Romping on Winter Break - Day 01

Writer's Note:

Years ago, when I was a student, I discovered erotica online, and while I enjoyed many of the stories I found, I had never written before. As an exercise to push myself past the fear of a blank page and to write for myself, I took an obscure storyline which was abandoned years ago, and seeing some potential in it, I took it and expanded upon it. I found editing an existing story as a useful segue way into writing my own story.

However, it was brought to my attention that I perhaps borrowed too liberally from the original work. Certain phrases, certain scenes, were used as the base. By the time I had finished several chapters, it had become a new story, but the first two chapters were not my own voice, despite being formatted and spell-checked rather well.

So going back, I decided to make drastic changes to the first two chapters, changing various details and changing the series of events and the scenes, to make it in line with the new story I had crafted. This is the first chapter.

The pages written below are completely my own creation, unless the idea of students having group sex is somehow copyrighted. Hopefully it is a decent read. Please message or comment after you read if you enjoyed it, as I am trying to improve as a writer and and feedback is useful.

Enough with the chatter, please enjoy.

MaiaEmpire

***

It was halfway through final exams week, and I was shifting through my AP History text book in the school library. I was still recovering from my Biology exam from the morning, and I was trying to focus on making it through the next part of the gauntlet: Pre-Civil War Politics. I exhaled, and brushed a wisp of dark blonde hair behind my ear. I was trying not to think about the upcoming senior cheerleading squad trip, but it was a losing battle.

I was enrolled in one of the higher-tier private academies in the greater New York metropolitan area. So naturally, our squad could afford to be flown to Florida for a week-long training exhibition between finals and the holidays. Honestly, I was just looking forward to getting some warm weather, because New York Decembers suck. But between now and arriving in sunny Florida, I had a week's worth of tests to push through. I sighed and massaged my temples.

"Hey, Beth!"

I looked up from President James Buchannan to see my best friend Brooke approach my table. Brooke was a couple of inches shorter than me, with thick, dark brown hair that flowed playfully almost to her elbows. She had smooth, pale skin with friendly light brown eyes. Her nose was slightly bigger than average, but it honestly made her even cuter. Her pink lips seemed to always be smiling sweetly. She was dressed in the same dark blue blazer and gray skirt combination I wore that encompassed our school uniform.

"Hey Brooke," I replied as she sat across from me. "Save me from this."

"History kicking your butt?" she asked.

"I am managing. I'm not sure why I need to know about Confederate economic policy, but I'm sure there is some horrible reason I need to suffer through it."

"I think all we really need to know is that the South lost. And that they sucked," joked Brooke.

"I just want to make it to Saturday so we can get away from snow for a week. I picked out a new swimsuit for Florida that I am dying to try out."

"Yeah...I wanted to talk to you about Florida." Brooke's voice took a conspiratorial tone as she leaned closer to me. "I think I'm going to be skipping the trip."

"Wait, what?" I gasped. "We've been excited for this for months! What's the point of me going without you!?"

"Well, Mark asked me if, maybe, I wanted to spend the week with him, instead." Mark was Brooke's steady boyfriend of about three months. They were practically joined at the hip. Mark was an outgoing and funny guy, and I think it balanced Brooke's quiet sweetness very well.

"I see. So you want to sneak off and spend the week with Mark?"

"This morning, Mark mentioned that he had plans to stay somewhere on Long Island, and he wants me to come with him!"

"Wow, a whole week alone with Mark? How are you going to get away with staying with a boy for a whole week?" I asked.

"Well, that's where you come in. If you covered for me, maybe take some photos to send to my parents so they think I'm in Florida..."

"Well, sure. Why the hell not. I can cover for you, I guess," I stated disappointedly. "My god, what will you be doing with him for a week on Long Island!?"

Brooke giggled. "I have no idea! I can't believe I'm even thinking about skipping out like this! Alone for an entire week with Mark, I'm so excited!"

"Excited, about little old me, eh?" said a voice behind Brooke. Mark appeared, his blazer and tie lazily askew. He was tall and broad, with spiky black hair and a permanent grin on his face. He sidled next to Brooke and gave her a peck on the cheek. She blushed and smiled. "I see you're telling Beth about my little plan?"

"I was telling her that we would be going to your vacation house for the week," replied Brooke, "and we're trying to figure out how to make it work."

"Actually, it's my vacation house," piped another voice shadowing Mark.

