The Prettiest Woman Read online

  “What are you doing?” I asked myself as I put on my eyeliner. “I’m going on a date with a rich man, and I’m talking to myself like a psycho.” I applied my Barbie pink lipstick from MAC, and headed to my room to get dressed.

  I felt like I was operating at a snail’s pace. I grabbed my things looked at myself in the mirror one more time and headed out of the door.

  *

  “Well good morning.” my professor said as I walked through the door. I cringed, feeling a little self-conscious. I always looked presentable but it was rare when I dressed up. There wasn’t any use to dressing up daily because I just had to go to the diner. When I did dress up, it was business casual for my internship.

  “Good morning.” I mumbled as I headed to my seat.

  “I’m sorry have you seen my friend? She looks a lot like you but less…decorated.” my classmate Rodney said.

  “Hush up Rodney. Can’t a girl look good sometimes?”

  “Shit, I would love it if you could do this every time. Now I’m happy that I got here early, I got a full view of you walking through the door.”

  “You are so full of it.”

  “I’m just saying, you’re looking good girl.”

  “What would you wife think about that sir?”

  “Well, my wife isn’t here and I’m still a man. I’m married but I’m not blind.”

  I laughed and shook my head, “I swear you make me afraid to get married sometimes.”

  “Why? I’m an excellent husband.”

  “Yeah, with wandering eyes.”

  “All men have wandering eyes.”

  “That’s what I’m afraid of. For my sake, I hope you’re wrong.”

  He shrugged, “You know I’m always going to keep it real with you, even when it hurts.”

  “It doesn’t hurt, it just makes me cautious.”

  “Go into everything with two eyes open, baby girl.”

  I’d met Rodney a year before and I just knew that he was going to be my man when I saw him. He was chocolate, tall, and had a set of pearly whites that would put Taye Diggs to shame. Our friendship got flirtatious really fast and I felt like an idiot when he told me that he was married. From that point, I kept things strictly friendly, much to his dismay. I have no doubt that I could have kept things going and had something physical but I didn’t want to share another woman’s husband. I wanted a husband of my own and nothing good comes to people that do stuff like that.

  Professor Yates cleared his throat, “Alright everyone, you know what time it is. Put everything away and get ready for the test. I hope for your sake that you studied because it’s comprehensive.”

  I heard the groans around me and I snickered lightly. I was made for this shit.

  *

  I walked out of the building with a smile on my face. I knew I kicked that test’s ass. Lord knows I studied enough. Then a slight grumble in my stomach started. The nervousness set back in, I considered flaking but I willed myself to go to the coffee shop, anyway. I couldn’t go home and tell Jessica that I flaked him out. I had to at least give it chance and I needed the money.

  I was a little early so I planned on scoping out a nice table and taking some time to collect myself before he arrived. When I stepped through the door, a man waved at me. He was sitting near the window and already had a cup of iced coffee in his hand. Ugh, he was early too.

  I gave him a once over and was severely disappointed which only increased the closer I got to him. He looked to be older than the photos he posted and about thirty pounds heavier. Why do people do that? But I was the sugar baby, so I guess I was the only one that had to look like my pictures.

  He extended his chubby hand, “Hi Roxie, it’s nice to meet you.”

  I smiled and shook his hand, “It’s nice to meet you, Chris.”

  “Do you want something?” He asked.

  “Just bottled water.”

  He rose to his feet and quickly got what I requested. I sat and stared out of the window as I waited for him to return.

  “You look exactly like your photos.” he said as he sat next to me. “Actually you look even better, I’m impressed.”

  “Glad to hear it.” I smiled.

  “So do you live in this area?” He asked.

  “No, I live in the Bronzeville area, I go to school downtown.”

  “Nice, what school?”

  “I go to DePaul.”

  “See, now I’m really impressed.”

  I laughed, “I take it that you like DePaul?”

  “Absolutely, it’s my alma mater. I bleed white and blue.”

  “Now that I’ll have to see for myself.” I giggled.

  “I like that.” he said as he looked at me intently.

  “Like what?”

  “Your laugh. It’s really cute.”

  “Thank you.”

  So far our little meeting was going well. I realized he was an average guy.

  “So what do you do for fun?” He asked.

  “Honestly I don’t have much fun. I work a lot so I don’t have time anything else.”

  “What a pity. Maybe I could help you out in that area.”

  “Maybe.” I said uncomfortably.

  “I can’t believe that you aren’t enjoying yourself. This should be the time of your life. I did nothing but party when I was in undergrad. I drank a lot, fucked a lot and went to class when I wasn’t hung over.” he laughed.

