Jack's Adventures 02: Margaret 01

This is the second story.

This is the story of Margaret.

Margaret was the bartender at an Italian restaurant in Santa Monica that I'd frequently pick up deliveries from. The first time I saw her behind the bar wasn't the first time I'd been at the restaurant, but she was so beautiful that I acted as if it was. I could never forgo an opportunity to chat up a pretty lady, and Margaret immediately drew my eye.

She was maybe 5'6" or 5'7", in her early twenties, and possessed a striking Irish beauty. Her hair was dark brown, her skin pale. She looked like a slightly older version of the actress Thomasin Mckenzie, with sharper features and dark eyebrows, but the same eyes, light blue and doe-like. She was wearing a white shirt under a gray vest, the shirt unbuttoned to a few inches below her neck. As I approached and she turned toward me, I spotted a smattering of freckles across her chest. I was tempted by what I would see if could undo a few more of those buttons.

She smiled at me and I immediately sensed mutual interest.

"How can I help you?" she asked.

"I'm here to pick up a delivery," I said. "Is this where?"

"No, around the corner there," she said, pointing.

I nodded and smiled, but kept looking at her, taking a slight pause to put her on her heels.

"Anything else?" she said.

"Where would I pick up a girl?"

Her face broke into a goofy smile and she blushed scarlet, red running up her freckled chest past her neck and into her cheeks. She looked around guiltily, as if a superior, a manager, God, might admonish her for something. Then she looked down at her feet before looking back to me, unable to meet my eyes.

"That would happen here," she said.

"But?" I said, feeling it coming.

"But," she said, then looking into my eyes, "I would need to see you in here a few more times first."

"Fair," I said. "My name's Jack. What's yours?"

"Margaret."

I extended a hand, and she took it. I held her hand for a second. Her fingers were slender and delicate.

"Well, Margaret, then I hope I get more deliveries here. See you around."

And I turned and went to get the food.

On my way out of the restaurant, I passed back by the bar, deliberately keeping my eyes forward at first, playing with her. Then when I sensed her watching me, I looked over. I caught her eye for a split second before she looked away, trying to stop herself from grinning.

I knew I had her.

A few weeks later, I got another delivery from that restaurant, but she wasn't working.

A couple days after that, the same thing.

Then, after two more weeks, the fateful order came through.

I walked through the door and there she was. She had her back to me, her hair pulled back into a loose ponytail. She was bent forward over something and her slacks were tight across her butt, giving me a wonderful view of it. It was perfectly shaped, full and round, not too big nor too small for her figure. She looked over her shoulder, we made eye contact, and she smiled in recognition. She quickly turned and came over to the end of the bar.

"Hey," she said, her hands brushing some loose strands of hair back behind her ears.

"Hey yourself," I said.

She was shifting back and forth, and bouncing a little on her toes.

"Picking up a delivery?" she asked.

I nodded. She looked around, then leaned in toward me.

"If you'd like to pick up something else, I think you'd have a good chance," she said. Her big blue eyes were especially big right now. Achingly vulnerable.

I leaned slightly toward her.

"I would like to pick up something else," I said softly. "Would she want to grab a drink when she gets off work tonight?"

"She would. She's off at 10:30."

"I'll see her then," I said.

She smiled and nodded quickly, then turned and returned to the other side of the bar. I went to get my order and left.

Finishing up deliveries that evening was torture. I watched the time tick onward, wanting it to move faster but my constant attention dragging it even slower, as I imagined what Margaret would look like naked, as I planned what I would do to her in bed.

At 10:30 I was standing outside the restaurant. She came out the front door, still in her shirt and slacks, but the vest was gone, and one more button had come undone on her shirt. I could now see the pale freckled skin just above and between her breasts, which were more prominent without the vest tamping them down. Her hair was out of its ponytail, spilling down in dark waves over the front of her shoulders. We hugged gently as a greeting, and I felt her boobs push up against me, their size a pleasant surprise.

There were a lot of bars close to her restaurant and we started walking among them. It was a warm summer night but we kept close to one other, not talking much but feeling a casual intimacy between us. We entered an Irish pub. It was a busy weekend night and packed to the gills.

