Lola’s Graduation Day

"Wouldn't it be hot?" I breathed, letting my tongue graze against his ear as I spoke. "Wouldn't it be so hot if you let him think he's going to fuck me..."

"Lola, please," he said, a pleading note in his voice as he cock began harden against my fingers, pressing insistently against the fabric of his shorts. "Not here."

"But then," I breathed, my hand stroking him faster. "At the last second, right when he's about to get what he wants..."

"Lola, Lola, stop--"

"... then you fuck me instead," I whispered, sticking my tongue into his ear.

"Lola, NO," he said, pushing me back and turning away.

"Baby, what's wrong?" I said. "Didn't it feel good?"

"Yes," he said in between deep breaths. "But I don't want to cum in my pants on a beach full of people."

"It turned you on that much, huh?" I smiled, sidling back up behind him. "I guess you like my idea."

"We haven't even had sex yet," Jesse said, still facing away from me, obviously trying to get his erection under control. "I just want us to have sex before we start exploring... other stuff."

"But didn't you hear me, baby?" I purred. "I'm talking about us having sex."

"That's really how you want to do it?" Jesse said, turning towards me. "That's how you want our first time to be?"

"Oh my god, yessssss," I hissed, smiling. "Can you imagine how hot that would be? We'll never forget it!"

Jesse looked down at the sand. But he didn't say no.

"Let's tease him together, okay?" I said conspiratorially. "Let's make him think that we're, like, open, or something. I'll get him so worked up, to the point where his body is just boiling, and then you'll swoop in and steal me away."

"Are you sure about this?" Jesse said, looking me in the eye.

"If we do all of that, I'll know for certain that you aren't the jealous type," I purred. "And then I'll finally be ready to let you fuck me, baby. It's gonna feel so good."

"Okay," Jesse sighed, shaking his head in disbelief. "But this is your plan, so I'm just following your lead here."

You don't know the half of it, I thought to myself.

...

After my conversation with Jesse, I felt exhilarated and emboldened. He had ceded control of the night to me. Now, I just had to be patient and wait for my moment.

We stayed at the beach for a couple more hours, but I mostly spent these hanging out with Jesse and Ravi. We played backgammon on a portable set that Ravi had brought with him, and then I walked around with them, helping the guys break the ice with some of the other guests that Chase had invited. Ravi had made me promise to do that for them, but I was more than glad to do it, because it also gave me an excuse to introduce myself to people as Jesse's girlfriend. You'll see why I was more than happy to do that soon enough.

I wasn't avoiding Chase, exactly, but I was following Yasmin's advice: Don't be eager. Be disciplined and patient. Make him earn it. But even as I was chatting people up with Jesse and Ravi, I was conscious of Chase, hovering just out of frame, his eyes never wandering very far from my body, stalking me like the lion he was.

Finally, it was time to go back to Chase's house, which turned out to be just a short walk from the beach. It was a beautiful, modern, bungalow-style home, the kind you see near many of the nicer beaches in Southern California. But don't let the word bungalow fool you--the house was spacious and airy, with an expansive private patio in the back.

"You own this place?" Ravi exclaimed in wonder as we walked in.

"The first million is the hardest," Chase laughed, wrapping his arm playfully around Ravi's neck. "Don't worry, man, you'll get there."

"God, I love working in tech," Ravi laughed. "Jesse, man, how many doctors do you think can afford a place like this?"

"How much does something like this even cost?" Jesse wondered aloud.

"Babe, that's rude," I chided.

"Nah, Lo, it's fine," he said, casually shortening my name like we were old friends. "It was a little more than a mil when I bought it, but now it's worth almost three."

"That's insane," Jesse gaped. "Three million dollars?"

"But that's what I'm saying, J-man," Chase said, clapping Jesse on the back. "The first mil is the hardest because you have to work for it. Once you start buying real estate, the money starts working for you."

"See, babe?" I said, touching Jesse's hand lightly. "It's not all about writing code. Now that Chase is helping you meet these VCs, you're going to be in more houses like this one."

"Your girl is right about that, as usual," he said, shooting me a grin as he squeezed Jesse's shoulder. "I think if you just listen to Lola, you could have a house like this someday, too."

As the sun sank below the waves and night fell over the house, the party began to turn up, and the alcohol began to flow in earnest. Outside the patio, Chase had a DJ booth set up, and one of his friends was on the turntables.

Although Jesse was a reluctant dancer, I had pulled him out onto the dance floor anyway. But after a couple of songs, I heard the opening bars of "Ghost Ride the Whip" by Mister F.A.B. began to blare over the speakers.

