Saturday Night Five

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

I was your typical inbetweener.

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 I included though, I would 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 basically, I was fucked if anyone ever saw it.

Life in general was tough and lonely.

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."

I knew a lot about Annie and she knew nothing about me, not even my name.

Part of that was due to an obsessive social media stalking 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 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 in bikini photos she posted online.

Yes, I had wrote about her in my diary before, 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 desperate. 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.

When I saw her walking my way, about to meet me at the library that afternoon, I knew she was taking this studying business seriously. But boy, I didn't know how much I could really help considering how distracted I was about to be. Annie came walking my way in a very tight black crop top that covered her breasts but revealed her midriff. Her hair was done up into a neat ponytail and she had spent plenty of time doing her make-up just as she did every day.

"Leonard?" she asked as she approached.

The blonde girl was squinting at me, but the slight smile on her face at least told me that she was pretty certain who I was. It took me a second to get my words out, "Um, yes.. uh yes.. I'm Leonard but you can call me Leo."

I stood up and pulled out her seat.

I would have loved to say that it would have looked like a nice genuine gentlemen-like action but instead, I looked like a bumbling mess as I dropped one of my books in the process and fumbled with her chair as I moved it for her.

Annie giggled as she took the seat, at least she knew what my intentions were.

"So I'm sure Miss Holland filled you in on everything?" she said to me as she opened up her expensive Mac book at the table.

"Uh yes, yeah I'm aware," he replied, "You need a bit of help to get your grades up."

She nodded, looking directly into my eyes, "I really can't afford to risk failing, I want to go to college next year, I really don't want to be stuck repeating these classes while everyone else graduates."

"Well I hope I can help you out," I told her.

"Oh I'm sure you can," she grinned, "I asked Miss Holland for her best student and you're who she chose."

The next hour and a half flew bye. As nervous as I was at the start of our lesson, I was feeling a lot more comfortable by the end of it. She had a cool calmness about her, suddenly I wasn't so afraid of her because of her social status.

She would ask me questions about the work while also asking me things about myself, wanting to know me better, "So you want to go to college in Houston?"

"Yeah, they have this really amazing IT program there that I think would suit my strengths, I'm not exactly talented in many areas," I admitted.

"Aww don't be like that," she said, brushing that aside, "I'm sure you're great at a lot of things, you're just being modest."

I blushed in response, smiling back at her. There was really something about her that got me going.

Before we knew it, it was half past five and the library was almost empty.

"Oh fuck," she quietly said to herself as she checked the time on her phone.

I looked at her a little confused, "Everything okay?"

"Oh sorry, I just didn't realise how late it was already," she said as she packed up her stuff, "Declan's house party's tonight, I've got to go right now, get changed and do my make up and everything."

I was about to ask why she needed more make-up considering what she had on already look good enough to me. But I didn't understand girls or know really anything about them to intrude.

"Oh I better let you get going then," I smiled, turning back to my own laptop screen.

Standing up with her belongings in hand, she looked down at me with a puzzled look, "You're staying longer?"

"Ah I mean... I haven't really got much else to do so I might as well get a bit more studying done before I waste the next five hours away playing PlayStation."

"Wait, you're not going to Declan's tonight?"

"No," I said straight away.

"You're kidding, everyone's going," Annie huffed.

That hurt a little knowing I definitely didn't get invited and Declan wouldn't know who I am. I had always found parties hard to get an invite for, I had basically given up trying to be noticed.

I just shrugged my shoulders, knowing there was nothing that could change the fact that I hadn't been invited.

Little did I know, Annie was already getting her phone out to make arrangements. She put her mobile up to her ear before I even had a chance to say anything.

"Hey Tay... yeah I'm good."

Tay... I was sure that was Tayla, another member of the Saturday Night Five.

"Declan doesn't care if I bring along another person tonight does he?"

Listening to her soft voice say that made my eyes widen, she was actually talking about me. I felt a little awkward if I was being honest, almost thinking it would be worth telling her not to bother.

"Leo," I heard her say before repeating it, "Leo... Leonard... Leonard Hawkins."

Ugh... Tayla certainly had no idea who I was.

"Okay awesome, I'll see you soon!"

Annie put down her phone and pulled her chair out to stand up, "Done... all sorted, you can come tonight."

I sat there a bit speechless, I had so many questions, when? where? what?

Seeing the blank look on my face, she raised her eyebrows as she looked down at me, looking a little intimidating, "You do want to come right?"

"I uhh... I dunno, I guess so... I just..."

"Oh come on Leo, you're coming," she cut me off, grabbing my hand and pulling me up from my chair.

