All characters and events found in this story are purely fictional. They are all consenting adults and are loosely based off real people and events that I've experienced or heard of.
The story was originally written on October 19th, 2013 for someone I used to know, but it was never really completed. I recently decided to re-write the whole thing so it's no longer the same story.
...
Anna graduated from high school with outstanding marks. She was also a popular girl because she was well-liked by pretty much everyone who wasn't jealous of her. Despite her participation in various school events, she wasn't a true extrovert. People had this expectation that she did her best to live up to.
The localized pressure was a secret reason why she wanted to go to another university to explore her horizons. She, of course, hated that she would probably lose touch with her friends, but she wanted to challenge herself. Her parents were aware of her underlying reasons and were still supportive. After all, she earned herself the right to make this decision.
Because of her exceptional grades, she was accepted at all the schools which she applied to, including an elite calibre university that was notoriously strict with admissions. She even earned a scholarship there too.
Leaving home was very sad for her, but she was confident with her decision. She knew this school was going to bring her one step closer to landing her dream job - a microbiologist. She felt empowered that she was going to be working with some of the brightest minds in the country, though she understood herself not to be a genius.
She had only a few boyfriends previously. She experimented a couple of things here and there, but she never did anything remotely close to what some of her friends and classmates did. Yet she was prepared in her mind about the possibility of sex and maybe finding a serious boyfriend.
September finally arrived. She deftly set herself up in her assigned dorm room, and purchased all her books for her courses. During this time, she met a number of new people, including her roommate Kylie. Kylie was a multi-sport athlete on a sports scholarship.
"What?! You've never tried field hockey? You should!" she shrieked.
"Maybe." Anna replied softly.
Just then they received a couple of knocks on their door. When permission was granted for the outsiders to open the door, there were two people standing there with clipboards.
The female said, "Hi! Sorry to bother you two. My name is Selina and this is Eamon. We are your assigned mentors and we would like to welcome you to the school!"
Eamon asked, "Who are you two? Please tell me about yourselves."
The two girls stood up and blurted out their names. The dorm leaders, meanwhile, were furiously writing down some of the details.
Selina said, "Very good. We'll be getting to know each other very soon. Toodles!"
The two waved goodbye to the girls before going to the next room to interview the other residents.
Though Anna and Kylie were diverging into vastly different career paths, they realized they were very similar in personality. After leaving their respective classes, they spent more and more downtime with each other. It was not at all unusual for them to hang out in the hallways for a few minutes between classes.
One semester turned into one year. Her adjustment at the school was smooth and without any problems. Anna became progressive more into fashion, especially as she met some more people, including two short term boyfriends. She learned more and more about herself each time, or so she thought.
It was in her third year that she met Riley because of Kylie's drunken dare. Riley was one of the leading scorers on the school's basketball team - and was very attractive. The truth was that Kylie was actually too scared to approach him, and Anna wanted to show her how she would do it.
Riley and his two friends were playing pool at the school's recreational center. Anna purposefully decided to set up a game with Kylie nearby. As their games separately progressed, eventually the guys came over to "talk".
"Hey - you wanna play a game with us? We can show you some trick shots." Riley winked.
"Sure." Anna smiled while pulling along an infatuated Kylie.
As the two friends were split up into opposite teams, everyone eventually learned each other's names. A few drinks later, everyone headed over to the boys' private afterparty. Anna was still very much in control of herself, though she and Kylie allowed themselves to sit on the guys' laps. Kylie, on the other hand, became wilder after each shot. Eventually, Anna had enough fun for the night, so she safely pulled away her reluctant friend home. Everyone exchanged numbers, so this type of fun was going to happen again for certain.
The texts turned sexually explicit, as one would expect, though Anna was significantly less involved than the others. While Kylie was practically ready to get laid with anyone, Anna was happy to play hard to get. Riley welcomed this challenge - and he was going to do everything to succeed.
In Riley's mind, his strategy for success was not to fail once. He simply ignored Anna entirely after picking up her desperate friend. His façade led him to go on more dates - and have more sex. Anna wasn't affected by his tricks though. However, on one night, Kylie invited Anna to join them at his place, which she accepted.
The three of them were having a good time, particularly as more drinks were consumed. Later on, Kylie proposed playing truth or dare, though Anna initially didn't want to participate. She didn't want to say or do anything stupid.
"Truth or dare" she asked Anna.
"Truth."
"What is the wildest thing you've done?"
"Um. I've had sex without a condom once." Anna answered nervously. She probably wouldn't have answered that in any other situation.
"What?! That's not that bad." Kylie flatly stated as she put the card down.
As the night went on, Anna became less guarded about the situation because Riley remained cool and calm. Having some alcohol probably was another factor for her too. Kylie later openly cuddled him. At some point, he decided to slowly undo his pants - and she looked at him in the biggest shock during this process because doing this in front of Anna was previously unimaginable, yet Kylie smirked afterwards.
"Omg! I'm gonna leave you two alone!" Anna declared in disgust.
"You don't have to." Kylie insisted as she proceeded to take the shaft out.
Anna really had the choice to walk out, but she stayed to watch instead because she was still trying to figure out how this all happened. Kylie was not ashamed of jerking him for some reason, so the dick proudly pointed up.
"Oh yeah, baby... that feels so good." he muttered.
She was pleased to hear that, so she rewarded him with her tongue and eventually the rest of her mouth. Anna still couldn't look away.
"Have you not seen this sort of stuff, Anna?" he calmly interrogated.
"Of course I have, just not like this!"
"If you want, you can come closer and watch."
"No it's okay, I'll stay here." Anna beaked.
