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Chapter 294
by
Samus1001
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Humiliating a Jock
"Aaaahhhh fuck yes. Fill me up Caleb," Chris moaned.
Angie giggled as she pulled Caleb's cock and fed it into her friends pussy for the entire class to see. She got a perverse thrill out of seeing her lesbian friend enjoy their masters dick. She gave Chris's ass a good smack of her own. She deserved it, she was no more a lesbian than Angie was. Chris called herself a Calebsexual, claiming she was a lesbian except when she was around Caleb, but that description fit every woman in his harem. Angie got nauseated just thinking about having sex with another man. Caleb was special though.
For years Angie and Caleb had been as close as a guy and a girl could be without actually crossing the line into something more. They were so close they even had a couple sleepovers, their parents trusting them to not cross any lines. Now she smiled up at him as he gripped Chris's hips and began plowing her over the desk.
Angie got her cellphone out of her pocket and moved around to stand in front of Chris. She started recording, saying to Chris, "Hey, we don't have any plowcam type videos on the new porn site. This will be the first one."
Chris looked up with a shocked expression, "But Angie, I, UH... I didn... UH... Fuck... Uh... I didn't... Agruh... Agree to... shhhiiittt... to this..."
Caleb rammed his dick hard and deep while smiling for the camera. "Make it look good Angie. I want to watch this with Kat later, even if we don't put it on the porn site."
At that, Chris suddenly became an enthusiastic partner, just like Caleb knew she would. Chris was devoted to Kathy, every bit as much as Kathy was devoted to him. She began to slam her ass back at him, bouncing her ass cheeks against his hips. She looked back over her shoulder at him and hollered, "Oh yeah, uh, give it to me Caleb. UH! Show Kathy, fuck, how much you, uh, love me. Show her, huh, how gouh, good you take care of me."
She turned back to Angie and her camera, "I love you Kat. Oh fuck! Caleb fucks me so good. He’s such a good, uh, master, letting me, uh, cream all over, uh, his cock. I hope you, uh, you suck my juices, ohff him next perinnnf… period. Taste me on his cock Kat. I love you. I love Caleb. I love being in the harem! Oh Fuck! Shit! Oh god yes! Pull my hair!”
Caleb was doing just that. Each of his girls had some quirk they enjoyed. Chris liked having her hair pulled right before orgasm. He could tell she was getting close because she was rising up on her tiptoes. Her feet always straightened right before she came.
Her cunt spasmed on his cock as he plowed her across the desk. Her back arched in a nice U shape and he could hear her titties slapping together under her. He loved that sound, especially from his bigger titted women. He yanked her hair and growled, “Look at the camera Chris. Show Kathy your ‘O’ face. Let her know how much you love being on my dick.”
“Oh fuck! Kathy! Kathy! It’s amazing! It’s so deep! It’s so thick! I love it! I love Caleb’s cock in me! I’m so glad you talked me in to joining the harem. Thank you! Oh fuck! I’m… I’m cumming!”
Chris dug her nails into the desk leaving scratch marks as she thrashed on his dick. She tried to keep her eyes on the camera but it was impossible once her eyes began to roll back in her head. Every time his cockhead stabbed her womb she felt a bomb of pleasure explode inside her. She was addicted to the cock inside her. When she couldn’t get the real thing she loved being fucked by the replica dildos Sonia made.
Caleb looked around the room and saw his classmates were intently focused on him, or more specifically his cock impaling in and out of Chris’s soaked snatch. A girl named Amy, a cute friend of Marilyn on the gymnastics team drew his eye. Not only was she finger banging herself, she was jerking her boyfriend off as well. Craig was one of the football players that picked on Zack. He also had his hand around Amy’s wrist using her hand to jerk him off.
Thinking of Zack and the problem he had gave Caleb an idea. A naughty idea. He liked hearing Chris talking to the camera so that Kathy could hear her later, but he wanted to do something even naughtier.
He gently lowered Chris onto the desk and slowed his hips while letting go of her hair. For all her strength she didn’t have a ton of stamina, not when it came to sex anyway. One or two big orgasms and she needed a break for a few minutes before she could fuck again, which meant he needed a new partner.
He pulled his dick out of Chris and headed in Amy’s direction. Her eyes grew wide as she realized he was looking at her. The. She looked at his cock pointing right at her and she licked her lips. He smirked and said, “Hey Craig, Amy looks like she needs a stretch. You don’t mind if I give her one, do you?”
Craig enthusiastically agreed just like Caleb knew he would. “Hell no man. Be my guest. She’s been wanting one since we started dating.”
Caleb looked back over at Amy and said, “If you want me to give it to you then stand right here and put your leg up on Craig’s desk. Keep jerking him too.”
Amy scrambled to get in position like he wanted. He jerked his head at Angie in a ‘come here’ motion. She hurried over and began a new video as Caleb lifted Amy’s skirt and rubbed his slick cock over her slit.
Amy was already soaking wet and Caleb’s cock was covered in Chris’s juices so without much preamble her began pressing himself into her. She had a tiny little pussy, but with her leg up on the desk she was spread wide. Wide enough that his cock head could pop inside. He chuckled as she let out a yip. “Don’t forget to jerk Craig. And talk to him. Tell him how it feels.”
“Craig, baby, it’s so big. Hooo! I can feel him stretching me. It feels like a baseball bat that’s about to tear me in half. He’s so much bigger than you too. His cock is as thick as my wrist. My kitty has never felt so good.”
Caleb grinned as Amy spoke. The slightly embarrassed yet happy look on Craig’s face was priceless. He glanced down and saw Amy’s hand slowly moving up and down half an inch or so as she squeezed Craig’s dick in a tight grip. There was barely any precum to lube his shaft and she was pulling his skin around rather than sliding along it. Amy obviously wasn’t trying to do a good job, but the goofy grin on Craig’s face said he didn’t care.
