Jack's Adventures 07: Jess 01

Maybe it's time for a little reminder of who I am.

I've spent a decade and a half in Los Angeles trying to make a career as an artist. In the course of things, I've met many beautiful women from all spheres of life. I've been lucky enough to sleep with a lot of them.

You can call me Jack. This is my seventh story.

This is the story of Jess.

Right out of college, I worked a summer at a chain restaurant by a popular Los Angeles tourist attraction. The shine that college puts on life hadn't worn off yet, and I had that early-20s feeling deep in my bones that I didn't really have to do anything and everything would still work out exactly how I wanted. So while this restaurant was an objectively terrible place to work, it ranks as one of the best summers of my life because I didn't have one goddamn care in the world. I spent the days getting blitzed by tourist business, then the nights getting blitzed with my coworkers.

My coworkers were a ragtag group, a coterie of lost souls nursing broken dreams, ranging in age from their late teens to their mid-40s. I'm ashamed to admit that even though I loved letting loose with them, I actively judged all of them, thinking myself superior, that I was the only true artist of the bunch. And sitting here years later - much older, somewhat wiser - I think, no I know, that on a moral and spiritual level I couldn't have been more wrong. We're all cut from the same cloth, some people are handed decks more stacked than others, there is no one true lifestyle that makes you better than everyone else.

But on a fuckable level?

Yeah, I was above them.

I had my way with the young female wait staff that cycled through our restaurant, their varying levels of competence meaning some only lasted a couple weeks before moving onto the next summer job. Usually I'd stake my claim the first night they'd join us all for a post-shift drink, my other male coworkers trying their best but the girls always finding their way to me.

I have multiple stories to tell from this summer, but we're going to start with Jess.

Jess was a Filipino girl, 21-years-old, very petite, maybe 5'2", with the regal face of a beauty pageant winner. Her skin was the color of caramel, her hair a dark brown with gold highlights. She always had it pulled back in a ponytail, showing off her gorgeous face, her smiling brown eyes, her bright white teeth. Her tits and ass were small but still big for her frame, and always pushed provocatively against her clothing. I knew from the moment I saw her I could absolutely manhandle her, and I made it my mission to prove myself right.

Her first week on the job we encountered each other sparingly, but I sensed a not insignificant amount of mutual interest. Some lingering eye contact, a bright laugh when I made a lame joke. While my other coworkers actively fawned over her or made fun of her, like kindergarteners with a crush, I played it casual, always there with an easy smile, reassuring her with my quiet presence.

Crossing paths with her always made my shift slightly better. She was always smiling, was forever optimistic, never said a bad word about anybody. When she looked at you you felt like you were the only person in the world, and you glowed.

She also was very bad at her job, racking up an unprecedented three walkouts in her first week. Management didn't give a shit about her sunny disposition. All they saw was lost profit, and it wasn't clear if Jess would make it to week two. If I wanted to sleep with her, I knew I might have to act fast or miss my chance.

We were both working on a Friday night, the entire staff overwhelmed by chaotic families and rowdy teens and bad tippers. I was standing near Jess in the service station when one of the servers, a skeezy guy (who willingly went by the name Scumbag) tried to convince her to come out after her shift. We usually took over a local dive bar on Friday nights, probably treating that staff as poorly as our customers treated us.

Jess was equivocating about joining us, likely because Scumbag was the one asking. I was filling a few sodas and I looked over, catching her glancing at me when Scumbag was mid-pitch.

"Come on, Jess," I said, "it'll be fun."

"You'll be there?" she asked.

I smiled. "Unfortunately."

She smiled.

"Okay," she said. "One drink."

"YES!" Scumbag said. He fist pumped. "Fuck yes, Jess!" And he turned and left the station.

I sighed, stacking my sodas on a tray.

"Isn't he something?" I said.

Jess looked down and pushed a strand of hair behind an ear.

"He is. Maybe a little too much."

As I passed her, carrying my tray, I leaned in conspiratorially, whispering: "Way too much."

She smiled, looking into my eyes, our faces close, and then I left.

Our shifts ended around the same time, and we sat in a back hallway waiting to close out with our manager. We traded brief glances and small smiles.

"Excited for the bar?" I asked.

"Very," she said. "You?"

