Anna's Debauchery Ch. 01

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.

Kylie stopped her BJs briefly, "Come over, it's fine."

Anna subsequently parked herself closer, though she repeated in her head that she probably wouldn't have done this in any other situation. Her curiosity had taken control of her now, at least for the time being.

Kylie's BJs suddenly intensified, like she was putting on a show. Riley enjoyed the situation as he had planned. He had been quite certain that Kylie was willing to do almost whatever he wanted. Anna, by contrast, was a lot less pliable.

"Good girl!" he playfully jeered. "Suck it like you know how!"

Anna saw the erection tower everything else as her friend kissed his balls. Kylie gradually removed her clothes, revealing her slim and toned body. Riley did the same.

"You wanna try this?" Kylie queried unexpectedly.

Anna shook her head fervently, "No, absolutely not! What's gotten into you?"

"Come on. Have some fun with this. This doesn't hurt anyone."

"Don't force her... she's probably scared." he sneered.

"That's ridiculous, why would I be scared?" Anna snapped. "I didn't know you were like this though."

"What do you mean by that?"

"Nothing, I'm just gonna go back. I'll see you when you return."

This time, Anna really did walk out. Throughout the rest of the night, she couldn't shake away the images from earlier. She thought she was crazy to watch her friend behave like that! Part of her wondered when she'll be back, but another part of her wanted to know what they did!

Kylie didn't return until the next morning. Anna was very prompt about talking to her.

"My god, you were so drunk last night! Everything okay?"

"Yeah, I had a bit too much." Kylie responded in her normal self.

"Do you remember anything?"

"Kind of. I'm so tired though."

Anna could tell Kylie was embarrassed, so Anna tried to act like she was cool about the whole thing.

"You two looked like you had a lot of fun." she giggled. "That was my first time watching."

"Sorry to put you through that. I wanted to prove something and I was acting stupid."

"Don't be sorry! I don't think you were stupid. It was definitely interesting though to watch." Anna cackled.

Anna let her friend have some peace and quiet. However, Anna still thought about Riley's cock. It wasn't that she was particularly impressed or horrified by it. She just couldn't 'unsee it'.

It had been months since she got laid. While she was far less adventurous about sex than other people, she wasn't naive nor completely innocent. Her goal, up to this point, had been to avoid any social stigma. Yet there had been days, such as the present time, that she might imagine cutting herself loose if there weren't any negative consequences. She then masturbated quietly underneath her sheets.

She recalled last night's events but decided to take her friend's place instead. Riley seemed like the type of guy who she could control if she really wanted to. She'd work him up and then make him beg for more. Her body was a premium product which she wasn't going to give away to just any handsome guy. When she imagined Riley going crazy over her, she would then make him eat her out. Only when she was satisfied would she repay the favour. Once he was hard, she'd ride him because she was the one in control - not him. She'd pound herself with his cock so she'd get the best sensations. At the same time, she'd be the reason why he's feeling good too. Her tight pussy would encourage him to fuck her more, or so she thought. He'd take her from behind or carry her in his arms. The list of things he could do made her more and more wet!

She thought of even wilder stuff - maybe she would be at the center of his friends! Although she had only been in monogamous relationships, she felt the spontaneous urge, at this moment, to have multiple cocks in her at the same time! The feeling of being ravished at the same time was somehow appealing!

Her friend woke up to use the washroom, which killed Anna's masturbation session. As Kylie started her day, she deliberately avoided the topic of Riley whenever she talked with her roommate. Part of her still felt embarrassment over her behaviour even though Anna evidently tried to comfort her. Anna couldn't really ignore the anxiety in the room, so she decided to address it in a productive way.

"Hey, if you don't mind, I wanna talk about guys with you."

"Sure. What do you wanna talk about?" Kylie asked.

"You know, I've been feeling lonely lately."

"Really? You don't seem like you are. You're always busy with something."

"That's the thing - I hide my loneliness through school and other things. Wouldn't it be nice to hang out with some boys for a night out?"

"Wow, Anna, is this because of what happened the other night?"

"Please, Kyls [affectionate nickname], don't feel embarrassed. I have to say I was kinda turned on when I watched you."

"I'm not usually like that." Kylie interjected.

"It's fine. People have a right to do what they want, so long as they're not hurting anyone else. And you weren't hurting anybody."

"True."

"So what do you say? Let's think about doing something next weekend - and we can let ourselves go if that's what happens. We're young."

"I'm down for that, Anna!"

The next week, Anna went to her classes, labs and studied hard whenever she had time. She felt really good about the two quizzes she did. When Friday came along, she called her parents to update them about school and life, as usual. She also facetimed with some old friends.

...

"You ready for tonight, Kyls?"

"Fuck yeah! I was looking forward to this day all week!"

The two girls prepped themselves for a night out. They were dressed to impress. Anna wore red gloss lipstick, a white club dress which exposed her cleavage from the top, and 3 inch open-toed heels. Kylie wore black lipstick, a silver tank and dress and black stilettos. At 9:00, they ordered a cab to go downtown. They walked in without paying cover, thanks to the bouncer.

The loud music slightly overpowered the youthful screaming on the floors. Despite the chaos, Anna and Kylie had plenty of attention on them. By the time they reached the bar, a bunch of guys already wanted to ask them to dance. Anna quickly realized that they were going to reject so many guys, but she wasn't going to be rude when doing it. Even at the bar, a couple of guys offered to buy them drinks. The girls refused them all.

