Jacks Adventures 18 Catalina 01

This is the eighteenth story.

This is the story of Catalina.

I was in my mid-20s, it was summer, I was between steady jobs, and I was supporting myself by driving for Uber. A lot. I was putting an insane amount of miles on my car, coming home absolutely exhausted, but I was meeting a lot of people, hearing a lot of unique stories, and I felt like I was really living. It's very easy in Los Angeles, too easy, to settle into isolation. But I was out there among the people, witnessing the breadth of the human experience, and my soul was on fire.

I was also having a lot of sex.

I listened for the signals and was respectful, didn't talk if the passenger wasn't up for it, didn't impose myself on anyone or make anyone feel uncomfortable. But if I'd had a great conversation with a woman, and the rapport was good and comfortable, I'd offer my number at the end and we'd see what happened. I'd drive a sexy blonde in a pencil skirt home from her law firm, and we'd meet up for martinis later in the week. I'd take a gorgeous brunette in jeans out to a bar on a Friday night, and I'd meet up with her later at the club. I'd pick up a beautiful redhead at 4 in the morning with her drunk and high friends, and when we arrived at her house she'd invite me inside.

And often I'd pick up a tourist, and if the vibes were good, I'd offer to show them the city.

That's how I met Catalina.

I'm waiting outside a hostel in Santa Monica, at midday on a Saturday, close to the Promenade, so the streets are absolutely swarming. I'm stopped in a red zone, drumming my fingers on the wheel, hoping this girl comes out sooner rather than later and I don't have to explain myself to a traffic cop. Then my back passenger door opens, I whip around, and I'm looking at one of the most beautiful faces I've ever seen.

She's South American but I don't know from what country. She's in her early twenties, has olive skin, beautiful wide eyes, full lips. Her hair is dark and curly, currently pulled back in a loose bun, but a few strands have escaped and hang jauntily around her face. She's wearing a peasant crop top, of white cotton, over small breasts. I can see a beautiful flat midriff beneath the hem of her top and above the waistband of high-waisted light blue jeans, which curve out over a prodigious ass and hips before tapering down some of the longest legs I've ever seen. Her entire being conveys health and a life well-lived.

"Jack?" she said, her voice tinted with a Latin accent.

"Catalina?"

"Yes."

She smiled, a Julia Roberts-wide grin, and threw a large backpack across my back seat and clambered in after it.

"Where you headed?" I said, looking at her in the rearview mirror.

"Hollywood and Highland?"

Classic. An absolutely awful part of town that every tourist feels the need to go to. But on the plus side, it was a very long drive away from where we currently were, meaning we had a lot of time to get to know each other.

"You got it," I said, and I pointed my way east.

We drove in silence for a minute, me glancing at her in the rearview mirror every so often, watching her look out the window with a dreamy smile on her face. Then her eyes met mine in the mirror and we held it for a split second and then both smiled.

"Where're you from?" I said.

"Colombia," she said, rounding the middle O gorgeously.

"First time in L.A.?"

"Yep!"

"How long are you here?"

"A few days, and then I go to Vegas!" she said, beaming.

"Vegas! How fun."

"Yes. Have you been?"

I was falling head over heels for the Latin lilt in her speech, the way she said the words combined with the slight hitch in stringing them together.

"Yes," I said, "a few times. It's wild."

"'Wild'! I like that."

"Yeah? Big fan of wild?" I gave her a sly side-eye in the mirror.

"Yes," she said, nodding emphatically.

"Did you come to L.A. alone?"

"Yes."

Her expression clouded over ever so slightly. I wondered if there was more to that story, some unfortunate reason she was here by herself. I persisted.

"Were you meant to come with somebody?"

She didn't speak at first, kept her gaze out the window, her brow furrowing slightly, before she leaned forward toward the gap between the front seats, her eyes forward.

"I had a boyfriend. We broke up a few months ago. I almost didn't come. But then I decided to come."

She leaned back and threw on, tried to throw on, a breezy smile.

"I'm so sorry," I said, shooting her my most empathetic glance in the mirror. "But I'm glad you still came."

"Me too."

"How's that hostel?"

"It was nice," she said. "But I'm not going back."

"Where are you staying tonight?"

She shrugged and smiled, carefree again.

"I don't know!"

"You don't know!" I echoed playfully.

"I don't know! I'm gonna play it..." she searched for the end of the phrase.

"By ear?"

