Will He Size Up Ch 04

The next morning came around and I woke up with Holly still on top of me and in my arms. Holly woke quickly after I did, and looked up at me smiling before she reached in for a long morning kiss. It was by far, the best way to wake up in the morning, I had no doubt about it. We stayed and cuddled in bed for almost an hour before we finally decided to dress and check if the other girls were awake. I quickly threw on a set of comfortable clothes and waited just down the hallway, shutting the door behind me so Holly could continue to dress in peace. I opened up my phone and scrolled through my Instagram feed, seeing a few photos that a couple of the girls had posted the night before. I remembered back to the last night after our swim, we had all gathered around to take photos in our swimwear. The girls in their small bikinis were already fresh in my memory and my dick once again began to harden as I saw the first part of Rachel's post, where I had posed for a photo in between her and Holly, their huge tits sticking out and my arm around each girls waist.

"That's a cute photo" a sweet voice behind me said. I turned around to find Holly looking at me with a smile and we once again immediately embraced in a hug.

"Yeah it's nice we managed to get a few yesterday afternoon, big day with us doing our final exam you know," I replied. Holly nodded as she pulled me back into her breasts for another cuddle before we broke and walked down the stairs, with my arm wrapped around her small waist. Holly was in a black tank top, with tiny straps, allowing her thick black bra straps to be seen underneath. The top showed a mammoth amount of cleavage and clung to the top half of her body. She wore a complimentary pair of black short shorts, that were extremely tight and only managed to cover half of her gigantic ass.

We walked down stairs to find most of the girls were already awake and in the kitchen, only the girls who slept upstairs (Gabby and Scarlett) hadn't made their way down yet. "Morning sleepy heads," Rachel called to us as we also made our way into the kitchen. "Morning Rach," we replied at the same time. Rachel had set about making everyone breakfast, a selection of hash browns, bacon and eggs and toast. We happily accepted her meal and sat at the table next to each other, as Holly quickly laid her large leg across mine. Scarlett and Gabby joined us soon afterwards and we all spent the morning together, laughing away, much like the previous night.

Today was the day before our formal, which meant the girls were all preparing themselves, so after breakfast they all left fairly quickly, leaving Holly and I once again. We waved Rachel off as the last to leave, before we closed the door and Holly once again pulled me in for a long kiss, resting her huge tits on my shoulders and reaching her long arms down my back. I pulled her into my waist by wrapping my arms around hers before we broke. Holly had asked if I could go back to my place until the next afternoon, to give her space to prepare, as she wanted it to be a surprise for both of us when we saw each other, properly dressed up for the first time. I thought this was a great idea and was only too happy to agree with her.

I left not long after the other girls, and smiled as Holly waved from her driveway as I backed out and drove down the road. I immediately thought it would be different lying in my own bed tonight, especially without Holly cuddling up to me. We had been together a lot over the last few weeks and I'd loved every part of it, maybe it was good to have some time away though. I pulled into my driveway and into the garage, and immediately pulled out my black suit. I thought it looked brilliant, it was the first time I had ever brought myself something this nice, and along with the red tie to match Holly's dress (which I still hadn't seen, as she also wanted that to be a surprise) I was getting more and more excited. I got to the point where I wanted to try them on for the last time, and I did just that, pulling on my long-sleeved, white, button-up, dress shirt before I slipped on my black suit jacket and the pants to go with it. I slowly and carefully did my tie and smiled at myself in the mirror. Tomorrow was going to be a good day, and I was looking forward to it more and more by the minute. I quickly slipped out of my suit, so not to do any unwanted damage to it before tomorrow.

The rest of the day went by slowly and I found myself messaging Holly for the majority of the afternoon anyway. I wrote myself a plan for the next day, which I thought was probably bound to go wrong somewhere, but I felt I might be a bit more prepared with it. We were all meeting at Holly's for photos and a few pre-drinks before we were to be picked up by two limousines to take us to the inner city venue. All the girls had decided they would put themselves up in nice rooms for the night, and Holly had also decided that I was to stay with her. This meant I had to drive over an hour into the city to drop a few things like clothes and toiletries into the room where Holly and I were staying the night, which I didn't mind doing. I also was taking Holly's things to help her out, as I knew tomorrow was going to be busy for her as well, as she continued to get ready. I was to pick up her corsage on the way back before going home, changing into my suit and arriving at her place in the afternoon.

