Will He Size Up Ch 01

Author's note: All characters in this story are over the age of 18. None of these characters are real characters. This is part 1 of a series and is fairly slow moving. Story set in Australia. Enjoy

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It all started again as I slowly rolled out of bed to the sound of my buzzing alarm, for the start of another school week. I hated Monday mornings. Who doesn't? I was still burnt out from a big weekend watching numerous sporting events throughout, and it looked like it too. The bed hair and tired eyes said it all. Realising I wouldn't make it through the day if I remained in this state, I quickly jumped in the shower to freshen myself up. I'd never been a big coffee drinker, so this was always the way to go for waking me up in the mornings. After the shower I quickly dried myself off while looking at my reflection in the mirror. I'm a slightly below average height - just below 5 foot 7 (173 cm) and a featherweight 58 kgs (130 pounds). My semi-erect 5 inch penis stood proudly out in front of me like it does most mornings. Unfortunately I didn't have time to take care of it though, as I hastily pulled on my school uniform and made myself some toast before hurrying out the door.

There were three more weeks left of school until graduation, something I was genuinely looking forward to. I had already decided on studying Health and Physical Education at university next year, and simply just couldn't wait to leave school. I didn't actually mind going to school. I was on a sporting scholarship and a capable member of the cricket team, and most of all there were plenty of good looking girls. I didn't have many friends at school but that didn't really worry me. My scholarship came into play as I simply couldn't afford to go to the school without it. I pulled into the school parking lot, parked between two expensive BMW's, and lazily walked up the grassy hill towards my locker.

I walked between buildings and made my way to my locker, passing plenty of people making their ways towards first period. Tripping over a loose brick from the ground, I stumbled around the corner, blindly bumping into one of the hottest girls at school. A straight 10, Rachel had flawless white skin, straight, long black hair which grew to about halfway down her back, big blue eyes and an amazing smile. These weren't even her greatest physical assets, as her large 30HH breasts made huge bulges in her school dress (and many guys pants) and an amazingly round ass that was always nicely accentuated by her school dress sat on her small 5 foot 5 frame. These curves were made all the more ridiculous with her flat stomach and toned legs. It was fair to say Rachel was the centre of attention for many of the guys. Unfortunately her books had flung out of her hands upon contact, which made me feel even more embarrassed. Red faced I bent down, apologising and picking up her books for her. As I did this she also bent down, and looked at me with those big blue eyes, flashing her beautiful smile.

"Honestly, it's fine. Don't even worry about it. It's a blind corner, you just can't see if anyone's there. It's all good." she said.

I smiled back at her, still red faced as I handed her books back over. "Hey by the way. Have you studied for maths by any chance? I was trying to do that practice quiz with Holly last night but we just couldn't figure out question 6" she continued.

"Oh maths. Yeah I was having trouble with that one too. It just didn't make sense to me, but I'm sort of glad I'm not the only one stuck by it" I replied, still red-faced but now grinning. I had never really been someone who talked to a stack of girls in high school, so whenever I had the opportunity to talk to someone like Rachel, my heart pounded almost out of my chest, and my face would often turn bright red.

We continued our short exchange for another minute, as we decided we'd help each other out if we figured out the answer, before going our separate ways. I was so late for class now, but that short exchange with the second hottest girl at school was completely worth it. Being a perfect 10, Rachel would have easily been the hottest girl at any other school in Australia, hell, probably even the world. She was simply gorgeous.

However, her best friend Holly was easily the hottest girl around in my eyes. With full, thick pink lips, on her large mouth, she had long flowing blonde hair, which grew to a little below halfway down her back and big blue eyes. Holly was absolutely stunning. She also had cute little dimples on the sides of her mouth when she smiled, which seemed like all the time. Her skin was absolutely perfect. However, there were a few points that turned a lot of guys away from her. Holly was a towering 6 foot 9 (205 cm), but unlike many girls of tall stature, had massive breasts (34M), easily bigger than what Rachel's were, and an absolutely humongous ass with a small, almost tiny waist. It got me hard just simply thinking about her, let alone when I saw her at school, with those perfect long legs and huge ass barely covered at all by her short school dresses. It seemed all of her fat went to her chest and ass. Due to these facts, many guys were actually afraid of her, and therefore, many also believed Rachel was much hotter. I had always had a major crush on Holly, but never thought I would be able to pursue a girl like her, so I didn't. I had dreamed of getting with her for a long time.