Rylan was Mark's best friend, and not only did he happen to be the richest kid in our class, he happened to be dating me. Well, sort of dating; I wasn't sure where we stood. We started hanging out since Brooke and Mark started dating, and even double-dated with them a few times, but I wasn't sure if Rylan was interested in taking it to the next level. He had taken me out a few times, but we hadn't kissed or anything like that.

In many ways Rylan was Mark's opposite. Whereas Mark's uniform was untucked and unconcerned, Rylan's tie was fastidiously fixed to his collar and his hair was stylish and tidy. His personality was as reserved and measured as his uniform. He wasn't as popular as Mark, but he wasn't the type to concern himself with that nonsense. But together they were quite a duo, with Mark's confident swagger and Rylan's self-assured aloofness. They were both handsome, with Rylan being slimmer and shorter, but still taller than me.

I had always crushed on Rylan. He was just so cool and collected, and not stuck-up like so many of the rich brats at our school. We always had good conversations when we were together, but I didn't know if it was Rylan's shyness that caused him to not become more serious with me. Maybe it was just disinterest in someone who wasn't as well-off as he was. But I dearly hoped he wanted to be with me, as I watched him take a place at the table his eyes met mine.

Brooke looked at Mark confused. "Wait, we're going to Rylan's vacation house?"

"Well, yeah. His parents are going to be in Paris next week so we'd be able to have the place all to ourselves. Which is actually why I'm glad Beth is here."

"I mean," started Rylan, "if you wanted to, the four of us could spend the week there." Rylan seemed uncharacteristically nervous as he spoke. "Er, obviously your trip to Florida would be really fun..."

"So, you actually want me and Brooke to stay the week with you on Long Island?" I squeaked.

"I know, it's a dumb idea..." trailed off Rylan, looking away.

"No no, I mean, that sounds like a lot of fun!" I didn't want Rylan to think I wasn't interested. Especially since it was obviously difficult for him to be this forward. "Brooke, maybe Alex or Sophia can cover for us on the trip?"

"I'm sure they would!" Brooke exclaimed. "Oh my god, could we actually get away with this?"

"You totally could, babe," reassured Mark, as smooth as only he could be.

Rylan smiled at me, and despite his calm I could see his eyes light up. "Then it's settled. I can make the arrangements. You're totally sure about this, Beth?"

"Of course!" I blushed. "This will be really fun!" My eyes fell to my textbook. "Great, now how the hell am I supposed to get through the rest of my exams!?"

"Sorry, can't help you there," said Mark, standing quickly. "We gotta get to next period. I'll see you later, babe." He leaned to give a playful smooch to Brooke, who in turn gave her trademark sweet smile.

Rylan stood to follow Mark. "So this Saturday, it is," Rylan said, with a grin I never expected from someone as serious as he was. I held my breath as my heart skipped a beat.

"Saturday," I managed to get out. "I can't wait!"

Rylan followed Mark out of the library, Brooke and I watching them until they stepped out of view. We simultaneously jerked our heads and gawked at each other.

"Oh my god!!!" we mouthed to each other in unison, and proceeded to freak the fuck out.

The rest of the week was a slog to get through, and I spent almost every waking moment thinking about that coming Saturday. One by one my exams finished, and by Friday I was mentally sucked dry. We had confirmed with the other girls on the squad, and they both reassured Brooke and I that they could cover for us. We didn't exactly tell them what we had planned, but we let them wonder.

Late Saturday morning, my parents brought me to JFK Airport where I would ostensibly board for Florida with the rest of the team. They dropped me off at the front entrance, gave their hugs, and once they drove out of sight I ducked a corner and hunted for Brooke. She was in one of the side terminals after successfully ditching her own parents. We clasped our hands shaking in nervousness as we waited for the boys to pick us up. After an eternity of sitting and internally doing summersaults, we got the text from Rylan. He was outside the departure gate.

Brooke and I practically ran to the gate, and when we exited we were greeted by an older chauffeur in uniform holding a sign saying "Beth Evans". We waved to him, and he gave a small bow.

"Ms. Evans? Ms. Fletcher? I'm Alan, the Hunts' driver. Right this way, please."

He took our suitcases, and led the way to a large black sedan parked nearby. I could see Mark peering out the window as he waved to us excitedly. Alan set down our bags to open the door for Brooke and I. Mark was grinning in the back seat next to Rylan, who was hiding a smile of his own. We piled in next to the roomy backseat. Mark immediately pulled Brooke onto his lap as she squealed.

