Will He Size Up? Ch. 02

Author's note: Unfortunately the second chapter to this story has taken a long time to produce, as I have been very busy lately, and therefore have had limited time to work on this. I never expected this story to blow up like it did so thanks for your patience, and as always all characters are over the age of 18. Enjoy!

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Holly and I began to get closer and closer over the next week. I picked her up the morning after our dinner so she could get her car, we sat next to each other at lunch, parked our cars next to each other and walked between classes together. Every time I saw her my heart pounded as if I'd just finished a marathon. The week went by quickly, with Holly and I warming to each other just as fast. By the time Friday came around, we were laughing hard at each-others jokes and we would use any excuse possible to sit next to one another. Physical contact between our legs as we sat was a given, and we would sit close enough to each other that our shoulders would almost touch too.

That afternoon I ran into Rachel again, but this time it wasn't accidental and she was accompanied by Georgia, Caitlin and Gabby. The four girls approached me confidently with Rachel leading the way.

"Mat, we have to talk," she said, as the small group of girls came to a stop close in front of me.

"Alright... what do we have to talk about," I said cautiously.

"Okay, I'm going to cut straight to it, do you have a formal partner?" Rachel continued.

Shit. Formal (prom for our American readers) was in our final week of school, and was something that I'd been quietly preparing for, for some time. I'd used a lot of my money buying a nice black suit, pants and a nice shirt and pair of shoes, but I didn't have a partner to go with.

"Um...no," I stammered in nervous response to Rachel's question.

"Well you need to ask Holly to go with you," she said.

"What? Are you sure?" I asked.

"Mat of course I'm sure. She doesn't have a partner, and well, she really likes you. It's obvious."

"You guys would be so cute together on formal night," Georgia added, while the others nodded in agreement.

My faced turned from a pale shade of pink to red. "Yeah alright then, I'll do it. Monday morning at our lunch spot? I'll get some flowers on my way to school. Just make sure she's there," I said.

All four of the girls smiled at the same time. Rachel stepped forward and gave me a hug, her huge tits pressed against my stomach. She squeezed me tight and told me how awesome this was going to be.

"I'll text you guys when I get here, how does that sound?"

"Yeah that's a good idea," Caitlin said. "That way someone can come get you as well, just in case we aren't in the same spot."

"Cool, see you guys Monday morning then," I replied. I was pleasantly surprised as I got hugs from all the girls before I left. Each girls huge tits pressing against my chest was almost enough for my now throbbing hard on to explode. Somehow I kept myself in check before meeting Holly at our cars in the car park.

"And where have you been mister," Holly said with a smile as I approached.

"Was just cleaning up a few things, sorry," I responded quickly.

"Ha, it's okay, no need to be sorry. I was just teasing," she laughed.

"Yeah I know," I said with a cheeky grin. "You didn't have to wait for me you know."

"I didn't, but I did want to," Holly said with a smile. Maybe she does like me, I thought as I smiled back.

"Anyway I better get going," she continued, walking towards me. She bent at the knees and reached her long arms around me, smashing her huge tits into my shoulders. I reached my arms around her thin waist and held her close as she continued to squeeze her huge tits against my shoulders. She backed out of the hug and smiled before slowly lowering herself into her car and driving away.

That weekend went by quickly. I spent almost every minute thinking about what Monday morning would hold for me. I spoke with Rachel often, and we perfected the plan. I was to text Rachel as soon as I arrived at school and she would come and find me, that way I'd be able to find Holly if the girls weren't in our spot.

Monday morning arrived, and after a stop in at the local flower shop I arrived at school and texted Rachel who met me outside within minutes. The shorter girl wrapped her arms around me, excitedly smashing her huge chest against mine. I hugged her back before we set off on the long way around the school, which meant we would avoid a lot of the students walking in.

"Nervous?" she asked as she looked first at the flowers and then me.

"Absolutely shitting myself Rach, but it'll be okay once I get it over with," I laughed.

We found ourselves around the corner from the girls lockers, right next to our lunch spot and stopped. I looked at Rachel as she went up onto her toes to kiss me on the cheek.

"Goodluck, you'll be fine." I blushed hard and gave her another long hug, feeling her huge chest against mine once again.

