Explorers Club Ch 05 Tight Spaces

Explorers Club Ch. 5: Tight Spaces

"Hey you two!" Hale said, waving, as Gracie jogged up to her and gave her a big hug. Hale chuckled and looked from me to Gracie. "So, how's your birthday minion situation working out, Gracie? Following orders?"

"I had to pry him out of bed, but he agreed to my terms, even if that took a little prodding," Gracie said, eying me ruefully.

"You have terms?" Hale asked, laughing, and turned to me. "Perkins, what did you agree to?"

"There are some various rules and conditions," I said, thinking. "Three... no wait, four rules, now? Is the 'no lying' rule officially the fourth?"

"Psh!" Gracie waved her hand dismissively and turned to Professor Hale. "So are we still going to the resort?!"

"We are, all six of us..." Hale said, and looked over to the pool.

"Six?" Gracie asked, annoyed, and spoke in a low voice. "We're including Frank's..."

"New Friends?" Hale finished her sentence, which surely would have ended in something more insulting. She sighed and shrugged. "I'm trying to be accommodating to all members of the Explorers Club and not have too much favoritism..."

"They're not in the club," Gracie said.

Hale sighed. "Well we are down a member since Alex left, and I'd rather Frank keep occupied, unless you want him hanging around and trying to get in your pants all week, Gracie?"

Gracie rolled her eyes.

Hale whistled to the others and walked over, beckoning them forward.

Gracie tugged on my arm as Hale walked out of earshot for a moment. "So you going to get me my birthday present today?"

I gulped. Gracie's present was to get Hale to fuck her, but I had no idea if I could make that happen. The idea was enough to nearly make me hard, especially after Gracie's promises on what would happen if I got her what she wanted. But I didn't know what to say and only nodded.

Professor Hale returned with the others in tow. My stomach growled, and Hale looked at me and smirked. "Looks like we need to get you some breakfast, Perkins."

I nodded. "Please. Do you have any bacon?"

"We can eat at the spa, right?" Gracie asked before Hale could answer.

"Oh sure," Hale said. "They've got a few restaurants on the property. I meant to ask if my friend could swing us an employee discount or something, at least."

"Great! Let's get going, we can eat there!" Gracie said. My stomach growled again.

"You going to last that long, Perkins?" Hale asked, stifling a laugh.

"I'll survive," I said. I debated pushing to eat here, but Gracie was nearly jumping up and down, eager to go.

Frank walked up to us and waved. One of the girls clutched his arm possessively- tall, blonde, and wearing lots of makeup. I could tell by her silhouette and her disdainful, disgusted expression when she saw me that she was definitely the one who saw me naked on the beach earlier that morning. Her friend trailed behind, shorter with dark hair, and was clearly the shyer one of the two. The blonde carried herself as if she was the pretty one, but both looked like rather plain, unremarkable college age girls to me.

"What are you two names again, girls?" Hale asked them.

"This is Henna and Jenna!" Frank said proudly, introducing them. "They were big fans of the sunrise, Professor!"

"I'm so glad to hear that," Hale said, trying and failing to look excited.

The blonde one rolled her eyes at Frank. "I'm Hannah,

not

'Henna'. Henna is the ink." She gestured to her friend behind her. "And this is my best friend Jenny."

"Well... that's what I meant to say..." Frank said to both of them and smiled weakly.

Jenny turned to Professor Hale and spoke softly. She seemed a little intimidated by the big group. "Thanks for including us in your plans today," she said, meekly.

"No problem!" Hale said, smiling at the shyer girl.

Frank looked at me and winked as he nodded to the two girls with a 'hey, I did pretty good, huh?' sort of expression.

I gave him back a nod, but I really wanted to ask him what actually was happening here. I sort of assumed they had a three-way, but judging by the obvious dominance of the blonde girl, and the fact that the other seemed almost lost in her shadow, it may very well be that he slept with this Hannah girl and the other one awkwardly was just... there? However I knew if I asked him for details he would start pressing me for details on my own nighttime affairs, and that could get dangerous...

Professor Hale clasped her hands excitedly. "So one of my oldest friends, Tessa, is the assistant manager of a small, but very nice upscale resort over on the other side of the island. They haven't hit full season yet and she's doing us a huge favor! We'll have our own room for the night, free reign on the grounds, a cabana by the pool, and well she can explain the rest, but I hope you all enjoy it... and happy birthday, Gracie."

Gracie beamed and ran forward, giving Professor Hale a strong hug. I could see Hannah looking excitedly at Frank and bouncing on her toes. It was clear why she was still hanging around him.

