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.
I certainly wasn’t a social animal but at least I had a little more confidence… It also helped that Annie was right there by my side half the night. Noticing how much she was drinking and how touchy she was starting to get with me, I was even starting to think I was a chance.
Me?!? A chance?! I mean… could you believe it?
With the sound of everyone belting out ‘Sweet Caroline’ on the deck, myself and Annie snuck out the back. Was this it, I thought to myself, was she gonna kiss me out here?
We sat out a low hanging swing that was set up, attached to one of the backyard trees.
“I’m glad you came tonight,” she told me, “I’m really looking forward to our study sessions… I mean I really appreciate your help.”
I didn’t say anything, just smiled, trying to work up the courage to kiss her. My kissing history was extremely limited and never anyone that were as anywhere near attractive as her.
It’s funny…
Funny how such a nice moment could be ruined in the blink of an eye. Less than a minute late, we were interrupted by Henry Foley, the unfriendly jock.
Again I sat there as if I was invisible to him. He flirted with Annie, making it awkward enough for me that I had to eventually move. Before you knew it, he was kissing her. The moment I saw it, I looked away and got the hell out of there.
I was upset to see that. But the alcohol made me angry, enough so that I could hit Henry or at least take my anger out on an object that couldn’t hit me back. But I controlled it enough that I could get out of there without making a scene.
What was I thinking? Of course she wasn’t interested in me in that way. I was being stupid.
Honestly, I was a little humiliated… it wasn’t even necessarily anyone’s fault but after an enjoyable night, I started to wish I never came. Maybe it’s better to remain invisible to all, this way your heart couldn’t be touched.
As I started to make my way out of the front driveway, ready to walk home, I heard a female voice telling someone to stop. Making my way off Declan’s property, I heard that voice louder.
On the side of the street, a car that was parked on the side of the road had two people next to it. It was dark out here so I couldn’t recognise either person but the male had the female pinned to the side of the car. His hand looked to be groping the woman, from her chest to the bottom of her skirt.
She yelled out again for the man to stop but he wasn’t listening.
I stood there in a panic, neither of them knew I was out there. Quite easily, I could runaway and pretend I didn’t see anything, it’s what I would normally do, too afraid of conflict. But I had this anger surging through my body and seeing someone being taken advantage was awful to witness. Something I had never experienced before.
Well… fuck it, I’ve got to do something.
“OI! LEAVE HER ALONE!” I yelled as I approached the car.
They both looked to their left to see me walking towards them. The man still had the girl pinned, “Yo one chance… piss off nerd or I’ll come over there and whoop your ass…”
I kept walking towards them. Close enough that I could see who the girl on the car was, it was Katie… she looked worried, breathing heavily, her right tit was almost hanging out of her lacy top.
“Let her go,” I said, sounding like I had been watching too many movies.
The man who I could now see was another guy that was at the party, slammed the side of the car with his right hand before coming my way.
“I gave you your warning…” he said, coming right at me.
As expected, I had no idea what I had gotten myself into. The jock pushed me straight to the ground with one push to the chest. I fell on my ass and before I even had a chance to get up, he was hovering above me.
‘WHACK’
‘WHACK’
Two big hits, his fist flying into my face, hitting just below my eye.
“I told you to mind your own FUCKING BUSINESS!” he yelled at me.
I was defenceless.
I laid there as this guy literally turned the lights out on me. All I could remember was hearing Katie scream, telling him to stop. But I was out cold.
My first ever fight, KO’d in seconds…
***
When my eyes finally reopened, I was staring up at a bright ceiling light. It hurt my eyes as they struggled to stay open.
A moment later, I realised I wasn’t alone, there were five faces that were now staring down at me. It took a couple of minutes for my senses to return. Then I realised I was in a bedroom with the five girls… the Saturday Night Five.
“Wakey, wakey,” I heard one of them to say.
“You poor baby,” I then heard Annie’s voice say as her hand rested against my chest softly, “We were all so worried.”
When I tried to sit up, the girls all held me down, not wanting me to move too quickly. Luckily they did because my head began to spin when it was lifted up. Eventually I was able to communicate properly, they all explained what had happened, how I had passed out from the punches and how the guy was eventually pulled off me from others from the party who heard the noise out the front.