  “Must have been nice.” I said with a lack of enthusiasm.

  Of course he was able to be an idiot in college, he was probably rich then, too.

  “It was more than nice! It was amazing.” he said with excitement. He obviously hadn’t picked up on my sarcasm. “One time me and my friends got so drunk that we pissed in Buckingham Fountain. It was like three in the morning and it was a dare. I even have photos. See, times like that are priceless. You have to make those kinds of memories now because when you enter the real world, it’s over.”

  It seemed apparent to me that he still wasn’t a part of the real world. Either that, or our worlds were just too different. Never in my life would I pee in Buckingham Fountain and think it was funny. What kind of person would do something like that? It was downright disgusting. My mom would whip my ass if she ever found out that I did that and it didn’t matter how old I was. Shit, she would probably haunt me from her grave if she were dead.

  He talked about his college shenanigans for the next fifteen minutes and I was less than impressed but I smiled and nodded, as instructed.

  He pulled a $100 bill out of his wallet and slid it over to me on the table. I discreetly picked it up and slipped it into my handbag. I felt like I was making a drug transaction and cops were going to burst in and arrest me at any moment. But it was the easiest hundred that I’d ever made in my life.

  “Thanks.” I replied in a whisper.

  “You’re very welcome. I’m really enjoying your company. Would you be willing to accompany me to an early dinner? I’ll give you another $100.”

  I would have preferred to go home but I decided that it was worth my time. He was going to pay for dinner and pay me. I could sit through another hour and a half of his boringness for cash.

  “Sure, I would love to.”

  “Cool, we can head down the street to Tamarinds. It’s a really nice little Thai restaurant on Wabash.”

  “That sounds like a plan. I’m a fan of that place.”

  We walked a few blocks to the restaurant and took our seats. I looked at my watch and silently prayed that I would be on my way home by five.

  “I know that this is unmanly of me but I love their Sweet Riesling. I’m going to get a bottle.” he said with delight.

  “Knock yourself out.” I said.

  I personally preferred red wine but he was buying so I would put up with whatever it was.

  When the server came, he ordered for the both of us. I tried to keep a straight face and then I understood why Jessica ate before she went out on her dates. He ordered us
different rolls of sushi and some pad Thai to share. I hated sushi, and their pad Thai wasn’t the best.

  “This small place has such good food.” he said as he scarfed down the rolls. I tried not to look at him with disgust but I wasn’t so sure if it was working. The only thing that was getting me through the dinner was the too sweet wine at the table. I ate a small plate of the noodles and drank and drank some more. We went through two bottles of wine. He spent the entire dinner talking about his glory days. He seemed like an overgrown child.

  After he’d finished annihilating all of the food he said, “We should have one more drink before we hit the road.”

  I was a little annoyed but if one more drink was what it took for him to give me hundred more dollars, then I would have another drink. We walked over to the bar and he ordered another drink, I had water.

  “You know I’m really enjoying myself right now.” he said.

  “I’m glad. I’m enjoying myself, too.” I lied.

  “I could see myself having a woman like you on my arm from time to time. You’re quiet, demure and hot. That’s just the way that I like them. So why are you single?”

  “Honestly, I haven’t really had much time to date.”

  I realized that it was the first time he’d asked a question about me since we first had coffee. He was very self-centered. I wondered if all rich men were that way. Maybe they were like that because they were used to everyone catering to their every whim. Now I knew why rich wives seemed so damned miserable. They had husbands who only thought of themselves. The world can be lonely when you only have Burberry scarves to keep you warm.

  “Oh right, all you do is work. What a waste.” he said as he slowly looked my body up and down. I suddenly wished that I wore loose fitting jeans and t-shirt. There was no way I was letting him get his grubby hands on me. I could see the debauchery running through his mind. Ew.

  “I don’t think it’s a waste at all. It’s my life and I have to make sure that I’m taken care of.”

  “Oh you’re one of those independent black women?”

  I scrunched my face up, “I’m a black woman that has had to take care of herself. If that’s what you mean, then yes.”

  “Well, it will be my job to help alleviate your stress.”

  He leaned in and tried to kiss me, I quickly moved away so that he missed his mark. I stared at him in shock. His expression mirrored mine.

  “I’m sorry but I don’t kiss on the first date.” I said in an attempt to spare his feelings.

  I could see his ears starting to get red, “You’ll do what I tell you do.”

  “I’m sorry? Okay, it’s clear that you’ve had a little too much to drink. You can’t be thinking clearly.”

  He pulled out his wallet, “Okay how much do you want? There is a nearby hotel that we can go to. Is $500 okay?”

