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I 32[M] picked up a half-Spanish hostess 23[F] with some of the biggest tits I'd ever seen - Part 1 - Jack's Adventures #12
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propmasterflex is a male
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This is the twelfth story.

This is the story of Sofia.

In my days as a delivery driver, my shifts would usually start with a pickup from a popular gastropub near my apartment. It was always a great start to the evening because the hostesses were always young women, always 18 and at least a little bit cute. They were fun to flirt with but most of them acted slightly too young for my taste and I never felt like taking things any further.

That is, until Sofia.

She was older than the others, 23 when I met her. She was gorgeous, ethnically ambiguous, almost definitely half-Spanish. She had olive colored skin, dark eyebrows, and dark brown hair. Her face was round but with sharp features, somewhere on the spectrum between a young Helena Bonham Carter and Penelope Cruz. She was 5'4" or 5'5", with a thin frame but very heavy breasts, to my eyes at least d's or double-d's. The first time I saw her it was an effort to not stare at them, and even if I got better at not doing that, I still spent most of the time in her presence imagining setting them free from the bra that held them.

And best of all she was fierce. If the place was ever slammed with customers, and delivery drivers were rudely trying to get her attention, she'd ignore them like the savviest bartender or put them in their place like the angriest mom.

She was so focused and so no-shit that for the longest time I didn't know if I'd made any impression on her. I just came in, waited my turn, didn't badger anyone, eventually got my food and left. My desire to be respectful to beleaguered wait staff far outweighed my desire to pick her up.

And then one night, as I stood off to the side and people churned around me, Sofia running this way and that, a delivery driver stepped in front of her and said:

"Hey, I've been waiting forever."

Big mistake, buddy.

"You've been waiting?" Sofia got up on her tiptoes, put a finger in his face. "You've been waiting? Everyone's been waiting. I work here and I've been waiting. Step back in line and don't say another word to me. I'll let you know when your food's ready."

The delivery driver bowed his head sheepishly, his face beet red, and stepped aside. Maria walked past him, looked at me, caught me suppressing a smile. I had a flash of worry that she'd misread that smile and lay into me too.

But no, she shot me a quick little smirk in return, rolled her eyes, and went back to work.

There. We. Go.

I pulled a spare receipt out of my pocket, snuck a pen from the host stand, and scribbled out my number. A few minutes later Sofia brought me my food.

"Thanks for all you do," I said, sincerely.

"Thanks for being patient," she said.

For once she was making eye contact and not immediately running off to the next thing. It further cemented what I was about to do.

I took the bag, and mid-exchange I handed her the spare receipt. She looked at it, confused.

"If you ever want to commiserate about impatient people," I said.

I didn't wait to see if the look of confusion turned happy or sour, I just turned and left the restaurant. I wasn't going to push her, just give her the space to make her own decision.

I did deliveries the rest of that night, clocked off just before 10, and headed home. Back at my apartment I poured out some dark rum over ice, threw on an NFL Network replay of some recent playoff game, and put my feet up.

Then my phone dinged.

I picked it up. A text from an unknown number. A 213 area code. Los Angeles. I opened it.

hey...jack?

Hi?

this is sofia. from [redacted]

I sat up straight on my couch.

Hey! How are you?

brutal shift! almost over tho

And she ended the text with the cheery emoji, the one with the rosy cheeks. I typed back quickly.

What are you up to after? I got nothing in the morning

me neither. going to a taco truck. wanna meet me?

Yeah. What do you drink? I'll bring a can of something. We'll celebrate on the sly

!! you're something. umm i like those canned margaritas? what are we celebrating?

The end of a brutal shift! Canned marg, you got it

She sent a crying laughing emoji. We agreed on a time and place, a late night truck thankfully not too far from me. I put my glass of rum in the fridge, bagged up a couple canned cocktails, spruced myself up, and headed back out the door.

I got to the taco truck and parked nearby, and ended up waiting about fifteen minutes in my car before Sofia pulled up. I got out of my car and walked to hers, noting how chilly the night had become. She emerged and looked at me, and we both smiled. She was zipping a hoodie up over her work shirt. I shivered.

"Smart idea," I said.

"Work smarter, not harder," she said.

We exchanged a brief hug, then went to order. As we waited for the food we chatted casually, her smiling every so often at how cold I clearly was.

"You should've brought a hoodie instead of those canned margs," she said.

I chuckled. "You say that now."

They called out our numbers and we grabbed the food. My teeth chattered slightly.

"Wanna eat in my car?" I asked.

She laughed. "Sure."

We scurried back to the safety of my car, I cranked the heat, and we sat and ate and drank the margaritas (I don't endorse drunk driving!). We shared restaurant horror stories, something any server or former server can easily connect over.

"I don't know how you deal with all us shitty delivery drivers," I said. "Respect."

She laughed. "Some are better than others."

She looked at me meaningfully. I looked back.

"And some hostesses are better looking than others." I smiled.

"We got a charmer here," she said, grinning.

"All the others seem like girls. You seem like a woman."

She smiled, taking me in.

