Sugar Daddy - Chapter #1 - Free To Read

3 Years ago

Ohmigod, what am I doing? I stood in front of the massive oak double doors, my knees trembling as I smoothed out the front of my short, tight, and slinky black dress. The restaurant was nice, extremely fancy, and I was extremely underdressed with so much thigh and cleavage exposed. That was the point though, to put the “goods” on display, as Jazmin put it.

She had talked me into this who ordeal. Jazmin had also told me she could get me non-sleazy clients if I actually wanted to go through with it. It’s just a date. I reminded myself. No money would change hands unless I liked him, and no sex was happening tonight. I had never met Mr. Hatzistefanis but based on his photos he was pretty hot for an old guy. Jazmin said he was nice and liked even more discretion than her usual sugar-daddies, but I still wasn’t sure about this whole thing.

Just as I took a deep breath and reached for the handle the door opened and I leapt backward. A laughing couple came out and apologized as they wove around me. The man glanced back briefly, giving me a once over with a cocked eyebrow. They know, holy shit. Was it that obvious? Would everyone know? As if on command my phone buzzed to alert me my phone bill needed to be paid. I closed my eyes for the shortest of seconds and steeled myself, stepping through the doorway and smiling politely at the maître ‘d.

The well-dressed man narrowed his eyes at me as I approached and my heart jumped into my throat. He knew I didn’t belong here too.

“Hi,” I greeted shyly. “Um, my name is Chloe, Chloe Jamieson, I’m here to see Mr. Hatzistefanis?” I said it like a question and I immediately wanted to kick myself for not sounding more sure of myself. “Alexander Hatzistefanis,” I corrected.

The server’s eyebrows shot up and the look on his face became incredulous as he gawked at my exposed skin. I really needed to try harder next time, I don’t think Mr. Hatzistefanis would appreciate me looking like I was trolling for a hot date if he wanted discretion. Whatever the server might have thought, he still composed himself and guided me down a narrow hallway to a private dining room. The confined space was all dark burgundy walls, black carpet, and warm yellow up-lighting from the sconces. I felt like I was about to walk into the Dragon’s Den.

“Here you are, miss.” He put so much emphasis on the last word I thought he would spit everywhere.

I stepped into the room and felt my stomach plummet. The room was painted a royal blue with gray wainscoting, dark hardwood floors, and a low hanging chandelier. But the man sitting at the circular table was most eye-catching thing; he was older, obviously, his hair was black with shots of silver and just long enough to be a little floppy, his beard was trimmed to little more than stubble, and he was tall. He was sitting but as he straightened and then stood up, I felt like a child. It’s because he’s like, as old as dad. Maybe older. He was Robert Downey Jr. type of hot though, so I wasn’t worried about that.

I stood rooted to the spot, watching with wide eyes and parted lips as he strode confidently towards me. My hands were clammy, and my heart in my throat. I was really doing this; I was actually about to introduce myself to a man looking for a sugar baby. My parents are going to kill me if I don’t die of nervousness.

“Miss Chloe,” he greeted. “It’s lovely to meet you, I’m Alex.”

My mind was blank and I’m sure I looked pretty stupid as I shook his hand with my mouth hanging open, floundering for words. “Um, hi, it’s nice t-to meet you.”

Alex smirked but he quickly rubbed his jaw to mask it. He gestured to the chair and slid it out for me. I’d never had someone do this before. I sat and quickly hid my trembling hands in my lap, he took the spot across from me and I had nowhere but to look but his dark eyes. The glimmering light from the chandelier reflected across the wine glasses and porcelain, giving the room a dream like feel.

“You look nervous, are you alright?”

No. “I’m sorry,” I blurted. “This is just new. I’m not sure what Jazmin told you but…” I trailed off and gestured helplessly.

Before Alex could reply, a woman in all black bustled in with a bottle of red wine. I didn’t drink wine, it wasn’t usually what was offered at my friends parties. But he was paying, and I wasn’t about to complain. Though I probably would have to tell him I wasn’t legal to drink in the state of California.

She smiled politely and poured us glasses before setting it on the little side table and excusing herself.

“I’m sorry I didn’t ask what you wanted, the menu is prix fixe but if you don’t like it, I’m more than happy to take us somewhere else,” he offered apologetically.

“No, no, it’s fine, thank you though.” I’d already looked at the menus online, as long as he didn’t order me the liver, I would be fine. I reached for the wine and took a tentative sip.

“Is this your first time?”

I choked on the wine. Very ungracefully. Smooth. Now start giggling and tell him that you aren’t that kind of girl. “Y-yes. I’m new to this whole thing, and nervous so it’s great that you ordered because I would’ve taken forever—” I stopped and clamped my mouth shut. I was talking to fast and saying too much, I was totally blowing this, and I barely been there five minutes. “Sorry, I’m not trying to be a complete weirdo right now.”

“Someone knows you’re here though, right?” he demanded more than asked. “You made sure to tell someone where you were going. Like Jazmin?”

I shook my head, my tousled blonde beach waves swishing around my shoulder. “No, I just kind of… did it… I guess.” Why did I tell him that? That was like, rule number one to not get kidnapped by your date.

