Saturday Night Five

“Ohhh fuckkkk yes… fuck me…”

Laying on top of the bed, a beautiful blonde hair 18-year-old school girl bobbed her head up and down at the level of my crotch. She had her mouth full of my hard cock, slurping away.

She pulled her head up and started to stroke me aggressively with her dominant hand, the girl smirked.

I knew the girl as Annie… my high school crush.

“You want me to make you cum?” she said in her most seductive tone.

I nodded, “Please.”

She kept jerking, I felt my orgasm building and building…

KNOCK KNOCK

“Leonard, you’ll be late for school!!”

Ugh…

My mother’s voice had put me off. I opened my eyes and Annie was gone, I was still half naked on my bed, my right hand wrapped around my hard cock.

I had built a nice imaginary fantasy world in my head where girls like Annie served me all my sexual needs. But that’s all it was… a fantasy.

***

High School hadn't been easy.

I was just beginning my senior year at Templeton High. Throughout my entire time here, I never truly found a place I belonged. I wasn't one of the popular kids, in fact, I wasn't even close. Most of them wouldn't bat an eyelid my way, I was physically invisible to them.

But I wasn't a complete oddball that everyone laughed at because there were plenty of those around.

I was very smart, I studied hard and had fantastic grades. But that all went unnoticed.

Instead of playing sport in my free-time, I'd rather spend time at home, playing video games. Adding to what many would describe as an 'embarrassing' daily life, I liked to write so I kept a diary.

I would write in this diary all the time, sometimes day to day, sometimes at the end of the week. The diary wasn't something to hold back on. I used it as a way to get out all of my thoughts on paper.

I would share my deepest secrets, my hopes and desires, my...

Oh god, just writing this down made me cringe.

It wasn't just that though, I would also write down my sexual frustrations of being an untouched virgin. Writing about girls I went to high school with, what I wanted to do with them, what I wanted them to do to me.

So to be blunt, if anyone ever saw it… my life would be over.

Things had been tough for me lately

However... in the space of a day, that would all change.

***

It all started one day after one of my classes. I was told to stay back by one of our teachers, Miss Holland, she was one of the senior year teachers at the school.

"I've got a task for you Leonard," she said in her serious toned voice, putting down a bunch of test papers on the classroom desks as I stood up the front, waiting for her to finish what she had to say.

"We've got several kids falling behind," she stated honestly, "Seniors that won't be graduating at the end of the year if they don't get their act together. I trust you enough as a student and as a genuine human being that you can really help these people out.”

I nodded, knowing where this was going.

"I don't expect you to help them all but I want to pair you up with one person that I know is capable of more than what she is achieving right now. Annie Rowland."

Wow.

I knew a lot about Annie and she knew nothing about me, probably not even my name. Unless of course you’re talking about the Annie of my fantasy world, that Annie knew everything about me.

Boy did I like her…

I had been obsessively stalking her social media over the last five years. That and the fact that she was a part of the Saturday Night Five. It was a group of five girls, arguably the most popular group of high school girls going around. Nicknamed the Saturday night five after the 'Saturday Night Live' television show, the girls were all known for their antics out on the town or at a local party on a Saturday Night.

The girls all had incredible reputations, Annie was no exception. She had beautiful blonde hair, these incredible long legs that led to a heart shaped backside that I had spent my own Saturday night's staring at via the bikini photos she posted online.

Yes, I had wrote a lot about her in my diary, quite frequently to be honest.

Major crush alert...

With the threat of failing her senior year at high school because of her poor grades, Annie had become . She wouldn't dare spend extra time at school if she didn't have to so I knew it was serious.

I accepted the teacher's request in a bid to help out and spend a bit of time with a girl I had always dreamed to be with.