"Oh, shit, this is my jam!" I screamed, throwing my hands in the air.

Then, seemingly out of nowhere, Chase appeared next to me.

"I always know how to bring out the Hyphy in a Bay Area girl," he smiled.

"What's Hyphy?" Jesse asked, confused.

"Oh, baby," I groaned, tilting my head disapprovingly.

"Sorry, bro, but it's a Bay thing," Chase said, sliding his large, muscular body between me and Jesse. "I think you better let me cut in for this one, okay?"

"Sure," Jesse said, looking at me as he raised his palms in surrender. "Go for it."

I gave Jesse a quick wink to let him know that this was all part of our plan. Then, I turned my attention to Chase, whose hands were already encircling my waist.

If Jesse was an awkward, reluctant dancer, then Chase was the exact opposite, confident and aggressive and in control. As the beat dropped, Chase pulled my hips against his, grinding the slab of his hard, angular body against the softness of my generous curves. My hands reached up, instinctively arching over his broad shoulders and around his neck.

As we swayed to the beat, our hips moving as one, I felt Chase's hands beginning to loosen the Hawaiian print sarong that was wrapped around my waist.

"Boundaries, Chase," I whispered into his ear, but my hands remained where they were, wrapped around his neck.

"I want you so bad," he whispered back, gently opening the front of the sarong so that there was nothing between his board shorts and my white bikini bottoms.

"Baby, we talked about this," I purred into his ear as I felt him gathering the fabric of my wrap into either hand.

"I just need you to feel it," he breathed, his voice low and husky. "How bad I want you."

As he spoke, he continued to gather up the fabric of my sarong, pulling it tighter and tighter around my waist. The effect of this was to bind my body closer and closer to his, pulling me towards him, grinding my mound against his rapidly thickening cock.

I let out an audible gasp as I felt him. I'd hoped, even expected, that Chase would be fairly well-endowed. He was tall, of course, but he also had that special kind of confidence. I'd never heard the term "big dick energy" back then, but that's what Chase had, and now I knew why. As I felt him growing against my mound, I knew he could surpass my loftiest expectations.

"I need you tonight," he hissed, our bodies meshed together, the sarong hiding the lurid details of what was happening between us.

"I won't cheat," I whispered, the hoarseness betraying my own arousal. "You need to earn it."

Chase just grunted in response, his ability to vocalize overcome by frustrated desire. This is a man who is used to getting what he wants, I thought. A man who is used to being the exception to every rule.

As the song ended, I disentangled myself from Chase, quickly retying the sarong around my waist.

"Let's get a drink," he said, taking my hand. "Come on."

Chase led me from the dance floor over to the fire pit, where Jesse and Ravi were having a conversation.

"What's up, boys?" Chase said, reluctantly letting go of my hand. "You guys having a good time?"

"Yeah, man," Ravi said. "This is awesome."

Jesse nodded but didn't say anything.

"Listen," Chase said. "Lola and I were talking, and there's something special I want to do for you guys, since you're just getting started with your company."

"Really?" Ravi exclaimed. "What is it?"

"Come inside with me," he grinned. "I'll show you."

Ravi and Jesse stood up, and together, the three of us followed Chase back into the house. He took us past the living room, where most of the other guests were hanging out. Chase said hello to several of them as we walked by, then he turned down a little hallway and opened a door.

"Is this your bedroom?" Jesse asked as we stepped inside.

"This is where I keep the good stuff," Chase smiled, closing the door behind us. "Can't have just anyone getting into my secret stash."

I took a look around. On one wall, there was a wet bar adjacent to an en suite bathroom. On the other wall was Chase's bed, and next to it, a loveseat that sat beside a sliding glass door. Beyond the glass door was a tiny private garden with a couple of chairs in it, walled off by a high concrete barrier that was mostly covered with vines.

"Sit down, boys," Chase said, gesturing to the loveseat. "You sit on the bed, Lola."

We all sat down where Chase had told us to.

"Guys, a successful startup is about more than just good tech," Chase said, walking over to the wet bar. "And it's about more than product-market fit, or VC money, or whatever else people talk about on their LinkedIn profiles."

Ravi nodded. He was eating up every word. Jesse was next to him on the loveseat, his expression completely blank.

"It's also about tradition," Chase announced, picking up a bottle and four shot glasses. "And it's about bonding, as brothers."

"Fuck yeah," Ravi said, giving Jesse a shove. "This is a brotherhood, man."

