Will He Size Up Ch 06

Author's note: Thanks for your patience, I hope this chapter is worth your wait.

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Sunday came around quicker than we thought it would. After shopping for snacks and essentials the day before we were packed and ready to leave for Rachel's beach house. We woke at 8, cooked and ate breakfast and were ready by the time Rachel and three of the other girls arrived at 9. Holly changed into a tight tank top, and short jean shorts that almost covered her ass. Another outfit that complimented her body extremely well, though I seriously doubted there would be an outfit that wouldn't. We were following Rachel to the beach house. We walked out the front to greet them, giving them all quick hugs before we opened the garage for Holly's car, which was already packed with our things. After a quick chat we decided to get moving as Holly slid into the drivers side of her Mercedes.

The two hour drive was a long one, but in good company it didn't feel that way. We called Rachel and the girls in front of us on the phone a few times when we got bored and pulled in a few times to get snacks along the way. We eventually arrived and took in a breathtaking view of the coastline. The beach was just across the road and looked fairly quiet for a warm summers day. The beach itself was fairly secluded, which meant we had a nice amount of privacy. The house was huge and beautiful. The large terrace could be seen from the long winding driveway. The view from up there over the coast line would be incredible, and Rachel had told us all about it many times.

Holly drove following Rachel up the extensive driveway and pulled in under a car cover next to the house. Holly and I got out of her car and started removing the suitcases from the back as the others did the same. We took a while to remove the suitcases and other bags before Rachel led us inside. The interior was just as beautiful as the exterior. Polished marble floors and matching bench tops in the kitchen and bathrooms. It was simply incredible. Rachel quickly showed Holly and I our room. It was impressive in size, similar to the size of Holly's bedroom. There was a king bed in the middle and a large, mirrored cupboard around the side. The other side of the room had sliding glass doors leading out onto a small balcony. It was the definition of luxurious.

After a quick look at the rest of the house we carried our suitcases to our room and unpacked a few pairs of clothes as we waited for the other girls to arrive. Not everyone had travelled with us, as Georgia, Abigail, Clare and Scarlett were making their way to us later in the day. Holly switched on the television to see that it also had Netflix, and quickly entered in her account details and bringing up the latest episode of Lucifer which we had started watching together not long ago. I joined her on the bed, propped up by the pillows and slid my arm around her thin waist. She pressed her body against mine in reaction and lifted her left leg so that the top part rested over my right and the bottom in the space in between my legs. We relaxed into each other and stayed like this until Rachel walked in, and asked us if we wanted to jump into the pool. On a hot summers day the only thing that beats watching Netflix in the air-conditioning is a swim and we jumped at the question. I grabbed two towels from our suitcases, one for myself and one for Holly, before lathering up with sunscreen.

I turned to walk towards the pool to investigate, since I hadn't taken much of a look at it prior before I heard Holly call out. "Hey Mat, wait for me!" she said with a smile and jogging playfully towards me, causing her huge tits to bounce around in her tiny yellow bikini, and my dick to spring to life. "Can you do my back?" she asked me as she picked up the bottle of sunscreen from the kitchen bench and walked towards me. She was followed by Rachel, Caitlin and Gabby who had all changed in to bikinis that showcased their curves tremendously. "Only if you do mine," I replied with a smile.

"I'll do it," Rachel called with a smile and a giggle. I looked up to find Holly smiling as well and welcomed her offer. In a line, we did each-others backs successfully. I gently lathered up Holly's perfect back, making sure to cover all of it. I looked down to her small bikini bottoms being basically eaten by her huge ass and my erection throbbed. I did this as Rachel ran her feminine fingers down my back, doing the same thing for me as I did to Holly. She slowly massaged the cream into the skin of my back and shoulders. "Oops," I heard her say as she squeezed more sunscreen onto her hands, obviously more than what she wanted. She proceeded to wipe it slowly along my sides and around the front of my body, her small, feminine fingers were almost feeling me up as she spread it along.

