Jacks Adventures 19 Sienna 01

This is the nineteenth story.

This is the story of Sienna.

To summarize some necessary backstory, I'd been at a charity luncheon with Lily (you might remember Lily? Hot mom? Wager of psychosexual warfare?) and her ex-husband Trent had shown up with a gorgeous young blonde on his arm. They'd come over to our table to say hi, there'd been a lot of awkward tension between all four parties, and I'd definitely sensed that Trent's hottie and I could've had some fun in another life.

That was Sienna, and we weren't going to have to wait that long.

About a half hour later I used the restroom, down a side hallway off the ballroom, and when I emerged Sienna was standing outside, across the hallway, despite there being an unoccupied restroom next to mine. I stopped in my tracks, looked toward the ballroom to make sure neither Lily nor Trent could see us, then crossed the hallway to her.

She was about half a head shorter than me, if balanced on very high heels. She was wearing a silver dress, studded with rhinestones, that hugged her tight body incredibly, her waist so thin that her hips had nowhere to go but out, a plunging neckline showing off ample cleavage, her breasts large on her frame and possibly fake. She was very tan and incredibly manicured, from her wavy blonde hair to her dark eyebrows to her full glossy lips. Everything about her was impeccably crafted, and I saw exactly why Trent wanted to flaunt her in front of his ex-wife.

"Hey," I said.

"Hi!" she said, smiling widely, breathy. "Jack?"

"Sierra," I said, messing up on purpose.

"Sienna."

"Oh that's right, I'm sorry."

"That's okay. It happens a lot."

She laughed, a bubbly rising thing. She was twisting her hands together in front of her stomach, looking at me with wide eyes, biting the inside of her bottom lip. I just looked at her, my gaze steady, wearing a half smile, waiting for her to speak.

"What?" she said.

"What?"

"You're staring at me." She lightly emphasized staring, while looking lightly scandalized.

"Sorry, you're just incredibly beautiful."

Her mouth dropped open.

"I-"

I shook my head, smiling. "Sorry, I meant, I thought you were gonna say something."

"I was," she said, nodding.

"Yeah?"

"Yeah."

"What were you gonna say?"

She narrowed her eyes at me, pursed her lips, and then shook her head.

"I have no idea," she said, laughing.

"You were gonna ask for my number."

She froze, her mouth hanging open.

"You're with that woman," she said.

"And you're with that man."

"We're not official."

"Us either."

I leaned in toward her, said under my breath, "Everyone here is so ancient."

She laughed, leaned in, whispered, "Oh my god! Right?"

"What are you, twenty?"

She blushed, started rotating her hips back and forth like a schoolgirl, her eyes locked on mine. "Twenty-three."

"I'm glad," I said. "Then we can grab a drink together. Give me your phone."

She obeyed without seemingly a single thought to the contrary, no hesitation at betraying the guy waiting for her in the ballroom, no matter how official or unofficial they might be. I felt only the slightest twinge of shame at what I was doing to Lily, but I had no misconceptions about our relationship, knew what we had was a purely sexual thing, a love of fucked-up fuck games and a willingness to participate in them. I also knew that, if she found out, she'd get some savage joy out of me stealing Trent's new toy out from under his nose.

I took Sienna's phone from her, typed in my number, and handed it back to her.

"Text me," I said. "We'll grab a drink. Or play some golf. I've heard you've got a good game."

"That'd be fun!" she said, before going suddenly serious. "We can't go to his club though."

"I wouldn't dream of it. Some other course."

"That'd be fun."

"I have to get back," I said, starting to walk away. "Talk to you soon?"

"Yeah," she said, nodding, her eyes wide, before she turned toward the wall of bathrooms and strode toward it, her high heels indenting the carpet.

I returned to the ballroom and sat back down next to Lily, and she didn't suspect a thing.

And that's how I found myself one early morning a couple weeks later idling in my car outside a very nice apartment building in Beverly Hills, waiting for Sienna to emerge for our first golf date. When she did, I wolf-whistled, completely alone in my car and for no one's benefit but mine.

