College Loser Ch. 05

Christopher bobbed his head up and down the cock in front of him and thought about how long it had been since he had been able to stretch his out like that, let alone cum. Justin had decided that, since he couldn't have pretty girls, he should at least get to be a pretty girl, so on most nights Christopher dressed up in clothes lent to Justin by his girls and went around the dorms calling himself Krysti and building a reputation as the dirtiest slut in the school. To keep people from discovering his true gender, Christopher had to wear a diaper whenever he was Krysti, and explain to the boys that they don't want to go in there as Krysti never learned to use the toilet. Krysti, the dirty slut who couldn't even master potty training, only went down on boys and never let them take off clothes or give anything in return. Krysti only liked making men cum, saying things like "all real men deserve to get hard and cum whenever they want" and "real men's penises need to be able to feel good," further reinforcing his status as not a real man.

Krysti's targets weren't even popular boys, either. Justin had Christopher please the fattest, ugliest, most unpopular, and nerdiest boys on campus. He felt that Christopher needed to understand that even these people weren't as big of losers as he was, and that even they deserved to have pretty girls suck them off because even if they couldn't actually get real girls to do it, at least they weren't as big of losers as Christopher. Some days, Christopher would have to service up to ten men. It all started with one of Justin's girls worrying that her boyfriend would get jealous, so they came up with the solution of making sure the boyfriend got action on the side. Next, another one of Justin's girls was having her obese younger brother—still in high school—visit the college, and wanted to make sure he had a good time there. After this, it became a regular thing.

Christopher heard the boy moan and felt the cock twitch as he prepared to swallow the whole load. Justin tended to ask around about Krysti, and if he heard about lackluster blowjobs, behavior not befitting of a complete slut, or failing to swallow every drop, Christopher would be punished. Sometimes, Christopher spent time sucking their balls, licking their toes, or rimming their asses just to make sure he wouldn't get a bad report. This was especially common when they'd try to grab at his breasts, to which he'd learned to say "sorry, I'm just an a-cup, but let me make it up to you". The idea was that these boys should get to experience complete sexual satisfaction from time to time, while Christopher never deserved any sexual joy whatsoever. Sometimes, Christopher would even take the time to pleasure people beyond those Justin assigned, so that he could practice and try out new things without being punished for how he performed.

This was Christopher's last of the night, so with a giggle and a wink, he left to go back to his room. Once there, he took off his diapers—soaking and dirty in case anyone tried to reach in there—and sealed them in a bag before heading off to clean up. Later, he would have to bring them to the girls' bathroom dressed as Krysti to reinforce the backstory (and face ridicule by the other girls there), but for now he had to leave them next to his pillow to humiliate him further while he slept. At least this time, it was only his own waste in the diaper. As Christopher wiped the last bit of feces off of himself using tissues and baby wipes—every one of which he was required to eat—he sat down at his desk naked and worked on his GIFs of Justin cumming, his pink and purple sparkly spiked cock cage on display for whomever Justin decided to bring back that night.

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Justin entered the room with a girl on each of his arms. Christopher went over them quickly in his head—the one on the Justin's left was Kelly, and on his right was Samantha. Kelly had a tighter pussy with a couple of notable bumps towards the top back inside her pussy, while Samantha had a tighter asshole and used more tongue in her blowjobs. He needed to know these things, as Justin would often quiz him on the spot.

"Christopher", said Justin, "I think it's time to let you out for a bit". Soon, Christopher was tied to a chair, his cock cage off, and both girls rubbing themselves all over him because he was told that even though his cage was off, he'd still get punished if he got hard. Eventually, of course, the girls won, and Justin got ready to dish out the punishment. He brought out another cage, this one longer and straighter, and clipped it over Christopher's cock. It had spikes on the inside right under the glans of Christopher's penis. Justin explained that with this cage, he'd get stabbed if he got soft, so he'd need to stay hard if he wanted to avoid that. Both girls laughed as Justin untied him from the chair.

"Now", said Justin, "come kneel behind me and pull down my pants". Christopher complied, and as soon as he brought Justin's pants down to his thighs, Justin let out a huge fart directly in Christopher's face. Christopher let out a squeak as he felt the points bite into his penis, and immediately tried to think of something to get hard again. He thought about one of the newer games Justin had been playing with him—multiple girls would bring in their used panties and make a pile, then Christopher, blindfolded and with his hands cuffed behind his back, had to sort them based on what he could discern using his nose and tongue. This had been incredibly difficult for Christopher, and would always be Hell on his penis. He took a deep breath and let himself get hard again. The girls, of course, were in hysterics.

The next few hours involved the three of them coming up with the most disgusting and pathetic things to make poor Christopher be aroused by, and spending ample time making fun of him for being aroused by these things. They figured out that Christopher was trying to imagine other scenarios to keep hard, so they came up with tasks that would require enough focus that this wasn't an option. There were tasks involving Justin's underwear, Justin's socks, Christopher's own diaper that he'd just put away, watching the most disgusting gay porn his tormentors could find, writing degrading things about himself, and even eating an entire cow pie in tiny bites. Eventually, they made Christopher beg to go back in his other belt—but wouldn't let him until he had re-sharpened all of the spikes.

After taking off the long cage, Christopher was made to scrape off all of the scabs he'd developed in his months of spiked confinement, submerge his bleeding penis in alcohol, and rub cream over it after the bleeding had stopped to help make his skin softer and more sensitive. After this, Justin held out Christopher's balls for the two girls to abuse until he'd gotten soft again, then made him lock himself back up and present the key to Justin on his knees. Christopher wasn't sure if he hoped he'd get released like this more often or never again.