I woke early the next morning, to make sure I was prepared. The check in at the hotel was 1pm, which meant I had plenty of time to drive back from the city and to Holly's, where I was supposed to be for about 4pm. The morning went by quickly, and I managed to drop off our things alright before picking up Holly's corsage as planned. The next hour and a bit went by and I carefully dressed, neatened my hair and tied up my shoes before I was out the door.

I arrived at Holly's just after 4pm with no other cars in the driveway, and strolled up to the door. I knocked on the large wooden door. I leant against the wall waiting, and heard footsteps as she made her way down her staircase, my heart pumping with excitement. I heard the door being unlocked and watched as she gently swung it open, back towards her. My heart skipped a beat before pounding harder than it ever had before as I adored her figure, accentuated perfectly by her bright red dress. The colour itself was outstanding, and the dress complimented her in every right way. It had thin shoulder straps and was extremely low cut, almost into a deep, V-shaped neckline. I could immediately see she was wearing no bra to conceal her huge tits, and they looked incredible in the dress. The most impressive thing about her tits was the extremely limited amount of sag they had to them, which made them stand proudly in front of her. The valley of cleavage was immense, but that wasn't all to the dress. It tightened immediately below her huge boobs, which showed off her flat stomach and small waist. It remained tight around her enormous ass, which made it look even more incredible than it already was. The dress loosened off after it hugged her ass, flowing down to her feet. It had a slit almost the whole way up her leg, which made her look even more ridiculously perfect.

"Heyyyy Mat!" She greeted me with a hug, pulling her huge tits into my face. I quickly managed to hug her back as I took in her long wavy blonde hair and her long extended eyelashes, which brought out her big blue eyes even more. She had applied light red lipstick on her lips and an easy, simple amount of make-up, which somehow slightly improved her look. It was clear she had gone to an extended effort for this.

"W-w-wow" I stuttered, as I quickly slid my arm around her waist. I couldn't believe my eyes. "You look incredible," I just barely managed to get out.

"You look fantastic yourself," she replied with a smile. "I've got to say you look very cute in that suit."

"Thanks Hol," I blushed, smiling back at her. To be honest, I did feel great in it. To be dressed up was quite exciting.

"The others will get here at around 4.30, could you help me set a few things up?" she asked.

"Of course Hol, what do you need?" I replied.

"Oh nothing major, I've just been putting out a few snacks. Can you help me finish them up?"

"Yeah easy," I quickly replied and we set to work, finishing off in no time. Holly pulled me in for a quick kiss, and felt up my chest under my shirt.

"I really do love your suit Mat," she complemented, "and the tie matches my dress really well, that was a good choice," I blushed hard again.

"I love your dress, it looks fantastic Hol," I replied.

"Aw thanks, I got it specially made for tonight," she said with a smile.

"That's awesome," I replied with a smile. I pulled her in for another hug, my head gently rested on her enormous chest and arms around her waist. Her long arms around my back and legs tangled around mine. We stood more than contently like this for almost fifteen minutes, before we heard a knock at the door.

The girls slowly started arriving one by one, with their parents accompanying them. Simply put, all of them looked incredible. It did hit me all of a sudden that Holly and I were the only ones without parents there to see us off, which was disappointing, but at least we had each other. I looked around the room to a view of incredible hotness, but none of the girls could even slightly compare to mine who was nestled beside me.

Rachel had fitted herself into a wonderful, tight, white, thin-strapped, tube-top dress. Her huge 30HH cup tits made an incredible amount of cleavage as the top seemed to tighten around them. The dress was tight the whole way over her body, much like Holly's after her chest, which accentuated her small waist and round ass nicely, and stopped a few inches above her knees. Her matching 4-inch heels brought her up to about 5 foot 9, a little taller than me.

