College Loser Ch. 01

Christopher tried to think back on how it had all happened. His first year of college was going so well: he liked his classes, found a girlfriend, got along well with his roommate Justin. In high school he was a nerd, never dated, and jocks like Justin would never want to spend time with him doing anything other than belittling him. It seemed like that had all changed, and he was on his way to a new life.

How wrong he was. His girlfriend, Sarah, had been secretly hooking up with Justin behind his back. He convinced her to talk Christopher into posing for some embarrassing photos of him in panties, in diapers, shoving vegetables and other objects up his ass and deepthroating them, him posing nude in humiliating positions... Sarah immediately went to Justin with the photos, and Justin in turn presented Christopher with a tiny pink chastity cage and an ultimatum: Christopher would wear the cage, and if Justin ever found the lock had been cut or any other reason to think Christopher had removed the cage, then all of the photos would be emailed out to the whole school and to Christopher's family. If Christopher was good and did everything he was told, Justin might let him out at the end of the semester and be cage free for winter break. Otherwise, he would have another semester to earn his freedom.

Christopher was now kneeling, naked, waiting to see Sarah get her reward. She had only ever sucked Justin's dick, as she wasn't pretty enough for Justin to want to fuck. After two weeks of coming over while Christopher was in class , sucking him off, and begging him to finally fuck her, he finally agreed to if she would do him this favor in helping him enslave and humiliate Christopher. Now, as she was naked and bent over the bed waiting for her reward, Justin smacked her ass and told her he decided he's only going to fuck her in the ass. Sarah beamed, "ooh, that sounds lovvveeelllly, but I still want to feel your dick in my pussy. Please do it, please," she begged, "please let me feel what it's like to have your cock up in my snatch. I told Christopher I wouldn't have sex because I wanted to wait, but I don't want to wait for you, I want it now, Please!"

Justin laughed. "You'll get to feel my dick in your cunt, all right, but it'll be with cum dripping out of your ass!" With that, he grabbed her hips and forced himself into her. His dick was so strong and hard, it busted its way into her asshole with one move. Sarah shrieked, giggled, screamed, and moaned as the pain and pleasure took over her. Justin thrusted into her with no regard, as if she was just a sex doll, and she loved it. With one final thrust, he tensed as he came deep into her ass. He pulled his dick out, covered in blood and juices, turned to Christopher, and said "lick it clean, loser."

Christopher had not even been caged for an hour, but he already understood his situation. He choked back his tears, hesitantly stuck out his tongue, and slowly licked Justin's penis clean. Justin and Sarah laughed at him, and Christopher saw a flash from the corner of his eye as Sarah snapped a picture, then another, then a few more, all with Christopher's own camera that he had saved up for through his senior year in high school. As Christopher was finishing the last little specks of filth on the head, Justin asked Sarah if he was ready to feel his dick in her pussy yet.

"Oh boy am I, I can't wait!" Sarah giggled, cum dripping out of her ass onto the linoleum floor of Justin and Christopher's dorm room. Justin laughed, then reached into a bag. "You don't need a condom if you don't want, I can just get the morning after pill if you'd rather do me bareback," Sarah said.

Justin smirked and pulled out a realistic-looking dildo, then handed it to Christopher. "This, loser, is an exact copy of my cock. Your girl wants to feel what it's like to have my cock in her pussy, and so you're going to fuck her with it." This wasn't quite what Sarah had wanted, but she found it highly amusing and laughed hysterically as she laid back on the bed and spread her legs. "Come on Christopher, I know you wanted to fuck me, and now you get to! Shame it's not with your own penis, but hey, I guess that's loser life, right." Christopher was shaking and staring at the floor as he slowly moved the dildo over toward Sarah. There was a handle on the end of the dildo so that holes would be able to feel the whole length of Justin's dick, and Christopher trembled as he clutched the handle with his right hand while his left hand slowly guided his roommate's penis into his girlfriend's vagina.

"You'd better give her a good dicking, loser," Justin said as he grabbed Chris's camera and started snapping photos. "I want to see her cum. My dick will give her a screaming orgasm if you use it right, and you will not stop until that happens." Christopher had never even fingered a girl before, so he didn't know how to get one off. This was going to take a while. Sarah didn't care, Justin's dick felt so good that she could do this all night, and probably into the morning.

She closed her eyes in bliss, moaned, and breathed heavily. "Justin, your dick feels so good, I want another one in me. Come over here so I can suck your dick."

"You may suck my balls," Justin replied. Sarah smiled, opened up her mouth, and stuck out her tongue. Justin straddled her face and began to lower himself. "Hey, looks like your girlfriend's mouth gives a great angle for photos," Justin laughed, snapping a few more pictures of Christopher sobbing as he thrust the dildo into Sarah. Her moans vibrated through Justin's nutsack, and he started to get hard again. He began stroking his dick, aiming it directly at Christopher.

An hour later, Christopher was devastated but finally starting to get the hang of this. He just wanted it to be over. Justin had came on him three times, and his hair, face, and chest were dripping semen. He would take breaks to sit on Sarah's face, his balls still in her mouth, then would kneel up so that Christopher could see the pleasure on the face of the girl he thought was his. Finally, with rhythmically deeper thrusts, Sarah began to moan louder. Her mouth opened as she was in too much ecstasy to keep her lips over Justin's nutsack. Her jaw widened as she kept moaning louder and louder. Each moan a higher pitch than the last, they turned into shrieks. Soon, her legs were shaking, then her hips, then her whole body. Christopher was sure everyone in the hall could hear her as he brought her over the edge.

Panting and exhausted, Sarah started to go limp. Christopher was slowing down his thrusts, now completely bawling as he saw his girlfriend experience greater pleasure from a model of Justin's penis than he had ever seen anyone experience in his life. Justin stood up and, with a swift shove of his foot, kicked Christopher onto the floor. He lay on his back, defeated, as Justin came and stood over him, giving Sarah a playful pinch on her nipple as he walked over. "This is how college is, there are winners and losers. Now you know what your place is," Justin said, smirking down at Christopher. "It's up to Sarah if she wants to keep dating you, but from here on, you belong to me. You're going to be my slave, and you're going to help me out with all the girls I bring over to fuck. Now, suck these sheets clean, it looks like your girlfriend's butt leaked a lot while my cock was in her pussy. Once you're done, you can lick up the rest of the dried cum off the floor." Justin shuddered, but realized he had no choice. This was his life now, and really, what else could a loser like him expect?