My heart rate continued to rise as Holly turned her head around to look at me. "How about giving me a hand to the bottom part as well?" she asked with a wink and a smile. I complied with her request and reached for the bottle. After squeezing some of it onto my hands and rubbing them together efficiently, I quickly spread it over the surface area of her humongous ass cheeks. I rubbed the cream in circles and massaged it into her skin, taking as much time as I possibly could. She gently shook her ass from side to side as I did this before she bent over at the waist in front of me to pick up a hair tie she had "dropped". My dick throbbed uncontrollably in my pants as I again took in the sheer size of her 56 inch ass, and the physical beauty of her 24 inch waist that matched it. It was simply surreal, but then again it wasn't. She was right in front of me.

Holly stood and turned around before pulling my head in between her huge tits and gave a slight giggle. The other girls had already headed towards the pool but had kept their eyes on us. Holly's show hadn't gone unnoticed and neither had my reactions from the looks on their faces. "Ready to jump in then?" she asked with a smile and releasing me from her enormous cleavage. I leaned back towards her breasts and quickly kissed the inside of her right one and smiled back up at her. "Let's go," I said enthusiastically as I took her hand and we almost jogged out to the pool.

Still holding her hand I guided her in down the tiled pool steps and into the water, when she slipped. Holly's hourglass, six foot 9 frame came crashing down on me, pushing me into the water. Her huge tits squished against my face. "Oops," she said with a smile as we came up for air and I realised that this was no accident.

"Are you guys alright?" Rachel and the other girls asked as we emerged from the water.

"Yeah Rach we're fine" Holly said with a smile while fixing her bikini top up. The sudden movement had caused both of her huge tits to pop free of the small yellow top. I gently slid my arm around Holly's waist and pulled her close, to which she didn't resist. Immediately everyone began talking and the time flew by. Holly remained by my side and rested one of her arms around my shoulders. Our legs tangled as we stood against the outside of the pool, her left leg in the middle of mine and my right in the middle of hers. I had no chance of controlling my erection, especially given the other girls were also all in small bikinis of their own. This meant everywhere I looked was a fit body in a small bikini. We laughed, talked and splashed for hours before the other girls arrived, though it didn't feel that way.

We climbed out of the pool at the sound of a few cars pulling into the driveway and car doors being shut. I handed Holly one of the towels I had picked up earlier but not before she shook her huge tits in my face, the water flicking off them as they shook. She giggled and I was almost frozen in astonishment as the girls walked inside to greet the others. We walked in slowly after as Holly wrapped her towel around her shoulders and bent down to give me a long kiss. I watched her enormous tits hang in her small bikini as she bent and met her lips with mine and kissed her back gently.

We all helped the other girls unload their bags before they all quickly changed into bikinis of their own and joined us again in the pool. Holly immediately jumped in and motioned for me to follow her. I complied and jumped in slowly swimming up to her. She embraced me in another warm hug, before wrapping her long legs around my waist and pushing her huge tits into my chest. I moved my hands from her back to her huge ass causing her to grin. I carried her over to the ledge and leant on it as we struck up new conversation with the girls. I slowly massaged her enormous 56 inch ass with each hand on a different cheek. I managed to hold her for a while before I got a bit shaky under her weight and began to struggle to keep her up. She felt this and looked down at me. "Struggling a bit there big boy?" she asked me, leaning in and whispering in my ear as the other girls continued the conversation. I looked up to her grinning face and I nodded, to which she responded by releasing her legs from around my waist. She then almost immediately turned around in front of me and squished her massive ass against my stomach and held me against the ledge like this. I wrapped my arms around the front of her flat, toned stomach as she held me there.

My dick throbbed and throbbed and my heart pumped hard. We made our way over to the pool steps where a few of the girls were sitting. I sat and expected Holly to sit beside me, however that wasn't her plan. She plonked her huge ass straight onto my hardened dick before moving around a bit, just to let me know she was in control. She stopped and made sure my hardness was in between her two enormous ass cheeks and relaxed her back into me. I hugged her around her stomach, and she guided both of my hands to the top and inside of her thighs. As her hands rested on top of mine we continued conversation. Holly knew that I wouldn't be able to last long like this and was enjoying every moment of my struggle. The weight of her massive ass was enormous on my much smaller body.