Caitlin and Gabby both wore similar, low cut, deep cleavage dresses to each other, only really differing in colour. Caitlin went blue and Gabby black. Again, they were tight around their waists and huge asses and finished at about the same spot as Rachels, and did an ample job of showing of the cleavage from their 32F sized tits. Their 3-inch heels raising them to just over 6 feet.

Scarlett and Georgia (34DD) wore similar styled dresses to each other, Scarlett in black and Georgia in red. Both were strapless with a plunging neck line, putting a large amount of cleavage on show. They were also tight around their waists and asses, the dresses loosened and continued almost to the ground. They did however have large slits at the thigh of the left leg, which was cut threateningly high. The only real difference between them other than the colour was their heights, with the heels on Scarlett having her measure up comfortably at 6 ft 3 and Georgia's at 5 ft 7, which brought us almost exactly to eye level. I was going to be one of the shortest in the group, but I didn't care as I was surrounded by the most beautiful women.

Claire (5 ft 7 with heels, 30C cup) Abigail (5 ft 6 with heels, 30DD cup) and Cass (5 ft 5 with heels, 30DD cup) were the last three girls. Clare wore a long green dress, with a slit almost the entire way up her thigh, which was tight around her waist and ass but loose everywhere else. Abigail's dress was silver and similar but tight everywhere, also promoting a fair amount of cleavage, while Cassandra's pink dress was a tight two-piece, which showed off her stomach and also put a fair amount of cleavage on show.

I sat next to Holly on the couch, trying to cover my erection which was becoming increasingly obvious. I slid my arm around her waist and we sat until the girls were ready for photos. "Hey Mat, I really want heaps of photos tonight so I'm sorry if I drag you in," she said smiling, but waiting for a response.

"Yeah that's alright, I'll be in all the photos you want," I smiled back at her.

I rose from my seated position next to her and helped her stand.

"Ready for some photos then guys?" Rachel asked us. I nodded and smiled.

"Oh, just hang on for a second I'll be right back" Holly said as she quickly walked out of the lounge room and up to her bedroom.

She returned a matter of seconds later carrying a pair of matching red heels. My mind and heart raced as I realised that these were for her, and she was going to tower over me even more. She quickly slipped her 4-inch heels on and walked over to me smiling. She was now just over 7 foot 2 tall, which was simply incredible. Her valley of cleavage was no longer at eye-level, but with the design of her dress I was still able to catch glimpses of the last bits of skin before her dress, given how low cut it was.

Holly bent down and hugged me again, kissing me on the cheek. "Wow, you look amazing," I said, trying to catch my breath.

"Thanks cutie, I hoped you'd like it," she responded quietly with a smile.

We all walked into her backyard and took a ton of photos. To put a ton into perspective, I had at least 10 alone with each of the girls, before Rachel's dad took a few group photos of us all. After our group photo, the only people who hadn't managed to get photos together were myself and Holly. The limousine's had arrived towards the end of our group photo shoot and were obviously keen to get moving. A disappointed look filled Holly's face as she realised we weren't going to get photos together, her eyes wide as she looked at me almost in despair.

"Alright" I said. "Can someone take a few photos of Holly and I before we go?"

"Have you two not already had photos?" Rachel asked shocked, to which we both shook our heads. Holly quickly gave Rachel her phone to take some photos, which in itself turned into a photo shoot. Holly wanted photos of us at our regular heights, then some with her heels on. She rested her large hand on my chest, as we posed and my heart continued to thump. To end our little photo shoot Holly wanted a few photos of us kissing, which I was only too happy to do. She bent down a long way in her heels and brought her mouth to mine. We held our kiss for an age before Holly tripped over her feet and fell on top of me. Luckily I was able to catch her alright and she managed to straighten herself up as we locked up and walked out of the house, making our way down the drive way to the limo.

We all quickly forwarded into our limos, as we had already arranged who would go in each one. Holly, Rachel, Caitlin and Gabby were with me in the first limo, while the other girls (Cass, Georgia, Claire, Scarlett and Abigail) were in the second. Neither of the other girls had dates, which I thought was interesting. Each of them could have had any guy they wanted, and all but three of them turned down proposals (the others weren't asked). Rachel was especially asked a few times, and said no each time.

