College Loser Ch. 04

Christopher was on his computer, working frame-by-frame through a video clip of Justin shooting his load into a girl's mouth. Every week, he had to make a new GIF loop that made it look like Justin was cumming continuously, and these loops would be assembled randomly into montages that Christopher would have to watch 45 minutes of every day. This was an idea from Mira a graduate computer science student Justin had been seeing who also taught tai chi. She even made an app that tracked Christopher's eye movements to make sure he was watching. She felt he needed to constantly be reminded of all the cool ways non-losers get to cum, while he hadn't even had an erection in months.

There was a knock on the door. Christopher quickly threw on a robe to cover his exposed chastity cage sticking out of his pants, and went to answer the door. It was Sabine. He stepped aside and let her in, then pulled off his robe after closing the door. "I have to pee," she said, pulling up her skirt with one hand and her panties aside with the other. Ever since that night when a girl Justin had over was too exhausted from fucking him to get up and go to the bathroom, so she called Christopher over so she could pee in his mouth, Justin decided that drinking pee was another function he should be able to fulfill. Christopher was punished for spilling on the sheets that night, so he made an effort to practice, even spending some of his free time going to the rooms of some of the girls Justin had brought over and begging them to pee in his mouth. Now, all the girls knew him as a toilet.

Christopher got on his knees and held his open mouth under Sabine's vagina. She sighed and let out a stream without regard, but Christopher didn't miss a drop. After swallowing the last of it, he knelt up to lick her pussy clean and blow it dry. He felt some stubble on his tongue and knew this might make Justin angry, so he looked up at her and said, "would you like a fresh shave before Justin gets over?"

"Sure," she replied, and he threw a towel over his chair, then gestured her towards it as he grabbed his pussy shaving kit. He lifted up her skirt and slid her panties off, then held them with his teeth as he went to work, careful not to damage them or get his spit on them. When he had finished, her pussy felt as smooth as silk, and she was happy she would be able to please Justin more. Christopher slid her panties back on as she stood up, then asked if she needed anything else.

"No thanks, I'll just grab a beer from your bed and chill out." Christopher nodded, and went back to making his GIF. A half hour later, he felt he had one that was adequate and would keep him from getting that particular beating this week. Just as he was saving the file, the door flung open, and Justin stepped in with his arm around a new girl.

"Hey, Sabine! Good to see you," Justin said, ignoring Christopher, "this is Jordan, I met her in the library. She's pretty cool, I think the three of us should get along pretty well. Jordan, why don't you drop off that paper you were working on when I met you, and we can go hang out on the bed?"

"Here," Jordan said in a flat, uninterested tone, "I might need a couple more sources, but the main thing is that the conclusion needs to be redone." As she reached over to drop off her backpack, she caught a glimpse of the purple sparkle of Christopher's chastity cage and smiled. "Looks like this is what Justin was talking about," she said giving one of the bars a quick flick, sending a couple of spikes into Christopher and causing him to gasp.

Christopher stared with his left eye through the lacy fabric on the edge of Jordan's underwear. While the other three had largely ignored him, Justin had thrown both of the girls' underwear onto Christopher's head as he removed them. He had gotten pretty good at it by now. The two pairs of panties had almost covered Christopher's vision entirely, but he knew better than to move them, so he made the best of what he had.

Three of Justin's condoms also sat in Christopher's mouth. He had obediently opened his mouth each time someone reached over with one of them, and since he hadn't gotten the order to swallow, he kept them there as he worked, the combined flavors of cum and two different pussies reminding him what he was now sure he would never get to experience.

As Justin was relaxing and cuddling with the two girls, he called Christopher over. Christopher immediately ran over and knelt next to the bed, waiting for his next command. Justin was sat up, leaning against the wall next to the bed, with one of the girls in each of his arm.

"Did you girls have fun?" he asked. They both nodded and leaned in closer to him, smiling. "Jordan, you think you'd do this again?" She nodded, and Christopher and Sabine both knew where this was going. "Well, then, loser-boy here is going to have to catalogue you."

"What do you mean, catalogue me?"

"I've been having him keep a record of every girl I get with, so I can figure out who I'm in the mood for. He's going to do a full-body inspection to try to guess what it would feel like to fuck you. Remember, he won't be getting anything out of it but pain," Justin said, nodding at Christopher's spiked cage, "but it helps me out."

