First-Time Challenge

College, as it turned out, was more difficult than Emma expected.

It wasn't the classes. Emma had a head for numbers, and engineering was second nature. She could do most of the equations in her head before her fellow students finished writing them down. What Emma was struggling with was the social aspect of higher education.

"Meet some people," she mumbled sarcastically to herself while trying to pick a dress. "It'll be fun."

"Did you say something?" Riley shouted from the bathroom.

"Just talking to myself."

Emma pulled out a simple black dress. It was lower cut than she would have preferred, but the skirt, unlike everything else Riley owned, did not threaten to expose her underwear if she leant forward slightly.

She tried it on, and it fit better than Emma expected. Of course, she was a cup size or two bigger than Riley, and it showed in the way the dress projected her breasts forwards.

"That looks great," Riley said, coming into the room.

"Do you have something I can wear over it to cover... these?" Emma asked, gesturing to her own chest and refusing to look her friend in the eye.

"Why would you want to? You're got great tits. Besides, we need to get going."

"Fine. Just let me go to the bathroom."

Emma, despite her intense sense of embarrassment, knew there was no point in arguing. She had met Riley in one of her classes, and the girl appeared to have made Emma her pet project; an awkward, nerdy caterpillar she intended to force into becoming a butterfly. Emma had a suspicion that, even if she did let Riley force her into a cocoon, she would probably come out closer to a moth, flapping wildly and getting in everyone's way.

She looked at herself in the bathroom mirror, straightened her glasses, and did her best to at least make her unruly, brown curls look symmetrical. The mix of fear and apprehension had given her skin a slight greenish tinge. She was about to go to her first college party. At least it would be over soon.

The party was being held off campus, and there was a fifteen-minute walk from Riley's dorm room to get there. Emma was mostly silent on the way, saying just enough to avoid Riley asking her any deeper questions.

Emma had seen enough movies to know what to expect: a house blasting generic rock music, keg stands, young men ready to fight at the drop of a hat, probably someone running nude across the front lawn eventually.

What she found was completely different.

For a start, there couldn't have been more than two dozen people present. The music was nearly inaudible under the steady sound of chatter. Riley introduced Emma to a group of four guys as they entered. They were friendly, intelligent, and did not seem like they were about to start hitting one another.

"Here," Riley said, thrusting a cup into Emma's hands. "Vodka soda. You'll need it."

Riley had a mischievous expression, but Emma had come to expect that. She was always plotting something. While Emma had not been to a college party before, it was far from her first time drinking. She and Riley spent at least one or two nights each week getting drunk and watching old horror movies. She sipped her cup slowly and tried not to be too embarrassed whenever she noticed a guy staring at her boobs.

She stayed close to Riley, not wanting to be left alone among people she didn't know. They chatted to the same group of guys for at least an hour. The party seemed to be made up of a few such groups, Emma noticed, small individual circles of five or six people. She also noticed that the guys significantly outnumbered the girls, twenty against four.

Most of Emma's conversation was a back-and-forth between herself and a guy named Mark. He was tall, solidly built, a couple of years older, and also studying engineering. This gave some comfortable conversational ground for Emma to cover.

At some point, people started moving from the main part of the house towards the rear.

"Looks like time," Mark said, gesturing for Emma to follow them.

"What's going on?" she whispered to Riley.

"It's time for the blowjob contest," her friend replied.

Emma's heart skipped a beat. She can't have heard that right.

"The w-what?" she asked.

"The blowjob contest. I couldn't tell you earlier, or you wouldn't have come."

Of course she wouldn't have come. Emma had enough trouble talking to a guy she'd just met, let alone doing anything else. Her hands were shaking, and she felt a hollow feeling in her gut.

"I've never given a blowjob," she hissed as loudly as she could without anyone else hearing.

"They're horny college guys who've been thinking about it all night," Riley said. "It won't exactly be difficult."

"That's not the point."

Riley shushed her. One of the guys asked for the room's attention.

"I see at least one new face in the room," he said, making eye contact with Emma. "Let's not scare her off."

Besides Riley, energetic and blonde, there were two other girls on the opposite side of the room. One was short and petite with hair a little lighter than Emma's. The other was a curvy black girl.

"For the benefit of our newcomer, I'll go over the rules," the guy continued. "It's a contest of speed. Guys will be split among the contestants and the first girl to get all of her guys off is the winner. The only prizes are bragging rights, though there is the usual penalty for coming last."

A few of the other guys chuckled.

"Last place owes each guy in the room a blowjob before the next contest," Riley explained. "It's a full month away, so plenty of time. The idea is it will help you get better."

"Do I have to do this?" Emma asked.

By now, she was feeling sick to her stomach and only slightly tipsy, nowhere near drunk enough to do what was expected.

"If you don't, you'll ruin the whole evening for everyone and ruin my reputation," said Riley. "Get through it this one time, and I promise I won't make you come back. These people are my friends, and I don't want them blaming me for you chickening out."

Emma felt a little angry. Riley knew exactly what to say to manipulate her. There wasn't time to dwell on it.

"Guys, if you could all sort out who you're going with?" the guy in charge said.