"Should be a pretty good time," Frank said to Hannah and Jenny, though of the two he was clearly paying more attention to Hannah. He puffed his chest and seemed very proud of himself.

"Now we're a bigger group than I anticipated... so we'll need to pile in. I think we're a seat short, actually..." Hale said, as a large jeep SUV pulled up in the driveway.

The driver got out, he was middle aged, with a salt and pepper moustache and stood tall as he opened the doors. He was wearing the white khaki outfit the other handful of staff members wore on Jessica's property. I wondered how expensive her place was when she rented it out while she was teaching.

"This is Gerard, our driver for the day. Say hi everyone," she introduced, and we all waved politely. "This is going to be a tight fit with all six of us but at least I don't have to be the designated driver all day!"

"Oh that's why you aren't driving, is it because you're already two mimosas deep this morning?" Frank asked, grinning wide at Professor Hale. "Nice way to get a head start."

"Frank!" Hale said, whirling on him.

"Good work professor, not wasting any time I see," I said, approvingly, and Gracie laughed.

"Oh my god, will you all just get in the car?!" Hale said, hiding her face with her hand as she turned towards the car. "We are a seat low, so..."

"I'll sit on my minion!" Gracie announced and quickly grabbed Hale's arm. "And Jessica can sit with us in the back!"

"Shotgun!" Frank said, calling the front seat quickly, and turned to give me a knowing look as his eyes shot between me and Gracie, who had just grabbed my arm. His eyebrows did a surprising amount of wiggling.

Gerard pulled forward the middle seat and I ducked into the back first, with Gracie behind me, and Hale followed us into the tight back seat. Frank's two friends got in the middle, and Frank went to the front seat as Gerard went around to the driver's seat.

Gracie sat on my lap, and laid back against me, in the corner of the small backseat normally made for two.

"Try to actually get that seatbelt over you," Hale said, turning to us. "So I can pretend there's some semblance of safety happening here."

"How long is the ride?" Hannah asked.

"About forty minutes, depending on traffic," Gerard responded.

Gracie pulled the seatbelt over the front of her, and after some struggling, I helped her click the seatbelt to our right side. The seatbelt squeezed between her breasts and pushed her backwards into me.

Hale took out her phone as we started to leave she called the resort. The beach began to pass by out the windows, and Frank debated with Hannah about what to listen on the radio. Hannah made him stop at a Dua Lipa song and they cranked the volume as we sped up on the beachside road. Hale bent over and turned away from us as she put a hand to her other ear, trying to block out the music so she could talk to someone from the resort.

"This is so pretty!" Gracie said, looking out the window as she nestled her butt into my lap. "Minion, what do you think?"

"Yeah it definitely is," I croaked.

Hannah and Jenny were singing loudly to the pop music. Gracie leaned forward, looking out the window and wiggled her butt a little. I felt myself harden slightly under her, though it was a struggle: I was half hard from the feeling of Gracie's soft body pushing into me, but I was still uncomfortably cramped and in an awkward position with the seatbelt over us.

Professor Hale was still looking away, talking to Tessa about employee discounts and alcohol. I concentrated on the feel of Gracie sitting on me, and held her stomach, pulling her into me. Her hands moved behind and under her, and I felt her fingers playing with the button on my shorts. She managed to undo the button, and I felt her fingers moving down and reaching for my fly. I hugged her midriff and breathed heavier as her fingers worked. Since I wasn't wearing underwear, I had to twist a little, so my dick wouldn't get caught as Gracie's fingers began to slowly unzip the zipper.

I glanced at Hale, who was still talking, as Gracie finished opening my fly. I could feel her wiggling above me, but the seatbelt was pushing us awkwardly together, and there wasn't much room to maneuver.

"I'm a bit cramped down here," I groaned.

"Yeah this isn't going to work," Gracie grumbled, and unlatched the seat belt. Hale looked over and raised an eyebrow as she put her hand over the phone.

She whispered.

"It was choking her," I said, nodding up to Gracie.

"It's fine, my minion can be my seatbelt," Gracie said, clasping my hands around her waist. She turned her head back towards me. "Hold on tight, alright?"

"Got it," I said, confidently. I already felt better without the seatbelt pressing on us.

Hale gave us a disapproving grimace, but didn't respond, and turned her head again and covered her ear to continue talking.

"Oh yeah, crank it up!" Hannah demanded, as a Brittney Spears song came on. Hannah and Jenny sang along loudly, and soon it felt like we were traveling in a cramped party bus.

