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I was catering a gala and got one of the guests to step outside her comfort zone - Part 2 - Jack's Adventures #14 [M27F27][Car Sex][Doggy][Cowgirl][Creampie]
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propmasterflex is in Creampie
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Part 1

As the gala wound to a close, I watched Harriet meander toward the exit with an assortment of women. Her head turned in my direction, we made eye contact, and I winked. She smiled and bent her head. She'd agreed to ditch her friends and meet me at a nearby cocktail bar as soon as I was off.

I hurried through the end of my shift, cleaning up tables like a tasmanian devil, impressing my coworkers, they'd never seen such enterprise from me. When I clocked out I changed into civilian clothes, left the hotel, and began to walk. The bar was further from the hotel than my car was, but not further enough that it would make any sense to drive and find a new spot to park. It was a winter night, my breath lightly fogging the air, but I didn't feel the cold, only excitement. And a little bemusement at what I'd look like in Harriet's company, she wearing a formal dinner dress, me a hoodie and jeans.

The bar had a nondescript entrance, just a door squashed between rundown storefronts, one you'd walk quickly past without a second thought if you didn't know what was behind it. I entered, showed my ID to a bouncer just inside the door. He didn't care about my casual attire, probably figured I was in music or in tech, and waved me past. I walked through a blackout curtain into the bar proper.

It was dark, narrow, very old Hollywood, with copper fixtures and green leather booths. The light was low, shadows pooling in the spaces between flickering candles. It was busy, every seat taken except for one, a stool at the bar with a coat draped across it.

Harriet's coat.

She was sitting on the stool next to it, her elbows on the bartop, one leg crossed over the other at the knee. She looked stunning, her skin, her hair, her dress, all glowing in the dark. I couldn't believe she was waiting for me, and that I was wearing a fucking hoodie.

I walked up behind her.

"Is this seat taken?"

She looked up, ready to shoo me off, then smiled.

"Hi," she said.

I leaned in and gave her a light kiss on the cheek. She pushed a strand of hair behind her ear, then moved her coat and I sat.

"This place is so cool," she said. "Have you been here before?"

"A couple times."

"Is this where you take all the girls you pick up at galas?"

I laughed. "Where do you take all the caterers?"

She bit her lip, picked up a coaster, tapped it on its edge.

"I've never done that before," she said.

"Me neither."

We shared a look and a smile.

"I'm sorry I look like a total schmo," I said, gesturing to my outfit.

"Oh, please," she said, rolling her eyes, "that's me every other day of the year. You caught me on a good night."

The bartender walked up, a mean-faced woman with severe bangs who turned out to be delightful, and we ordered drinks. We watched as she embarked on a complex mixological quest.

"So how is a gorgeous woman like you alone at an event like that?" I asked, not looking away from the bartender's work.

Harriet chuckled. "Stop it."

"I'm serious."

"No."

I turned to her. She was staring resolutely at the bartender's hands.

"Hey," I said, my voice soft but firm.

She looked at me out of the corner of her eye before angling her head slightly toward me.

"What?" she said. "Why don't I think I'm gorgeous?"

I nodded.

"Well," she said, but didn't continue.

My hand found her knee under the bartop. I gently squeezed it. Her mouth opened slightly.

"We're gonna need better self-regard from you," I said.

A smile worked its way across her lips. She leaned her head further toward me.

"How do you do it?" she said, her voice soft.

"Do what?"

"Make me want to do anything you say."

I smiled, and drew my hand up her leg, pushing up under the hem of her dress and onto her thigh. Her head tilted, her eyes staring deep into mine.

"I don't make you want anything you don't want already."

I could feel her pulse under my grip. I felt it quicken. I briefly wondered what the bar bathroom was like, what it would be like to fuck Harriet in this one too, if we had time before-

"Your drinks."

We turned, and the bartender placed our drinks in front of us. I took my hand off Harriet's leg and pulled out my wallet.

"Thank you," I said, and handed the bartender a card.

"Thank you," Harriet said to me.

I lifted my glass, and Harriet lifted hers.

"Least I can do for the best shift of my life," I said.

She laughed. "Most fun I've had at a gala."

We toasted, we drank, and we talked, turned to each other on our stools, our knees interlocked. She'd worked at the non-profit for a little over a year, and never expected anything about it to involve that level of glamor. She just wanted to help people, truly. I watched her talk, enraptured with her, with this lovely, idealistic, caring person.

"How often do you cut loose?" I said.

She laughed. "Not often."

"Maybe let this be the night?"

She took a last sip of her drink and put it on the bar top. She held out a pinky.

"Pinky promise."

I smiled, and wrapped my pinky around hers.

"Let's get out of here," I said.

Her eyes twinkled. "Let's go."

She put on her coat and we left, heading for my car. I put an arm around her and she leaned into me, and we talked and laughed as we walked into the surrounding neighborhood. We reached my car and she turned to me.

We were close. My car was under a tree, the canopy just above our heads. I put my hands on Harriet's waist, pushed her gently up against the car. My crotch pushed into hers. Her face tilted up and I leaned in and kissed her. She kissed back, and we made out for a minute in the quiet of the night, enjoying our bodies pressing together, not feeling the cold air around us.

