Anal Only Journey

Hi! I’m Cassandra, but most people just call me Cassie. This will be a collection of short stories from my sexual experiences as I was going through the last year of Highschool, and beyond.

All of these stories are at least a little embellished, but we wouldn’t want you to go in dry!

Chapter 1: I don’t lose my religion

Oh no he did not just “No. Listen. John! No! I can’t. You know why.”

“C’mon Cassie, we’re both adults here. Everyone is doing it. Plus, this is the perfect opportunity, nobody will be around for hours!”

“John please take your hand out of my skirt. You’re not even close, it’s lower.”

Slap “That was not an invitation!”

“Ow Cassie! Why did you even show up then?”

“No. I’m not doing it with you. I thought you asked me to come here to make out or something. You know I’m saving myself until marriage, and I’m definitely not losing my virginity in a church choir box.”

“I’ll just put it in a little…”

This has been a long time coming. “Shut up John. You know what? We’re done. This is clearly all you want, and you don’t care about me.”

I didn’t hear the rest of his pleas as I swiftly exited through the vestry. Walking quickly, I made my way through the maze of rooms that sprawled out behind the Church Nave (Sanctuary for you protestants) smoothing down my school uniform and trying to control my breathing as I went.

Screw him. Ugh. And now I’m all worked up too. It’s not like he isn’t hot, and I couldn’t see us…OK no. Stop. Don’t think about that.

I made my way towards the nearest restroom, dodging students and keeping my head down. I knew I was blushing hard, and that John would immediately spread word about our breakup. He was a pretty popular guy, and if he couldn’t get me to spread my legs for him he would just find someone else.

In a big Catholic School like this one, there are bound to be a few girls who put out before marriage. A few mental images of girls I knew in my class stripped naked flashed through my head as I pushed open the bathroom door. Thank god it’s empty.

I stepped over to the mirror, and worked on making myself look presentable. I was supposed to be on a study hour, but my next class was coming up far too quickly. The girl that stared back at me in the mirror looked like a mess. I had, in fact, gone to make out with John, and not only was my shirt and skirt rumpled, but he had messed with my hair too. God, why is it so hard to be the good girl who doesn’t mess with boys? …or girls?

I had my kit in my backpack, so I quickly brushed my long red hair and reapplied the bit of makeup that I wore. It wasn’t much, but with my pretty porcelain skin, freckles and green eyes I was a central focus of most of the boys in class. I just added some mascara and lipstick, and I was done.

Pulling my shirt tight as I stepped away from the mirror, I looked at my chest. Someone is going to make me get a bigger shirt soon, but maybe I can make it through the rest of the year…I really have grown up. Now sporting 32DD breasts, my shirt was too “form fitting” for the regulations. My skirt however, was within the rules, as I hadn’t grown an centimeter past 5’4” and it still hung down to my knees. I wish it showed off my butt more… woah. No. Stop. You don’t need to show off for anyone. My butt was a nice bubbly heart shape, and I had no reason to flaunt it. Because I’m not looking for anything. Definitely.

How am I supposed to be good? I have all these sinful thoughts, about boys and girls.

Consumed by my mini-existential crisis, as I exited the bathroom I wasn’t looking where I was going, and ran straight into someone.

“Oh! Wow I am so sorry…Father Preston!”

“There you are Cassandra. Follow me to my office.”

Shit