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WTWG Chronicles | Ch. 17: "MILF Pt. 1"

July 13, 2018

Worth The Wait Guy Chronicles Ch. 17

"MILF Pt. 1"

JimDre Westbrook  

 

A few weeks went by and Stephanie and I were having great times on Match, even though she didn't live in Vegas. Stephanie lived in Oklahoma but was actually from Vegas, so my living in Vegas didn't draw any red flags for her. Stephanie was headed to Vegas to see her family and felt it would be the perfect opportunity to meet one another for the first time. I happily agreed that it was right on time to meet Stephanie and couldn't wait to see her in the flesh. According to her Match profile, Stephanie was a tall, short-haired, slender, biracial woman who was a few years my senior. She reminded me of a vintage Halle Berry (think Boomerang or Strictly Business) - Stephanie was gorgeous.

 

 

 

On the night we met, I had to report to work at the nightclub. I worked as a VIP Table Busser on the Las Vegas Strip. The job wasn't glamorous but it did have its perks. Stephanie and her friends wanted to party over the weekend and I knew I could hook them up with a comp table and free bottle of liquor at my spot. Stephanie and her girls agreed to the free offer and it was on. My manager even let the girls sit in my section so I could take care of them.

 

 

 

Before the club opened, I made sure I had enough cologne on and fresh breath for Stephanie. I was pretty excited to meet Stephanie and her friends and wanted to show them a good time in Vegas. Once I met the girls, Stephanie immediately stood out from the pack. From a physical standpoint, she was as good as advertised. Stephanie definitely had the Halle Berry thing going on.

 

 

 

 

After I set up their table, we spent time chatting until I left work early - we were slow that night. So, I took advantage of the slow night and decided to party with Stephanie and the crew. Lucklily, I didn't drink so I knew I wouldn't get too carried away but I was about to get it in!

 

By the end of the night, Stephanie and I were making out on the dance floor and really feeling this match.com thing. After spending an hour on the dance floor, Stephanie and her girls were hungry and I offered to take them out for a late dinner. We went to the local wing spot because they wanted some chicken wings and fries. After we laughed a lot and straight killed the food, it was getting late. I was starting to fade but looking at Stephanie made me alert every time I felt like dosing off. Man, the things we do for the opposite sex I tell you. When sleep should have been the only thing on my brain, I couldn't help but to wonder "how far could I take this without having sex?"

 

So, after we dropped off her friends at the hotel, I walked Stephanie to her hotel room. Before we stood in front of her door, I already knew that I shouldn't have gotten out of my car. Big mistake. I was trying to be a gentleman but I knew it was the wrong move that night. She invited me in, and of course, I accepted her invitation. Before I knew it, we were back to kissing, touching and rubbing on each other like were husband and wife. See, this is where curiosity and a lack of discipline and judgment fail you every time. I was wide open again - I was at the point of no return. My only misson at the moment was to please her and I only knew one way to make it happen.

 

 

 

You remember that crazy rule I had? The one where I only went down on a girl if she was my girlfriend (Natali)? Yes, that one. Well, I broke it that night. I had to find out if I could work the same magic with Stephanie like I used to with Natali. Natali and I had established a certain level of chemistry, so when oral sex took place it always ended in climatic fashion. I wanted that same exact feeling with Stephanie but I didn't get it, y'all. Though she thoroughly enjoyed it, Stephanie didn't respond the same way Natali did. Because of it, I was disappointed and shook. Did I lose my touch? Was she used to better? Maybe I'm just too tired?

 

After I finished, I didn't know what to think of myself or my situation with Stephanie. I'd never been in this position before. I felt like a total loser. I felt like a complete failure. I felt like a big dummy. I needed a win in my book and this definitely felt like a loss. I was so disgusted with myself that I hadn't thought about how Stephanie felt about the situation.

 

I wonder if she's going to speak to me ever again?

Or was she going to ghost me because I was something like a one-night stand?

Yo, how in the heck did we even get here? Smh.

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