I pulled back, we smiled at each other. She looked back and down at my car.

"How big's your back seat?" she said.

I laughed. "Look at you."

"I'm letting loose."

I unlocked the car, opened the rear door.

"Well, let's find out."

She climbed in, I climbed in after her.

When the door was closed behind me I wrapped an arm around her and pulled her into me and we started making out. We were still sitting up, our knees pressed together, our upper bodies pushing at each other. Then I pushed forward, she fell back, and we were lying across the back seat, our heads pressing against the inside of the far door.

I pushed a hand up under her dress and between her thighs. She spread them for me and I found her underwear and I pushed my hand up against her pussy. I rubbed my palm over her vulva for a bit, causing her to moan into my mouth, and then I pushed the underwear aside and pushed a finger up into her.

She gasped and pulled her lips away and looked down to where my hand disappeared up her dress. She pushed her head back into the door and looked up at me, our faces close, as I started to finger her. I pushed my head down toward her bent neck and started kissing it, and she turned her head into the corner between the seat and the door to give me more access. She'd gotten wet very quickly, my finger making suction sounds as it ran in and out of her. She moaned as I worked, as I pulsed my finger up over the top ridge of her pussy, aiming for her g-spot.

I kissed across her neck, down across her chest, down into her cleavage. I let my face rest here, turning it back and forth, dragging my lips over her skin, smelling her perfume. I felt her chin press against the top of my head, felt her hot breath ruffle my hair.

I rose up and looked down at her, my hand still pushing up under her dress, my finger still inside her. Her pale arms were straight, her hands lightly grasping the wrist between her thighs, her eyes wide and beseeching. Her head was still pressed into the corner, her light red hair tousled around her head. I pulled my finger out of her slowly, with a soft squelch, and started unbuckling my belt. Her eyes watched as it came undone, then as my pants were unbuttoned, as I pulled them down my legs and fully off. They watched my cock spring up, watched it stand at attention as I took off my hoodie and t-shirt, watched my naked body loom over her, my torso bent against the ceiling of the car.

"You're so sexy," she said.

I shimmied forward, one knee between her and the seat back, one foot on the floor. She lifted her torso and craned her neck forward and took my dick in her mouth and started sucking me off.

"Fuck," I said, pushing the back of my head up into the ceiling.

Her eyes were closed and she was bobbing her head forward and back the best she could. Her hands came up to my shaft and started pulling on it with each movement of her head. I put my hands under the back of her head and neck and supported her, letting her take some of the strain off her muscles, and she moaned as she kept blowing me. It felt amazing, not because she was particularly skilled but because of the weird arrangement of our limbs, of having certain muscles tensed that I hadn't had tensed during a blowjob before, of having quiet sex in a car on a quiet street on a quiet night.

She came off of it and took a deep breath and I lowered her head gently back down to the seat. Without speaking we both started shifting around so that she could get up and me down. I half-sat half-lay across the seat, my upper back and shoulders against the door. She dropped to her stomach across the seat, her legs bent down to the side, and dove her head between my legs and back onto my cock, her hands continuing to tug up the shaft as she bobbed on and off. Her hair had fallen around and in front of her face so I put my hands in it and pushed it back behind her ears, and her eyes opened and looked up at me briefly as she kept sucking. They were such a stunning shape and color, two pale green diamonds. I held the sides of her head as she kept working, still letting her control the movements, but feeling the shape of her as she moved on and off my dick.

She popped off of it and pushed herself up into a seat, and pulled the straps of her dress off her shoulders. It fell down around her waist, revealing her pale torso, her light blue bra. She stripped that off quickly and I looked at her perky b-cup breasts, at the freckles across her cleavage. I sat up and reared forward and put my hands around her thin back and pulled her chest toward my mouth and took a breast into it, drawing my lips over it and out across her nipple, before extending my tongue and flicking it back and forth quickly.

She moaned, her hands clutching my head, and I moved to her other breast, letting my teeth run across this one, feeling the flesh push around it. I pulled her toward me and scooted my hips down and my butt across the seat, lying back down, my mouth still on her tit, and she swung a knee over me and straddled me, and I pushed my hands down her body and found the bottom hem of her dress and raised it, pushed my hands up underneath it, pulled her underwear aside and directed my cock toward her pussy. When I felt my head push through her labia I put my hands on her ass and pulled her down and my cock slid up into her easily, her pussy tight but soaking wet. My mouth came off her breast and we looked into each other's eyes, our faces close, our bodies curled together in the cramped back seat.

I started thrusting up, my motion limited, only able to get the upper half of my cock into her with the positioning of our bodies. She moaned and started kissing me and I kept thrusting as far as I could, my hands wrapped over her ass and the curve of her lower back, knowing that the pushing of my head through her hole was still doing enough for her.