"Thanks Rach, I appreciate it." With that I walked down the nicely cleared but narrow pathway next to the lockers, and found the group of girls standing in a circle. Holly was side on, back against a wall and only turned her head when she heard me talking to Rachel. We immediately made eye contact. I continued to walk over until I was just in front of her, my head in line with her massive tits as I looked up into her deep blue eyes.

"Holly, I was just wondering if you would come to the formal with me?" I asked, much more confidently than I thought possible. Before I knew it, those huge tits squeezed up against my face as she threw her long arms around my neck, pushing my face into her tits even more.

"Yes Mat, I'd love to, but on one condition." The group fell silent as we waited for Holly's next words.

"I'll go with you Mat, if you say you'll go out with me."

I continued looking into her beautiful eyes, and her large, thick-lipped mouth curled into a smile. I smiled a huge smile back at her.

"What? On a date?" I stuttered out.

"Yes silly," she returned quickly, still smiling.

"I'd love to," was all I managed to get out before I once again was pulled into her mountainous chest. I handed her the flowers, before she bent her legs and hugged me properly, kissing me on the cheek. I wrapped my arms around her small waist and muscular back as she wrapped her arms around my neck.

"Thank you for the flowers, they're beautiful," she whispered into my ear as she released her long arms from around me and stood back up. We smiled at each other as we parted ways. I was now more keen for maths than ever, which we had together at the end of the day.

We walked into maths together with Rachel also with us. Holly and I sat down and didn't stop talking for most of the lesson.

"Hey Mat I was just wondering if you wanted to come over this afternoon and study a bit. We usually have study sessions when we can and seeing as exams are next week we could always use an extra brain."

"Of course Hol, I wouldn't miss it, what time should I be there?"

"Um, maybe around 4 30 if that's alright for you, but really any time is fine with me."

"Yeah I can be there for then. Do you want me to bring anything?"

"Just you're cute little self," she said, almost seductively before releasing a little giggle. That comment almost sent me over the edge, as my now rock hard dick throbbed almost uncontrollably underneath my desk. "Oh and a change of clothes, bring a change of clothes too" she added.

"For what?"

"I've got a pool, and it's hot" she laughed in response. Wait did she just say she had a pool, I thought. Immediately I thought of Holly's hot body in any type of bikini. I closed my eyes and moaned slightly under my breath at the thought. I was dangerously close to an embarrassing climax in my pants at that stage, and had to focus incredibly hard to cool myself down.

With that the end of the day was upon us and we walked side by side out to our cars, once again parked next to each other. As we reached them, Holly bent down and hugged me, her arms around my neck and kissed me on the cheek. Feeling her damp limps on my skin was enough to have my heartbeat rise once again, let alone the fact her arms were hung around my neck, with her two huge tits pushed into the top of my shoulders and chest. Holly steadily rose to her feet, bring my eyes into line with her huge boobs once again. She placed a large hand on my chest as we confirmed our plan for later. We then departed with our goodbyes and a "see you soon," as we got in our cars, Holly in her expensive BMW and myself in my old ute.

I pulled into Holly's drive way at about quarter to five that afternoon and parked next to a Mercedes. I jumped out of my car with my bag slung over my back and walked casually up towards the grand doors of her house. Holly greeted me in the doorway, obviously hearing me arrive. She was wearing a small white crop top (which I realised was actually not small at all, her tits were just popping out of it), showcasing a huge amount of cleavage and her slim midriff, along with a cute pair of short shorts that stopped just below her ass. I also realised that these were actually a normal pair of shorts, at a normal, non-rolled up length (however her huge ass made them look tiny). She towered above me as she wrapped her long arms around me and once again thrusted her huge tits into my face, pushing me into her huge, deep cleavage. My dick quickly returned to a fully hard state as I reached up around her tiny waist and hugged her back.

"I'm so happy you came, come on in," she smiled looking down at me, as she placed one large hand on my shoulder.

I breathed deeply trying to compose myself as she turned to shut her door, granting me another look at her massive ass.