He tsked. “It might help your nerves if you text your friend, Chloe,” he said more gently.

I don’t know why I listened to him but I did, and instantly Jazmin texted back an affirmative – she would check on me in an hour. And Alex was right, it did help some of my nerves. Just as I tucked my phone away the waitress returned with our plates. The food was complex and artful looking, I was almost afraid to ruin it.

“So,” I began as I picked at my plate. “Can I, um, ask you what exactly you’re looking for in a—in a uh…” I trailed off and chewed on my bottom lip, not sure how to phrase it.

Thankfully he laughed. “A companion?” Alex offered. “It’s not complicated, honestly. I just travel a lot, my wife and I have been separated for about two years now, I like to have company on my trips. Discreet company, I usually refer to women I travel with as my assistants. I need someone with a lot of free time and is willing to put a certain effort into her appearance.” He cringed as he said it and it made me smile. “I’m very sorry, I didn’t mean that in a rude way. I meet politicians and businessmen and I prefer to have my assistants well-dressed and made-up whenever we’re out.”

Okay. That’s not bad. “And the other stuff?” I wanted to stab myself with the fork, I was talking to a grown ass man, I should be able to say sex.

To his credit he smirked and glanced up at me, his eyes glittering. “That doesn’t need to be discussed tonight, I have no intention of trying to pressure you into anything and I certainly don’t expect anything right away.” He paused long enough to have another bit of the veal. “You don’t have to be so clinical. Tell me about yourself, your hobbies, what do you like to do?”

I swallowed my mouthful and thought on it for a minute. I didn’t think he was supposed to care but he seemed genuinely interested. “I live with my parents, I dropped out of university last year, but I was doing journalism, right now I’m getting into photography and blogging. It isn’t like a career or anything but it’s fun and I really like seeing all these people read my poems.”

“You write poetry?”

I nodded eagerly. “I do. I studied a lot of John Keats and William Blake in high school, it just sort of stuck with me. My mother hates that I focus on it so much, she wants me to go to Greece to stay with family and work with my cousins, but I want to stay in the city. Poetry doesn’t exactly pay the bills…”

Alex pushed his plate away and leaned across the table with his arms folded. “Would you ever share your work with me? I wouldn’t mind seeing it.”

I knew my face lit up like a Christmas tree based on the way he smiled back and his eyes kept searching mine. “Of course! And um, yeah, I have a lot of writings you could read. Do you like poetry?”

“I do, I confess that I don’t have much time for it lately, but I do enjoy the classics,” he said happily. “I focus most of my free time on woodworking, my father used to build clocks and he taught me to as well. You said your family is in Greece?”

“Yeah, my mother’s side anyway. Most of them are in Athens.”

His smile grew wider and I couldn’t help but return it. “Mine as well, lovely place really. Have you been recently?”

“No,” I said remorsefully. “I haven’t been since I was a kid.”

His face fell a little. “A shame, it’s quite stunning, I’m sure you’d love it.” Alex paused and a wistful look crossed him face as he poured himself another glass. “Perhaps you and I could go.”

Oh. I could swear that he could hear my heart, it was beating so loud. “That sounds amazing actually.” There was an elephant in the room that neither of us was addressing though and I knew he knew it.

As if he could read my mind, he cleared his throat. “I have to ask; you said you were new to this… Have you travelled as a companion before or anything of this sort?”

I shook my head again. “No. This is my first date like this I guess.” I had to bite my tongue on the virgin joke, I didn’t know if he would like it or if it would even be funny.

Alex visibly paled. We sat through another few awkward minutes as the waitress came for our dishes and then brought the next course. “Why did you come here tonight?”

Because I need money and I thought I could do this. I wasn’t so sure anymore, but I certainly wasn’t about to run out the door. “The obvious reason, I guess.” I paused and smirked at my now empty plate. “Why do actually want a companion?”

“Excuse me?”

“You heard me. Why do you actually want to pay someone my age to travel around with you?” I allowed myself to glance up at him and we locked eyes. The music that had been softly playing over the speaker seemed to drift out while Alex stared me down, I wasn’t going to crack though, I wanted a real answer.

“I can’t meet women easily,” he said after a moment, not breaking the eye contact. “I find it difficult. My money is attractive and using it from the get-go makes me more comfortable.”

“So, you think all women are just after your money?”

He couldn’t hold my gaze anymore and smirked. After a minute he started to laugh and leaned back in his chair. “Oh, you are a treat, aren’t you?” He shook his head and crossed his arms as he continued to chuckle. “No, I don’t think that, but I am paranoid, and it makes me feel better to know the money is upfront.”

“That way your trust isn’t broken.”

“Exactly. I know you’re here for money, you know that I want the trappings of a relationship without the fear that you’re faking it. Because, quite frankly, I already know you’re faking it and then my feelings won’t get hurt.”

“Including sex.” No sooner had I said it than the waitress came back for our plates. My face flamed and I looked down at my lap guiltily. She came back a moment later with dessert and we thanked her.