Without any notice Holly began to bounce up and down on my dick. Obviously she wanted to speed up the process. It didn't take long, only a couple of bounces of her huge meaty ass before I dug my fingers in deeper to the inside of her thighs. I could barely see her huge tits bouncing up and down in front of me but I knew that would also be a sight to behold. That tiny yellow bikini was struggling immensely to keep her huge tits inside it when she was walking, let alone bouncing and jumping around in the water. Holly continued bouncing away, almost as part of some sort of game the girls seemed to be playing, however it was quite obvious to all what her goal was. I looked around and saw eight flushed faced girls watching Holly as she claimed me as her own. She stopped as I loosened my grip on her thighs and fixed her bikini up before again settling on my dick. Holly turned around and gave me a quick wink before the girls quickly struck up some small conversation once again. My dick rapidly hardened with the weight of Holly's enormous ass still upon it. She felt my hardness and removed herself from my lap. "You're going to need that for later," she said and kissed me on the cheek before we decided it was probably time to head inside and plan something for dinner.

It was now well into the afternoon and the sun was beginning to sink lower into the horizon. "So do you guys want to go out for dinner tonight?" Rachel asked us. "There's a few small but nice restaurants along the coast, probably not even fifteen minutes' drive from us." We all quickly agreed that nobody really felt like cooking and that we could go scout out possible eating spots for later on in the week. We gave ourselves an hour before we had to get ready and Holly led me by hand back to our room. She closed the door behind me as I walked in, and she removed her tiny bikini, leaving her naked in the middle of the room. She walked teasingly, shaking her humongous bare tits before turning around and walking to the large mirrored cupboard where we had unpacked our clothes. I watched as she took out a massive black bra and pulled the straps up to sit on her shoulders. The bra offered a nice amount of cleavage and she pulled out a pair of matching bottoms. She looked smoking hot.

I walked over to grab a shirt and pair of shorts. I stood next to her, at eye level with her bra-contained breasts. I wrapped an arm around her fit, tight waist and picked out my clothes with the other before turning to her. I reached onto the tips of my toes and managed to kiss the inside of her left breast before I lost my balance and had to hastily retreat into a normal standing position to avoid sprawling myself over the floor, causing Holly to first blush then giggle. She pulled my head into her bra contained tits and held me there as I wrapped both of my arms around her fit upper body. My dick throbbed and my pulse quickened before Holly released me and pulled out a fine black dress and hung it over the door handle. She smiled as she turned around and walked towards the bed and settled down. "Come on," she motioned with her hand to me with a smile. I quickly accepted the invitation and laid next to her on the bed. The air conditioner cooled the room and we quickly reverted to watching Netflix under the bed sheets. Holly was still wearing her enormous black bra and her matching pair of panties and nothing more, while I only had on a pair of shorts. My arm was wrapped around her waist as we laid half naked and propped up by pillows.

Fairly shortly after covering ourselves in the blankets Holly laid a large, smooth leg on me. "I think we're going to need to take those shorts off," she said with a wink. "I like it far better when I can feel your smaller, uncovered leg under mine." I looked up at her and quickly pulled off my shorts leaving only my underwear between my now throbbing erection and whatever Holly decided she wanted to do with it next. Holly again rested her large leg on top of mine, this time also resting part of one of her enormous ass cheeks to sit partly on my lap. It was sitting barely an inch away from my dick which by this stage was absolutely rock hard and leaking more precum by the minute. My heart rate continued to rise and I knew she could feel it as she reached an arm slowly and effortlessly across my body, sliding it down my stomach. Her large hand grabbed hold of my throbbing hardness through my underwear and she smiled at me. The tease was driving me insane.

Holly had decided not to go much further than this though, only giving my erection a light squeeze every few minutes to make sure I stayed hard as a rock for as long as she wanted. I would moan every time to which she would follow with a light giggle. She knew the effect she had on me and she was using it to her advantage as much as she could. We continued to watch Netflix while Holly kept this up for almost another twenty minutes before she decided it was time for us both to get ready to go out to dinner. Holly released me from her grasp and I sighed my relief, though my dick was screaming for attention to be allowed to finish off. I looked up at Holly as she now got up off the bed. "I'm going to want all that cum later baby so don't you dare finish that off," she said with a wide smile. I nodded and got off the bed myself. My balls were as blue as they'd ever been and Holly continued to tease me as she walked towards the door where her dress was hung.