"As I said, I wouldn't miss it," I said with a smile. As Holly turned I followed her enormous figure into where Rachel was sitting on a couch. Feet on the foot rest and knees drawn up to her chest, as she looked lost in thought. Holly walked in and Rachel looked up immediately, and jumped off the couch as soon as she made eye contact with me. Rachel also greeted me with a hug, as she pushed her big tits against my small chest.

"Just us three this afternoon I think," Holly said as Rachel and I broke away from each other. The three of us immediately set to work on our maths study for the rest of the afternoon. Laughing away at each-others wrong answers and celebrating our right ones. After about an hour and a half of solid study we decided to pack things up and relax for a bit.

"Did you bring that change of clothes like I told you to?" Holly asked me.

"Yeah I did," I quickly responded.

Holly smiled at my response, obviously sensing my enthusiasm.

"Keen for a swim Rach?" she asked.

"You know I normally would but it's 6.30 and mum wants me back home for dinner tonight so maybe next time," Rachel replied.

"That's alright Rach there'll always be a next time," Holly smiled back at her.

With that Rachel packed her books, hugged us both and slung her leather bag over her shoulder before Holly and I walked her to the front door. I stood in the doorway in front of Holly, with Holly resting her tits on the back of my head and stroking my chest and stomach with her large hands, as we saw Rachel off. After watching Rachel drive away Holly reached out and shut the door.

"Do you want to come for a swim though?" Holly asked hopefully, almost pleadingly. I looked up at her big, beautiful blue eyes and slid my arm up around her waist, as Holly rested a hand on my chest again.

"Of course, I'd love to" I said with a smile.

"Awesome, alright well I've just got to get changed, I'll be there in a second. You can jump in if you want," Holly said, flicking the pool lights on.

"Oh cool thanks, I'll see you out there." With that I slid Holly's back door open and swiftly took my shirt off before bomb diving into her huge pool. It was bigger than any other backyard pool I'd ever seen, and I took full advantage as I swam around madly for minutes, before coming to a stop. Once again my heart raced and dick hardened as I waited in anticipation. Just as I was about to jump out to check if she was coming, Holly emerged from the back of her house wearing a tiny black, two-piece bikini, and a matching, equally tiny pair of bottoms. My dick quickly returned to full hardness as Holly ran towards the pool, her tits bouncing everywhere and jumped in. She emerged from the water and slowly swam towards me.

"I was just about to come check if you were coming out I said," trying to calm myself down.

"Of course I was silly," she said. "I just had to figure out which bikini I was going to wear," she continued with a wink and a smile as she slowly swam up next to me.

"Fair enough," was all I could get out, as I swallowed, trying even harder to keep myself in check.

"Come over here so we can stand up a bit better," Holly said, taking my hand and guiding me towards the shallow end.

"What do you mean we?" I asked. "You were doing just fine standing up there," I laughed.

"Yeah I just thought I'd make it a bit easier on you shorty" she laughed in return. "So, did I choose right? Do you like it?" Holly asked as she slowly stood up out of the water, allowing me a full, close up look at her top and bottom.

"Wow!" was all I managed to get out, as Holly smiled and pushed her body against mine, embracing me in a hug. She slowly wrapped her smooth, large legs around mine as she continued to push her massive 34M sized tits into my much smaller chest. She clung to my shoulders and back. Her long arms easily surrounded my back and neck, and she continued to push her humongous tits against my chest as her large lips meant mine. Holly continued to feel up my shoulders as I rubbed her back. Our tongues met as she opened her mouth to allow her much bigger and longer tongue to wrestle with mine. Holly slowly pulled away from the kiss and planted a hand on my stomach as she smiled at me again.

"Wow!" was all I managed to say once again.

"You're cute," Holly laughed before we embraced in a hug once again. As she let go she guided my hands to her enormous ass. I grabbed on to the ridiculous amount of flesh on offer as she wrapped her legs around my waist, bringing her pelvis into contact with my hardened 5-inch dick.

"Mmmh, you really like this bikini," she giggled.

"Yeah well, I really like you," I replied. Holly grinded herself against my readily hard cock, harder and faster until her huge body relaxed over mine. She breathed heavily, clinging to my back and shoulders.

"Mmmmh I really like you too Mat," she replied after a while, my dick on the verge of explosion. Holly twisted out of my reach and with one hand, slowly pushed me towards the side of the pool. With my back against the edge of the shallow end she preceded to bend her knees and arch her back before slamming her huge ass against my dick.

