Explorers Club Ch. 01: Maui

Explorers Club - day 1 - to Maui

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Note: This story was submitted as a stand-alone story for the 2024 Summer Lovin Contest. If you want to see the series continue, leave a comment to let me know, and subscribe to see future updates.

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The loudspeaker blared: Flight 1331 to Maui had begun boarding.

Professor Jessica Hale, our group's faculty advisor, clapped her hands, waking us up. "Alright Explorers, get up! One last flight, then Hawaii!"

It was already past midnight, and the delays and layovers were finally over. The four students in the Explorers Club who joined this trip, including me, were splayed across the nearly empty boarding area in the San Francsico airport. The group's big summer adventure was about to truly begin.

I was lying across a row of seats, using them as a bed. I had been dreaming of Gracie, one of the other Explorers, and was a little annoyed as the dream faded. Professor Hale bent down in front of me and I blinked. In my half-wake delirium, the first thing I saw were her big almond eyes, peering at me from behind her black-rimmed glasses. The second thing I noticed was her cleavage, which I had a clear view of as she bent down over me.

"Come on, Perkins," she said, and grabbed my shoulder. I enjoyed the feeling of her hand, and I felt my blood and consciousness return.

"We've got to get..." she paused mid-sentence.

I followed her eyes, which were staring down at my crotch. My hard-on was pushing an obvious bulge in my pants. Shit.

"Well I see you're already waking up, aren't you, Perkins?" she whispered.

"Oh god, professor, I didn't mean to, I just, uh..."

She just flashed me a grin and stood to go wake the others.

"Frank, Gracie, Alex!" Professor Hale yelled, clapping. "You know how Marines have that phrase 'leave no man behind' or whatever? Well we're no Marines, and I will leave you behind if you don't get your asses on the plane!"

"Okay Jessica, I'm awake," Gracie said, as she stood up and pushed out the creases of her sundress.

Gracie's dress showed off her incredible cleavage and hung short at her mid-thigh. Her warm smile, kind eyes, and killer body meant that she was the kind of girl that boys easily obsessed over. She was also a senior, and the club's veteran member. She had developed a close friendship with Professor Hale and was on a first name basis with her. But even after joining four hikes with Gracie this year, I doubt she knew my name.

I was just a Freshman, and I joined the Explorers Club as a way to meet people. I liked hiking, but I really stayed for Gracie. And I joined this summer trip to Maui because of Gracie, as well. Professor Hale had been hyping up the Maui summer trip all year. She was Hawaiian and considered the trip a sort of homecoming, as well as a way to celebrate the end of the schoolyear.

But most of the Explorers Club wasn't coming along. There was a $2,000 fee to cover the cost of flights, travel, food, and all the other expenses, so usually only a small group went each year. It was 'cheap for a beautiful Hawaiian vacation' Professor Hale would say, but even so, people at our college generally vacationed in places that were cheap and drivable.

But when I heard Gracie signed up, I paid immediately- even if it did represent most of my savings account. This would be the perfect opportunity to get close to her: a small intimate group, hiking in the beautiful jungles and mountains of Maui. Then after paying the non-refundable fee, I saw the attendee list. There would only be four of us: Gracie, myself, my friend Frank (who I had coerced into joining), and Alex: Gracie's boyfriend.

I had no idea she even had a boyfriend. He wasn't even part of the Explorers Club, but due to the small group, Professor Hale was happy to add an outsider, especially as a favor to Gracie. I spent the next week kicking myself for spending $2,000 on absolutely nothing. Even if I didn't know for sure that Gracie had a boyfriend, I was a moron to think that she would be single. But the fee was non-refundable, and I had already roped Frank into it, so I was stuck.

"Come on lovers, save it for Hawaii," Professor Hale said, splitting up Gracie and Alex who were making out. I tried to avoid watching them.

"I wish we had done direct flights like last year," Gracie complained, still groggy. "Jessica, remember the hike we did to the volcano-"

"Gracie come on, we have to get on the plane. We can reminisce when we get there," Professor Hale said, sharp and commanding.

"Tough but fair, I like that in a woman," Alex said, tipping an invisible hat to Professor Hale. Gracie poked him as they moved onto the jet bridge. They were arguing in loud, very easily audible whispers.

I do not have a crush on her! Alex protested.