"Very."

When it was my turn to see the manager, I turned to her and asked.

"Do you want me to walk you there?"

She lit up, and nodded quickly.

"Great!" she said.

"Awesome," I said. "I'll wait for you outside."

As we walked the few blocks to the bar, I asked her more questions about her life. She still lived with her parents, was trying to save up money to move out, but hadn't been able to keep a job long enough to do so. She hoped this restaurant would be different. I didn't have the heart to tell her I didn't think so. I told her how I was trying to become a filmmaker, and she was very excited by that. She started looking at me slightly differently, like I'd passed a quality test. Up against the likes of Scumbag, it wasn't hard.

We reached the dive bar and looked in the front window.

"Oh boy," I said.

"Oh boy," Jess said.

Scumbag was standing on a table, shirtless, chugging from a pint glass. Our other coworkers ringed the table, cheering him on. I looked at the next bar down.

"Do you wanna go in there instead?" I asked.

I was half-joking, but she said, brightly:

"Sure!"

So we hurried past the window and into the safety of the next bar.

And we proceeded to have a fantastic time. Jess was incredibly fun to hang out with, matching me over a couple beers, at one point ordering us tequila shots. We ended up playing darts against some regulars and she was a surprisingly wicked shot. When we won she hugged my torso and I hugged back, and we looked into each other's eyes...and I kissed her. She kissed back hungrily, and then we stopped and looked into each others eyes again.

"Are you going home tonight?" I asked.

"Not if I had somewhere else to go."

The noise around us faded. The world was just the two of us, looking into each other's eyes, wondering what the night had in store.

"How 'bout mine?" I said.

She nodded.

A half hour later we were in a taxi heading back to my apartment, vigorously making out in the back seat. I'm sure the driver was disgusted with us, but I didn't care. We were young, she was hot, we could do no wrong.

When we were deposited from the taxi, we ran up to my apartment. At this point in my life I was sharing a gross apartment with a couple roommates, but I thankfully had a bedroom to myself. This night no one was home, maybe also working late restaurant jobs, maybe also drinking with their coworkers. We rushed into my bedroom.

I closed the door behind us and turned. Jess was already on the bed, leaning back on her elbows. I ran and climbed on top of her, spreading her legs and dropping my hips between them, and we started making out. She tasted like stale beer and tequila, the taste of darts at a tourist bar. I felt her petite body writhing beneath me, her tits brushing against my chest, her crotch against mine.

She was an eager kisser, her lips really pushing against mine, her tongue running wild. I reached up and lightly grabbed her chin, and looked at her.

"Slower," I said. "Easier."

Her eyes were big and vulnerable. I kept holding her chin and kissed her lips softly. Once. Twice. Three times. Showing her the pressure to exert. Then I let go of her chin. She closed her eyes and kissed me softly.

"Better," I said.

My cock was swelling in my jeans and I started moving my hips, pushing its hardness against her pelvis. She moaned into my mouth and pushed her pelvis back against me, denim brushing against denim. I started moving my hips more quickly, rubbing the hardness of my cock rhythmically up and down against her crotch.

I reached down and put my hands on the bottom hem of her shirt and started lifting it. She took over, lifting her torso off the mattress and pulling the shirt off over her head. She was wearing a tan bra slightly lighter than her skin. Her shoulders were bony, her stomach flat.

I pulled off my own shirt and she looked up at me, then lifted herself up and planted her hands around my lower back and started kissing my stomach. I put my hands on the sides of her head, massaging her scalp with my fingers. She reached up and pulled off her hairband, and her hair cascaded in dark waves past her shoulders. She continued kissing my torso and I reached behind her and undid her bra. She shook out of it, I tossed it aside, and I looked down at her tits. They were b-cups, shaped like small oblong mountains, pointy with a curved underboob and hard brown nipples.

I cupped her breasts in my hands, easily encompassing them, and rubbed them in circles against her chest. She moaned and bit at my stomach, an actually hard nip that made me exclaim in surprise.

She looked up at me, smiling naughtily.

I immediately moved off of her and her smile turned to concern. I was now on my knees on the mattress next to her.

"I'm sorry," she said, her tone earnest.

