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.