She was dressed exactly as I'd dreamed she'd be, wearing a polo shirt and a pleated skirt, pure white Adidas and a sporty visor. Her hair hung down past her shoulders in perfect waves, and all of her face and arms and legs had a deep golden tan. Her breasts looked slightly smaller than they had been at the luncheon, but I was happy to see they looked a lot more natural. I wondered what pushup bra dark arts had been used on them at the event, and whether Trent liked, possibly demanded, a bustier, faker gal by his side.

I got out, walked to the back of my car and popped the trunk. She had a bag of clubs over her shoulder.

"Hi!" she said brightly.

"Hey you," I said.

I leaned in and we exchanged a quick hug, and then I took the bag from her and and nodded at her outfit.

"You know what you're doing," I said.

Her hands found a strand of her hair and played with it.

"I've been golfing so long," she said.

I looked at the bottom hem of her skirt, at her thighs, skinny and tan, her skin utterly flawless, then turned away to put her clubs in the trunk.

"I think you're gonna kick my ass today," I said.

"Stop it." She rolled her eyes.

"Will you give me pointers?"

"Of course."

"Do that thing where you wrap yourself around my back and swing the club with me?"

She laughed, holding a hand just in front of her open mouth. "I don't want you pretending to be bad," she said. "I want a good game."

"Trust me," I said. "I'll be bad, and I won't be pretending."

A few hours later we were about to tee off on the ninth hole at Rancho Park, coming off eight straight holes of Sienna Lydia Ko-ing me up and down the fairway. She was amazing, regularly outdriving me and with outstanding precision, and no handicap was going to be needed for her to absolutely kick my ass on the scorecard.

I watched her line up her tee shot, watched her swing, every motion of her athletic body fluid and coordinated, watched her latest drive sail perfectly down the middle of the course. I gave her a polite golf clap and she turned to me, beaming, and did a little curtsy.

I walked up to set up my own shot, sighing deeply, giving her a high-five on the way.

"I could use a little bit of that instruction now," I called back over my shoulder.

"You should've asked eight holes ago," she said.

I sighed again, and began setting my feet, looking down the course.

"Here."

And suddenly she was behind me, reaching her arms around me to hold my hands against my club. I felt her breasts press against my back, her head pressed sideways against my shoulder.

"Like this," she said.

She pushed her crotch against my butt, connecting the movement of our bodies.

"You're swaying way too much," she said. "Your hips are your axis."

Her left hand dropped off the club handle and came down to my front hip, held the outside of it firmly.

"When you swing," she pushed her right hip against my right butt cheek, making my right leg give, "don't lock this leg, and rotate."

We lifted the club together and I brought it down in a gentle arc, feeling her hips pressing against me again, helping me learn the movement. We did it a couple more times, her left hand still riding along my left thigh, her face still pressed against my shoulder.

"How am I doing?" I said, looking back over my shoulder, trying to catch her face in my periphery.

"Good," she said softly. "Finally."

I smiled at that. Then she stepped back.

"Go for it."

I lined up my shot, determined to put into practice her instruction and hit my best drive of the day. I raised my club, swung...

And sliced that shit right into the trees.

Sienna doubled over laughing, and I dropped my club and charged her, reaching for her waist, tickling her. She shrieked and turned her body and I wrapped my arms around her midsection and lifted her off the ground, so light, laughing, her legs kicking, and I lowered her to the ground again, and she turned to me, smiling, flustered and flushed, put her hands on my chest and gave me the lightest of pushes.

"Stop," she said, without an ounce of conviction.

"Let's go find my ball," I said.

I did slightly better over the final nine, but only just, and the bigger story was the growing comfort between us, the growing friskiness. Sienna had a single less-than-ideal shot and I took the opportunity to pretend that she was the one who needed help with her swing, came up behind her, wrapped my body around her, put my hands around hers on her club.

"See, what your problem is..." I said.

"Oh yeah? What's my problem?"

She wiggled her butt against my crotch, and I pressed back, feeling the firmness of her butt cheeks.

"The hips," I said.

"My hips are bad?"

I put a hand on one of her hips, held it firmly, patted the front of her thigh. "Nah, the hips are fine."

"What is it then?"