"I'll get us drinks," I said. "Will you find us a table?"

She looked around at the flood of people.

"I don't know if that's likely," she said. "How about a place to stand?"

I laughed.

"That works. What do you want?"

"Guinness?" she said.

I couldn't believe it and my face showed it.

"What?" she said, turning pink with embarrassment.

"A girl ordering Guinness," I said. "It's just...very hot."

She smiled, that goofy side smile again. She put her hands on my bicep, said "I'll find a spot for us," and turned away.

I pushed through to the bar, got us two Guinnesses, and then searched for Margaret. I found her sitting at a small table in a back corner, and she raised her arms like "can you believe it?"

"Amazing!" I said, sitting down across from her.

We then drank our Guinnesses slowly and chatted, speaking loudly to be heard over the din of the pub. We continued getting along smoothly, but the inability to have a quieter conversation was interfering with our chemistry. Once we'd finished our beers, I asked if she wanted to find someplace quieter and she nodded eagerly.

We perused the other bars but everything was noisy and overflowing with people. When it was obvious there were no quiet options around, I stopped and turned to her.

"I don't want to be presumptuous," I said, "and feel free to say no, but do you want to come back to mine?"

"Oh!" she said, her eyebrows rising. "Um-"

"I live alone, so it'll be quieter. I've got Guinness, or wine, or water, whatever you'd prefer."

She looked away, thinking. I had no desire to pressure her, but I was still worried she'd walk through the exit door I'd provided. Then she looked at me, confidently or trying to appear confident, and said:

"That sounds great."

We drove separately, her following me in her car. I was disappointed she wasn't sitting next to me, for us to do what I had once done with Selena, but I don't think that was in the cards anyway. This was going to be a different kind of game.

I let Margaret use my parking spot and I parked on the street, and we went up to my apartment.

I have a very well-appointed space, a sleek mix of modern and the old-fashioned, all dark browns and burnt coppers, and I could see she was impressed. And when she took a seat on my couch, putting one leg underneath her and lounging back on the dark red leather, I was happy to see it had made her more comfortable too.

While I poured us drinks from my bar cart (I switched to whiskey, she to red wine) we learned more about each other. She wanted to be a musician, a singer-songwriter, and had only been out in L.A. a few years. She'd been a bartender the entire time, and didn't necessarily enjoy the steady procession of drunken idiots but tolerated them for the paycheck. She seemed more at peace with people and the complexities of life than most girls I'd met, and this all made her even hotter. I brought the drinks to the couch and sat next to her.

She took a sip of her wine and looked over at me. I took a sip of my whiskey and looked back.

She wrinkled her nose cutely, and said: "I haven't done this before."

"Done what?" I said.

"A random pickup like this. I've always known the guy a while before we..."

"I get it," I said. "I want you to be comfortable. We'll go at your pace, and if you ever want to stop, we'll stop. If you ever want to leave, there'll be no judgment."

She nodded, exhaled, and her shoulders visibly relaxed. She sat back into the couch, looked at the ceiling, and took another sip of her wine.

"Picked up for random sex by a perfect gentleman, what are the odds." She gave me a playful side-eye. "Do you do this a lot?"

"A fair amount."

She nodded, and ran her tongue very quickly around her lips. She looked down at her glass.

"You'll take care of me?" she asked, her voice meek.

I put my whiskey on the coffee table and sat back against the couch.

"Come here," I said.

She took another sip of wine, a big one, and put her glass next to mine. She then scooted over on the couch toward me, until the sides of our bodies were touching. I reached up and touched her hair, then moved it back over her shoulder, revealing a smooth slender neck.

I leaned in, slowly, giving her time to stop me if she wanted. But she didn't, and I brushed my lips over the base of her neck, right at the top of her shoulder. She shuddered gently and put one of her hands on my thigh. I then kissed her neck, softly, once here, once there. She leaned her head away slightly, opening up more neck for me, and I kissed it again, holding it, sucking very lightly on the skin. Then I pulled away to look at her face and gauge how she was doing. She was staring at me with deep longing, her beautiful wavy hair framing her face.