"Don't think I forgot about you shorty," she said with a smile. She held her ass in that position as I quietly moaned just about to release my load.

"Do you know how big this thing is Mat?" she asked, with an innocent tone and look on her face.

"No," I moaned out.

"It's 56 inches, and surrounding your cock," she replied quickly in the sexiest way possible. She shook her ass as my 5-inch dick remained in her huge crack between those two massive cheeks.

"Uh," I moaned as I came the hardest I had ever before, sending spurt after spurt of cum into my pants which had remained on.

"Did you like that?" Holly asked after waiting for me to calm down, making eye contact with me as she looked back over her shoulder.

"Oh my god yes that's the best feeling I've ever had in my life, you're seriously amazing," I replied.

"Thank you Mat, you're amazing too," she said back sweetly, finally releasing my dick from its prison between her huge ass cheeks.

"Do you want to stay for dinner? I'm cooking sausages, they won't take that long and I like having you around."

"Oh nothing's better than a sausage sizzle, of course I'll stay," I replied.

With that Holly stood up to full height to hug me, pushing my head between her enormous breasts. My dick stirred in my pants once again, as I followed her out of the pool and into her house.

"Feel free to have a shower too," she called over her shoulder, as I walked into the bathroom to change. I turned the tap, feeling the hot water relax my body. I took my time in the shower to regather myself before I changed and walked back into the kitchen, where Holly was still standing, cooking in her tiny bikini.

"Would you like me to take over for a while so you could jump in the shower?" I asked her.

"That's such a sweet offer Mat, but it's ok, they're almost done," She replied with that sweet smile once again. Her face was truly the most beautiful thing I had ever seen, and it was matched with a ridiculous hourglass shaped body, that one could only ever think of seeing in anime. She finished off cooking and we sat down next to each other at her beautiful wooden table, her much larger leg over the top of mine as I rested my hand on her upper thigh. We finished eating and remained like that for another half an hour telling stories, jokes and just chatting about anything that came to mind.

"Do you want to stay the night Mat?" she asked suddenly, looking down at me with hope in her eyes.

"Well it'd mean I'd have to get up pretty early to get home and grab my stuff for school so what do you think of that?" I replied.

"How about you go get your stuff now and then come back?" she countered.

"Good idea. Want to come for a drive?" I asked her back.

Holly flashed her amazing smile before answering with a wink; "Yeah I'd love to come, just let me get changed out of this bikini first." With that she removed her leg from the top of mine and walked up her grand staircase and down the hallway towards her bedroom. I stood up, took out my keys from my bag and waited by the door for her to come back out. She returned in a matter of minutes in a pair of tight black leggings and a matching black tank top, showing almost as much of her tits as possible. It really was an incredible sight. As she walked down the stairs her tits jiggled and bounced an amazing amount, threatening to unleash themselves from the tight tank top. She slipped on a pair of thongs (flip flops) when she reached me at the front door and we walked out onto the driveway.

"So how long do you reckon it'll take to get there and back?" she asked, walking closely by my side, seemingly just to show off her size.

"Probably about an hour of travel time, but maybe a bit less with the amount of traffic around at this time of night," I said back, looking up into her eyes.

"Ok cool," she said with a big grin on her face.

"Why does that make you so happy?" I laughed, asking her.

"Sorry if this sounds a bit cliché," she said, "I just really like spending time with you," she continued after a lengthy pause. I blushed and my heart beat once again increased. This girl was absolutely incredible, and she's telling me she really likes being around me.

"I really like spending time with you too Hol," I smiled back at her as we got into our respective seats in my ute. I quickly jumped into the drivers seat as Holly slowly lowered herself in on the passenger side, legs first and then the rest of her. Her legs looked fantastic in the moonlight and I watched as her tits jiggled all over the place as she readjusted her position. My dick was once again, unashamedly at full erect status. I placed a hand on Holly's upper thigh, to which she responded by placing her hand on top of mine, as I backed out of her driveway and started driving. I often looked over during the drive to find Holly's eyes concentrated on my face and her lips turned in a smile.