She looked up sideways into my eyes. Our faces were very close. I could've leaned in and kissed her.

"Your grip," I said.

"Really?"

We both looked down to where our hands were wrapped around the golf club.

"Let me try something," she said.

I moved my hands to her wrists. Her top hand remained wrapped around the handle, but she pushed her bottom hand a few inches down, twisting around the shaft as she went, and then she drew it back up.

"How's that?" she said, looking back at me, smiling slyly.

My dick was stiffening in my shorts, starting to press against her ass. I did nothing to hide it, instead pushed my crotch more firmly against her.

"Oh," she said, her eyes dropping in that direction. "It must be pretty good."

She pushed her bottom hand back down the handle and drew it up again. I moved my hands off her wrists, brought them to the outsides of her thighs, started playing with the hem of her skirt. I wanted to pull it up, see what color panties she was wearing, see how the fabric looked up bunched up between her ass cheeks.

"I don't want to finish this round," I said softly into her ear.

"We know who's gonna win anyway," she said.

"True. I forfeit."

We grabbed our gear and left the course, striding quickly back toward the clubhouse. When we reached my car, we put the clubs in the trunk, and Sienna automatically moved around the passenger side.

"Wait a second," I said.

She stopped, her eyes fixed on me as I came around the side of the car toward her. She turned her back to my car and bumped back against it, and I moved in, cupped her chin, and kissed her. Her lips pressed back against mine, and I felt her chest press out, felt her breasts against my stomach.

"Wow," she said softly, her eyes still closed.

I looked around. We were parked amidst a long strip of cars between the course and a busy thoroughfare. There were a few golfers far off on the course, and cars rushing by on the street, and nobody currently walking through the parking lot.

I moved a hand around to the back of her neck and gripped it firmly. Her eyes opened and looked at me, and I dropped my other hand down between us and onto the bottom hem of her skirt, lifted it up and pushed my hand up between her thighs. Her mouth fell open but she didn't say anything, didn't protest. My hand pushed up against the crotch of her panties, and I dragged a few fingers up it, feeling the softness of her mound beneath it. She made a soft gasping sound, and her eyes fluttered, and then she looked around us as well.

"Should we be..." she started to say.

"Why not?"

She looked back at me, with a tinge of fearful excitement.

"Did Trent ever finger you in a parking lot?" I said.

She shook her head quickly. I found the waistband of her underwear with my fingers, pulled it downward, and she reached up under her skirt and wiggled her hips as she helped pull her panties into a bunch around her thighs. She put her hands up around my shoulders and stared into my eyes as I ran my hand over her bare pussy.

She made a long mmmmm sound, the back of her head coming to rest against the roof of my car, and I ran my hand in a circle, drawing the pads of my palm against her labia, letting the lengths of my fingers drag up between her lips. I found the small bead of her clit, let my fingers rest against it before very gently moving it from side to side. She let out another soft gasp, pulled on my shoulders, brought my body even closer to her, my head coming next to hers over the car. My cock was stretching firmly down one leg of my shorts now, and it pushed into her thigh and caused her face to bend forward, to try to see down between us. As I kept playing with her clit she dropped one hand from my shoulder and pushed it against the front of my thigh, wrapped it around the shape of my dick.

I let out a small happy grunt, and she held it tightly and started moving her hand quickly up and down, stimulating that small stretch of my shaft. I worked her clit faster, started moving the pads of my fingers in a rapid circle against it. Our breathing was becoming husky and heavy, us tuning out the busy world around us, lost in touching each other.

At the exact same time, with no advance planning or collaboration, we both took it a step further. I curled a finger up between her labia and into her hole, and she dropped her hand down to the hem of my shorts leg and dragged it up my thigh and the head of my cock sprung out into the open air beneath it. We looked into each other's eyes, breaking out in huge grins, both surprised at the timing. Her fingers wrapped around the ridge of my dick, and I ran my finger against the upper ridge of her pussy, and I leaned in and kissed her quickly, biting her lower lip as I pulled away.

"Someone's gonna see us," she said, anxious excitement in her voice, her hand starting to work the end of my cock.

"Probably," I said, keeping my finger hooked in her, drawing my whole hand in a circle around her vulva.