I didn't say anything, just reached down and unbuttoned her jeans and shoved my hand under her waistband. She looked down in surprise, and then, as my hand felt under her panties, she looked back up at me, her expression unreadable.

My fingers ran through soft pubic hair, then I pushed one down between her labia. Her mouth fell open and I raised my other hand to the back of her head and gripped it. I started playing with her clit, rubbing it in slow circles. Her teeth clenched together and released again, and I felt her quickly grow wet. Then I moved my finger down and inserted it up into her pussy.

She gritted her teeth and let out a high-pitched whine, staring up into my eyes, her head still clasped in my hand.

"This is your punishment for biting me," I said.

She nodded very gently, her eyes wide.

I started moving my finger in and out slowly. Her hole was incredibly tight, and at that moment I didn't know how I'd possibly fit anything bigger in there. I started moving my finger faster, and she started whining again. Then I let go of her head and pushed her flat on the mattress, moved my hand around the front of her neck, and leaned down and took her entire left boob in my mouth.

Her whining moans had become incredibly loud, sharply piercing, and I was the glad the apartment was empty. I sucked on her breast, running my tongue over her nipple, my finger still working her pussy. Her arms flailed around wildly, sometimes going to the hand that was lightly pressing on the front of her throat, sometimes running over the front of my jeans, where my hard cock pressed out down my leg.

I briefly let go of her throat to reach down and unzip my fly and pull my penis out through it. Then I grabbed her hand and moved it to my dick, and then put my hand back on her throat. Her hand started to pull on my shaft in rapid strokes. I moved my mouth to her other breast. I sucked on this one now, running my teeth over her skin and her nipple. I sped my finger up, her pussy was drenched now. I figured she was close to coming, even if she wasn't saying anything.

I ran my tongue wildly over her nipple and increased my finger's pressure on the top of her pussy...

And she did come, her whining ending on a single high-pitched yelp. Her body jerked once, and then fully stretched, and I took my mouth off her breast to look up at her face. Her eyes and mouth were open wide and she was staring at the ceiling, moving her head slowly back and forth. She looked down at me, her hand releasing my penis. I pulled my finger out of her pussy, pulled my hand out of her jeans.

I stood up and, while I took my jeans off, she shimmied out of hers. I watched her naked body reveal itself, her gorgeous brown skin, her body thin and bony, but with a lovely suppleness to her tits and ass. I then stood next to the bed, my cock hard, and she stood on her knees on the mattress, putting her hair back into a ponytail.

She then leaned forward, dropped onto all fours, and extended her mouth toward my cock. I stepped closer to her, but our aim was off and she missed, the tip bumping against her cheek. I laughed, she smiled, then she course-corrected, turning her head and wrapping her lips around it. She moaned, closed her eyes, and, her head still turned sideways, pushed the end of my cock out against the inside of her cheek. She then dragged her cheek up and down over it for a second, before straightening her head and starting to bob back and forth, properly blowing me. She continued moaning, as if getting to suck my cock was the greatest pleasure in the world, the sound punctuated by each push in of her head. I ran my hands through the roots of her hair, then looked up her slight body to her ass poking up in the air, her cheeks perfect curves.

She pulled off my cock for a second and looked up at me, lifting one hand and jerking it off quickly.

"How was that?" she asked.

"Perfect," I said.

She smiled, put it back in her mouth, and continued. I'd lied, it wasn't perfect, her form leaving something to be desired, but it didn't really matter. It was a blowjob, and I was finding her eagerness to be very erotic, was loving ogling her body, sexy and tight.

After a couple minutes I put my hands on her shoulders and she took my dick out of her mouth again.

"Flip around," I said.

She turned on the bed and I put my hands on her waist and pulled her ass toward me, her knees ending up on the edge of the mattress. Her ass was small and firm, and I looked at her cute slit of a vagina, fringed with pubic hair. I remembered how tight her pussy had felt around my finger, and wondered how it was going to feel around my cock.

"Are you ready?" I asked.

She looked back over her shoulder and nodded.

I pushed my cock slowly into her pussy. She gasped and threw her head back, even though I'd hardly entered at all. I didn't know how this would be possible. It felt like I was trying to push my cock through a wedding ring.

I put a hand on my shaft and moved it back and forth slowly, trying to loosen up her opening, and then pushed in further. Only half my head was in and I saw her grit her teeth, saw her fingers clutch at the sheets.