"We almost thought you'd change your mind and fly to Florida!" laughed Mark, as he kissed Brooke hello.

"I'm glad you made it, Beth," said Rylan as I scooted next to him and out of the cold.

"I wouldn't miss it," I replied shyly. "Thanks for agreeing to pick us up." I was pressed up against him on the seat as Alan closed the door behind me.

"I convinced Al to turn around and pick me up after he dropped off my parents early this morning. He gets paid either way, not to mention I may have slipped him some cash to keep it quiet."

"So your family has a private driver?" I asked.

"We have a private staff. I already had them prepare the house for when we get there."

My mind boggled. My dad was an engineer and my mom was a doctor, but we didn't have anything near what Rylan casually brushed off. Alan had loaded our bags in the back and got into the driver's seat.

"Ready, Master Rylan?"

"Yes please, Al."

The ride was non-eventful, with Brooke staying on Mark's lap with her arms around his neck. Mark was teasing her and nibbling her neck, and I felt slightly awkward with them playing around. I tried to play it off as I chatted with Rylan, who also looked a little uncomfortable. I did like him sitting scrunched together with me, and his hand met mine as he gave it a little squeeze.

Rylan looked past me out the window. "Looks like we're almost here, guys."

Brooke, who had been playing her boyfriend's neck and earlobe, dislodged from Mark as we pulled into the driveway. "Wow, look at this place!"

The house was situated in a wooded area away from the beach. From the front, it was a long, two-storey house in a classic brick style. There was a hedge running the property, and a large glass enclosure connected to the side. The driveway ended in a roundabout, in front of a white stone entrance. Snow covered the property, but the path had clearly been recently plowed for our arrival.

"If this was just Rylan's vacation house," I thought, "what did his actual house look like?"

Al pulled to the front door and ran around to open the door for us. Brooke had to scoot over Mark, and Rylan helped pull her up. Al went to retrieve our bags, as Rylan took my hand and led us up the steps and through the double doors. The entryway was massive, with two marble staircases on either side leading upstairs. The floor was marked with an engraved H in the center. Brooke and I stood gawking as Alan carried in our suitcases.

"Will there be anything else, Master Rylan?" he stated.

"Have Maria and the groundskeepers finished preparing?"

"Yes, this morning sir. They'll return a week from now, as you requested."

"Excellent," said Rylan, slipping some bills into Alan's hand. "Thank you very much, Al. I'll see you next week. If there are any issues, please expect a message from me."

Alan nodded, and headed back outside into the cold, shutting the doors behind him and leaving us in the house.

"Wow, Rylan, this is a nice place!" said Brooke, as Mark put his arm around her waist.

"We usually come here in the summer. It's usually empty for the rest of the year. Last time I was here was in August before my sister went back to Berkley. Mark's been here before."

"Yeah, I have! C'mon babe, I'll show you around!" He guided Brooke, who had now put her own hand around his waist, and headed into one of the side rooms, leaving Rylan and I alone.

"Well," said Rylan, "would you like the tour?"

"Lead the way!"

We walked past the staircases and took a right. There were various rooms Rylan pointed out, but he led me to the massive kitchen. Rylan loved to talk about food and cooking, so it's no surprise he led me here first. It was huge, with clean, white cabinets and an island in the center paired with stools. The fridge was chrome and massive, and nearby was a table with a little breakfast area. I peeked into the fridge and found it stocked with food. In fact, all of the cabinets were filled.

"Wow, where did all this food come from?"

"Our housekeeper, Maria. I made a list and had her pick up a truckload of food to stock up the place. Can't have my guests go hungry!"

"I was hoping to see a little cooking from you! I'm tired of just hearing about it!"

"Your wish is my command," Rylan said with a bow. "Come, this way."

Rylan took me past the kitchen island and through a glass door. It led to the large glass area I saw on the way in, and inside was a massive pool area. There was a stone barbecue area, as well as tables and tanning mats littering the area. In the corner there was a raised, stone area with a hot tub. The entire area was nice and toasty, despite the snow resting on the glass above our heads.

"Wow, this is amazing! I'm surprised you don't have this pool outdoors."

Rylan shrugged. "Dad doesn't like the outdoors. Prefers keeping the bugs outside. Not that we'd have them in December. I had the staff switch on the water and start warming this place up earlier this week so it wouldn't be frozen by the time we got here."

