Jack's Adventures 02: Margaret 01 - Sex Stories

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 ...