Emma turned bright red as Mark and two other guys immediately moved next to her, one of them staring intently at her cleavage.

"How are you at deep throat?" the other asked.

Emma stammered gibberish in response, and two other guys joined them. Once the groups were all established, five guys per girl, they made their way down into the basement.

It was quite a comfortable place, Emma thought, despite her panic. Each girl had a pile of cushions to kneel on, and there was a scattering of IKEA furniture more reminiscent of a trendy loft apartment than a creepy sex dungeon.

Before she could fully process the situation, Emma found herself kneeling in one corner of the room. The guy standing in front of her unzipped his pants to reveal his cock, hard and throbbing, with a bead of liquid positioned right at the tip.

In the middle of the room, a buzzer sounded from someone's phone. Emma had the realisation that it was really happening.

As the cock approached her, she tried to remember everything she knew about blowjobs. It admittedly was not a lot, just stuff she'd read online: suck, don't blow, use your tongue, be careful of teeth. Emma had watched a few videos out of curiosity, but they didn't exactly explain how to do it.

She put her hand around the shaft of the guy in front of her and licked his cock gingerly. In response, the guy grabbed the back of her head and pulled her mouth down over his member. Emma felt it hit the back of her throat and gagged. Oblivious to her discomfort, or just not caring, the guy pushed deeper, until Emma's nose was buried in his pubic hair.

She struggled not to vomit as the guy pulled back slowly and then quickly thrust again. Tears formed in Emma's eyes. They weren't out of fear or anger, but purely in response to the foreign object being rammed down her throat.

Two more thrusts and the guy groaned loudly, grinding his crotch into Emma's face. When he pulled away, Emma tasted an odd mix of salt, bleach, and traces of her own vomit. As soon as air hit the back of her throat, she coughed and spluttered.

Emma tried to look around the room, but her eyes were watering, and her glasses were smudged. She felt another cock brush against her cheek. She put her lips around it and sucked. This new guy started to thrust, but not as hard as the first one had.

Was he trying to tell her something?

Emma moved her lips up and down the top couple of inches of the guy's shaft, meeting his rhythm. He pushed a little deeper, and Emma felt her gag reflex kick in. She put her hand around the base of his cock to control the depth. She kept bobbing up and down, not looking up. Her hand, wrapped around the shaft, was dripping with her own saliva.

After a few minutes, the guy's thrusting picked up pace.

"I'm gonna cum," he said, breathing heavily.

A thick, salty glob shot into Emma's mouth, immediately followed by a second, smaller spurt. It was like an oyster gone bad. There was nowhere to spit, so Emma forced herself to swallow it. She was sure a little came straight back up, but she ignored it.

The third cock went relatively smoothly. Emma had developed a rhythm and, as Riley had explained, horny college guys weren't notoriously difficult to please. The guy's breathing picked up, as did the pace of his thrusting. Emma braced herself for another mouthful.

Instead, the guy pulled away. Emma experienced a few moments of confusion before ropes of cum shot across her face.

By now, the tears had cleared from Emma's eyes, mixing with the saliva and cum on her face. She took off her glasses—her vision wasn't great, but her lenses were obscured by the third guy's load—and looked around the room. Riley had already finished. The two other girls were both going, and it was hard to tell how many guys they had left to get through.

"Are you doing okay?" a voice asked.

It was Mark, the older engineering student she had spoken to earlier, before the party had turned into a teenage boy's fantasy.

"I'm sick, nervous, and have no idea what I'm doing."

Emma was shocked by how hoarse her voice was.

"You're doing fine," said Mark. "Try licking around the head. That usually works. And use your hands more."

Mark's cock was out, meaning he was next in line. Once she dealt with him, there would only be one more to go. Then Emma could go back to her dorm and never think about any of this again. She took Mark's cock in her hand and started to pump it rhythmically.

Taking his advice, Emma circled the head of Mark's cock with her tongue. It spasmed in her hand as she did so. Emma couldn't stop herself smiling at the involuntary reaction. She wrapped her lips around Mark's member and took it as deep as she could.

"Fuck," he said with a gasp.

Emma oved her mouth in time with her hand, licking around the head on each upstroke. It didn't take long for Mark's breathing to speed up.

"Nearly there," he said. "Nearly there."

As soon as Mark's cum hit her tongue, Emma swallowed. His cock slipped from her mouth with a shudder.

The black girl was finished. Emma's only competitor was the petite girl, and she looked to be on her last guy.

Emma took the fifth cock into her mouth. She was almost ashamed at the rush she felt as she worked it. A few minutes, and the guy thrust frantically into Emma's mouth, filling it with cum.

She swallowed quickly and looked around the room. The entire crowd was watching her.

"Nice work, new girl," one of the guys said.

"You nearly beat me," the petite girl added. "You should be proud."

Emma was proud. She'd gone from never having sucked dick in her life, to awkwardly fumbling through it, to developing some basic technique in the space of an hour. She'd taken a facial. She'd swallowed cum. Last place didn't matter.

Then it hit her.

Last place.

Last place had to blow every guy in that room over the next month. Twenty more blowjobs. Emma's next thought wasn't how rough it was likely to be or that she felt Riley had cheated her into this situation.

It was that she'd better get good.