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Looking for The Waitress

adreamer529

Super-Earth
Joined
Nov 1, 2018
Location
America
My name is Drew Smithson. I'm pushing 40 but very successful, and not bad looking for my age. Women seem to like the flecks of gray in my scruffy beard. I'm 6'1, with the body of a clearly former athlete - strong but not as toned as I was in my 20's.

On this random Tuesday night I am out at a super classy steakhouse - Del Frisco's. I have a really large group because I am treating all of my employees to celebrate our recent successes. Dinner is my treat. As everyone knows, for a group of 10 people at a place like that, usually you will get your own personal waiter... or waitress. That person works hard for about 3-4 hours and walks away for the night with a pretty significant tip - especially when we are drinking some expensive bottles of wine, like we are.

I'm sitting on the corner of the table, and its clear pretty early on that I'm the one in charge, the one paying the bill, since I order the wine and group appetizers. We have one main waitress for the evening. Of course she is nice to me, as anyone would to the guy who is clearly paying the bill for their one table for the evening. But there's something about our interactions that are extra special because I'm extra nice to her. Unlike most corporate men who oggle the waitress and let her serve them, I'm different. I do the little things to help her out. When we are ordering appetizers, I tell her to just get a little of everything and make sure everyone has enough - she can essentially charge as many as she wants. I order the expensive seafood tower appetizer, which will help with her tip, and in fact tell her to bring two so we don't have to reach over each other. I'm clearly not worrying about how much this dinner costs the entire night, wanting my people to be happy, which has the benefit of making our waitress happy. When its time to clear the plates, I've not only stacked my own plate, making it easy to clear, but I've gotten the rest of my group to clean up after themselves too. She is nice to me when we chat from the corner of the table, and I'm nice to her back, confirming we are her only table of the night, asking what its like to work there, and how we can make her night easier.

Of course the waitress is sexy as hell. I peg her somewhere between the ages of 21 and 25. I know she's 21 because towards the end of the dinner, I offer to share some of the leftover expensive wine with her, and even though she shouldn't, she does pour herself a glass that she hides as my one of my own, finishing it off over the course of 3 visits. Shes a short brunette with curves to die for, and the tight black tank top she's wearing clearly shows off some cleavage on purpose to help with her tip. Her face is made up to perfection, but not overboard, and she's also wearing a short black skirt that barely covers her ass, black stockings, and black leather knee high boots. All meant to attract the generally older men who will be giving her tips... but tonight, its really just for me.

I don't oggle her like other men, treating her with respect, looking her in the eyes and not blatantly checking out her body. Of course she sort of wants to, and I can't help myself when she leans over close one time to look at the menu, basically putting her cleavage on view for me to see. I look at them and then look up at her, and she's been watching me... wanting me to look at them, and smiles, happy that I looked.

There is one extra thing here though. I'm married. I clearly have a wedding ring on my finger, although that is not mentioned or spoken of in my interactions with the waitress at all. In a way, she doesn't seem to care. She knows her job here - keep me happy to get a good tip, whatever it takes.

It's now time to pay the bill. Will there be some message handwritten on it by my friend the waitress? Or is there nothing, and do I leave my number for her? Her shift is now technically over and I certainly have the rest of the night free to do what I want. What happens next?

(If you are interested in continuing this story, just contact me with the next scene and we will jump right into it. I play on email - adreamer529@gmail.com - and discord: adreamer529#0028)
 
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