I guided Holly into the limo, realising how difficult for her it was going to be to get in, much like the time we went to the movies. She looked up at me and thanked me as I got in next to her. She quickly cuddled up next to me, sliding down in her seat to rest her head on my shoulder. She rested a large, heavy leg over the top of mine, and I brought her waist close to mine as I easily slid my arm around it.

"Love you Mat," she said, looking up at me.

"Love you too Hol," I replied, whispering in here ear. We remained like this for the 40 minute drive to the venue, while engaging in conversation with the other girls.

We arrived at the venue in what seemed like no time, and I quickly managed to tuck my obvious hard on under my belt. I assisted each of the girls as they got out of the limo this time, and we thanked the driver as we walked in. The venue was a tall building, with us situated on the second level from the top. We were directed by security guards and teachers to the lifts and patiently waited outside the lift, waiting for it to return to the ground floor to take us up to the top.

We quickly found our table as we walked in and sat down, Holly pulling her chair right up close to mine. Her tits were absolutely popping out of her dress, and I was finding it increasingly hard to calm myself down, even when I closed my eyes, let alone when I was staring directly at them. We sat and talked for half an hour before we decided to explore the rest of the floor. The school had hired a professional photography team to take photos for us, and we ended up there, as Holly quickly took my hand and walked me towards them. They had set up on a balcony area, with views of the city lights in the background. In reality it was the perfect spot to set up. The girls and I again got plenty of photos, even though the photographers found it obviously hard to position themselves for the photos of Holly and I, which we both found increasingly funny. We continued to explore the balcony, which ran around the entirety of the floor, and found a quiet space where the ten of us relaxed over the edge. The girls and I casually engaged in conversation as I once again pulled Holly close to me with my arm up around her waist.

We were called back into the room, for speeches and meals before the music started up again. The meals were nice and we enjoyed each-others company, before the music turned slower. I felt Holly's head, which was rested on my shoulder turn up and I caught her eyes looking up at me.

"Would you like to dance then?" I said quietly, looking down and smiling at her.

"Yeah!" she said, as a huge smile filled her face and I helped her to stand up. We positioned ourselves in between the other couples already on the dancefloor. Girls heads on the guys chests or over their shoulders, arms around their necks. It was different for Holly and I but we seemed to adapt to the challenge after a bit of perseverance. She dropped her arms down around my neck, and I responded by pulling her closer, wrapping my arms around her waist as we swayed to the music. After a while I rested my head on her huge tits, which only made my dick throb more in my pants.

Slow dance completed, we made our way back to our table, where the girls grinned at us, after obviously watching the whole thing. "You guys are so cute," Georgia said smiling, the comment followed by a host of giggles from each girl.

The night was quickly wrapped up after that, and we made our ways out onto the street. Luckily enough for us our hotel was only a few blocks away, meaning we would get there in no time by walking. As we walked we were greeted with more than a few wolf-whistles and crude comments in the street, out of building windows and from cars which were obviously aimed at the girls. I could see it was having an effect on them as they all became quickly unsettled and were visibly shaken from the experience.

We sped up our pace and reached the hotel, walking straight into the lift. We were all on the 16th floor of 20, and almost all next to each other which we were quite happy about. I hugged each of the girls, some of them still shaken, making sure they were okay. Rachel was especially shaken, and I pulled her close. Her huge tits pushed into my chest as I managed to calm her down.

After a while we all said goodnight to each other and I followed Holly into our room. It had beautiful city views and was nice and quiet, just what we had hoped for, but this was overshadowed by something. Holly who had done a great job being the supporting friend for the other girls broke down in front of me. Some of the comments made towards the girls had even made me feel awful, let alone them. I quickly pulled her into my arms and she rested her sobbing head over my head, and her huge tits pressed into my face. I held her for a few seconds until her body calmed down and rested over mine. I had never seen her like this, but at that moment I was going to do anything she needed me to do. We remained like this for a long time before Holly stirred.