I was working as a real-estate agent and one time I asked out a flirtatious secretary for drinks on a tuesday after work. Her name was Kelly, and she was cool, and smart, but a little trashy. We got to the restaurant late because I had just done a closing. And neither one of us ordered very much to eat, so when the drinks hit us, we started getting drunk pretty quick. I wasn’t a drinker. And Kelly was… well Kelly was Kelly.
After about three drinks, Kelly had to go “powder her nose,” and when she did, the waitress came up and asked me if  I needed another drink, so I asked her to bring me another tequila margarita; no salt on the rim.

I hated that, messy. And I couldn’t be bothered with the lime either.
Before she left the waitress mentioned that had seen me before,  this pseudo sports bar was a familiar haunt, because it was close to the office where I worked. Their food was a step above the other fast-food restaurants, that had drive-thou’s, plus they had WI-fi, so a lot of times I would work there or meet other agents, but not clients. If it wasn’t too busy, I would just work thru my lunch. Real common.

You have to understand, being a Real-Estate Agent is not a 9 to 5 job. You have to arrange everything around your clients schedule.  You could work days, afternoons, nights, or a combination of all three, and this night was no exception.
I looked at the waitress for the first time and then I recognized her. She was quite striking, young, attractive, but she had a hard look about her, not angry but an intensity that really drew my attention, and she kept it.
She was full-figured and she wore her blonde hair up, the way I preferred a woman too. She might have been the bitchy prom queen back in high-school, who would never have given me a second glace, but we weren’t in high-school anymore.

I had ten years on her easy, fifteen wouldn’t be a safer number, but that didn’t seem to bother her any.
“Yea, I’ve seen you too, but I don’t remember you ever being my waitress before, I think I would have remembered you… “Leigh,” as I glanced at the large swell in her uniform top to read her matching name badge.”
“Well your one of the few people who comes in wearing a $500 suit, every time he dines, she said with a straight face.
Actually the suits were closer to $1000, because I had a friend who worked as a salesman at a higher-end Men’s Apparel store, and he always gave me his employee discount.

“And you tip well, she said.”
“Thank-You, for the compliment, I replied, but its only for work, I’m a Real-Estate Agent, and the office is right over there I said, pointing to the building outside of our tables window, otherwise I would just wear street clothes just like everybody else. I tip well when I can afford to do so, so don’t be too impressed.”
“Are you a good real-estate agent, she asked.”
“I’m okay, but I wonder if you would have noticed me without me wearing my suit, I said.”
“I think I would have, she replied.”
“I doubt it, I said.”
“Why do say that, she asked?”
“Because up until now, you never went out of your way to say, “Hello” or try and make an effort to get my attention, or make it a “coincidence,” that you just happen to always be my waitress no-matter what section I’m sitting in, that’s why, I said.”
“You always looked so busy, I didn’t want to be rude and interrupt you, she said.”
“Are you trying to tell me that you have been interested in me all along, I asked?”
“Maybe, she replied, looking away.”
I had to laugh.

I was cute, but I wasn’t that cute.
“Why did you decide right now while I’m on a date with another woman to let me know this, I asked?”
“Because I don’t want you to wind up in her bed tonight, she said.”
Now she had my full attention.


I just don’t think she’s right for you, Leigh replied casually as if she were a friend looking out for me.

If she wasn’t hotter than hell she could have NEVER gotten away with this.

But she was.
“Is that any of your business, I asked?”
“There’s a certain way I think of you, and if you slept with her, then it would tarnish that image, that’s all she said.”
“Suddenly whatever she was saying was direct enough, and inappropriate enough to sober me up at the same time.”

None of her business who I fucked.
“Well, I’m sorry I don’t live up to the expectations of a waitress, I said.”

I shouldn’t have said that, you never insult the people who serve you your food, no matter what they say or do, or send it back either, they spit in it.

Or worse.

It would make you sick.