The two girls didn't always have it their way though. Both of them were bullied out of the "popular" group during the earlier years of high school as they both developed early and were often teased about it by the girls. Most of the guys made attempts to have little "accidental" squeezes here and there which also made them both squirm a bit. Eventually they formed their own group with a few other girls in similar circumstances. I looked back up to see the locker area deserted, everyone was long-gone towards their first classes.

The rest of the day flew by and immediately I knew what the first thing I would do when I got home would be. After a quick snack I headed straight to my room and started question 6, with a newfound desire to figure out how to do it. Sure enough, within a solid 15 minutes of work I managed to find out the right answer, while doing it the right way. My heart rushed as I grabbed for my phone, opened snapchat and immediately sent the two pages of working I'd done to Rachel; "I finally figured it out. Hope u can understand the mess" I wrote at the top of the screen. My hands were shaking. I didn't know whether it was excitement or nervousness but I was smiling knowing I'd helped her out.

A few minutes later my phone buzzed, a notification from Rachel. I opened the snapchat to see Rachel's beautiful smiling face and a slight bit of cleavage showing from what looked to be a very revealing tank top. "Thank you sooo much Mat!!"she wrote. Our conversation ended as I sent back a snap of me smiling and "no worries, c u tomorrow". Yeah that's pretty smooth I thought.

There was some unfinished business I had to attend to. My raging hard-on was throbbing in my pants. From not being able to take care of it this morning, to speaking with Rachel earlier, to the picture she had just sent me, it was more than enough to send me over the edge. It was true that I had jerked off just imagining the touch of those huge tits, and how they might feel around my throbbing dick a number of times. Even more often I thought of Holly's huge ass and tits and those amazing long legs as well. I'd also seen the two walking side by side about 50 metres in front of me earlier on in the day, asses shaking as they walked. It was pure perfection. Between the two, it was less than two minutes before I shot my load into the toilet bowl, just thinking of them. It was two days before I spoke to one of the girls again, apart from small talk, a smile and the nod of the head on the way past. I couldn't wait to get out of bed to get to school now, keen that I might not just get to see the girls every day I went, but also because the more I turned up, the more chance there was of having a conversation with one of them.

I walked into maths the next morning wondering why I was still in the class. I wasn't getting the best grades but was still comfortably passing. My problem with it was the stress that it made me feel. I never felt I could study for any other subject apart from maths due to the difficulty. Therefore, I often took hours reviewing and attempting to understand the content that we "learned" in class. Between school and my commitments to sport, I rarely had much time to myself. I walked over towards the desk I had been sitting at all year, a two-person desk, right up against the wall and three rows back of a classroom able to capacitate about 30 people with four rows of desks. I opened my book and put my legs across the empty chair next to me with my back against the wall and waited for the teacher to begin his inevitable attempt to make the work we would be covering seem important.

Just as he started to get up from behind his desktop computer, Rachel and Holly walked in. Every day since the beginning of the year I had tried to get to class before Holly, just to try and catch a sneaky glimpse of that huge ass that generally stretched her school dresses to their limits. They always sat at the back of the room but on the other side. Not today though. Holly looked in my direction, (though I was unsure whether she looked straight at me or just generally towards my side of the room) and confidently walked over to the unoccupied desk behind me. I looked intently at Holly's fantastic legs as she walked past me, immediately feeling blood rush to my dick. Rachel quickly trailed behind her, as they both took their places at the desk behind me.

After about 10 minutes of copying from the whiteboard and endless chatter from behind me, Rachel leant forward over her desk and whispered; "Hey Mat, just with the practice test again. How'd you end up doing number 5? Turns out that Holly and I both got different answers and we were just wondering who was right, if either of us is" Rachel said.

"Hang on let me check" I quickly replied. "There you go"

"See. I told you!" Holly exclaimed. "Thanks heaps Mat" she said as she handed the book back to me.

