Dylan and his siblings while his parents were in Europe. Dylan eagerly dropped his pants first and sunk into a chair. After the previous night, they knew they'd have to change who went first and had decided unofficially to use last night's order as a rotation. Sam blinked in surprise at Dylan's mammoth cock. It was already hard and she hadn't even touched him. Younger boys are insatiable, she thought. Sam was an aggressive cocksucker. In college, she had perfected her skills as a way of avoiding sleeping with everyone. She had sucked huge ones and tiny ones, but hadn't had one as big as Dylan's since college. While she didn't love to deep throat, she worked wonders with her tongue and fingernails. Again Dylan took a long time to milk out. After 15 minutes, her mouth was getting exhausted and there were three boys to go. So she shoved a finger in Dylan's ass and he tensed up immediately. The last girl to stick Underage Tits a finger there was the grad student 4 years, he though. Maybe this is a secret only older girls know. As she massaged his hole, she intensified her sucking until he burst out into her mouth and then all over her face. Brandon again wanted to be sucked while lying down. Sam did all the work and Brandon lay back dreamily while she controlled every moment. As he had spent the past quarter hour staring at Dylan's dick, he was already pretty wound out and easily shot in Sam's mouth. Nick seemed a little less tense than the previous night perhaps because he had no hang-ups about being with Chet's sister as had with Austin's. Again he handed over a glass of water following her time with Brandon. He asked her to sit on the floor with her back against the couch. After removing all his clothing, revealing his evenly tanned body, he fed his cock to her waiting mouth grabbing her hair and aggressively face-fucking her. The Underage Tits other boys were again surprised that Nick was such an aggressive sexual partner. It didn't talk long before he covered her face and blouse with cum. Sam was kind of pissed about the blouse and removed it revealing her perfectly shaped small breasts. Chet stared in amazement. He hadn't seen his sister naked before and found himself incredible aroused by seeing her suck on the pledges. His right hand began to gently rub the front of this jeans. Austin was ready to bust having watched his roommate's facial. He was delighted to have Underage Tits a chance to fuck Chet's sister's face. The only way to make it better would be to fuck her. Or maybe to have Chet doing the blowing. Taking a cue from Nick, he told Sam to lie on her back on the floor with a couch cushion under her head. He proceeded to straddle her, having her Underage Tits suck his balls and rim his crack. Sam found it kinky to be licking the ass of a 19-year-old boy. She let him feed his cock to her and also played with his balls in her mouth. As she switched from one ball to the other, Austin exploded in jets of cum across her face and hair. "Thanks," he said as he stood up from Sam's prone floor position. After Sam returned from another trip to the bathroom to wash, Dylan loudly whispered to Brandon, "Now, it's Chet's turn." "No fucking way," Chet said although the huge hard-on he was spotting said otherwise. "Just the four of you." "That's not what you said to me last night," Austin reminded him. "How about it, Sam?" "Well, my brother could certainly use some reminders in how to give a blowjob. On Monday, he did such a piss poor job with Trevor that my boyfriend had to fuck him to get off. So he deserves a reward." The silence in the room was deafening. All four boys looked at Chet whose lack of response told them everything. Sam pushed her unusually silent brother down onto the couch in a seated position and proceeded to remove every piece of his clothing. He offered no resistance. He had fantasized this moment in many of his earliest masturbation sessions. Now it was happening. But wasn't this wrong? This shouldn't be. Sam seemed to have no moral objections and pushed apart his knees and dove in for the kill. The four other boys stood surprising close to each other watching their trim friend's quivering body under his sister's tutelage. They began to massage their own cocks with pulsing erections despite their own blowjobs earlier. Nick, working his own shaft with his right hand, dropped his left on top of Austin's hand and began to join with his back and forth motions. Austin was stunned, but said nothing. After a few seconds, Austin removed his own hand letting Nick continue the jack-off. Brandon, seeing this out of the corner of his, likewise grabbed Dylan's monster in his right hand. Dylan tensed up, but offered no resistance as Brandon pleasured him. Then, as Dylan enjoyed Underage Tits the sex-charged event before him, Dylan found his own left hand reaching for the blond boy and he started to rub Brandon in rhythm with the hand that was on his own dick. Chet's resistance to his sister's mouth weakened with every passing lick and slurp. Finally, he dropped any emotional hang-ups and leaned back on the couch. Sam swallowed his whole cock about the time she also shoved two fingers into her brother's deflowered butt. As they disappeared from view, Chet squeezed his buttcheeks and let out a small gasp of delight. He began cumming into her mouth, more than he had in weeks despite the frequency of sex he had enjoyed. She moved off his member and let the cum shoot onto his legs and chest while she moved her fingers in and out of his ass. Seeing Chet shoot was too much for the other boys. Brandon, already in delirium with Dylan's hand on his dick, let loose with Dylan following. Nick felt Austin's dick tense and he increased the pace as Austin exploded. Nick, the only one massaging his own tool, then ejaculated as well. The smell of cum in the room was overwhelming. Sam got up, pulled her cum-stained shirt back on, and smiled at the four naked boys standing in front of her. She then leaned in and gave her brother a full mouth on mouth kiss as his cum went from her tongue to his. Like most every boy, Chet had tasted his own cum at some point, but this kiss was surprisingly appealing despite the source and transfer of his own fluids. Sam walked out of the basement ignoring Austin's hints for a fuck. Chet remained naked on the couch. After assembling their clothes, the four standing boys got dressed and departed quickly except for Brandon. "You got fucked by a guy?" he quizzed. "Yeah." Chet said, the breath finally returning to him. "How was it?" "Honestly&It wasn't bad. But I still prefer being on top." "Have you ever fucked a guy?" "No. That was my first time with a guy in any fashion. What about you?" "I had a few experiences growing up. But never any fucking," Brandon life. "I'm naked and covered in cum, aren't I?" Chet noted. "Yup. Get dressed. We'll be back here tomorrow for Nick's turn."
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