Today is Friday

MondayTuesdayWednesdayThursdayFriday
Political Science LectureEnglish Literature
Calculus
Laboratory 101
Soccer
Biology Lecture
Trigonometry Remedials
Women Studies Discussion

Go to your classes before doing other things...

You can read our short FAQ, check our cast of character page or check our locations page

Save and close your game Load a saved game

Niles Chapter #1 : Getting into trouble

Cassandra has a big news

I finally finished that stupid long lecture when I decided to drop at my girlfriend's dorm room.

I was lucky enough to get a room in the same section as her, but sadly, we are quite a few doors away from each other.

Cassandra and I have been in love for a few years. I've been loving her since before I even knew what love really is, but she's been in love with me since she figured out what it was.

She's always been wiser like that than me.

We actually began dating in 7th grade. That's stupid, they said. It will never last, they said. And they were right! We broke up soon after. And came back together. And broke up. And decided it would be forever, that third time was the charm!

Turns out, forever is 2 weeks for a 13-year-old.

But we persevered. During frequent breakups, she would make other boyfriends, but I would remain single. Still, eventually, I always won her back.

Always.

Our last breakup was early in our senior year, for about... 20 minutes. Ok, I count it as 20, she counts it as 22, but that's because it took me a minute to realize we were broken up, and it took her a minute to realize we were back together.

I count our breakup from 7h23, she counts from 7h22. To me, we were back together at 7h43, and to her, it was at 7h44.

It's trivial, but we joke about it, still to this day. Oh, not in that first month. Or even in the second. But by Christmas, it was a running joke.

She gave me a watch, with a note to check the time, and I gave her the full timetable of the bus stops in town. You know, those little flyers you can get at the various terminals? Well, you can't get all of them in the same place, so it was a chore to find each of them! I also gave her a gold necklace, I am not a cheap bastard.

Sure, we don't have much money, but she was the love of my life!

Ever since, we managed to not only stay together, but to have a good sense of humor about ourselves. We also trust each other fully, and completely.

I get to her room before I even get to mine. I always do, despite her annoying man hating roommate, Yana. You keep hoping she will be gone, but she is always there. Always.

Upon knocking, you hear Yana reply "Enter" because, like I said, she is there. Always.

When I open, I find Yana helping Cassandra zip up her sexiest, sluttiest dress. Wow, Is Cassandra dressing up for me?

Did I forget an anniversary? No, but I think fast.

"I've always loved that dress", I say.

I bought it with her. She admitted that it made her feel sexy, but also that she should never wear it in public.

And yet, eventually, she did. We went to a dancing club twice with her wearing it, and well, really enjoyed when she stopped wearing it, once in her room, the other in my room: it's tight enough to not allow wearing panties, and has an included bra.

Sexy... and the sex? Spectacular. She would deny it, but I think that for her, feeling sexy, makes her more open with her sexuality.

"It's not for you", says Yana, with a harsh tone, as she finishes zipping it up.

"Huh?"

"Come sit down", says Cassandra.

And so, I do.

It's clear to me, and almost everyone, that Cassandra is a gorgeous and hot woman.

A natural red head, she always had (and still does) carefully unkempt wild hair, which just looks fantastic. You know she spends a lot of time on it, but makes sure it doesn't look like she does.

For example, it naturally curls a little, but she enhances their natural curl.

Oddly, the discoloration is entirely natural. She was accused of coloring them because the color was uneven, but it's 100% natural.

"So", she says, nervously

"So", I reply. Her wide smile always makes me melt. She is so warm and happy. It's weird isn't it? As a tween, many guys argued about whether tits or ass were more important, but dating Cassandra makes me see that her happiness is even sexier.

Because a happy girlfriend, is nice, friendly and more open.

"I found a guy", she says, all nervous.

"You found a guy?", you ask, confused

"For what you asked me. I found a guy, and I can go see him now"

"Huh?"

Yana decides to intervene. "You fucking asked her to cheat on you, and she found a guy to fuck"

Ok, let's rewind.

There were a few moments I was separated from Cassandra and she saw other guys. She even had sex with one of them, a guy I also knew.

This was fine, we weren't together, but I still felt something. Deep inside, seeing them together, laughing and having fun.