Then I scooted my butt further across the seat and came fully onto my back, and she scooted with me and was able to put her knee down, and she slid fully down onto my cock. I watched her eyebrows push up her head with each inch I pushed into her, and she let out a deep shuddering moan and just sat there for a second, feeling all my cock buried inside of her, her body quivering, her tits shaking. I put my hands on her waist and pushed my hips around and then she started raising and lowering her body, her head pressing up at an angle against the ceiling of the car. My cock slid in and out of her tight pussy, her slender frame.

She bent her upper body forward, put her hands down on my chest, and started riding me faster, grinding her hips against mine, my cock pushing around her walls. I pushed my hands up through her hair and held it in a mess around her head and we stared into each other's eyes as she rode me. The air in the car grew hot, the glass of the windows, still cold, now fogging. Her hair grew damp in my hands, our bodies sweaty, sliding against each other as we fucked.

Eventually she rose off of me, my cock sliding out and falling against my stomach. She held her dress in a bunch around her waist, and maneuvered herself around to face the other direction. She swung a knee back over me and leaned forward, her ass hovering above my dick. I raised it and directed it toward her pussy, pushed it against her hole, and she sat down fully onto it. She moaned and leaned forward and started raising and lowering her hips, and I watched her pussy skin gripping my cock, her ass cheeks spreading in front of me. I put my hands on her waist and helped her up and down for a bit, before moving my hands down and gripping her butt cheeks, sweaty under my hands. She looked at me over her shoulder and slowed up her movements, staring into my eyes as her pussy slid slowly up my shaft, revealing a surface shiny from her juices, then back down again, taking it deep into her.

I rose up and pushed her forward onto her knees and put a hand on the back of her head and bent my head under the ceiling and started fucking her doggy style. She pressed her head down into the seat, her back twisting in front of me, moaning as I drove my cock into her.

"Pull my hair," she said.

I reached forward and grabbed a handful of her hair and pulled her head up. She rose up onto her hands, and her back and her neck arched up and she groaned.

"That good?" I said.

"Perfect."

I drove my cock into her harder, loving the feel of her damp hair in my hand, her body under my control. Her pale ass slapped against me, every inch of my cock pushing deep into her pussy. I moved my hands off her hair and around the front of her neck and she turned her head this way and that, before I moved my hands down and groped her breasts, pulled out on her nipples.

I pulled out of her and pushed her down and flipped her onto her back and spread her legs and drove my cock back into her pussy. She looked up at me as I fucked her missionary, her head pressed up against the door, her tits vibrating on her chest. Her eyebrows pushed up her forehead, her mouth hanging open. I felt an orgasm building, knew I could get her there too, wanted us to come simultaneously.

"Start touching yourself," I said.

She nodded, or tried to nod, the door restricting her, and pushed a finger between her legs and started fingering her clit as I kept fucking her. My cock was swollen so hard, having this beautiful woman pinned underneath me, her expensive dress just a pile of fabric around her waist, her body sweaty and flushed, watching her touch herself as I slid in and out of her tight wet pussy.

"Let me know when you're gonna come," I said. "And I'll come too."

She nodded, and her hand sped up. I started snaking my hips, driving my cock the best I could against the deep upper reaches of her vagina. Another minute, another five minutes, another ten minutes, who knows, both of us lost in the sweaty pleasure of the fuck.

Then she cried out, "I'm coming," and I let the dam at the base of my cock give way, and my orgasm swelled, and we came simultaneously, her body starting to shake, me ejaculating deep inside her.

"Oh fuck," I said, the pleasure incredible, her pussy spasming around my cock. "Oh fuck oh fuck."

She shrieked and cried and I pushed myself down and wrapped my limbs around her and she held me tightly as she kept coming, as I kept coming, every sensation magnified by our bodies shaking together.

Then everything slowed, everything relaxed, and we just lay there, breathing deeply, our sweaty bodies entwined in the hot car. I raised my head and looked down at her, and we kissed, long and slow.

"I'll never forget this," she said.

"Me neither," I said. "Thanks for having some fun with me."

We didn't say anything else for a while, just stayed intertwined, her fingers trailing up and down my back slowly. At a certain point I pulled out of her and she sat up and we watched as my cum dripped out of her pussy and onto my seat, neither of us feeling any desire to prevent it.

Eventually we moved from our reverie, finding our clothes and dressing again, me wiping the cum off my seat, worrying about any stains at a later date. Harriet had taken an Uber to the gala, so I drove her home, neither of us saying much, neither of us needing to.

When I pulled up to her building, she leaned toward me and we shared a kiss.

"Can I get your number?" I asked.

She nodded eagerly, and entered it into my phone. She handed it back to me.

"Text me," she said.

"Yup," I said.

She smiled and got out of the car. I watched her walk to her building, her tottering slightly, adjusting her underwear, her hands running through her hair.

"Well that was a good fuck," I said out loud, even though I was the only one around to hear it. I put the car in drive. "Yeah, that was a good fuck."

And I left.

---

Thanks for reading! If you want more stories like it, plus NSFW AI-generated images of Harriet and the other girls I write about (now with hardcore versions), please consider subscribing to the Jack's Adventures Patreon. If you just wanna show a one-time appreciation for my work with no commitment, feel free to buy me a coffee.

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