"Oh he's absolutely got a hard-on for Professor Hale," Frank said as he came up next to me. "I mean, I can't blame him. Hale is a stone cold fox."

He wasn't wrong. Professor Hale was wearing her customary khaki short shorts and her tight fitting white top that really showed off what an amazing, toned body she had. Her tight butt pushed proudly against her shorts and both Frank and I stared at the round curves of her ass as she talked with the desk counter staff. Her skin also had this sun-touched honey tone to it that made it look as if she was always glowing, just a little bit.

"I mean she spends so much time hiking, no wonder she's in incredible shape," I said.

"Makes sense..." Frank nodded. "Goddamn. I could bounce a quarter off that ass."

"I mean, technically you could bounce a quarter off anyone's ass," I said.

"Yeah, but it would really like... bounce off that," he said. "Like, it would get distance."

"More than Gracie's, you think?" I asked, curious what he would say.

"See, that's different," Frank said, speaking with the tone of a distinguished professor. "You see Gracie's ass is soft and supple- judging solely based on visual data of course- but Hale has more muscle tone back there. That gives her a very high bounce quotient-"

"Wait so 'bounce quotient', is that the official terminology?"

"Yes it is Perkins, now keep up. For an ass like Gracie's with a higher 'squish quotient,' the most efficient way to properly appreciate the ass is to take the quarter and just nudge it in there, between the cheeks."

I snorted. "It sounds like you've really spent time working this out."

"I have Perkins, I've done the calculations."

"So you've been doing the calculations at night, in your bed, I assume?"

"Of course, where else am I supposed to do them?"

"Wait..." I thought for a moment. "Why would you want to put a quarter in between someone's ass cheeks? What's the point?"

"Why wouldn't you want to do that?!" Frank said, sounding almost offended.

For a few minutes, we debated whether sticking a quarter in someone's ass cheeks is something most men secretly want to do, or whether it's a strange, degenerate activity only the most craven of perverts would be interested in. We were locked in this heated academic debate when a clap came from right next to our face, and we turned. The line was empty in front of us, and we were the last ones to board.

"Two things," Professor Hale said. "First, I'm going to have to try very hard to forget the last ten seconds of my life where I accidentally overheard some of that conversation. Secondly, get on the goddamn plane unless you want to make a new life for yourselves living in the San Francsico airport."

The plane was small and only had two rows of two seats on either side. As we boarded, Frank found his seat first, towards the front. I looked at my ticket for my seat number and fumbled my way towards the back.

Alex and Gracie were sitting together, Alex by the aisle and Gracie by the window. Gracie put her sunglasses over her eyes and had nestled into the window ledge to sleep. Her cleavage was barely held up by her thin sundress, and those tits were incredible. I kicked myself again, and regretted spending $2,000 to go after this girl who still didn't even know who I was. What an idiot.

I felt a quick pain in my gut and gasped. Alex had sucker punched me in my stomach. It wasn't really that hard, it was just... weird.

"What the fuck?" I said.

"I see you, nerd," Alex said, looking at me. He winked.

Gracie turned briefly at the noise, then nestled back into the window.

Great. So Gracie paid no attention to me, and yet her asshole boyfriend was watching me closely.

"Keep your hands to yourself, Alex, or you're on the next flight back," Professor Hale said, from behind me.

"As you say, professor," Alex replied, giving her a salute. What an asshole. Where had Gracie found this jerk? I couldn't deny that he was handsome, and he had that carefree attitude and confidence that came naturally to these California boys. He moved through the world as if it owed him. Maybe that was just the kind of guy she liked. I didn't know.

"You'll need to hit harder next time," I said, and began to walk back to my seat.

"I can do that," Alex replied.

I moved to the back, with Professor Hale behind me, and we were soon alone at the back of the plane.

"Hey look, when you woke me up..." I began, feeling like I had to make some kind of apology. I honestly didn't know what I was going to say, and thankfully she interrupted me anyway.

She shook her head. "Perkins, I know how college boys are, it's fine. You know, I'm actually glad you came. You've been a good personality to have on our hikes this year. Steady, no drama, and you appreciate the outdoors."

"Oh?" I said, surprised. "Well, thanks."

"Just uh... try to keep an eye on Frank for me, alright? He needs an adult around."