On the floor, the girls swayed their body and hips together. A circle had naturally been created for them. While most guys were somewhat respectful about touching, an occasional guy would grope one of them, of course 'accidentally'. As unfair as it was, the girls couldn't let these types of guys ruin their night. Harassment and unwanted advances were an unfortunate reality for women.

Later on, two tall guys came by and happily danced with some other girls nearby. The fact that those guys were accepted by the people around them was important. When they invited Anna and Kylie to join, they accepted. After numerous song changes that involved fast beats, the DJ methodically slowed down the songs to allow some intimacy to develop on the floor. The guy that had been dancing with Anna was now resting his face on hers. Soon, Kylie let her guy do the same. Eventually, the pairs kissed. Anna, in particular, was really into it. The moment just seemed so natural for her, even though she didn't know this guy at all. Unfortunately for her, the guy said he had to leave, which left her uncharacteristically upset. Before he walked away too far from her, he turned around and asked if she would come with him to another party. She said yes, and Kylie came along too. The guy who with Kylie couldn't come, but he did get her number at least.

Inside the taxi, Max, as the guy called himself, sat in the middle, so that the girls could flank him. He called them beautiful, and claimed that they would love this party. When the taxi stopped, they were in front of a mansion. All the houses in the area were similarly huge. Inside, there were two guys in their thirties and one woman in her twenties.

"Hey girls, how are you doing? I'm Ed."

"I'm Tina"

"Welcome girls, I'm Rick. This is my place. You can drink whatever you like. I can whip you up something too. Nothing too crazy though."

Anna and Kylie were amazed by the modernity of the house. They talked to Tina who also said she enjoyed crashing the place. Tina was a full-time social media model. Anna and Kylie were sure they wanted to get into it too, but felt they weren't likely to succeed on Tina's level.

After the girls requested their drinks, everyone chilled on the spacious leather couches. It didn't take long for Anna to resume her makeout session with Max. She had been feeling him all night. Then everyone else joined in on the kissing.

Max asked Anna if she wanted to go upstairs with him, which she agreed. Her body was aching for him. Kylie wanted to come along too, so she brought over Rick. The host, Ed, remained downstairs. As it would turn out, him and Tina were going to snort lines.

In the same large bedroom, Max and Rick began taking off their clothes. The girls did the same thing, which led to some foreplay. After Max brought Anna to the bed, he dove his face into her pussy! Rick and Kylie did the same thing on the other side. The girls moaned together.

When the guys asked for their dicks to be sucked, the girls were more than happy to do it. Anna had the benefit of having Max fingerbang her too, which Kylie didn't receive. Regardless, she was just as enthusiastic as Anna about what was to come.

As the condoms appeared in front of them, the girls silently lay on their backs. Just before the men put their cocks in them, the girls reached for each other's hand. The men loved the sight of that and were more turned on than before.

Anna and Kylie panted loudly together. Nothing else mattered to them right now except taking dick! Part way through the intense sex, the girls were turned over into the doggy style so they could see each other get nailed - and how good they felt!

"Yes, take a good look at each other, you sluts!" Max uttered.

The insult seemed to add to the experience. Anna, for instance, rolled her eyes back. This encouraged more degrading talk.

"The bitch likes it when you talk like that. Fuck her good!" Rick exclaimed.

Anna didn't seem to care what her life purpose was anymore. Max mercilessly unleashed his piston-like thrusts on her. At some point, the overwhelming power caused her to drop her head in awe. He then pushed her face into the mattress to continue. When he was close to orgasming, he violently pulled out of her. Then he flipped her over and jizzed on her pretty face. She knew she was never going to be the same after this.

Kylie also went through a similar process, though she had more awareness. She watched Anna submit entirely to Max. When Rick pulled out, Kylie opened her mouth widely for him. He then shot almost everything there. Afterwards, she tugged on his cock to slurp him dry.

"Shit, that was a good fuck!" Rick declared.

"You okay there, Anna?" Max asked in a surprisingly caring tone.

She nodded with a big grin. Kylie checked up on her too. Both girls knew they were beyond satisfied. Afterwards, they were left to rest there while the men went back downstairs.

"Anna, how was he?"

"He's amazing. If I could get this like everyday, I'll be a happy girl."

"Same."

Anna and Kylie both cackled uncontrollably.

They got dressed and joined the group downstairs.

Tina asked while using her e-cigarette, "Did you girls have fun?"

"Yes, I had an amazing time." Anna remarked.

Anna realized at that moment that Tina was probably hinting them to leave. As a result, Anna indicated that they were going to leave. Of course, the men were disappointed.

"So soon? How are you gonna get back?" Max queried.

"We'll just call a taxi." Kylie responded.

"Why don't I just drive you two back? Do you two live separately?" he offered.

"Actually no, we're roommates at the dorm."

"Oh, perfect. You're at which school?"

"Royal Oaks."

"Damn, smart girls. I knew you two were special. Anyway, we can get going now if you like."

Max, Anna and Kylie had a pretty good conversation in the car. He indicated that he ran his own business, yet he didn't specify exactly what he did. Max seemed like a nice guy, despite what he did or said to Anna. This was certainly not going to be the last time that the girls would see him and his friends again.

To Be Continued...

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