I couldn't stop myself. I leaned in and kissed her full on the lips.

She responded eagerly, kissing back with gusto, tasting of dark cherry. Our bodies started to search for one another, our chests pressing toward each other, our hips angling up off the couch. While still kissing, I gently pushed her over onto her back, and followed on top of her. I put one knee between her legs and let it press ever so gently against her crotch, and she moaned and pressed it back against my knee, as if her pussy was straining to break through the fabric of her slacks. I then started moving my knee gently up and down, and she started to kiss me harder.

She grabbed at my neck, ran her hands through hair. She grabbed my shoulders, pulling down on my torso. She grabbed my lower back, raising her hips up, as I kept grinding my knee against her pussy. She started moaning louder, muffled against my mouth, then she broke away and said "oh my god...oh my god," and her body started to shake, an orgasm coursing through her. I kissed her again and she tried to push me away feebly but I kept my lips locked to hers, my knee still gently massaging her, until the shakes subsided.

Then I sat up. Her face was flushed and shocked. Her hands flew to it, covering it.

"That was so embarrassing," she said. "I came so fast."

"It's not embarrassing at all," I said. "Look at me."

She lowered her hands, just revealing her eyes, those big blue pleading eyes.

"It's okay," I said.

She nodded quickly.

Then I reached down and started unbuttoning her shirt. Two buttons revealed her cleavage, the inner curve of her breasts, and the strap of her skin-colored bra. Another couple buttons revealed a flat, sexy belly. It felt like I was unwrapping an incredible Christmas present. When her shirt was fully unbuttoned, I let the sides fall away, revealing everything underneath. I looked from her skinny waist to her cute belly button, up her abdomen to her boobs, which spilled out the edges of her bra.

She was looking at me lustily now, biting her lower lip, ready now for whatever I would do next. I reached under her and unclasped the bra, pulled it off her arms, threw it on the coffee table. I looked down at her naked breasts. They were beautiful c-cups, pillowy and perky, with fluffy pink nipples. I lowered my head and gave one nipple a soft lick, then moved over and licked the other. A quick intake of breath told me this was a pleasure spot for her.

I rose up and pulled my shirt off over my head. Margaret stared at my body and ran her hands over my chest and abs...then down over my belt buckle, over my jeans, to where my dick strained against the denim.

"I can tell someone thinks I'm sexy," she said.

"We both do," I said.

I unbuttoned her slacks and pulled them down off her hips, revealing lacy black underwear that were dark and wet over her pussy. I pulled the slacks down further, down her two pale slender legs until they got caught on her small, cute feet, and Margaret wriggled them free and I threw them to the floor.

I looked at her lying across my couch, naked except for her black panties, her body gorgeously proportioned and the color of marble, her dark hair falling loosely across her freckled chest. She looked like a statue of a Greek goddess, or a painting of a forest nymph.

I put my hands on her hips and pulled her underwear off, revealing a perfect little pussy, just a beautiful small mound, pink and shaved clean, that already glistened with wetness.

"I've been hoping you'd come back for weeks," she said. "I've stayed ready."

My dick was in legitimate pain now, so I stood up, unbuckled my jeans, and pulled them off. Margaret rose to her knees on the couch and put her hands on my briefs and pulled them down, my dick springing out at her. She giggled, and raised her hands to touch it, but before she could I pushed her onto her back again. She frowned, but then I put one hand on the outside of her pussy and brought my dick close to her face.

She had no more fear, no more hesitation. She opened her mouth and closed her lips around my cock, and I simultaneously inserted a finger into her pussy. She moaned and started to slowly move her lips back and forth over my head, then raised both of her hands and started to work my shaft, her delicate fingers twisting back and forth over it lightly. Her eyes were closed and everything was being done almost lovingly. It wasn't the best blowjob I'd ever received, but she was working my whole cock well enough, and with such care, that I was more than content. I kept exploring her pussy with my finger, it getting wetter by the moment, while I ogled the gorgeous shape of her nubile body, her raised arms pressing her tits together, those fluffy pink nipples seeking the sky.

