LUCKY |Modern Sugar Daddy AU|

Shared Nostalgia

The Arrangement 

Chapter One: World's Worst Sugar Baby 

The perfect sugar baby is gorgeous and perky with a bright, fake smile and the ability to completely disconnect from any temptation of attachment to her sugar daddy. She can spend nights and weekends at her sugar daddy's home, she can meet his kids and learn about his past, and through it all she doesn't fall for him, even if he's attractive. The perfect sugar baby is a lot like my closet friend, V, who introduced me to the world of arrangements. 

In my experience, and the experience of those I've interviewed, the title of sugar baby tends to be looked down on in day to day life. If the woman checking out your groceries asks you what you do for a living and you say 'I'm a sugar baby', the conversation is doomed to end almost immediately. 

The reality of being a sugar baby is that it feels like dating, only you have to try a little harder. Sometimes I was nicer than I really felt. I always dressed up and looked presentable. I spent my time with him trying to guess what he needed, so that I might fit into that mold of his 'ideal' partner. Being a sugar baby is fun, until it's not.

I met him in a low-lit bar in November. V's sugar daddy at the time was kind enough to help me find an arrangement at a work event. I was sitting at the bar, fully prepared to meet a series of balding, lonely, slightly pathetic yet utterly rich, men in boring suits. Imagine my shock when instead I found someone young and gorgeous. For the sake of discretion, I will call him a different name--Ben. I once promised that if I wrote something about him, I would use a name he would hate. He said he wouldn't expect anything less of me. So apologies to Ben, who's going to hate being called Ben. You can't say I didn't warn you. 

I knew Ben was nothing but trouble from the moment I saw him. With his well-tailored suit and over 10k watch, he was too handsome for his own good. Ben's hair must be the most distracting thing about him, and when I first laid eyes on him I couldn't stop staring at his collection of dark waves. 

When I look back at my first impression of him, it all seems like a different world. He was cocky and arrogant, uncaring and cold. I was naive and scared. I'm still scared most of the time, but I'd like to think I've gained some knowledge since then. 

At first, I truly believed Ben didn't like me. He wasn't much of a conversationalist. He still isn't. And while I was impressed by his customized Porsche, I was disappointed by our lack of immediate connection. Despite our lame conversation that first night, he still gave me his card and said to call. 

And I did. I called. I went over to his apartment that first night, wondering if things were going to get intimate right away, or if these things usually went slower than that. A part of me was nervous he was some sort of serial killer that got away with his crimes by paying off the people in charge. The actual outcome of the night was some mixed signals and tense conversation. After that night, I started to become curious about Ben and who he really was. I could sense a facade of disinterest he was using to hide something else within. For the first month, I'm not sure he really got past that stage of pretending with me. There were tiny steps forward, glimpses of a softer side, but nothing truly exciting. 

And then we broke it off.