That was the catalyst to starting a conversation, and the three of us hit it off for the remaining half an hour of the class, where we talked about everything from the funny shape of our maths teachers head, to what we were going to do after school. Both the girls were on the school netball team and didn't mind their sport which was quite similar to me. Obviously Holly's height came at a major advantage for her, and she had played a lot of representative netball for our region, the state and even country.

The bell rung for the end of the period much quicker than we had all anticipated. "I guess time does fly when you're having fun" Holly said with her gorgeous smile filling her face. "We should sit here more often." All I could do was look up to her eyes and smile at that comment. I casually started to walk out of the room, trying to avoid any positions which may make my boner more visible to the eye. I had been hard for a good 30 minutes and totally unable to do anything about it. I had never even considered jerking off in the school toilets before but right now it seemed a valid option. My cock was absolutely throbbing.

"Hey Mat..." Holly nervously started as I turned around to face her imposing figure "what are you doing this lunch?"

A little shocked by the sudden interest I replied "Ah I was just going to work on that English assignment in the library."

I'd never really had too many friends at school, due to this I often spent most of my lunchtimes in the library doing assignments or watching YouTube. It wasn't because I'm not a likeable guy though. The problem was that this school was so prestigious and expensive to attend, that many of the students were quite stuck up. There were basically three groups at school. The "cool guys" generally pretty good at a specific sport but often very stuck up about everything, and not the nicest guys around. The school bitches were always very popular with them, often almost throwing themselves at the guys. Then there were the nerds who were friendly enough, but I never really had much in common with them. I always tried my best at school, but I never really took it as the end of the world if I didn't do as well as I'd hoped on a piece of assessment. The third group were the stoners. The guys and/or girls that were almost constantly high. They seemed to be decent people, but I'd rather have a conversation with someone who isn't high. It's just not my thing. There were a few smaller groups mostly made up of girls. There really wasn't one that I fitted in with.

"Oh cool, I was just going to ask whether you'd be interested in working on English at lunch. I hate doing schoolwork alone and most of the girls have meetings during the break. Could I maybe sit with you?"

Immediately taken aback and definitely blushing hard I nodded and tried to say "yeah sure" as casually as I could. I couldn't help the slight bit of excitement in my voice when I spoke though. Hopefully she didn't notice and if she did, she didn't say anything about it. All three of us; Rachel, Holly and I walked out of the room together. "I guess I'll meet you in the library at lunch then" Holly smiled at me. "I can come at the end of my meeting. It shouldn't go for too long. I should still have about half an hour left of lunch by the time I come out" Rachel said. "Cool that sounds good. See you guys then" I replied smiling, and walked off in a different direction towards my next class.

Holly and Rachel were a part of one of those smaller groups. The group was made up of all girls, mostly ones who had been outcasted from the "cool" group, or ones that didn't really want to be there. Fair enough I thought. There were 9 girls in their group, all of who I had barely ever talked to, though they had seemed nice the times that I'd had quick general chats with them. The other thing about that group was that all of them were absolutely stunning, each with pretty faces and fantastic bodies.

Cassandra, or Cass as she preferred to be called was neither academic, artistic or sporty, but was incredibly funny and just seemed a pleasant person to be around. She stood at 5 ft 1 (155cm), had lengthy, curly black hair and large 30DD cup breasts, a round perky ass, and nice (albeit short) legs. Everyone always thought it was funny when Cass walked along with Holly due to the massive height difference.

Claire, Georgia and Abigail were all very similar in height to each other. Also just over 5 feet, all standing at about 5 ft 3 (160cm). Georgia had 34DD boobs, Abigail wore a 30DD bra and Claire had smaller but perky and still large enough 30C cups. All of the girls had straightened light brown hair, that had grown to about halfway down their backs, and were very slim.

Scarlett stood a fair bit taller than the other girls (and myself) at 5 ft 11 (180cm) and had large 34DD tits. To go along with this Scarlett also had a huge ass and knew it, often shaking it when she walked just for a tease. Scarlett's hair was black and was between shoulder and mid-back length, and swished lightly as she walked.