“Are you okay Katie?” I finally managed to say, remembering the position she had been in before I was attacked.
I saw her there now in a grey hoodie, “I’m fine, I just feel bad for you, I’m so thankful you said something.”
While the five girls all had a chance to speak to me and tell me how thankful they were for me standing up for one of their own, I just laid their very dizzy.
“Girls, I think we need to leave him to sleep,” Tayla eventually said.
They all agreed, but before they all left, they gave me a kiss. Every single one of them, Tayla who was the only one currently with a boyfriend, kissed me just on my cheek, then Milly changed it up by putting one right on my lips, I could taste her cherry lip gloss. Rose did the same, I almost thought she was going to full on make out with me by the way she pressed her lips down on mine.
Then Katie thanked me one more time before a peck to the lips. Annie finished it off with one last kiss. It was interesting how this all started by her not kissing me and kissing someone else.
But maybe sometimes nice guys do win?
“I’ll talk to you tomorrow, get a nice rest,” she said, smiling as she ran her hand through my hair.
***
“What the fuck happened to you?” Michael asked me.
It was Monday and we were back at school. My right eye was battered and bruised and now everyone was noticing me.
After waking up in the spare bedroom at Declan’s house on the weekend, the girls again thanked me for standing up to the guy. He was from another high school, a friend of a friend of Declan that shouldn’t really have been there in the first place.
The girls were all keen on me meeting them for lunch at school. Something that Michael couldn’t grasp when I told my best friend.
“The Saturday Night Five?? You’re lying… how?? I mean… you? Why would they want…”
“Thanks for your vote of confidence,” I said, opening up my locker.
“I mean, sorry dude but seriously, they’re the most popular girls at school, I hear that Rose gives the best blowjobs of any chick south of the Mississippi and don’t get me started on Milly Milkers and Katie Cannons…”
He wasn’t wrong, they were way out of my league even if they did just want to be friends. This group didn’t allow anyone like me to just hang out with them, it wasn’t normal.
But as others around the school congratulated me for standing up to the asshole on Friday Night, I walked a little taller, a little more confidence than I ever would when walking down these corridors.
At lunch, I was welcomed by the girls with open arms. I didn’t say a whole lot, just listened quietly and ate my food. Just being there with them was a thrill.
It was also a good chance to get to know them a bit more. Rose and Milly were certainly the loudest of the five, both had so many boy troubles to get off her chest and complain about. Tayla was more of the non-official ‘leader’ of the group, she was the smartest of the five and was the only one that definitely didn’t need any help studying. Milly was the opposite, hearing that Annie was getting help from me, she was quick to ask if she could get some too.
Katie was more standoffish, I sort of thought that the first time I met her properly at the party. Although she was thankful for saving her on Friday night, she still seemed to keep her distance.
Then Annie of course, I hadn’t worked her out yet. The way she spoke about me or spoke to me, it felt like we were best friends. After seeing her kiss Henry on Friday, I didn’t know whether she was fake or not… she was difficult to work out.
It turned out only to be the start of things though. Over the next few weeks, I basically became the sixth member of their group. I was helping Annie and Milly study every night, Rose would join on occasion.
I was also a sounding board for all of Rose and Milly’s problems.
Tayla also appreciated that I was smart, someone who could actually challenge her on an intellectual level. It wasn’t something she was used to with the other girls.
“It’s so nice having a genuine conversation that doesn’t involve make-up, boys, clothes or why the NFL is rigged when Declan’s team doesn’t win,” she told me as we walked back from class.
“You two been together long?”
She shrugged, carrying her books tightly to her chest, “We’re on and off… we fight a lot so we have broken up multiple times before.”
It didn’t surprise me, honestly.
Especially considering how vastly different IQ’s they would have. Can anyone really be that different and manage to work as a couple? I doubt it.
Anyways, whether I was friend zoned or looked at as a ‘gay best friend’, it didn’t matter to me. I had five new friends to hang out, five very hot friends.
As nice as it was to hang out at school, things didn’t hit another level until I was finally invited around to one of the girls houses….