"Do you boys know what this is?" Chase said, holding a bottle of brown liquor aloft as he set the shot glasses down on a little side table. "Lola, will you read it for them."

Chase handed me the bottle.

"Pappy Van Winkle's Family Reserve," I read. "Twenty years old."

"You guys ever heard of this?" Chase asked, sitting down next to me on the bed. "You know what this bottle represents?"

Ravi shook his head.

"This is one of the rarest bottles of bourbon in the world," Chase smiled. "A bottle like this, if you can even find it, will set you back $5000, sometimes more."

"Holy shit," Ravi said.

"But that's not what makes it special," Chase continued, taking the bottle back from me. "What makes this bottle special is that it's like the holy water of Silicon Valley. Peter Thiel gave a bottle of it to Mark Zuckerberg when he made the first outside investment in Facebook. Whenever a new person joined the C-team at Uber, Travis Kalanick used to welcome them with a shot of Pappy 15-year. And I got this bottle from Marc Andreessen after a16z bought a stake in my last company."

"Wow," Ravi said, his mouth hanging open. "You're, like, Valley royalty."

"You could be, too," Chase grinned. "Lola says you guys have what it takes."

I shrugged my shoulders, smiling at Jesse and Ravi.

"That's why I want to give you guys a proper welcome," Chase said. "Lola, will you pour for us?"

He unscrewed the cap and handed the bottle back to me. I bent carefully over the side table and filled each shot glass. Then, I handed them to each of the three guys.

"To new beginnings," Chase said, raising his glass as we all followed suit.

"Hear, hear!" Ravi yelled.

"To brotherhood," Chase said, looking at Ravi and Jesse.

"Brotherhood!" Ravi echoed.

"And to beautiful women," Chase said, smiling at me. "Bottoms up!"

We all threw back our shots. The brown liquor glided smoothly over my tongue and down my throat, warming me from inside.

"Dude," Ravi said, smacking Jesse on the chest. "I'm so fucking hyped right now, bro!"

"Yeah, man," Jesse said, managing a weak smile.

"Let's go dance," Ravi said excitedly, standing up. "There's this brown girl out there who was making eyes at me all night."

"Oh, you mean Padma?" Chase smiled. "She just became single, actually."

"Bro," Ravi said, smiling wide-eyed down at Jesse. "Bro, I gotta go! Tonight feels like my night, man."

"Go get her," Jesse said, giving him a perfunctory high-five.

"Chase, man," Ravi said, walking over to the bed. "You're the fucking king, man."

"Nah, dude," Chase said, pulling him in for a bro-hug. "I'm a kingmaker."

"This fucking guy," Ravi said as they disengaged. "Unreal night, bro."

"Go get her, Ravi!" I cheered. "Padma's waiting for you!"

"Yo, I gotta get there before some other brown guy swoops in," Ravi smiled, reaching for the door. "These Desi girls don't stay single for long."

And then, Ravi stepped out the door, letting it close behind him with a gentle click, leaving the three of us alone in Chase's bedroom.

"Lola, pour another round," Chase said.

"That's too generous," Jesse said, sitting up.

"Nah, man, don't worry," Chase said, waving him off. "It's liquor. You're meant to drink it."

I looked at Jesse and he looked back at me. I could see that he was waiting to see what I would do. To follow my lead.

"If Chase wants to share with us," I said, picking up the bottle. "Then we should let him."

"Exactly," Chase said as I poured three more shots. "The whole point of having nice things is so that you can share them with your friends."

I handed a shot to Chase, then I got up and sat down next to Jesse on the loveseat.

"Lola, I think you should do the toast this time," Chase said.

"Hmm," I said, pondering it a moment. Then, I raised my glass. "To sharing with new friends."

"I'll drink to that," Chase smirked, downing his shot as Jesse and I did the same.

The second shot went down just as smooth, but it hit harder than the first. Now, the warm feeling inside me had become a roaring, crackling fire. I stretched my arms out over my head, feeling the languid, lazy calm of the liquor flow through me.

"Lola," Chase said, setting down his shot glass. "I noticed your tattoo earlier while we were playing volleyball, but I didn't have a chance to ask you about it."

"Oh, this?" I said, a tiny smiling forming on my lips as I touched my manicured fingers to the black Roman numeral II on my left wrist.

"Yeah," Chase nodded. "I like it. What does it mean?"

"Well, that's a very personal question," I smiled, blushing as I looked away.

"Only if there's a very personal answer," Chase smiled.