"And all the other delivery guys seem like boys."

There was a moment of us just looking at each other, the only sound the AC blowing.

I leaned across my center console, brought my face close to hers. She looked down at my lips, then up at my eyes, took a nervous gulp. I kissed her. She immediately responded, her lips pressing back eagerly. I closed my container of food and placed it on the dashboard, and she did the same with hers, her fingers fumbling with the styrofoam latches.

When our hands were free I wrapped an arm around her upper body and pulled her toward me, and her arms went around my upper back. We sat there, making out across the middle console, one of my hands buried in the hair at the back of her head. She tasted like Mexican food, like onions and tomatillo. Her lips were soft and she was an eager kisser, pushing her tongue into my mouth. I wondered how often this confident young woman got laid, if guys too often avoided her for being a hard ass bitch.

I decided to test how far she was willing to go. One of my hands was resting on her waist. I lifted it and placed it on one of her breasts, outside her hoodie. She made a surprised little sound into my mouth and pressed her chest toward me. I pressed my body back, pushed up on her breast with my hand, feeling how amazingly heavy it was, how thick the bra was, had to be, that was holding it. Her tongue probed deeper in my mouth and one of her hands slapped down on my crotch, started rubbing roughly over my bulge. I started getting harder.

And then she pulled away, took her arms off of me, held her hands to her face.

"I'm sorry," she said. "This is fast."

I took my hand off her breast and sat back. "That's okay," I said, meaning it.

She looked down at my bulge, my cock starting to press down my leg, then she looked up at me lustily, leaned in slightly, seemed on the verge of jumping back on me...and then she sat back.

"Can we wait?" she said.

I nodded. "I don't do relationships, but I also don't do pressure. I'd only want to do this if you really wanted to too."

She nodded, taking this in. I tried to intuit how interested she'd been in me, what she thought or imagined this could've become.

"I get that," she said. "Cool if I think about it?"

"Absolutely."

She smiled weakly. I smiled back, trying my best to reassure her that it was truly okay.

I picked up my food. "How's your food?"

She smiled, picked hers up. "So good."

And we kept chatting, still comfortable with each other. If anything, her enthusiasm and her interest in me seemed to have grown. Respecting someone's boundaries can have a strong effect. When the food was done, and the drinks were gone, I walked her to her car, we shared a brief hug, and she left.

I drove home (not buzzed! You shouldn't drive buzzed!), not expecting I'd ever hear from her again, but happy that we avoided anyone doing something they didn't want to do.

A week went by, and then I started a delivery shift and like clockwork an order took me back to her gastropub. I was slightly anxious, wondering what her response might be when she saw me.

I walked in and there she was, flying from one place to the next, barking orders. And then she looked over, saw me...and her face broke out into the goofiest shiniest grin. It might've been the first time I saw her truly smile. She stopped what she was doing and beelined for me. The other delivery drivers watched in awe as she got to me, brushed hair from her face, started speaking to me breathlessly.

"Hi," she said.

"Hi."

"How are you?"

"I'm good."

"Good."

"I've thought about it."

"Yeah?"

"Wanna get tacos tonight?"

I smiled. "Absolutely."

"Good."

She nodded briskly, turned on her heel, and walked away.

"I'm picking up for Sam!" I called.

She turned on the spot, blushed, nodded again, then turned and hurried off.

I caught the eye of a delivery driver standing nearby. He was nodding, impressed. I winked.

She brought me the food, we made quick eye contact again, co-conspirators with a secret, and I left.

I texted her later that night, around the time she'd texted me the week before. She let me know when she was getting off, and I offered to pick her up. She accepted.

I waited in my car outside the restaurant, and when she emerged we made eye contact and I waved. She waved back and hurried over.

"Hi!" she said, getting in.

"Hi."

We leaned in and hugged, and held it slightly longer than necessary. I felt her breasts pushing against my chest. Then we broke apart.

"Let's get some food," I said.

"I'm starving," she said.

I drove us to the taco truck, we got out and ordered, we sat back in my car and ate. We didn't talk as much this time, I think both expectant of what was to come. When the food was done, we put the containers aside, wiped our hands, and sat back.

"Mm," I said.

"Mm!" she said.

We looked at each other.

"So," I said, "you're comfortable with this?"

She nodded. "I need it."

I nodded, and leaned across the center console slowly. She leaned in, I took her chin gently in my hand, and we kissed. We explored each other's mouths, sensually, really enjoying the taste of each other, the textures of our lips and tongues.

I moved my hand to the back of her neck and gripped it lightly, and the intensity of our kissing increased. Our mouths pushed together, faster, her lips pushing over my upper lip, over my bottom lip. Her tongue started to run into my mouth, and mine pushed back. I pulled my head to the side and dove in on her neck, kissed the curve where it met her shoulder, sucked on it, bit it roughly. She moaned, her arms tight around my shoulders, her hands and fingers running sharply up and down my back.

"How tinted are these windows?" she said, softly.

"Very," I said.