I pushed her body forward and I mounted the bed on my knees behind her. I held her waist tight and pushed my cock in further. She whined, it was probably equally painful for both of us, and then, finally, my entire head was inside of her. We both exhaled at the same time and then laughed, and her pussy shook around my cock.

"Should I keep going?" I asked.

"Please," she said.

I pulled out ever so slightly and then pushed in again. Jess let out a high-pitched gasp, an "aiii," and put her hands up on the wall, and I held her tiny waist firm and kept driving myself in slowly.

A quarter of my cock was now in, Jess' breathing was slow and measured.

Now half of my cock, her mouth open in a silent moan.

The walls of her pussy were clamped like a vice around my shaft. I pulled out a millimeter and then kept pushing in, and one of her hands slapped against the wall.

I was three-quarters in, I pulled out slightly, I kept pushing in. The heel of her palm pounded against the wall, her head hanging down.

Finally, my entire cock disappeared into her pussy.

"Got there," I said.

She looked back over her shoulder, her body trembling.

"Now the fun part," I said.

She half-smiled, and I started moving my hips side to side, up and down, pushing my cock around every surface of her vagina. She moaned, and I felt things start to loosen. I started pulling my penis out, her walls and pink pussy skin gripping me tightly, and she closed her eyes, breathing deeply. Then I pushed in again, she let out a high-pitched gasp, I pulled out, pushed in, and I started to work into a rhythm.

I gripped her tight waist with my hands as I started properly fucking her. It would be an exaggeration to say my hands could fully encircle her waist, that my fingers could touch each other, but not much of one. I held her firmly as my cock started to pump into her pussy, faster and faster. Her hands were still flat against the wall in front of her, and she stared at the space between them and started yelping, her ponytail bouncing.

I moved my hands to her ass and placed them flat across each firm cheek, massaging them with my fingers. Each push of my cock felt incredible, my entire length being gripped and stimulated. I wasn't sure how long I'd last, so I wanted to savor every second.

I reached forward and grabbed her ponytail and pulled back on it gently. She arched her neck and her back, and I wrapped my hand in her hair and held it firmly. I fucked her like this for a minute, her yelps growing more and more ragged, her pussy growing wetter around my cock.

Then I dropped her hair, leaned forward and grabbed her around her upper arms and pulled her body up to me, my cock still buried in her pussy. I rested my chin on the top of her head and, my fingers digging into her biceps, held her torso back against mine, thrusting up into her, her ass pressed against my stomach. I then moved my hands to her chest, fondling both her boobs while holding her tight to me, and then pushed one hand down her stomach and started rubbing her clit. She started turning her head back and forth, her teeth gnashing, trying to bite me. I moved the hand on her tit up to her chin and gripped it, holding her head still.

"No more biting," I said.

But she wriggled her head quickly, too fast for me, and got two of my fingers in her mouth and bit down on them. I shouted in pain but then her tongue started to work around my fingers, and she started to suck at them, and any displeasure was forgotten.

We stayed like this for a minute, my cock pumping up into her tight pussy while I rubbed her clit and she sucked on my fingers, until I turned her away from the wall and we fell forward onto the bed and she was lying facedown, prone, me on top of her. Her face was on its side on the bed and she looked up at me, my fingers buried to the hilt in her mouth, as I continued thrusting into her. I raised myself up and put my other hand on the side of her head and held her firm to the mattress as I started fucking her faster and harder, knowing I was only seconds from coming.

She moaned around my fingers and started sucking on them faster, and I enjoyed one final moment of getting to hold her petite body down and rail her tight pussy. Then my orgasm swelled, and it was time. I pulled out, her pussy gripping me the entire way, and I held my cock up and came, shooting cum up her ass and back.

She let out some high pitched moans as I continued to rope her with my semen, and when I was empty I pulled my fingers out of her mouth. I fell over onto my back and lay next to her, both of us breathing deeply.

We made eye contact and I leaned in and kissed her. She started giggling.

"That was so much fun," she said. "Can we go again?"

"Absolutely," I said. "But I'll need a few minutes."

"Get me a towel, and when you're back I'll play with you."

"I like the sound of that," I said.