Caitlin and Gabby were the last two girls in the group and both had similar features. They both had huge 32F tits and big juicy asses on their 5 ft 9 (176 cm) frames. Both girls also had straight, light brown hair with strands of blonde, which grew down to mid-back length. Everyone in the group except Cass played a sport. Holly, Rachel, Scarlett, Caitlin, Georgia and Gabby were all in the netball team. Claire played soccer and Abigail was a state level swimmer. Holly and Caitlin also swum representatively, but it wasn't their first sport. Scarlett, Caitlin and Gabby had all played representative netball but not to the level of Holly.

Lunch time came around quickly, and I swiftly made my way to the library. The back corner was where I generally sat. It was a spot that I'd sat at for almost the whole time I had been attending the school. I opened my laptop, plugged in my earphones and got straight to work. After two or three minutes I got a light tap on my left shoulder. It was Holly, standing there right next to me. I could smell her beautiful perfume, it wasn't overly strong, indicating she hadn't put much on, but she had put on just enough to ensure its smell was blissful. I looked up at her and smiled, motioning for her to take the seat next to me. She quickly pulled out the single chair next to me and sat down less than 30 centimetres from me. By this time I was as hard as a rock and my heart was beginning to beat faster, which was why I had moved my chair further underneath the desk, in the hope it would limit the visibility of my cock. Holly then opened up her laptop and we started talking as I unplugged my cheap earphones from my laptop. She adjusted her sitting position and moved in a little bit closer. Her right leg brushing up against my left making my heart thump and sending my whole body into overdrive. For twenty minutes we didn't stop talking, barely getting any work done. I simply just couldn't believe I was sitting down next to and talking casually with the most beautiful girl at school. My cock didn't stop throbbing for the whole time.

A few more minutes passed before Rachel entered the library and made her way over to where we were sitting. Smiling as she approached, she pulled up a chair to sit on the other side of the desk. The desk was fairly small, only meant of two people, but we made room for her. Holly definitely took up a lot of room on my side of the desk (which was fair enough given her size). "Gabby, Georgia and Caitlin said they would be on their ways once their meetings finish if you guys don't mind" Rachel said as she sat down, her knees gently bumping into mine under the table. "Yeah that's all good" I managed to get out, somehow without showcasing my obvious excitement. "Have you guys done much" Rachel asked. "Yeah heaps" Holly quickly replied before looking at me and bursting into laughter, her smooth, humongous, leg rubbing up against mine as she laughed. I smiled back at her as Rachel sat back confused before asking "Hang on so what? Have you actually done a lot!?"

"Hahaha no Rach, we've done barely anything but laugh since we've been here" Holly said, maintaining the wide grin across her face, with her large, smooth, hairless leg coming to a rest slightly pushing into mine. My cock pulsing and pushing at the fabric of my school pants with all its strength. Rachel started talking about the meeting she had just come out of. I risked a look down to where Holly's legs were touching mine, to see the massive size difference between them. My cock continued to pulse increasingly fast, and my heart rate continued to rise as I saw that Holly's leg was at least twice the size of mine in diameter, maybe more. She had huge legs, but surprisingly they weren't particularly muscular. They were definitely toned and defined, but not over the top with muscle, which also left them soft to the touch. I continued listening to Rachel and contributing small comments to the conversation. I was majorly focused on trying to calm myself down. My dick continued to throb.

My struggle certainly wasn't helped as Gabby and Georgia walked in. The girls all greeted each other and I nodded and smiled at both of them as they sat. I was now sitting with four of the hottest girls at school with the biggest hard-on I have ever had. Gabby pulled a chair out and sat next to Rachel on the other side of the desk. Georgia retrieved a chair from elsewhere and sat at the head of the table between Holly and Gabby. I moved over to the very side of the table, right up against the wall, allowing Georgia to be able to fit her legs under the table. Holly also moved along with me, and made sure to once again rest one of her amazing legs up against mine. She leant in to me to make sure my shoulder was touching her arm and we continued talking with the others. My heartbeat continued to rise. Still somehow on the outside I had maintained a calm persona. I was struggling immensely to hide my excitement.