"Yes!"

We'd gotten on the 10 and were heading east. It was a relatively clear day, but the mountains to the north were still smudgy with haze.

"I love your courage," I said. "I don't think I'd be that brave."

She shook her head. "I'm not brave."

"You're being spontaneous. In a new city, in a foreign country. That's brave."

She blushed ever so lightly, but kept shaking her head. "No. No, no, no."

"Yes. Yes, yes, yes."

She didn't respond, just kept looking out the window, but now seemingly with a more concerted effort to seem more interested in what was outside the car than what was in it.

After a minute or two of silence, she asked:

"Where do you live?"

"Close to where we're going."

"Hollywood?"

"-Ish."

"Huh?"

"Close to there, yeah."

"Is it a nice area?"

"It has its charms." I gave her a sly, knowing grin in the mirror.

"Everyone says you have to go to Hollywood and Highland."

"I think you have to go once, and then never go again."

"Oh no! Is it bad?"

"It's just very busy."

"With tourists like me?"

My brain flashed in the direction of agreeing with her, continuing with the safe pitter-patter, but I took a detour, took a small risk.

"There are no tourists like you."

I caught her expression in the mirror, her brow slightly furrowed.

"What do you mean?" she said.

I stayed pointing in the same direction, but took the foot slightly off the gas.

"Most of the tourists I drive around are too safe. They're not really seeing the city. They stay in tourist hotels and they would never risk not having a place to stay."

"You're too kind."

"Just honest."

I caught her smiling again, her gaze lingering slightly longer on the back of my headrest. I saw my chance.

"If you'd like any company this weekend, just let me know. I'd love to show you around."

"I couldn't bother you with that."

"It's no bother. Here, take my number."

A slight pause, then:

"Okay."

She pulled out her phone and I recited my number and she typed it in. Then she stowed her phone and we were silent again, just now with a slight charge in the air.

"So what happened with your boyfriend?" I asked.

She let out a huge groan. "You don't want to know."

"I do."

"He slept with another woman."

"Fucking asshole," I said.

"'Fucking asshole,'" she repeated, turning the phrase over in her mouth. "Yes. He slept with an American woman."

"No!"

"Yes."

"Don't hold it against me."

"I won't. She was nice. Just a whore."

I laughed loudly at that. "That's funny."

"Do you have a girlfriend?" she asked.

"Nope."

"Why not?"

"So she can't cheat on me."

"You're very smart."

"And it lets me hang out with cool people when they come to town."

"Cool people. Like me?"

"Yeah."

"Are we hanging out?"

"That's up to you."

I caught her eyes in the mirror. Her mouth was hanging open slightly, as if she was shocked at my boldness. She looked out the window briefly, then looked back up at me.

"Do you want to come to Hollywood and Highland with me?"

"I'd love that."

"You don't have to drive more?"

"I need a break."

"I don't know how..." she searched for the word, "relaxing I am."

"Yeah? You seem pretty relaxing."

"Maybe right now. I smoked some weed at the hostel."

I laughed. "Well I'm excited to meet your darker side."

"It's not darker. Just, more energetic."

"That even more so."

"Huh?"

"I'm excited to meet your energetic side."

We held eye contact in the mirror, the air crackling, then she smiled and looked out her window again. I looked forward and focused on the road, focused on getting to hell on ear- I mean Hollywood and Highland. I was gonna get to spend the afternoon with one of the most beautiful women I'd ever seen, and if I played my cards right, even longer.

We chatted happily for the next thirty minutes, until we finally reached the heart of Hollywood.

"Holy crap," Catalina said, looking around at the masses of people swarming down the sidewalks and across the intersections.

"See?" I said.

"This is a lot of people."

"You gotta go once."

"But yes," she said. "Never again."

We parked in a garage, I ended her Uber ride, and we both got out of my car. She was tall, only half a head shorter than me, and she looked me up and down approvingly when her eyes first landed on me standing up. We walked out to the street and navigated our way through the masses of people, me sometimes putting a hand on her lower back as we tried not to be separated. We walked around the front of the Chinese Theater first, and she laughed and pointed at the superhero impersonators, paid to have her photo taken with one. Despite all my cynicism about the area, it was fun to watch someone see it with fresh eyes, to see those eyes fill with joy.