I laughed and nodded. "Sure thing. And you know what, I'm actually excited for this week, Hale," I said. It was a half-lie, but I knew she was excited for it and so far, it had been a rough start.

"It's good to hear you say that! So you're just calling me 'Hale' now, huh?" she said, smiling. I was struck by how pretty her smile was. She was usually so serious, always planning, organizing, and gathering her students, that I rarely saw her smiling like she was now.

I shrugged. "Seems only fair, since you call me 'Perkins'."

"Well I am the teacher, and it's my prerogative. And besides... I kind of like it when you call me 'professor,'" she said, with a grin.

"Happy to do it, then," I responded, and checked my boarding pass. "So where are you?"

"Looks like we're sitting together," she responded, checking hers.

We both looked at the two seats next to each other and hesitated. All the rows around us were empty.

"Well you can sit over there if you want more space," she offered. "No one else is getting on the plane, and it will be easier for you to sleep."

"Are you tired?" I asked.

She shook her head. "Not really, but I know you are."

I hesitated. "Well, I could keep you company. It would be nice to have someone to talk to."

She smiled back. "That would be nice."

"Then, I'll sit with you, Professor Hale," I said, and she smirked.

The lights went out soon, and I settled in for the long flight. A stewardess brought over blankets, and we both placed our blankets over our laps.

I forced myself to stay awake so that I could talk with her. We got to know more about each other in the next two hours than we had in the entire year previously. I was taller than her and I tried to avoid dropping my gaze down into her cleavage. But her low cut blouse had the top two buttons unbuttoned, and her cleavage was almost inviting my eyes in. Her breasts were firm and well-proportioned, and they strained against her tight blouse. The more tired I got, the worse I was at being subtle, and I was getting very tired.

"You're falling asleep," Professor Hale said with a chuckle.

She took off her glasses and put them in the pouch in front of her. "I admit I'm getting tired too. It's just hard to get comfortable in these seats."

"Yeah I know what you mean," I said, and then I froze as she rested her head on my shoulder.

"Is this okay?" she asked, nuzzling into my neck. "I don't want to make you uncomfortable."

"Oh yeah, no problem," I whispered. She turned and placed her arms over my stomach. I felt my cock twitch and move. I wanted to adjust and fix it, but I didn't want to grab my dick right in front of her or do anything that would make her move her off me.

For a few moments we lay there, doing nothing but breathing. Then, her hands began to move across me, slowly. I couldn't tell if her eyes were closed or not. One of her hands found its way up my chest. Her slow arm movements could almost have been mistaken for her just shifting or trying to get comfortable... except that she kept squeezing me lightly.

"You're in good shape Perkins, you know that?"

"Thanks," I whispered. "You, too."

She snorted but said nothing. Her hand undid a button on my shirt and slid inside. She moved over my chest, and her hand slid around, feeling my chest hair.

"You've got some hair on you, too," she whispered. "I like that."

At the touch of her soft, warm hands, my cock was now pushing very obviously against my pants.

"I recognize that bump," she groaned low, just barely a whisper. Her eyes flitted up and looked into mine. "I'm not sure that's an appropriate way to greet a teacher."

"I uh... I can't help it," I admitted. I was breathing heavily.

"Yeah, I've noticed you can't help staring at my tits either," she said. "We need to work on your self-control."

"Sorry..."

She grinned. "So tell me, Perkins..."

I waited. One of her hands slid just barely under my blanket and fingered my belt buckle.

"Are you always this horny when you travel? Or is it only on my account?"

"Look, you're just..." I stammered.

"I'm just what?" Her fingers explored slowly, under my blanket, as her head rested on my shoulder.

"You're just... incredibly fucking hot," I said.

I could feel her grin as her cheek was pushed into my neck. "You know, I get horny when I travel too... and when I hike. The longer I go, the worse it gets."

"So I guess we've been traveling for what... twelve hours?" I said.

"Yeah," she responded, breathing heavier now.

She smelled like flowers, sweat, and sex. Her fingers brushed against the bulge of my hard-on. It was light, but I still gasped. I was so horny now that any touch on my cock sent shivers through my body. She brushed against it again, then again. Her fingers were growing bolder each time, seeing if I would stop her. When I didn't, she unzipped my fly and fished inside.

I groaned with pleasure as she pulled my cock out, but she held a finger to my lips and shushed me.