Gracie sat up a few inches and I kept my arms around her waist but let my grip loosen to allow her to move. No one was looking at us, so she pulled off my shorts over my knees and they dropped to my ankles. My bare cock was released, but I was somewhere between flaccid and hard, having been crunched and a little uncomfortable for the last ten minutes. Gracie sat down again and nestled her butt into my lap. The thin fabric of her sundress separated my dick from her ass cheeks.

I bit my lip, stifling a moan as Gracie put a hand behind her and positioned my cock between her butt cheeks. She let herself bounce with the car and pushed her butt against my hardening erection. Her fingertip slid along my shaft, but her eyes didn't move, and she continued to look out the window, but I saw a smile creeping into the side of her mouth.

As I hardened I pulled her into me, grinding my hips to better enjoy the feel of my growing erection pushing against her soft butt. But I wanted more than the feel of cotton, and after her teasing this morning I was desperate. I released her midriff for a second and pulled up the back of her dress. For a second I saw her bare ass, and her head quickly turned to me, wide-eyed. I draped the dress over my lap, and it hid the fact that my dick was now shoved up against her soft bare ass cheeks.

I nodded to the window and smirked. "You can keep looking at the scenery, if you want," I offered, my low whisper hidden to the others by the sound of the music.

'Pervert' she mouthed silently and nestled herself into my cock as she turned again out the window.

For awhile, the car rocked as it ascended a hill, and I let the bouncing of the jeep grind my shaft against her. Her finger slid underneath the side of her dress and began to caress my cock. I was already leaking precum and her finger touched the tip of my dick, and moved around in a slow circle, wetting her finger.

Hannah and Jenny were singing loudly along to the chorus.

Gracie removed her finger, looked at it, and leaned back to whisper to me, showing me her wet finger. "Rule 3, Perkins," she whispered: a clear warning.

I sighed, barely able to speak. I knew what she was telling me: she had to come three times before I was allowed to cum, and I only had only gotten her to one so far today. So, I wasn't allowed to come yet. We both knew I was on the edge.

I nodded and took a deep breath to control myself. She smirked in response and looked to her wet finger. She sucked the tip of it, slowly, licking the precum off my finger as her green eyes stared at me. She then turned back to the window.

As she looked out the window, she sat up slightly and reached under her dress, pulling my cock forward. She pushed her butt back nearly onto my stomach and leaned so my cock was now nestled between her thighs. One hand was under her dress, holding it still. My cock soon felt wet and warm as the lips of her pussy pushed against the side of my shaft. She grinded her hips, and I could just barely feel the little soft nub of her clit flicking to one side of the head of my dick, then the other. The warmth and wetness of her pussy felt incredible pushed up against my aching cock, and I had to bite her neck to stop myself from groaning. Gracie began grinding harder, pushing her pussy against my erection, like she was finding the perfect angle to push against her clit.

"Thanks Tessa, that's great to hear! Sorry it's so loud! Yes, see you soon!" Hale said, and turned to us, excitedly. "Good news! We're getting comped some drinks on the house! And employee discount for food..."

Hale's looked over to me and Gracie and she looked down. Gracie's dress blocked a direct view of my cock on her, but Hale saw my shorts around my ankles and she opened her eyes wide. I was also not making much of a poker face: I was breathing heavily as Gracie's clit grinded against my erection. Gracie turned to Hale and smiled, but did not stop moving her hips. She was shaking a little and my cock was getting soaked so much that it was honestly a little hard to tell if I was actually inside her.

'Gracie!' Hale mouthed, jaw open wide.

Gracie smiled wide as she breathed heavily. Hale looked at her, wide-eyed, unsure what to do. Gracie's left hand was under her dress, holding my cock steady, but her other hand reached out to Professor Hale. Hale looked down at the hand, confused.

"Hold my hand," Gracie whispered. Her tone was hoarse, and nearly a moan. She mouthed the word 'please.' Her hips were moving of their own accord it seemed, a little faster and faster, and she seemed to be on the verge of an orgasm.

"Hey, Professor!" Frank yelled from the front seat, and Hale turned as she took Gracie's hand.

Gracie put her head down so her forehead was on the back of the seat in front of her, hiding her face from the others.

"Did you say we're getting free drinks?" Frank asked.

"Yeah," Hale said, trying to sound normal, and I saw Gracie squeeze her hand hard. "Free round on them, and we'll all get employee discounts on food."