Friday night at Tayla’s place.
I didn’t originally get an invite, it was a meant to be a girls only night at her place. Some drinks, movies, snacks, girl talk… I don’t know, I wouldn’t know, I’m not a girl.
Anyway, when I was sitting in Michael’s basement, playing PlayStation, my phone began to buzz.
Text after text came through from Annie.
Annie: Tayla’s place, now!
Annie: We need you to come round!
Instantly, I felt excited. I paused the game to send a reply, asking for her address.
“What the fuck are you doing,” Michael asked, knowing I never did this.
I ignored him, too busy trying to get the address. Maybe I was just thinking with my cock but I wanted to hang out with them, friend zone or not. Once I had an address, I was set, “Sorry Michael, bit of an emergency, got to get home.”
“What sort of emergency?”
I gathered my belongings, trying to think of an excuse but I blanked out, “I’ll talk to you about it tomorrow,” I lied.
Michael had been my best friend for over a decade so I felt a little guilty to lie to him. But I didn’t want to explain where I was going, just to be bombarded with questions and be told that I don’t belong with them. I had heard enough of that from him at school over these last few weeks.
So off I went, 15 minutes later, I was knocking on the door of Tayla’s house. It was an expensive looking property, double storied, with fancy exterior and interior. I could hear giggles from inside the house after I knocked at the door.
They were obviously inside without any parents home. After a few minutes, Annie opened up the door, she had a white robe on which made me wonder what was underneath. She didn’t say anything, just grabbed me by the hand and led me upstairs.
“Annie… what’s…”
“Just wait a second hun,” she said, taking me into a bedroom I presumed was Tayla’s.
In the middle of the room, near the queen sized bed was a black office chair. Annie led me to it, making me sit down. Again I was about to speak, but she stopped me, this time putting her finger to my mouth, “Just let me explain…”
From the smell of breath, I knew she had been drinking. Whatever was going on here, I had assumed they were all at least a little tipsy.
“We have something we want to settle…” she told me quietly, “All we need you to do is sit here and once we’re all done, you’ve got to vote for a winner…
A winner? What?
Annie leaned in one last time, getting up close and personal, whispering softer, “Just don’t forget who was the first of us to speak to you…”
She then pulled away and called out to the hallway from the doorway, “Contestant number one please!!”
Annie quickly skipped over to Tayla’s stereo speaker and flicked a switch. On came music, some sort of party track that I hadn’t heard before. Annie waited by the side of the room, shaking her hips on the spot.
That was hot enough on its own but when Milly entered the room, I lost it. I was ready to cum in my own underwear when I saw the busty blonde walk inside wearing a white lacy corset that made her large breasts bounce. I was so focused on the way her tits moved that I didn’t realise at first that all she had on below the the corset was a tiny white thong.
Milly did a little 360 spin on the spot which gave me the view of her big white butt cheeks. Coming up to me, she wasted no time to grind her ass back on my lap. As soon as I felt it touch the outside of my shorts, I flinched.
Yes, I know… I haven’t had much experience with girls, I’m a nerd.
But for the next minute, I took it all in, Milly leaned forward to shake her boobs in front of my face. There was an urge inside of me to reach out and grab them but I would never do anything that would risk my relationship with these girls.
When Milly was done, she was replaced by Rose who came in and immediately was ready to put on a show. My boner that Milly had given me wasn’t going anywhere. Rose’s long brown hair was flowing down, just past her shoulders. She was leaning against the doorway, stretching her legs out. I noticed the black stockings that Rose had running up to her thighs, she ran her fingers up them, pulling them up a little higher.
Without any warning, she pulled away from the door and danced over to me. She had the moves of a classy stripper. I now had a better view of what she had on, the black stockings were attached to a black garter belt and it was matching the black lacy panties and bra set that she had on as well.
She kneeled on the chair over me and gave me a bit more of a show, shaking her tits up against my face. When she plonked her butt back down on my crotch, I knew immediately that she could feel my boner. Rose began to grind up and down slowly which made me panic that there might actually be enough friction to make me cum.
“Time Rose…” Annie said.
“Already? I’m not done yet,” Rose said, while still sitting on my lap.