"You don't care?"

"Not in the slightest."

She shuddered, her hand wrapped firmly around my dick, and she leaned in and nipped at my neck, then stayed there, started kissing it, letting her lips push sloppily against it. I pushed my jaw against her hair, moved my hand to the back of her head and held her to me, and imagined the pink lip gloss being left across my skin. I started pulsing my finger quickly in and out of her pussy, adding a small rotation to it, feeling the tightness of her walls, my hand gripped firmly by her skinny thighs. Everything about her body pressed against me felt tight, manageable, fuckable.

At some point my eyes lifted briefly and I saw two middle-aged people, a man and a woman, standing a few cars away, looking back at us. Their body position indicated that they'd walked there from our direction, that they'd maybe passed by us and neither of us had noticed, and their expressions indicated that they didn't care for what we were getting up to. They turned and started walking quickly toward the clubhouse.

"We've been spotted," I said.

"What?" Sienna looked up and around, shocked, and took her hand off my dick. But I didn't loosen my hold on her, not on her head nor on her pussy.

"Look at me," I said.

She did, anxious and unsettled. I smiled, projecting calm.

"I'm gonna make you come before we get kicked out," I said.

Her mouth fell open, her eyes dancing between mine. I pushed my finger deep into her pussy, drew it down along her upper ridge, and then hooked my hand up to press firmly against her clit as well, and started moving everything in a fast circle. Her vagina had constricted at the fear of getting caught, but was starting to relax again, was becoming soaking wet.

I moved my hand off the back of her head and held her jaw firmly, made her stare into my eyes from a couple inches away.

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

She moaned, and I pushed my fingers up against her cheeks, pinching her lips out and together.

"Do you like having my finger up your pussy?"

She nodded, and then turned her head and brought her mouth to my thumb and wrapped her lips around it, keeping her eyes open and fixed on me. I sped up the motion and pressure of my hand, feeling the wetness run across every part of her vulva.

"Are you gonna be a good girl and come for me?"

She mhmed, sucking hard on my thumb, her tongue licking all around it. I kept working her pussy in rapid circles, squelching noises starting to emanate from it, wet spots appearing across her skirt where juices were flicking out against it.

I scanned the far-off clubhouse, saw the couple emerge with a staff member, point in our direction. We had a minute at most.

I pushed my mouth against Sienna's ear, licked her lobe, bit it. She moaned around my thumb.

"I wanted to bend you over on the golf course," I said, directly into her ear.

She made a loud, surprised moan.

"Pull your panties down and fuck you from behind, put my cock into your tight pussy."

She moaned again, high-pitched and drawn out.

"Rail your tight sexy body until you-"

Her mouth came off my thumb and she emphatically whispered "yes" and I felt juices flood around my finger and her pussy convulse as she started to orgasm. Her body began rocking against mine and I held her tightly, kept working her gently, maximizing her experience, my eyes fixed on the staff member advancing down the parking lot in a power walk, maybe thirty seconds away from us. And then Sienna moaned and sighed and her muscles relaxed, and I drew my hand out of her with a final squelch.

She looked up at me dreamily, I smiled, and I opened the passenger door and said, "In you go," and she fell back into the seat and I closed the door behind her and hurried around to the driver side, pulling my shorts down over my cock. I hopped in, started my car quickly, and whipped back out of the space. The front of my car swung out, and now the staff member was about ten yards in front of us, and I could see the reflection of my car in his sunglasses. I accelerated past him, giving him a cheerful wave through my tinted windows, and then we were turning out of the parking lot and turning onto the thoroughfare, scot-free.

Sienna started giggling in the passenger seat, looking back over her shoulder, her hands pushed down between her thighs, still savoring her orgasm and the thrill of escape.

"That was amazing!" she said.

"That was very close," I said, almost not believing myself how we got away with it.

I looked over at her. She was flushed, staring at me in wonder.

"Take you home?" I said.

"You better be coming upstairs," she said.

She leaned over my middle console, and put a hand onto the bulge of my cock, still pressing out against my shorts. I groaned, shifted in my seat.

"Yeah," I said. "I'll be coming upstairs."