“That is my deal breaker,” he agreed. “I won’t push you; I won’t ask you to be available every second of the day, but I want a relationship that involves sex.”

I nodded and pushed my spoon around in the chocolate sauce, making dainty swirls. “How much?” I asked finally.

“Two thousand a week.”

A week! I almost started crying at the table. By the end of the year I could pay off my school debt and easily move out of my parents. I could keep writing fulltime and not worry about the awful waitressing job at the diner.

“I have expectations,” he reminded. “I can send you photos or put you in touch with a stylist, but you need a variety of gowns and jewellery for my business, and you need to be regularly working out along with getting hair and nails done.”

“What exactly do you do?”

“Real estate mostly, I broker sales for land and properties among many politicians and government figures around the world. I also own a contracting company, but I don’t do much, my son is the one that controls that.”

“You have a son?” I asked, shocked.

“I do, but he really isn’t someone I want to talk about.” Alex paused and downed the rest of his drink. “That’s my other deal breaker – I don’t discuss family, it’s not important and I keep these lives separate.”

I nodded. I guess that made sense, it would probably be weird to tell people that you were paying someone for a fake relationship. “Can I ask one more personal thing?”

“Of course.”

“If you aren’t fully divorced from your wife, does she actually know about this?”

“She does,” he confirmed slowly, as if thinking on his next words. “She doesn’t know their names, she doesn’t ask for details, but she understands that I have needs and this suits it for me. She’ll be getting married again sometime after the divorce is finalized and I’m happy for her.”

That was actually pretty cool of him if he was telling the truth. At least he wasn’t mad at his wife for moving on. I was pretty certain that I would’ve slept with him without the money; he could’ve passed for thirty-five and we were able to talk so freely that we quickly lost ourselves in conversation.

Alex fell into realty, he didn’t pursue it, his relationship with his family was strained like mine, and he had a passion for the arts. If I was being honest with myself, this guy could probably charm his way into my panties if we just met in a bar. I had no idea why he said it was so difficult to meet women.

We kept drinking and chatting and before I knew it, it was nearly one in the morning. “Oh my gosh,” I whispered as I glanced down at my phone. “We’ve been here for four hours.” I started to giggle and covered my mouth. My cheeks were flushed from the wine and I realized that I was somewhere between slightly drunk and mostly tipsy.

“Have we?” Alex asked, startled. “We can go if you like, I understand if you want to get going.”

I shook my head a little to enthusiastically. “This is dumb, but do you want to go get coffee or something? Somewhere just a little less formal maybe?”

He laughed and butterflies filled my stomach. He had a nice laugh, hell, he had a nice everything. “That sounds wonderful, let me have the car brought up.”

Somewhere between Alex getting the cheque and finding our way to the waiting chauffer, I texted Jazmin to say that everything had gone really well and now we were going for coffee. She seemed pleased and promised to check in again later.

The only place we could really find that was open was a hipster cafe in the arts district. It was pretty cool with the exposed brick and general steam-punk sort of theme.

“I got you a cappuccino, I think? I’m not sure, they called it something weird but it looks like a cappuccino,” he said and placed the cup in front of me.

It actually looked like a macchiato, but I wasn’t about to correct him. Instead I just thanked him and tucked my feet up on the bench seat. “You know,” I began, pausing to take a sip. “You’re actually pretty normal.”

“Uh, thank you?” he offered with a cocked eyebrow.

“Well, okay I know how this sounds, but I didn’t expect…” I broke off and gestured to him as if it was the only explanation I needed.

He smirked and threw his arm over the back of the chair and crossed his knees. “Oh no, you have to be specific.”

I rolled my eyes but giggled when I saw him waggle his brows at me. “Like, attractive, okay? And you aren’t as creepy as I expected. I thought you’d be full on Buffalo Bill about this.”

“Buffalo Bill?” he asked in horror.

“Don’t judge me! I just figured that guys like you didn’t have to resort to stuff like this.”

“I’m not resorting to anything,” he defended. “It’s unconventional, I know that, but it just makes me feel better—”

“To know for sure that they’re there for your money?”

“Yes. I just…” He trailed off and looked sad as he stared down at his mug. “People ask for things, and I like being generous don’t get me wrong, but it gets to be a lot. I like to believe that this is more real than someone acting the part of my friend before they start asking things of me.”

I hadn’t really thought of it before, but I got it. The feeling of people only being there for that one thing they want only to leave once they get it had to be hard. It was uncharitable but I wondered if maybe his soon to be ex-wife had something to do with his trust issues.

“I get it,” I offered, reaching across the table and holding my hand out in invitation.

Alex took my hand tentatively and turned it over, letting his thumb brush across my knuckles and sending little bolts of lightning up my arm. “You’re very easy to talk to, Chloe,” he said quietly. His face flamed and he wouldn’t look up at me, instead focusing on our clasped hands with a look of fascination.

I just smiled and squeezed his hand in mine. Alex finally looked up and we locked eyes, my heart skipped one long and painful beat but I didn’t look away. I could do this, I decided dazedly, I can do this with him.