Just the soft touch of her hand on mine made the hair on my skin stand up. We were now face to face, even closer than at the table, the smell of her perfume even stronger, her smile so infectious. She had such beautiful white teeth.

"But Uhh," I started to speak again, trying not to be sucked too far into her beauty, "I don't know when to get there or..."

Annie was quick to take her phone off me, entering her number into it.

She passed it back with that same smile, "I'll text you the details... you come and find me when you get there."

The popular blonde then said goodbye as she left the library in a hurry to get ready. I had a look at the contact in my phone, smiling seeing her name was now in there with a real phone number and everything.

I gathered up my stuff and left not long after her.

Back home, I then stressed myself out for the next couple of hours. It wasn't long after the library that I received a text from Annie, stating the address and time it started.

In the back of my mind, I was worried it might be some sort of a set up. Was I being sent to a different house to where the party actually was or was I about to walk into something I would regret like one big set-up?

Even if it was a normal invite to a party, the most reasonable option... I was still worried. My friends wouldn't be there, I doubt Annie would want to hang out with me for very long and I didn't have much experience with alcohol.

I told my parents that I was going to my friend, Michael's house, just to keep them off my back from asking me too much. Then I set off on a walk to Declan's house, not far from the school.

***

Music blared.

The backyard was packed... the entire back deck full of eighteen year olds drinking. I walked around slowly, looking out for Annie. I felt like I was invisible, nobody seemed to notice me walking around which was certainly better than be stared at by everyone.

There were so many people here, mainly from Templeton High but also quite a few unfamiliar faces, presumably from nearby schools.

As I crossed the back deck, a guy that was a full head taller than me stumbled back into me. Because he was so much bigger than I was, I could barely keep my feet as I was pushed into the back of a girl on my right.

She made a noise as I crashed into her, her red plastic cup in her hand spilled out her drink all over herself.

"Oh my god, I'm so so sorry," I exclaimed in panic as she turned around, her purple top visibly wet.

She looked at me a little confused at first, trying to work out exactly who I was. I for one knew exactly who she was, it was Rose Parker.

Rose was another member of the Saturday Night Five crew. There wasn't a single person at school that didn't know who this sexy goddess was. She was reasonably short in stature, perfectly skinny like a model but still had what looked like a fantastic rack.

Without trying to be rude, she was seen as a bit of a slut around school. There was always rumours about her in the early high school days of the things she had done with guys. It had always intrigued me, always.

There wasn't a time or day that she didn't have at least one guy perving on her or chasing her around for attention. She made it tough for all of us when she'd strut around school grounds in short skirts that weren't meant for teasing. I couldn't tell you how many times I had stayed up late in my room, getting off on her online social media photos which were just as 'slutty'.

Now here she was, staring back at me after I ruined her nice purple top with stained alcohol. It was the first time she had ever given me any form of attention...

"Do I know you?" she asked, raising one eyebrow.

I shook my head, "I'm Leo... and again, I'm so sorry for..."

"Leo? You're not from Templeton right?"

Again... another person who had no idea that I went to their High School. I nodded, still worried about what I had done to her top and what the consequences may be.

"You're kidding..."

"No, I am, ask Annie, she's the one who invited me," I replied quickly, wanting to prove who I was.

Now she really looked confused, trying to figure out why one of her closest friends had invited him along as a plus one. She ran a hand through her long brown hair, still staring at me. Her beautiful blue eyes were even more intimidating than Annie's when she stared.

"Come on then," she said, starting to walk around.

For whatever reason, I didn't move. Maybe it was because I was now staring at her ass in the tight leather black jeans she had on. But seeing me standing there still, Rose came and grabbed me by the front of my shirt and pulled me forward, through the pack of people.

I didn't know where we were going but now that I knew she definitely wanted me to follow, I stuck right to her as she entered the house.

"Nice top Rose," another tall guy said as he noticed the big stain on the front of it.

"Bite me!" she called back of her shoulder, continuing to move through the house.

The inside hallways were at least a little less packed and you could now hear people a lot more clearly. I followed her right into a bedroom where two girls were already inside.

Immediately I noticed Annie who was standing in front of Tayla who was seated on the edge of the bed.

"Oh my god, you made it!" Annie smiled brightly, coming over to give me a hug.

The blonde had a nice tight black dress on, her high heels almost putting her on equal height with me. As she embraced me with a hug, I again got a nice whiff of her scent while her breasts pressed up against the front of my body.

"What the hell happened to your top," I heard Tayla ask Rose.

"Ask this dummy," she pointed back at me.

Tayla politely smiled at me after Annie had let go of my body, "You must be Leo right?"