One of her hands promptly landed on my crotch. I kept kissing and biting her neck, getting harder now. Her hand pushed up and down my growing bulge, her fingers clawing at the denim, feeling the growing length of my cock, trying to wrap around it.

"Holy moly," she said.

I smiled, paused what I was doing to her neck. "Holy moly?"

Her other hand playfully slapped my shoulder. I gave her neck a single light kiss.

"That's what I thought when I felt you up last week," I said. I kissed her again.

"Why aren't you feeling me up now?"

"Yes, ma'am."

I put my hand up on her breast, on the outside of her shirt. I lifted it in the same way I'd done the previous week, felt the weight of it, truly in awe. Then she took her hand off my crotch, grabbed my wrist, pulled my arm down, and pushed my hand up under her shirt. I cupped her bra, pushed up on the breast again.

"Holy moly," I said.

Sofia giggled and her hand went back down to my crotch, gripped my bulge harder.

Well if she was going to try to speed things along...

I took my hand off her tit, brought it down to my fly. I unzipped it, pushed my hand into my pants, and pulled my dick out. I grabbed her wrist, moved her hand to my dick and it wrapped around my shaft.

"Holy moly," she said.

I then put my hand back up under her shirt, pushed it under her bra, and felt her bare breast. She moaned.

"Hey," she said softly into my ear.

I stopped kissing her neck, looked at her. Her hand was still on my cock.

"I want to do this," she said, "it's just been a while."

"I totally get it," I said. "Best you can, don't worry about it. We're just having fun."

She nodded, leaned in quickly and kissed me. We started making out again and she started jacking me off. Her hand was small but strong, and moved up and down my dick in a quick steady rhythm. I kept playing with her breast under her bra, squeezing it, pushing it around, feeling her nipple, pinching it. I then took my hand out and pulled her shirt up her torso, over the top of her bra, and let it sit there bunched up above her tits. I stopped kissing her to look down. 

She was wearing a red bra with big cups but her breasts were bigger, massive, pooling around the sides. I didn't know if they were Gabbie Carter level, but they were close. I couldn't wait to see them set free.

"You have amazing tits," I said.

She smiled and grew bashful. "Pssh, they're too big."

I gasped. "Don't ever say that."

She laughed. "You have a big penis."

"I'm not gonna say it's too big."

"Damn it."

I laughed and she smiled and I leaned back in and we continued making out. I dropped my hand to the inside edge of her thigh, let it rest against the denim of her jeans. She spread her legs, everything about her hungrier now, and I pushed my hand onto the seam of her crotch, right over her pussy.

She moaned, and her hand slowed down on my cock, her mind elsewhere. I dragged my hand up her crotch and undid the top button, then pulled down her zipper, and pushed my hand into her jeans. Her skin was warm and smooth, everything shaved bare. I pushed my fingers down onto her vulva. She was already wet.

She moaned again and leaned her head into the crook of my neck, breathing quietly. I moved a finger across her clit and her hand tugged once up the length of my dick, slowly, lightly twisting. I held her firm by the back of the neck with my other hand, and pushed a finger up into her. She gasped and let go of my dick and brought that hand up to my cheek. She looked into my eyes wordlessly, then put her head back next to mine. Her pussy was tight and wet, suctioning my finger, and I started to rub her upper wall, my hand gripped to her by the front of her jeans. Her hips started to push back and forth on her seat, her breathing hot and loud in my ear.

I sped up my finger in the limited range of motion I had, feeling the grip of her pussy around it. Her hand briefly returned to my cock but just held it, all of her focus on what was happening inside her. I looked down to her tits, bunched up behind her bra, the edge of one dark nipple showing over one. I looked down her tan belly to where my hand was clamped around her pelvis, my finger hooked up into her.

I turned my head slightly, brought my mouth close to her ear.

"You have such a tight pussy," I whispered.

She moaned softly.

"I love having my finger inside you," I continued. "I can't wait to make you come."

"Are you gonna make me come?" she said slowly and quietly into my ear.

"When's the last time a guy made you come?"

"It's been forever."

I sped up the motion of my hand and the movement of my finger. It started to make suction sounds as it pumped in and out of her, everything tight and increasingly wet. She gasped, pushed her far hip off the seat toward me, held me tight with her arms, and I kept blasting her.

"Yes, yes, yes," she said.

Her breathing quickened, and in a few moments she came. She let out a soft sharp gasp but that was all, and then she shook quietly, her breath hot and loud in my ear. I started to slow the motion of my hand, she shook a little longer, these cute little vibrations, and then it all subsided, and her hand fell to my wrist, and I pulled my finger out of her.

She leaned away from me and collapsed back against the passenger door, her eyes closed, her breathing slowing. I watched her breasts heaving over her bra.

"How are you?" I asked.

She half-opened her eyes, looked at me, and nodded.

"Good," she said.

I started working my dick back into my pants, and she looked at it. Her head came off the window.

"Are we done?" she said, worry in her voice.

"No, I was just gonna ask if you wanted to go back to my place."

She nodded, closed her eyes, and put her head back against the window.

"Yes. Whatever that was, I need more."

Part 2


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