“I couldn’t schedule all my classes in the morning this semester, or the evening this term, and the classes I need for my Masters are only offered once a year, I had to find a job that allows me to have a very flexible schedule, she explained.”
“Just the same you shouldn’t be so judgemental, I said.”
“Is she a friend of yours, Leigh asked.”
“She works with me at the office as a secretary, I said.”
“So if you sleep with her first, and then we started
dating, I would always feel threatened by this woman that you had a history with, especially now that I know you see her everyday, she said.”
“Wait a minute, I think your getting way ahead of yourself Leigh, first of all, I don’t like a relatively unknown stranger telling me who they approve of disapprove of me “seeing,” In fact your way out of line girlie.”

“Look get rid of her, and I can make arrangements to meet you tonite instead, she said, I won’t go to bed with you, but we can talk and see if we have anything in common.”

Her green eyes held promise, they were compelling.
“No, I shook my head.”
“Why not, she asked confused?”
“Leigh, your better looking than she is, and I would be crazy not to take you up on that, but that would be incredible rude on my part, to say the least, because I already have plans with her, which may or may not involve us getting together tonight, and I’m not going to blow her off. I would never do that to a woman that I’m currently on a date with.
“Your never going to be serious with this girl anyway, even if you sleep with her, and you’ll probably regret it,
you shouldn’t get involved with somebody you work with, and when it dosen’t work out your going to regret that you blew your chance with me, Leigh said.”
“That’s not the point, I’m not going to drop her just because you told me too, there’s a certain code a man has to live by, I don’t know what its called: rules, ethics, morals, none of the above, all of the above, but I’m not going to change my entire world and flip it upside down, just because you shake your ass down the aisle.
“I was hoping that maybe you would show me a glimpse of who I thought you were, she said.”

I am.

Too bad, she said.

Was this crazy bitch testing me, I thought to myself, I couldn’t help wondering what she was like in bed. And I was beginning to weaken.
“Look, why don’t we make a date for another time, another night, not tonight, and I will give you the same courtesy that I giving her, I said.”

Just then Kelly came up from behind  her, oblivious,

“Are you ready to go baby, she asked?”
“Yea, I think I am, you know what Ms. (gesturing to Leigh), just cancel that drink, I said. I’ve think I’ve had enough.
About three days later I called the restaurant and asked if Leigh was working that day, and they said, she wasn’t, so I asked when she was working again, and the time she started.
Two days after that I came in for lunch and asked the hostess to sit me in Leigh’s section specifically. After I sat down I ordered a coke, and waited for her. To my surprise another waitress showed up instead to take my order instead, and this was not by accident.
I figured that Leigh saw me and had another waitress intercept me, so I told the second waitress that I changed my mind and that I was going to sit at the bar instead where Leigh was working that day.
I grabbed my stuff and sat down on one of the stools, still holding my leather briefcase. Suddenly Leigh came out from the back of the bar, and before she could say a word, I told her that I wanted to order a drink, and I wanted to talk to her, I had caught her off guard.

Or so I thought.
“Yes sir, she said when she returned with my drink, as if she had never met me before, what did you need to talk to me about, she asked?”
“The other night, I mean last week, I said.”
She shook her head as if she had no idea what I was talking about.
“When I came in with Kelly the redhead, I ordered the margarita’s right before you guys were closing, I said.”
“Is that the drink you’d like to order now, she asked?”
“No, I’m working, I came in to finish what I wanted to ask you that night, I would like to see if you after work, if your not busy, I asked?”
“No, she shook her head.”

“No your not busy, I tried to clarify?”

“No, I’m not interested, she said.”

“Well you said you were the other night, so why don’t you give me another chance, I asked?”
“Sir, I have other customers that I have to wait on, I can’t stay here to explain why I do not want to go out with you, but I would be happy to get you another watress from here out if that would make you more comfortable, Leigh said.”

I already knew the outcome but sometimes you have to go thru the motions.
That’s up to you I said, drinking my coke and opening up my laptop.

I didn’t see Leigh again until the other waitress waited on me, but I threw a “Jackson” on the counter just the same.
I came in twice afterwards and tried to approach her again, but my reception was just as cold, or colder if that was possible, until the manager asked me If I had a problem, then I stopped going there altogether.

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