Gripping Amy’s hips he pulled her ass back to him. His cock worked deeper inside her and he felt her cervix kiss his cockhead when he was most of the way inside. He briefly wondered if she had been previously stretched or if she just had a deep love tunnel. Not that it really mattered, he pushed himself deeper, shoving her internal organs out of the way.
Amy cried out, “Oh god! Oh god! Yes! He’s doing it Craig! He’s stretching me! It feels so good! How can it feel so good? Thank you! Thank you Caleb!”
Caleb began pumping long deep thrusts into Amy as she gave her boyfriend a mediocre hand job. She continued to babble about how good it felt, stroking Caleb’s ego while at the same time showing Craig how much she loved getting fucked by a big dick.
“Take her shirt off so I can have her bra Craig. I don’t want it getting dirty.” Caleb grinned as Amy had to pause her hands long enough for him to get her topless. Caleb let go of her hips and unhooked her bra. Not letting it fall he tossed it to Angie who caught it one handed.
Amy resumed jerking Craig while Caleb reached around and grabbed her small titties. They were not quite big enough to fill his hands, but there was enough for him to get a good grip. He used that grip to give him leverage as he sped up and rammed her cunt hard and fast.
Amy grunted and groaned as her pussy was pounded. Her hands were on autopilot which actually improved her efforts on Craig's dick. She slid one hand along his shaft as the other squeezed his balls.
Caleb could feel her cunt begin to flutter, telling him she was about to cum. The grunts Craig was making told him Craig was about to as well. Caleb squished Amy’s tits in his hands saying, “Cum together you two. I want you to cum at the same time.”
Amy squealed as Craig stuttered, “I’m cumming!”
Amy yanked her arms back, letting go of Craig’s dick. Caleb pulled her away as Craig’s cum fired up onto his desk, his dick bobbing with each spurt. Caleb continued to pump Amy as she creamed on his cock, all the while Amy grinned as Craig’s orgasm was ruined.
Caleb didn’t expect Amy to start laughing. She laughed uproariously looking down at the tiny amount of cum that puddled on the desk. When she stopped laughing she said in a soothing tone, “Aww baby, did you make a widdle mess? Do you need Caleb to show you how a real man cums?”
Quiet laughter broke out around them as Amy belittled her jock boyfriend. She twisted her body and kissed Caleb hard, shoving her tongue in his mouth. Caleb was technically fucking her from behind but her flexible gymnast body had her turned enough to kiss him with no effort at all. When she broke the kiss she whispered, “You're everything Marilyn said you are. That's the first orgasm a guy has given me in month. Cum in me Caleb. Just enough to knock me up. Please. Then you can spray the rest of your load on my face. Please.”
He saw the pleading look in her eyes but that warred with his sense of responsibility. He whispered in her ear, “But what about college?”
She smiled and whispered back, “Don't worry about that. I’m taking a year away from school. My mom is going to leave my dad and move away after I graduate. He’s an abusive asshole. Mom and me are in love. I’m going with her and I want us to have your baby. Please Caleb. This might be my only chance. I may never see you again.”
He felt his heart go out to her. He had slowed his strokes as they whispered to each other. Nodding to her he smiled and hooked his arm under the leg that was still propped in Craig's desk, then lifted it up onto his shoulder. Using her leg as a brace he began hammering her cunt once again. He kissed her nose and said, “Smile for the camera.”
Amy looked over at Angie and blew the camera a kiss as she stood on one leg. She wrapped her arms around Caleb’s neck and let him give her even more ecstasy.
Caleb waited until she was on the verge of another orgasm before he let his balls boil over. With one last deep slam he smashed his cockhead against her sucking cervix and pulsed two thick ropes into her womb before he let her leg down. She was so lost in her orgasm that she didn’t feel him pull his cock out of her, or noticed when eased her to her knees. All the while his spurting snake coated her in cum from her belly to her tits.
He finished himself off on her face, unfortunately her glasses blocked him from getting it in her eyes. She began smearing the cum around on her cheeks and chin then licking it off her fingers even as her small breasts began to swell.
He looked over at Angie and said, “Make sure you give her a copy of the video so she can watch it with her mom. Amy, let Angie get a picture of you.”

Mrs. Garcia stumbled over to them on unsteady legs. Her dew ran down her thighs as she said, “Caleb, did you breed her?”
Caleb nodded sheepishly, "Yeah, she asked me to. I know I'm not supposed to breed all the girls in school, but don't worry, she can get a hold of Marilyn if she needs my help with anything. I'll make sure her and the baby are okay."
He turned back to Amy to make sure she knew he meant what he said, but she was in the middle of arguing with Craig. "Of course I asked him to breed me. I may never get another chance to have his baby. Besides, it's my body, not yours. If you don't like it we can break up right now."
Craig's face fell, "Baby, no! I'm sorry. I... I didn't mean to get upset. I just thought we would date for a while and maybe get married and start a family after college, not right now."
Amy crossed her arms and said, "Well too bad. If you want me and mom to get an apartment with you when you start college then you better to get used to the idea of being a father. If not, mom and I will raise this baby alone. We don't need you, we would be perfectly happy not sharing our bed with anyone. Hell, most guys would kill to have two women share him."
Caleb was still chuckling when the bell rang ending class.
Thank you for reading. Please leave a comment if there is something you would like to see. If you loved the story please consider buying me a cup of coffee at https://ko-fi.com/samus1001
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Don't mind the fucking, nothing to see here
Once upon a time, on a bet and while very very drunk, a higher power of some kind made a very special item.
Updated on Jun 14, 2026
by Krakatowa
Created on Sep 6, 2014
by Murakami
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