We went to Madame Tussaud's, wandered among the wax sculptures, then to Ripley's Believe it or Not! before heading to the lobby of the Roosevelt and grabbing food. Catalina was flushed with happiness by the time we sat down, the Los Angeles experience clearly being all she had wanted. I bought us food and a cocktail, paying her back for the Uber ride she'd just paid me for.

"What a day!" she said, taking a sip of her rum and coke.

"Thanks for letting me come along," I said. "It was fun to not be cynical for a bit."

"It was fun to be with someone."

Her eyes lingered on me, and then she put her drink down.

"I wanted very badly to be alone," she said. "I wanted a romantic, moody trip." She laughed. "Have you seen Paris, Texas?"

"You've seen Paris, Texas?" I said.

"Yes! I imagined walking across the desert like that."

"You can do that in Vegas."

She laughed, took another sip of her drink.

"But it's better to be with people," she said, nodding firmly at the end, like she'd come to a decision.

"I agree," I said. I took a sip of my own rum and coke. "If you can't find a place to stay tonight, you can always stay with me."

Her foot shifted under the table and suddenly our feet were touching. "You are very nice. I'll think about it."

I looked into her wide brown eyes, her gorgeous open face. She wasn't hiding from me, which made me think the answer was closer to a yes than a no. I lifted my drink and took a sip.

"But that's a long way off. I have to take you out tonight."

"Yeah? A club?"

"A club? Sure."

She squealed excitedly. I guess we were going to a club.

After we ate, we returned to my car to head back to mine, and she climbed into the front passenger seat.

"Do I have to pay for this ride?" she asked, smiling slyly, as I pulled out of the garage.

"No, you ride free now."

I drove her back to my place and led her inside. I'd only recently graduated from the "having a roommate" era of my life and moved into the apartment I would have for the next several years. It was still coming together, but I was already proud of the decor I was assembling, of the vibe it conveyed, of how good it made me feel to come home to every night.

But Catalina was in fucking awe of it, like she'd walked into the Sistine Chapel, twirled around and looked at all my furniture.

"Yeah, I'm staying here," she said, almost to herself. I don't know if she even knew she'd said it, so I didn't follow up, even though my heart soared.

We relaxed for a couple hours, starting out lounging on my couch and watching TV, me giving her another drink, and then we both took a late afternoon nap. She sprawled across the couch, her body looking long and limber, and I laid a blanket over her and went into my room. When I woke and reemerged, she was sitting by the window, reading a book. She'd changed into a tank top and a pair of athletic shorts, showing off her incredible legs, which were currently propped on my coffee table.

"What are you reading?" I asked.

She looked up, initially startled, then smiled. "I took it from you. I hope that's okay."

She turned the cover toward me. It was On the Road.

"Fitting," I said, settling on the couch.

"I know," she said. "I'm such a cliche. But I've never read it."

"Take it with you. To Vegas."

"Really?"

"Yeah. I can get another one."

"No, I can't."

"I'm giving it to you. A gift."

She smiled sheepishly, put the book down, then stood up and bounded over to me. She bent her head down right next to my face and gave me a quick peck on the cheek. I turned my face toward her and we looked at each other, close, for a second.

"Thank you," she said.

"You're welcome."

Then she stood up straight. "I want to buy you dinner. Then you take me to a club."

I saluted. "Aye aye."

She dug into her backpack, pulled out a few pieces of clothing, and then went into my bathroom to change. I changed in my bedroom, into slacks and a nice shirt, and then made myself an old-fashioned while I waited for her to emerge. I was about halfway done with the drink, sitting on my couch and reading a book, when she came out. I looked up, and my jaw dropped.

She was wearing a sparkling black halter top and mini skirt combo, her olive skin standing out gorgeously against it. Her midriff was bared, as was most of her cleavage, as was almost every inch of her legs. She was holding a pair of black heels in her hand, ones that would make her legs look even longer. I wanted to bend her over my kitchen table and fuck her right there and then, and something about that thought must've registered on my face.

"Is it too much?" she said.

I shook my head, my mouth hanging open like an idiot. "Just right."

We did a shot of tequila and then headed out the door, catching an Uber to a local seafood restaurant. I spent on her, giving her the luxury treatment, making sure she tried all the best food and drinks. And we talked and laughed and I stared at her gigawatt smile, unable to comprehend how this had all worked out.