She ran her fingers along my naked, exposed shaft. I thought I had been completely hard before, but with my dick released, somehow it felt like I continued to grow harder under her touch. She smiled and kept stroking until her fingers were wet from pre-cum. I was aching.

"I thought you would be a big boy..." she murmured.

I nearly orgasmed as she said that.

"Please finish me," I murmured, but she shook her head.

"Teachers before students," she said, and put my cock back inside my pants, much to my dismay.

She pushed up against me and pulled my hand down to her stomach. I ran my hand underneath her blanket and unbuttoned her shorts. I pushed them down and found her panties already wet. I hesitated for a second. Maybe this is as far as she wanted me to go?

She shoved my hand underneath her panties and arched her back. I couldn't reach far enough to get my fingers fully inside of her, but her clit was hard and engorged, and when my fingers found it, she sighed softly into my neck. I was no expert at fingering, but I went by her cues. It wasn't long before I found a spot that made her gasp, open-mouthed. I stroked that spot harder and faster, and she began to shake. With my right hand working her sex, I ran my left hand underneath her bra and pinched her nipple as I grabbed her breast, hungrily. At that touch she shivered again, soaked my fingers, and collapsed onto my chest.

She pulled her shorts back up just as a stewardess walked by us. We sat up and watched the stewardess as she dealt with someone at the front of the plane. When the stewardess returned to the back of the plane behind us, Professor Hale turned to me, and directed me to hold my blanket at chest height. She pulled some loose strands of her jet black hair into a bun behind her head, preparing.

Her movements were smooth, silent, and confident as she undid my belt buckle and placed my belt on the ground, without letting the buckle clatter.

Her mouth slid up to my ear as she whispered: "I'm going to devour you." My cock twitched immediately in response.

She pulled my jeans and boxers down to my ankles, and my cock sprung free in the cool air. I held my blanket up, as directed.

Her head disappeared under my blanket, and when I felt the warmth of her mouth envelop me, it took everything I had to not moan loudly in response. My cock strained against itself, hardening to its full length inside her as she sucked.

I lost control, arched my hips, and thrusted. I expected her to gag, but she only grabbed my thighs harder and dug her nails in. I thrusted again into her mouth, and again. When I felt the tip of my cock press against the back of her throat, I started to cum. It felt like the lower half of my body was melting into a wet, hot, furnace as she sucked my trembling cock. For a few moments, all I could hear was the hum of the jet engines and the faint sound of Professor Hale gulping as she swallowed load after load of my cum, until I was spent.

"This is home, everyone, welcome!" Professor Hale yelled and waved an arm outside the taxi van.

The rest of us were still groggy, and mostly slept in the van. Hale's property was nearly an hour from the airport, over roads that wound around the seaside. As the first tendrils of dawn poked out from behind us, I realized how beautiful it was here, and began to understand why the trip was so special to her.

Hale seemed brighter and happier since we touched down in Maui, but it could have just been her happiness to be back home. She didn't acknowledge our little adventure in the back of the plane, and I followed her lead and didn't say anything about it either. So she was, once again, just our faculty adviser and tour leader... though I couldn't get the memory of her sucking my cock or the smell of her sex out of my head.

The five of us groggily got our luggage out of the van and looked around. Her property was nestled just between the coast and the forested mountains behind, and while it was no five star resort, it was undeniably beautiful. She showed us around: a small main house, square and white, a small pool with a few chairs, and access to a private beach that stretched out behind us. She even had a little spa on the property, and a couple of staff to run it all. Two of them, a man and woman dressed in white shirts and well starched pants came to take our bags.

"There are only two bedrooms in the main house, and I'll be staying in one of them," Professor Hale announced. "We can all use the kitchen and bathroom in there, but we have the bungalows set up for you all." She pointed out to a handful of squat little one-room, thatched roof cottages sitting on the beach.

"Damn, this is incredible," I said, looking around.

Hale smiled wide. "Thanks, the land has been in my family for generations. I grew up here."

"I call the second bedroom. After all, we're a couple," Alex said, pulling Gracie close.

Professor Hale hesitated but nodded. "Well, Gracie is the senior member here, so it's her call."

"Thanks, Jessica," Gracie said.

"So you LIVE here?" Frank said, amazed, as the staff took our bags.