I nodded, nervous to now be in the same room as three of the most attractive and intimidating girls of the school. Tayla was dolled up to the nines in a very sparkly gold dress.

She was Declan's girlfriend, the birthday boy and host of the party. So naturally, this was a chance for her to show off what was a killer body. Her long legs were similar to Annie's but her ass stuck out her further in what was something Declan must love getting a piece of every night. She didn't have the same blessings above the waist but it didn't matter with what was a beautiful face.

"Well Leo here says you invited him along," Rose said as she opened up a cupboard full of clothes, "I didn't even know the kid was from Templeton."

"He's helping me study," Annie said, "He probably needs to help you too Rose if you want to graduate this year..."

Rose just chuckled to herself as she started throwing out clothes behind her from the rack. She searched through the female clothes, looking for something to change into.

Getting off the bed, Tayla started to pick up her mess, cleaning up the clothes off the carpet, "Will you stop throwing my stuff everywhere."

"Did you move your whole wardrobe to Declan's or something?" Annie asked, amused by the amount of female clothing.

Tayla shook her head, putting her clothes on top of the bed, "Just a quarter of it..."

Eventually, Rose finally pulled out something she liked. A white blouse that was low cut enough that would show off her cleavage. She smiled as she put it down on the bed and immediately began to pull up her purple stained top, grabbing it by the bottom.

In awe of her body and the skin she was now showing, I watched very closely. Rose was taking her top off like it was nothing. She now stood in the middle of the bedroom in just her black leather pants and black bra that covered her tits.

I couldn't stop staring.

They looked so nice, a couple of decently big orbs in the safety of her bra, lightly moving around every-time she would move.

"There is male company here... Rose," Tayla spoke softly to her, raising her eyebrows at me.

Initially, I wanted to tell her to shut up, concerned Rose might ask me to leave right now. But the brunette changing just glanced over at me and gave me an ever so subtle but cheeky look.

Whether it was on purpose or not, Rose picked up her white top off the bed and dropped it at her feet. Bending down slowly, her boobs hung off her chest giving me the greatest view I had ever received throughout my high school years so far.

She then picked it up, slowly taking her time to put the new blouse on, giving me more time to stare at her tits in that lacy bra.

I didn't even realise the fact that I was sporting a giant hard-on now. Luckily none of the girls had noticed, as far as I was aware.

"Come on Leo, I want to introduce you to a few people," she told me, grabbing me by the arm on the way out of the bedroom.

Annie escorted me back outside through the crowd, introducing me to all different types of people. Most of them I knew or had seen around but almost none of them knew me.

We met Declan Walker, Tayla's boyfriend. The guy was stocky, built like a brick house and again, taller than me. It was a shame that inside that big meaty head of his, there wasn't a single smart thought inside.

Then there was Travis, a star of the high school football team. He was quick to notice I didn't have a drink and gave me his newly open can. I appreciated the kindness even though I was worried about drinking myself, I hadn't been to too many parties to have done so yet.

His friend Henry wasn't as friendly, his brown hair parted, smug look on his face, he only wanted to speak to Annie, not the quiet nerd besides her.

"Alright Foley, we've got more people to meet, I'll speak to you later," Annie eventually had to say to him, calling him by his last name as everyone here did.

And then she introduced me to the last two members of the Saturday Night Five... oh my goodness.

I already knew a lot about of them due to how much I stalked both their Instagram profiles but my goodness, in the flesh, up close and personal at a proper party, neither my eyes and cock couldn't control myself.

There was a reason for it.

It started with B-O-O and ended with B-S.

They both have unbelievable tits. Perfectly large breasts that were spilling off their chest tonight. Without a doubt, they both had the two of the best racks at Templeton. I had already wrote this down in my diary somewhere, comparing the best breasts in school.

Yes I know, lame and weird... I'm not denying that.

Making things even more interesting, they both have the same lace top that allowed for a lot of cleavage, just in different colours.

Milly Kempson and Katie Bronks...

The way to tell them apart was that Milly had blonde hair and Katie had brown. But none of this mattered because I was still staring at their incredible milkers. I didn't know how obvious I was making it but both girls knew what I was doing. Milly liked it, loving the attention but Katie kept looking at me like I was a big creep... which I guess is true.

"Well... it was nice to meet you even if your eyes didn't leave my tits," Katie muttered when the two girls left.

Annie just giggled, but I stood there with my cheeks red, feeling utterly embarrassed. She told me not to worry about it but it was hard to get off my mind.

The rest of the night flew by way quicker than I thought it would. Maybe it had something to do with the power of alcohol which not only made time fly but also calmed my nerves.