“Everyone gets a minute only.”
She sighed, having more up her sleeve but she didn’t leave me empty handed. Rose grabbed my cheeks and kissed me on the lips, slipping a tongue into my mouth before finally hopping off.
This was incredible…
“Contestant number three!!”
They may have been drunk but my god was I loving every second of it. It only got better when Katie came out next, looking a bit like a brunette tinker bell. She had this tight green dress on, just covering her boobs enough to hide her nipples but still giving me all the cleavage in the world to look at.
The dress was flowy at the bottom like a loose skirt but it was still incredibly short that I had a peek of her green panties underneath when she moved too quick.
Katie may not had her heart in it quite as much as the first two, seemingly a little more lacklustre but she stole the show when out of nowhere, she grabbed the top of her dress and pulled it down. Standing in front of me, the girl was now officially topless.
The brunette pushed her chest out in front of me and shook those beautiful melons all around. I couldn’t stop staring at her pink nipples, that looked tantalising to touch. They were so big, they bounced around like crazy when she jiggled her chest.
I was genuinely drooling over them.
“Ah what the hell!” Milly called out, now sitting on the bed.
“Yeah what the fuck, I call foul play,” Rose chipped in, “We didn’t agree that flashing was part of the rules.”
Pulling up her dress to cover her tits to my sadness, Katie shrugged, “There were no rules here.”
“Never mind ladies,” Annie said, changing the track again, “Contestant number four!!”
It was hard to focus after just seeing Katie’s bare breasts, I don’t know how anyone could top it.
In strolled Tayla. In the back of my mind, I wondered if she would be involved in this considering she had a boyfriend. But she strutted into the room as hot as any of the first three, she had a light blue skirt on that looked more like a thin towel. Above the waist was a blue tube top that covered her smaller breasts.
Getting closer to me, she pulled at the skirt like material and it came off in a second. Now I was staring at lacy blue panties that looked unbelievable when she spun around.
Her best asset had always been her ass. She bent forward, pointing her butt in my direction. Putting her hands on her knees, she began to wiggle and shake that backside to the music.
It was taking all my strength not to touch my throbbing cock. It had never been put through this type of strain before. When Tayla slapped her right ass cheek hard to leave a handprint on it, my dick began to twitch.
Without thinking, she turned to face me, walked up and planted a big kiss on my lips. I could smell vodka on her, it was strong. It must have been playing a reason in why she was now making out with me. I didn’t do much, just tried to keep up with her tongue that was inside my mouth.
Her hot breath, the movement of her tongue against mine… what was going on…
“Move aside Tayla, it’s time for contestant number five!” Annie then said, pulling her friend backwards to take front position.
Like a full on strip show, Annie ripped open her white robe to both sides to reveal what she had on underneath. It was a pinkish-red coloured lacy corset with a black lacy thong.
She spent the first part of her minute, dancing and shaking her hips in front of me. Annie was the best dancer of all five girls, even more so than Rose who had stripper like skills.
Annie who originally had her hair up in a bun, removed a hair clip and shook her head to let her blonde hair fall down. Like the others she took some time to grind up against me. At one stage she had her crotch right up against mine, leaning back while holding onto the back of her chair.
She slid up and down, testing the strength of my cock to hold on.
After seeing Tayla kiss me before, Annie then did the same. But this time she grabbed my hands and planted them on her ass. They had all touched me tonight but this was the first time my hands had ever been involved.
I couldn’t believe they were there, my palms resting up against her heart shaped ass cheeks. She kissed me harder when I lightly squeezed them so I did it again, a little more.
I was so aroused, like never before.
“Time Annie,” said Tayla who switched off her stereo.
For the next few moments, I just sat there in disbelief with what had just happened. I was physically panting and the girls could see that look on my face. Breaking the silence, one of them giggled, then making all of them laugh.
“I’m sorry Leo!” Annie finally exclaimed, “I hope we didn’t scare you with any of that.”
Sorry? They never had to be sorry for that.
I shook my head, “Uhh no, trust me… I loved every second.”
“Well then?” Rose asked.
I had forgotten what Annie had told me before the whole show. She wanted me to pick a winner.