We left the restaurant and went to a club, waited in line for a bit before walking into a dark, thumping room. We got more drinks, yelled at each other a bit, then took a turn on the dance floor. Catalina ground her huge ass into my crotch, I put my hands around her and down the front of her thighs, and she turned her face sideways toward mine as we started moving our hips and moved as one. Purple and blue lights were flashing across her face, across her wide eyes staring at me, her lips slightly parted in a small smile. I leaned in, she closed her eyes, and we kissed.

Her lips felt so good, so full, with power in them. Her ass pressed harder against me and my cock stiffened slightly in my slacks, pushing up into her butt crack. She moaned slightly into my mouth, I ground my crotch harder against her, and then our lips separated and we stared at each other. We kept dancing, just looking at each other as our hips swayed, our bodies interlocked. I leaned into her ear.

"How long do you want to stay?" I said.

"A few more songs," she said back.

I nodded, leaned in, and kissed her again. She responded fully, her face melting into mine, and then we separated and focused on dancing, on our bodies grinding together, on where my hands were running across her body. I was unabashedly hard now, letting her feel how much she was turning me on, and she didn't complain, just pushed back against me harder. After a few more songs, she turned to me, threw her arms around my neck, and we stared into each other's eyes for a second before briefly making out.

"Can I stay at your place tonight?" she said.

"Absolutely."

One of her arms fell between us and her hand found my bulge, found my cock pressing out down my leg. Her fingers groped down its length, her face going into my shoulder.

"Oh wow," she said.

"You're so fucking sexy," I said into her ear.

She lifted her face, pushed her lips into my ear. "Follow me."

She took my hand and led me through all the other writhing bodies and off the dance floor, down the hallway toward the bathroom, and shamelessly into the women's restroom. It was dark in here too, the walls reverberating with the sound from the dance floor. I made eye contact with two girls touching up their makeup in the mirror, I waved, their mouths opened in surprised shock, and then Catalina had pulled me into a stall and bolted the door behind me.

The girls outside ow-owwwed but I didn't pay them attention much longer, because Catalina had pushed my back up against the side of the stall and was working on my slacks' zipper, and then her hand was wrapping itself around my now fully-hard cock and pulling it out my fly. It sprung free and her eyes widened and she started twisting her hand up and down its length, staring from it to me.

"You like it?" I said.

"Yes."

She scooted up next to me, pushed her other hand down my back and jammed it under the waistband of my slacks. She gripped my bare ass cheek tight as her other hand started working my cock faster.

"Holy shit," I said, watching her hand twist and pull down my shaft, the feeling unreal.

I looked at her face, at the glorious curls of her hair, down her chest to her skimpy halter top, down her midriff to her skimpy skirt, down her incredible legs to her fuck-me heels. Then she took her hand off my dick, spit into her palm, and then wrapped it around my cock again and kept jacking me off.

"Fuckkkk," I said, her lubed up hand running freely down my cock.

She smiled and looked up at me. "I like what you say."

"This feels so good."

"I'm happy I make you feel good."

She leaned in and kissed my neck fiercely, her chest pushing against me, her hand continuing to work my cock, her other hand still gripping my ass hard. I ran one hand up through her hair and pushed my other hand down her back, pushed it under the waistband of her skirt, grabbed her ass in return. She moaned, her hand came off my dick and she spit into it again, then wrapped it around my cock again and jacked me off even faster. I squeezed her ass cheek, feeling how firm and heavy it was, couldn't wait to see it naked and in all its glory.

"I like your penis," she said into my neck.

"It's a big fan of you."

She was so sexy, her confidence and her forthrightness so hot, that I was already very close to coming.

"I'm gonna come soon," I said.

In response her hands gripped me even harder, worked me even faster. Pleasure was surging through my groin, I was pretty sure I was gonna blast a hole through the wall with my cum. I took my hand out of her skirt and leaned toward the toiler paper and pulled on it, causing the roll to unfurl wildly. I ripped off a huge stretch, wadded it up, and settled in to enjoy the end of the experience. Catalina's hand settled around my ridge, just started pumping over my head, and pure ecstasy surged through me, and I came.

I cursed loudly, held the toilet paper in front of my dick, and started shooting jizz into it. She giggled, her hand continuing to work my head, and I kept coming, my eyes roving over her gorgeous face, her stunning body, and I'd never felt so perfect in my life. Then I was empty, her hand came off of me, and I leaned back against the stall, groaning. I tossed the paper into the toilet, and looked at the ceiling as I worked my dick back into my pants.