  It took me a few moments to gather myself. I couldn’t be extremely upset because I put myself in a position to be disrespected. But I got to choose how far I allowed it to go.

  “I’m not that kind of woman.”

  “Then why would you come and meet me if you weren’t prepared to have sex? What kind of games are you playing?”

  “Okay, I no longer feel comfortable. You have a great evening, I’m going to go home.”

  He looked shocked that I was preparing to go home, “I can give you a $10k a month allowance. Most girls would jump at that opportunity. It would change your life.”

  “Well, I’m not most girls. I’m a grown ass woman.” I replied as I lowered myself off of the bar-stool.

  He grabbed my arm, “You’d be stupid to leave.”

  He caught me off guard; I grabbed my glass of water and splashed it in his face. I took that opportunity to run out of the restaurant. Everyone stared but I didn’t care. As soon as the Chicago breeze hit my face, I felt better. I headed directly to the train station and didn’t look back.

  I tried to call Jessica when I got on the train but it went straight to voicemail. I then tried Jaime who picked up immediately. She suggested that I come over to her place so that we could talk about it. Her home was quite a few stops before my own so it didn’t take me long to get near her house.

  Soon I was sitting on Jaime’s couch and spilling my guts about what occurred.

  “Oh my god, what a dick!” Jaime exclaimed, “You probably need to get off of that site, or maybe next time I can come with you and be your security.”

  “I don’t know. Maybe I just got unlucky. A guy can be an asshole no matter where you meet him.”

  “That’s true. Lord knows that I’ve had my fair share of broke assholes. So I guess if you have to be with a broke asshole and rich one, you may as well get paid for it.”

  I shook my head, “I thought that you were against all of this.”

  “I am, I’m just trying to look at the bright side.”

  “Mm hmm.”

  #Chapter5

  The following morning, Jessica did the walk of shame into our apartment. She didn’t come in the night before. She looked quite pleased with herself and was humming a little tune.

  “Good morning beautiful.” Jessica said when she saw me.

  “Hey, I called you yesterday.”

  “Sorry, I was all tied up.” she snickered.

  “I don’t even want to know.”

  “You’re right, but check out these shoes!” She said as she opened up her shopping bag and showed me her shiny new expensive heels.

  “Wow, so did Steve get these for you?”

  “Ummm, no. Actually these are from James.”

  “Have you no shame woman? What in the hell happened to Steve? When I saw you leaving this morning, you were going out to breakfast with him.”

  “I know, and we did. I then got a text from James and I just can’t say no to him.” Her eyes took on a dreamy look.

  “I don’t know what I’m going to do with you.”

  “Don’t worry about me. What happened with you and that guy yesterday? Did you make anything?”

  “Well, I got $100 dollars. I was supposed to make another $100 but I splashed my drink in his face before we got that far. It wasn’t even worth it because of what happened. That asshole offered me $500 dollars to have sex with him.”

  Jessica didn’t look shocked, “Well that happens from time to time.”

  “What would you have done in a situation like that?”

  “If he was hot I would have probably done it. Granted, I would have made him at least double his offer. But if he was ugly, I would have gone the same route that you did. How did he look?”

  “It doesn’t matter how he looked!” I said in disbelief. I couldn’t believe that my friend was actually trickin’ for cash. “Having sex for money makes you a prostitute Jessica and that shit is illegal and fucked up.”

  “Calm down Mother Theresa. It’s not the same. Being a sugar baby is different. Prostitutes will sleep with anyone for money. I only sleep with men that I have a connection with. Which means that I get to know them. They give me gifts because they want to, not because they have to. If that man just so happens to leave me cash in the morning, then it’s considered as a perk. He gave it to me as a gift.”

  I gave my friend the major side eye. She knew that it was all semantics and that she was toeing a dangerous line.

  “I only got into this because I thought sex wasn’t going to be involved. Now I don’t think I can do this anymore. I can’t go out with men that think that they get to fuck me just because they took me out or gave me money. I was naïve but now that I know the truth, I just can’t do it.”

  “Don’t be so quick to give up on it. You may meet a really hot guy that wants to give you cash and gifts, and sex will just be a bonus for the both of you. Who knows? You just may meet a man that you genuinely like, stop overreacting just because you had one bad experience. Assholes are everywhere. Besides, I know that it’s been ages since you’ve gotten laid. Imagine getting laid on the balcony of the Trump Towers. I get all tin
gly just thinking about it.”

  “It has been a while since I’ve gotten some and it’s been tough. But I just don’t see myself being attracted to any man that uses that website. All of the men on there were old and ugly. The ones that were attractive weren’t from here or they seemed like pricks.”