How could I really? They were all sexy in their own way.
“Pick a winner, no fence sitting,” Milly stated.
Again I just sat there looking at each of the five girls. They weren’t making things any easier as they sat there in their lack of clothing, all staring at me seductively.
“Don’t forget that kiss…” Tayla said but was immediately cut off my Rose, “Please… that’s barely a kiss, I’ll show you a proper one if you pick me.”
I would have loved to have seen that as I would have with all of them but my heart was still set on Annie. She was right, without her, this night wouldn’t have been possible.
“I’m sorry girls,” I said to the other four, “But I’m picking Annie.”
The blonde got off the bed, clapping and coming over to hug me. The others groaned or booed me as they got off the bed. It was hard to let four of them down but it was the nature of the contest. The rules made by then, not me.
“Alright back downstairs,” Katie said, “Let’s put on a movie.”
“Yeah, alright, I need to change first,” Milly then added.
The girls all made their way out of the room, leaving me with Annie alone. The blonde smiled as she sat on my lap in the chair. My cock was still at full mast and I was hoping for the love of god that she wouldn’t leave me hanging.
When they had all left, she spoke to me, “Sooo… had fun? Worth the trip?”
“Of course but… I mean… I have so many questions…”
I asked her first about why they wanted to do this, what was this meant to prove. Annie explained briefly that it was something they had always argued about, who had their best affect on guys. Now that I was somewhat apart of their group, they trusted me to use me for this test. Annie admitted that their drinking tonight was another reason why they decided to text him to come over.
“But what about Tayla? I mean… what would Declan think if he found out his girlfriend was in her underwear, on top of me, kissing me… if he finds out, he’ll kill me… he’ll…”
“He’ll never know,” Annie told me, “He’s been a dick recently… they’re on a temporary break again, they’ll be back together but until then, Tayla’s going to let loose, this happens regularly.”
“So they really do break up often?”
“All the time,” she confirmed, “She may be smart but she sure is dumb when it comes to picking partners, always the same types with no brain inside.”
It reminded me of Annie getting with that Henry guy at the party a few weeks ago, I wanted to bring it up and ask her why she would do the same thing and waste time getting with someone like him. I bit my lip though, not wanting to risk anything between me and her.
She was still sitting on my lap, the back of her legs very warm rubbing up against mine.
I wanted her to initiate the next move. Was she going to reward me for picking her? Or was this all just a big tease with no grand finale.
“Well… I still picked you over her.”
She looked and me and gave me that great smile again, a thing of beauty. But like what had happened outside at the party all those weeks ago, the mood was about to shift.
“That’s sweet of you,” she said, kissing me on my forehead, “You’re my go-to-guy.”
That would have been okay if she stopped there but she didn’t…
“I’ve never had a good platonic male friend that can have a bit of fun with like this and know you won’t try and take advantage of me.”
Platonic… yep, locked away in the friend zone with her. I started to regret my pick for the little teasing competition. Rose would have almost certainly given me something in return, Milly too!
I tried not to look disappointed in front of her, it was still an amazing night with what they had done with me.
“Annie,” Milly’s voice echoed from the door, “You guys coming downstairs? Board games and horror movies!”
“We’ll be there,” Annie said, hopping off my lap, “Come on Leo, you head down, I’ll meet you there in a second.”
It was a little bit of a disappointing finish to what was one hell of a show. I headed downstairs where the other girls were all changed into some more comfortable clothing, mostly sleepwear.
For the next hour or so, we played different board games while the girls had their last drinks of the night. When Milly and Rose began to argue over a game of Cluedo, everyone agreed it would be better just to put on a movie in the lounge room before bed.
As blankets and bowls of popcorn came out, I had to pinch myself. I was at a girls sleepover, not just any girls sleepover, the Saturday Night Five girls. There were countless amount of men who would have wanted to be in my position right now.
In the large lounge room, I found myself on one of the couches by myself. The cheap horror film flick that Katie had picked turned out to be a fizzer. I didn’t spend a single second watching it properly, my mind was just replaying the events of the night over and over again. I mean seriously… I can’t believe I saw Katie’s bare tits!?