"Well, I am certainly glad it's not outdoors! Would be a waste of a perfectly good pool."

"Come, I'll show you upstairs."

We went through the hall and back into the entryway. I went to pick up my bag, but Rylan quickly grabbed it to carry up for me, as well as his own. We took a left at the top of the stairs, and went to the end of the hall. Rylan pushed open the door into a large bedroom, the master bedroom I assumed. It had a very large, comfortable-looking bed with a small sofa facing it at the foot.

"So, what will the sleeping arrangements be?" I asked. "I'm assuming that Mark and Brooke will be sharing a room..."

Rylan dropped the bags. "Oh, geez, I'm sorry Beth, I, ah, didn't think of that..." His eyes darted around anxiously.

I sucked in my lips and studied the floor. I realize that Rylan had invited me for the week, but I didn't want to presume anything. I had hoped to maybe share his bed, but I was way too nervous to suggest it. By the way Rylan was looking awkwardly at the window, he didn't want to suggest it either.

"I can just -"

"You could go -"

There was another pause as we attempted to not speak over each other.

"It's fine if -"

"I could always -"

We did it again. Another pause ensued. I resigned myself to finding a guest room and hiding in embarrassment, and reached for the handle on my bag. Rylan leaned down at the same time, and his hand stopped on top of mine. We looked at each other, our faces inches away from each other. The butterflies in my stomach went into overtime as he stared into my eyes.

"Fuck it," muttered Rylan quickly, and his mouth landed on mine. My legs went limp, as Rylan's tender lips caressed my own. I sighed into his mouth, and I wrapped my arms around his neck to enjoy our first kiss. His arms went around my waist, and he pulled me tight against him. Rylan's hesitance and mine were gone, and our kiss became hungrier.

We kissed for several minutes, with no signs of slowing. I was so wet as Rylan kisses me harder. It had been a while since I had had sex, but I wanted Ryan more than anything at that moment. I walked backwards towards the bed, pulling Rylan with me and he gently laid me on the bed. Our mouths never left each other as I scooted up on the bed and Rylan's body moved on top of me.

We continued to make out like this, and I lifted up his shirt in the back and slid my hands over his lower back. I felt Rylan twitch like he received a shock, and I thought I had scratched him or something. I resumed stroking his back under his shirt, and Rylan shuddered again.

"Are you okay, Rylan? You're shaking a little."

"I'm sorry. I...I'm new at this." He shook harder.

"You mean, you're a - oh! Oh, Rylan, it's okay. Hun, it's okay. Do you want to keep going?" I looked up at him in concern.

Rylan nodded. "I want to, Beth. I really want to." His mouth returned to mine.

I hugged him close on top of me, and I started to bunch his shirt on the bottom to lift it up over his head. He lifted up, raising his hands and letting me pull it all the way off. Rylan was slim, but his hairless chest had some good definition. Soft, but firm. As he stood up, he lifted my sweater and pulled it over my head. Once it was off, I decided to do him a favor and reached behind me to unclasp my C-cup bra for him. I shrugged out of it, and Rylan's eyes were glued to my pink nipples.

Wordlessly, I took his cheeks in my hands and lowered him to my breasts. He began to tease my nipple with his tongue, like he was trying to figure out what to do. Letting him experiment, I stroked his hair and smiled down at him as he went from one nipple to the next. I could feel my temperature rising, and I gently pushed him towards my belly button. He kissed his way down, and began to fiddle with the button on my jeans. He grunted as it tried to get it open

"Fuck, goddamnit," Rylan swore, trying in vain to loosen it.

I stroked his cheek, and went to my button and flicked it open for him. I slowly unzipped my fly as he watched. Rylan yanked my jeans and panties down a few inches. I swayed my hips, and Rylan pulled them all the way off.

"Get my socks, too," I reminded him. In seconds he tossed them aside. Rylan's eyes soaked in my naked body. I was fairly toned and in shape from the cheerleading practice, and I loved having Rylan stare at my curves. Rylan's eyes came to my now flared pussy, and he lowered his face to my crotch.

Rylan started licking all over, trying to figure out what to do. I tried to help him out, letting loose a moan when he hit a good spot. It was adorable feeling him try to figure it out, but he eventually got it. My breathing became heavier, and as Rylan found my clit I began to rub and pinch my nipples.