Jordan giggled. Christopher had no idea how Justin managed to get girls to agree to these things; he was just so hot they couldn't resist. "Alright, so what do I do?"

"Stand up, feet spread apart, hands at your sides."

Jordan slowly got up, and once she was in position, Christopher grabbed a notebook from under the bed and began his inspection. After marking down physical characteristics, he began to feel her legs to get a sense of how fit she was and how soft her skin was. He worked his way up her thighs, stroking and squeezing and marking things off on a chart, and reached around to her butt. He felt around her cheeks and jiggled them a bit, then slipped his fingers in her crack to estimate depth.

Justin and Sabine relaxed and watched, occasionally groping and kissing each other. The next time Justin fucked Jordan, he would compare his experience to what Christopher wrote, and if there was a discrepancy, he would make Christopher grab the stash of sriracha bottles he was required to keep stocked by stealing from the cafeteria, and have the girl he misjudged punish him by pouring a certain amount into Christopher's asshole, held in place for a minimum of six hours by a locking butt plug Justin's sister designed. Christopher would always receive his punishment lying on his upper back with his legs in the air and ass over his head. There would almost always be a discrepancy, but Christopher was still relieved he had managed to make them minor enough that he only had to take a quarter of a bottle usually, much less than the two-bottle punishments he had been getting when he first started doing inspections.

Christopher worked his way back to Jordan's front, gently massaged her slit to watch how quickly it got wet, how wet it got, and how much her clitoris swelled. He then slipped two fingers into her. He felt Jordan clench to try to get a better tightness score so Justin would want to fuck her again sooner, but Christopher knew this trick and made a mental note to account for it. He also felt around the sides so he could map out any bumps and irregularities on his chart, as well as whether he though those irregularities would feel good during sex. Christopher wished he could try to avoid thinking about what it would feel like if his penis got to experience what his finger was feeling, but that was exactly what his task was. Afterward, Christopher put those fingers in his mouth so that he could try to make note of how she tasted.

Next, he moved behind Jordan, shifted the three condoms around in his mouth, spread her cheeks, leaned in, and stuck his tongue in her asshole. Justin preferred to have Christopher do this test with his tongue, just to make things extra humiliating. As he pulled his tongue out, Jordan let out a fart, and the three non-losers all laughed. Christopher stayed focused, working his way up to feel the tightness of her stomach, the firmness and jiggle of her breasts, the softness of her hands, and a host of other metrics.

When he had finally finished, Christopher started to fill out Jordan's chart. "What about my mouth?" Jordan said, "Shouldn't he keep track of how good that feels?"

"Warmness, wetness, tongue texture, stuff like that. Hm. Good idea, Jordan."

"Wait a minute," said Sabine, "giving head is about technique."

"Easy enough," said Jordan, "just have me give his finger a short blowjob, show him how I use my tongue and stuff."

"Yeah, but Justin's so much bigger than Christopher's finger, obviously he'll need to know how I do on the sliding up and down, and how deep I can take it."

"Well then," said Justin, "I can have each of you give him a finger blowjob, then you can each suck me off and he can make notes of how you do that. Not sure yet what I'll measure, but when I decide later, I'll read his notes and punish him for everything he left out. For now, I'll just have him try to guess whose head I liked more, and punish him if he got it wrong."

Tears welled up in Christopher's eyes as Jordan picked up his left hand and slipped his finger into her mouth. Christopher wrote about his experience with his right hand: her tongue flicks and swirls, any tooth contact, how hard she sucked, any moaning...

After both she and Sabine had a go, Jordan got to work sucking off Justin. Christopher tried to note things like how quickly she moved her head back and forth, how far she moved it back and forth, how much she varied her movements, eye contact, ball rubbing, and anything else he could think of. When she had finished, and swallowed it all, Christopher darted over to the computer to finish up the last paragraph in Jordan's paper and save the file while the two girls lay over each of Justin's legs kissing his balls until he got hard again. Christopher expertly managed to finish this just as Justin's cock began to twitch back to life. He crawled back over to kneel in front of Justin again so that he could take notes on Karyn's blowjob, shifting the condoms around in his mouth and hoping that Justin would let him swallow them after his second blow job. Just as Christopher had begun to get used to his situation, someone always managed to think of a new awful thing to do to him.