I seemed to find a particularly good spot in her pussy, and after working it for a bit she broke off from sucking me with a breathy "damn." She put her hands flat on the couch and closed her eyes briefly as pleasure coursed through her. Then, as if determined not to come again, she opened her eyes and looked up at me.

"Please fuck me already," she said.

With those eyes I would've done just about anything she asked. I took my finger out of her pussy and put my arms under her and flipped her onto her stomach, then raised her onto her knees and positioned her so she was facing the back of the couch. She put her forearms on the top of the couch, and arched her incredible, perfectly round ass up into the air. She craned her neck to look back at me, hair curtaining the side of her face.

I lined up my cock with her perfect pussy and started to push it in slowly. She was tight, and I watched her mouth open briefly in pain.

"You're so big," she breathed, her hands going up to the wall and pressing flat against it.

I took it slow, not wanting to hurt her. I teased her with just the tip of my cock for a minute, warming her up, and then I pushed deeper. She gasped as I got fully in, my girth pushing out against her walls, her body bucking forward. I put an arm under her breasts and pulled her torso up to me, her back now a gentle curve from her ass to her neck. She looked back at me and we held eye contact as I started to fuck her, again starting slow, but slowly picking up the pace and the vigor. Her mouth was hanging open, her eyebrows were raised, and her eyes were begging me to keep going, so I sped up even more, until I was pounding her pussy hard and fast and she was yelping with every thrust. I felt so powerful having this beautiful creature completely under my control, watching total pleasure flit across her face in all its forms. At one point she leaned her head back onto my shoulder, her eyes half open, and she briefly became a ragdoll, my arm holding up her torso and caressing her breasts as I plunged my cock in and out of her tight pussy, her perfect ass slapping against my stomach.

After a few minutes, I bottomed my dick out in her pussy, then held her face close to mine, her hair bunched in my hand, her ear close to my mouth.

"I want to fuck you while looking at your perfect tits, at your perfect face," I whispered.

I pulled out of her, my cock coated in her juices, and put her down on her back again. She stared at me in breathless awe as I got on my knees in front of her and lifted her legs up slowly, testing her flexibility, until I was able to put her knees over my shoulders. I then lowered myself over her, pressing the top of her thighs to her stomach, and laid my penis across her belly. Her eyes widened at the sight of it, imagining how deep it had been going in her pussy, and she looked up at me.

"I'm gonna give you every inch of this cock," I said, "slowly, no matter how long it takes, until you come again."

She nodded quickly, biting her lip. I dragged my cock down her belly, leaving a glistening trail of my pre-cum and her juices, and slowly inserted it into her pussy. She moaned and I kept going, slowly, making sure I didn't go too deep. We both looked down at my wide throbbing shaft penetrating her small tight pussy in the gap between her slender legs, until I lightly grabbed her chin and pulled her head up, so she was looking right into my eyes. We stared into each others souls as I kept giving her my cock slowly, methodically, grinding up against the top of her pussy to stimulate her clit as well.

I don't know how long we were like this. I think we both got lost in each other's eyes, becoming nothing more than pleasure machines, me to fuck her, she to be fucked by me. At a certain point she said, or maybe just breathed:

"I'm going to come."

"Me too," I said. "Where can I come?"

"Inside me. Please."

A second later her body started to spasm, her shaking legs still pinned over my shoulders, her mouth open wide and those blue eyes staring at me. And then my cock tensed inside her and I came, shooting loads deep into her pussy. We both vibrated there together, completely open to each other, until our orgasms finished.

I slowly pulled out and she stayed splayed on the couch, her slender legs akimbo. As I cleaned up, she stared at my body, one finger lazily playing with her clit. When I was done, I went back to her, leaned down, and kissed her, slow and full. When I pulled away, she looked up at me.

"How was I?" she asked.

"Incredible," I said.

"Maybe we could do this again sometime?"

I looked at her, confused. Confusion then crossed her face, as she wondered if she'd misread the situation.

"What?" she said.

"You're acting like tonight's already over."

She smiled, and blushed.