"I'm sure it's still expensive though," Hannah said.

"I'm sure it is," Hale agreed.

Gracie bit her lip. Her grinding slowed, but didn't stop. She arched her back, and adjusted herself, getting the exact position right as her clit grinded against the head of my cock.

"Is she alright?" Hannah asked, looking back at Gracie.

"It smells weird in here," Jenny said, sniffing.

"Yeah, Gracie can just get a little car sick sometimes," Hale said. "Don't worry about it. Frank you want to put something else on the radio? Gerard can show you how to change the music."

"Yeah! How about some Chili Peppers?" he suggested. "We've listened to enough chicks."

"Whatever you want, and you can turn it up if you want, I'm off the phone," Hale said. "Out the windows to the left is an incredible view over the waters, by the way..."

"Ooh!" Hannah said, turning to the windows and no longer paying attention to us.

I felt my cock slide just inside the lips of Gracie's pussy as she rocked over it. My cock felt like it was burning, either from it's own desperate warmth, or Gracie's, or both.

Soon 'Scar Tissue' came blaring over the radio, and Frank blasted it and started singing along.

"Ow!" Hale whispered as Gracie squeezed her hand hard. I saw her knuckles go white.

Gracie turned to me, and my face was pained, as her mouth went to my ear.

"Rule three," Gracie whispered, arched her back, and shuddered as she came on me. As she came, her ass pushed against me while her clit shoved over my shaft. It must have taken her a full minute to finish, and her juices dripped down my shaft and wetted both our thighs. I felt like I could burst any second, and was barely holding it in.

I bit her neck, trying to control my own urge to come, as Gracie rode out her orgasm. Hale shook her head in disbelief as Gracie smiled sweetly at her, still holding her hand.

Gracie opened her mouth and while she made no sound I could feel her sigh deep and slow. She turned and twisted sideways to rest her head on Professor Hale's lap. Hale just shook her head in disbelief. My cock was still poking between her thighs.

"How much longer till we get there?" Gracie murmured.

"About fifteen, twenty minutes or so," Hale responded.

"I'm going to take a nap, then," Gracie said. She held up two fingers and winked at me. "You're at two, minion," she whispered, and nestled her head into Hale's lap.

I couldn't believe she was really going to sleep but I soon heard her soft snoring, and my erection was still poking up between her thighs and constantly sliding around between them. If the car shifted on a left curve, my cock slid sideways, towards her knees, but around a right curve it slid up, against her pussy, still wet and warm.

Hale patted Gracie's head and took out her phone once Gracie started snoring. I held Gracie's legs together and let my cock twitch against her inner thighs as Hale typed. Hale turned her phone towards me, and I saw she wrote on her notes app:

Did u two just fuck?!?

"Phone," I whispered and motioned for my shorts. Hale took my phone out of my shorts pocket and handed it to me. I typed into my own notes app:

Kinda... she grinded on me and came.

Hale looked at the message, thought for a minute, confused.

I typed again

: I wasn't completely inside her

.

Hale smirked and typed.

She used u like a dildo?

I nodded and shrugged.

She thought for a moment and typed.

What does rule 3 mean?

I typed:

She has to cum three times before I'm allowed to.

She shook her head, and brushed Gracie's hair sweetly. She looked up at me. "How many are you at?" she whispered.

I held up two fingers.

Hale stifled a laugh and looked down at Gracie's dress and shook her head. My dick was poking up between Gracie's thighs, making a tent in her dress. The tip of the tent was wet where my cock was leaking precum.

Hale typed again, snickering. Her eyes flitted down between Gracie's legs, and she showed me her phone:

It looks like Gracie has a dick!

I grinned and shrugged, typed:

Well, we all have our secrets.

Hale grinned, and her tongue swirled around her lower lip as she typed again. Her eyes looked to my tent, and we made a hard right turn, up a hill. I stifled a groan as my cock felt Gracie's wetness. I heard her snore a little on Hale's lap. Hale showed me her phone:

That cock looks really fucking hard. Maybe she needs to cum again?

I stared at Hale's eyes for a long few seconds. When she looked right at me like that, those pretty almond eyes were a deep well I easily lost myself into.

Gracie snored a little and I saw Hale bite her lip a little, thinking. Hale's hand caressed Gracie's thigh casually, over the dress, and Gracie didn't respond, except for a few soft snorts. Her hand moved down Gracie's thigh a bit more, caressing Gracie's leg, just beside the tent. My stomach rumbled again and I winced a little, in pain from not having eaten.