The thoughts remained as I got tired, just like the others. Annie was first to fall asleep, on the recliner chair, her mouth wide open. Rose had another couch to herself where she dozed off not long after. Then it was myself who started to close my eyes. They kept flickering until they shut permanently.
I must have started dreaming not long after.
Annie was in my vision, wearing the same lingerie outfit she had on just earlier tonight. She was in front of me, stroking my cock which was now free from its confines.
Her hand was soft, she moved so slowly up and down my shaft, I begged her to hurry up, I wanted to cum. But she was just playing with me, not wanting me to finish yet.
Suddenly my eyes started to flicker again.
The feeling of my cock being played with hadn’t disappeared yet.
Holy shit… someone was touching me down there, there was a hand inside my shorts, someone was grabbing my cock. I looked around the room, everyone was asleep except for Tayla who was now sitting on the couch with me, with her hand down the front of my shorts.
“Shhhh…” she whispered to me as I woke up.
It took me a while for it to sink in. This was a huge deal to me, I had never had a proper handjob before and as I came to my senses, Tayla began to grip her hand tighter on my hardening shaft.
I looked at her, the light of the television screen the only source of lighting in the room, it reflected against her face. Tayla didn’t make any reactions, she looked back at me, didn’t even crack a smile.
The brunette was in her silky pyjamas, the pink material top was unbuttoned half way, I could just see a hint of her breasts inside but it was still too dark in the room to see much. She kept looking back and fourth from the television to me.
Her hand underneath the blanket continued to move. She was going so slow, knowing just as well as I that if she wanted to, she could make me cum in an instant. I was throbbing so hard, Tayla would have been able to feel its movements in her hand.
“Oooh,” I muttered as I felt her hand move a little quicker down my shaft, pulling my foreskin back.
She stopped, still holding onto my cock, squeezing it hard but not moving it. It was her warning to me to stay quiet. I got the message quickly and waited for her to pick up where she left off.
The girl was multitasking between the movie and jerking me off. I know she didn’t care what was happening on the screen though, it was all about teasing me. My worry was that she wouldn’t finish the job because I didn’t pick her.
At this slow pace, she could do this for hours with no release. But luckily for me, Tayla was in a forgiving mood. She slowly began to ramp up the pace again.
Edging closer to that orgasm, I did my best not to make a noise as my head leaned all the way back and my heavy breathing increased. Tayla had her eyes back on me now, watching the way my chest moved with every breath.
Her right hand pumped faster and as a virgin with no sexual experience who went through a show of a lifetime, I couldn’t hold on any longer.
But then she took her hand off… to scare me.
Releasing my cock just before I had a chance to cum, I gave her a shocked look which she couldn’t help but smile in return. Tayla reshuffled her position on the couch so she was now sitting down on her knees, facing me. Her long brown hair resting calmly past her shoulders.
She pulled down my shorts, underneath the blanket along with my underwear underneath. My cock free, she grabbed it once more, her right hand had control of it while her left hand undid another button of her silky night time pink blouse. Tayla’s left hand slipped inside it and grabbed her right breast.
I pulled up my shirt, knowing I was oh so close.
While jerking me off again, Tayla was massaging her breast, pinching her hard nipple as she did so. It was a fantastic sight to finish on.
Her hand pumping at a normal rate, my body twitched and it was followed by the head of my cock opening up and the first load of cum shooting out. Tayla continued to stroke as I shot out white liquid all over myself.
I had never had an orgasm this good… maybe it was because it was the first time a girl had physically got myself off with her hands but still… it was an amazing feeling.
Tayla seemed to be surprised with just how much cum I had sprayed. It was all over my stomach and chest. She tiptoed around the room to grab some tissues for me. Even having her clean up the cum off my own body was hot viewing for me.
The brunette was subtly smiling as she did this. I couldn’t believe what had just happened, even wilder than the events earlier that night.
Tayla left the room shortly after, presumably off to her own bed. As I laid there quietly as the credits on the screen rolled through, I wondered if I should have followed her up. Was I meant to return the favour?
What did I know? I was the virgin here… I didn’t know shit.
All I knew was that this was one of the best nights of my life so far. I was going to need a bigger diary to keep all these thoughts inside…