Sure, I was sad it wasn't me, but it was more than that. Cassandra was my long-term girlfriend, not his. This guy was a blip on her radar, and I was the base where she went to sleep. I was her rock, her anchor.

And yet... it was hot. That she had sex with another guy. Not that she was dating him while not dating me, that sucked.

No, just the having sex with another guy part. That was hot.

Wait, don't leave yet. Let me explain.

Did you ever play a video game you really loved and wanted to share it with a friend? What about a rare local indie rock CD?

Well, the thing is, the hottest thing I ever had to myself was Cassandra. Caressing her, having sex with her. Sure, she is the only girl I ever had sex with, but still, it felt like it was something.

Imagine you made a painting. To you, it's perfect, but there is still a nagging feeling in the back of your head that perhaps, it's not as good as you think it is. It's not good enough for the museum, but that doesn't mean anything about how good it is. So, you show it, and the praise you get? Wow, that's the real pleaser.

Well, to me, my painting is Cassandra. And my dream, my fantasy, is that other guys will discover how Cassandra is special, which make her feel that much more precious to me.

"Ah, a guy", you say.

"You are still ok with that, right?"

"Cassandra, I have been begging you to do this for what, a year?"

"About that. A little less, about 10 months", she says

"Sure. But I am not about to chicken out"

"He doesn't want you to be there", she says. Yana laughs. You both ignore her.

"I am fine with it."

"But he says he'll ask me to send pictures of us, you know, for you"

"Wait, pictures?"

"It's not his first experience, you know?"

"Having sex?"

This time, it's Cassandra that laughs.

"Yeah. Having sex with girls who are in a relationship. Like we are"

"Oh, right"

Yana speaks up. "The term is bull. He is a bull"

I heard that term, it's popular in the cuckolding community, only, this isn't really cuckolding. I am not asking Cassandra to cheat on me to humiliate me. I am asking her to meet other guys because I love her so much that I want to share her? Does that make any sense?

"And", Yana says. "He is coming to pick her up in a few minutes"

"Yana, please. ", says Cassandra. But then turns to you. "It's not too late to change your mind, you know?"

"Are you kidding? As long as you get back to me, I am all in"

Cassandra laughs. "Come on Niles. We've been dating forever"

"Intermittently", adds Yana, but Cassandra ignores her.

"It's you I love. I mean, it feels to me like he's a jerk. I mean, great for sex, but not really boyfriend material, you know?"

"I guess", I add.

"Now, I'll be honest, I did find other guys before, but the thing is, they were all potential boyfriends and well, I already have one", she says, nervously laughing.

"You do", you say, grabbing her hand.

"This isn't about getting rid of me, right?", she asks

Yana says, "No, he's just a little cuck", but once again, you both ignore her.

"Not at all. It's simply that you are so hot, that I can't dream of just keeping you for myself."

Cassandra plays with her hair, which is always a good sign.

After a few seconds, she says, "Thank you. You have no idea what this little stupid idea of yours is doing for my self-esteem"

"Huh?", I asked.

"Well, ok, most guys are possessive, but that's not good for their girlfriends. We feel constrained, limited. We wonder is there is something better, you know, better than a jealous possessive boyfriend."

"I get that"

"So, it's not so much that I want to have sex with another guy, Niles. It's more that I would like to get the freedom to do so. I know, it's weird. Like, I am not looking forward to having sex with him. I am rather looking forward to going back to you"

"God, Cassandra, you suck", says Yana

"Shut up Yana, we know what you think", says Cassandra

"Fine"

"Well, I am happy that's how you feel. I admit that there is some joy in knowing you can see another guy, and still come back to me"

On that, Cassandra kisses me. And in that kiss, I can feel all the love she has for me, and that's enough. More than enough. That's bliss.

What is your choice?

Choices from Niles's Point of view

Statistics

There are currently 2335 steps in 328 chapters in the system, with a total of 3007169 words

This is your th day in college, a Friday

Your last unlock was days ago (or 0 weeks and 0 days ago)

Your last orgasm was days ago (or 0 weeks and 0 days ago)

Your last ejaculation was days ago (or 0 weeks and 0 days ago)

You currently have 1 flags set

You do not currently have a main exclusive character

You currently have the key to your chastity device...