"What do you think?" I whispered, turning to look at Jesse. "Should I tell him?"

This, of course, was a trap. I hadn't told Jesse what the tattoo meant yet, and I knew he'd be curious to find out, too.

"If you want to," he nodded calmly.

"Okay," I smiled, putting my hand on Jesse's thigh as I turned back towards Chase. "But this is very private, Chase. Not very many people know what this tattoo means."

"I can keep a secret," Chase said, leaning forward on the bed, hanging on my every word.

"Can you?" I asked, softly. "Because a lot of guys say that, but when they hear something juicy, they can't wait to go tell their friends."

Chase said nothing, but gestured as if he were zipping his mouth shut.

"Well, since you shared your liquor with us, I guess I can share a little story with you," I smiled coyly. "Are you ready?"

Chase nodded his head, his attention rapt.

"Once upon a time, there was a pretty girl," I began, rubbing Jesse's thigh as I spoke. "And when this girl went to college, a lot of boys paid attention to her. And the girl liked all of the attention, but she had a problem. She wasn't sure which boy she should pick to be her boyfriend."

I could see the fire burning in Chase's eyes as I spoke.

"Some boys were sweet, and others boys were cute, but one of the boys was more clever than all the rest. He could see how hard it was for the girl to choose, so he came up with an idea. He said, 'If you pick me, then I won't make you choose.'"

Chase licked his lips as I let my fingers slide to the inside of Jesse's thigh.

"He told the girl that if she picked him, she could still see the other boys, but only while he was there. But she was only allowed to see one other boy at a time. There could never be more than two at once."

I could feel Jesse's cock beginning to harden as I rubbed him through his board shorts.

"The pretty girl thought about it, and the more she thought about it, the more she liked the idea of never having to choose. So she decided to accept the clever boy's offer. And when she did, he gave her a tattoo to symbolize the promise he had made, that she could always have two, never just one."

Chase bit his lip. The room was completely still. It was as if both men had stopped breathing.

"So, Chase," I said, looking directly at him as I rubbed the tent in Jesse's shorts. "What did you think of my story?"

"You're open," he growled, his eyes gleaming at me. Then, he looked over at Jesse. "Fuck, you guys are open, aren't you?"

I turned to look at Jesse, too, and now both sets of eyes were on him. He looked at me, and I gave his cock a squeeze. Then, he turned back to Chase and shrugged his shoulders.

"I should have known," Chase smiled, shaking his head back and forth. "It makes so much sense now."

He stood up off the bed, his height suddenly towering over the room.

"You're a good man to share her, Jesse," Chase said, peeling his shirt over his head to reveal the hard, lean slab of his chest. "You're even smarter than I thought."

I stood up from the loveseat.

"Sit down, Chase," I breathed. "I want to show you a game we like to play."

Chase moved past me, reaching out and grabbing my ass softly as he took the seat I had vacated next to Jesse on the loveseat. Seeing the two of them seated there, Jesse looked small, almost frail beside Chase's tall frame and broad, muscular chest.

"This game is called the Queen's Guard," I said, gently slipping the jean jacket from my shoulders. "Jesse knows the rules, but they're quite simple."

I began to unwrap the sarong from around my waist.

"I get to speak," I continued, "but you don't. I get to move, but you don't. I get to touch you, but you don't get to touch me, or yourselves. If I ask you a question, you can nod, or shake your head, but that's it. If you break the rules, the game ends, and I put my clothes on."

Slowly, I let my grip slacken, and the sarong fell softly to the floor. Now, I was standing before them in only my white bikini and a pair of high-heeled wedge sandals.

"Now," I smiled. "Are you boys ready to play?"

Chase nodded his head eagerly. Hesitantly, Jesse nodded as well.

Slowly, I turned around, facing away from them. Then, I reached behind my back and began to loosen the strings on my bikini top.

"Chase, baby," I purred, looking over my shoulder at him. "I want to know what you first noticed about me, what made you approach me by the bar last week."

Chase was sitting stone-still, but he was grinning like a madman. Jesse, just two feet to his left, wasn't moving or speaking either, but he looked more uneasy than excited.

"Was it my long, black hair?" I said innocently, turning back to face the two men. I was holding the untied bikini top in my hands now, cupping it against my breasts, the strings hanging down uselessly from either side. "Was it my pretty face?"

Chase shook his head from side-to-side.

"It wasn't, was it?" I smiled mischievously at him. "Oh, you're bad, aren't you?"

Chase nodded his head vigorously, drinking me up with his eyes as I moved towards him.