She gently picked it up and walked towards the mirrored cupboard where I had thrown back on my shorts and a nice but casual shirt. I turned to watch as Holly slipped the black dress over her head and large breasts. The dress had thin straps on both shoulders which stood to allow a mammoth amount of cleavage to be seen as she pulled it over her huge tits and let it slide down her stomach towards her massive ass. It was very tight around her top but even tighter around her bottom as she pulled the end of her dress over her 56 inch butt. There wasn't much left of the material as she managed to pull it over her ass. Her long, muscular legs accentuated by the beautiful dress.

"Wow Hol. You look beautiful," I said as I stared at her unashamedly in the mirror.

"Thanks Mat," she said with a smile as the rest of her face lit up even more. "You look quite dashing yourself," she continued to grin.

"Well thank you," I said smiling back at her and bringing the much larger girl in for a warm hug to which she quickly accepted. As we broke from our hug I walked towards the door as she stayed to brush her hair and "tidy herself up a bit more". I was the first one down in the kitchen, so I whipped out my phone and started to play a game to pass the time. Almost immediately Rachel, Abigail, Clare, Caitlin and Gabby. All of them looked incredible in dresses similar to the one Holly was wearing - tight and showing plenty of cleavage. Rachel's tits looked gigantic in her tight pink dress. Caitlin and Gabby's tits also looked larger than life although when next to Rachel's they didn't seem anywhere near as big. I looked up to see Holly walking down the stairs towards the kitchen.

As she arrived I once again took in her beauty and marvelled at the fact her tits dwarfed all the other girls, including Rachel's impressive rack. My dick had remained hard and now continued to throb at the sight of my beautiful giantess I called my girlfriend. We quickly took up conversation and I complemented the lot of them on how fantastic they all looked before the rest of the girls emerged from their rooms and we took off in two separate cars towards the restaurants.

The rest of the night was brilliant as we found a quiet place with a beautiful view over the moonlit sea. To say the girls turned heads would be an understatement, but the locals here seemed few and far between and it was obviously a quiet night in the restaurant. The food was good and we agreed we would have to come back later on in our stay. We quickly arrived back home and Holly immediately put forward the suggestion that we walk across the road and down to the beach. The moon was almost full and it was a beautiful, clear night. The stars were out in full force and everyone quickly agreed that it was a great idea. Holly lead me by hand up the stairs and to our room before once again shutting the door behind us. She slowly and teasingly pulled off her beautiful dress as I replaced my shirt with one I didn't mind getting sandy.

Holly was quick to pull out a crop top she had worn before, which left almost nothing to the imagination at the top half, and a small pair of booty shorts that could barely even be considered more than an accessory on her bottom half. She slowly pulled off her bra, leaning over towards me and maintaining our eye contact as she smiled and temptingly licked her lips with her long tongue. Her bra came off and she maintained her eye contact as she squeezed her humongous tits towards her body before picking up her top and pulling it over them. She then quickly pulled on her booty shorts and with effort pulled them up over her huge ass which almost immediately engulfed the shorts between its two massive cheeks. We met the other girls in the kitchen and walked down to the beach.

The walk wasn't long, less than two minutes until we got to the beach's soft sand. We found a spot with a high sand mound that we could lean back into and Holly slid down and pulled me close next to her. I gripped her waist and pulled her close in return as the rest of the girls joined us on either side. We laid there and continued to chat with the ocean breeze and the gentle crash of the waves in the background. The girls continued to talk as Holly began pointing out different constellations she recognised to me. We quietly slid a little further down the beach to where we were lying almost flat on our backs and looking straight up at the sky. I looked over to see Holly's enormous chest pointed towards the sky and I squeezed her waist which caused her to turn her head from the stars to me. "I love you Hol," I said with a smile.