The Prettiest Woman

by Lena Skye

  “No, I suppose we couldn’t have that.”

  He turned his face and I kissed him lightly on the other side. His face turned towards me and I was scared that he was going to kiss me on the lips but at the same time, I wanted him to. The chemistry between us was electric; he took a look at my lips, shook his head slightly and pulled away.

  Was something wrong? I was being silly. One minute I didn’t want him to kiss me, then the next I was disappointed that he didn’t.

  “I can see that you’re going to be trouble already. You’re dangerous.”

  I smiled as we stepped off the elevator. Jessica was right; he did want to rip my clothes off.

  We walked to the hostess and she smiled at the both of us, “Hello, table for two?”

  “Yes we have reservations.” Vincent said.

  “Great! What’s your last name?”

  “Caruso.”

  “Okay.” she replied as she checked the system, “Follow me please.”

  We followed her to the far end of the restaurant and my breath was taken away. We had a corner table. Under any other circumstances that would have sucked because I hated being in the corner. But this view allowed us to see the city from two different angles. It was amazing and I couldn’t get enough of seeing my city at night from so high.

  “Coming here was worth it.” he said.

  “Why is that?”

  “Just to see that look of wonder on your face, it’s gorgeous. I would want to show you new things all the time if I get to see that look.”

  “So you like showing women new things?”

  “I don’t mind. This is something that’s really exclusive to you. You’re just…beautiful.”

  I blushed and looked him in the eye, “You’re leading me to think that you’ve never been with a beautiful woman before.”

  “Of course I have. The key is that I’ve never been with you before and I really want to get to know you. I hope that you’ll allow me the opportunity.”

  “We’re on the same page. That’s something that I would enjoy as well.”

  He smiled brightly, “So tell me about you. I know that you’re a busy woman, but who are you outside of that? Where are you from?”

  “I’m a constant work in progress, I’m still figuring out who I am, and it’s an interesting ride. I don’t know if I told you but I have an older sister and I’m from the south side of Chicago.”

  “How much older than you is she?”

  “She’s 26 years old. So what about you? Any siblings?”

  “I have two younger brothers. I grew up in Orland Park.”

  “Nice. How much younger are your brothers?”

  “One is 30 and the other is 15.”

  “You’ve got to be kidding me.” I said.

  “Nope.” he laughed, “apparently my parents weren’t done yet.”

  “I guess not. That’s a huge age gap!”

  “Well what can I say? We Italians are a passionate bunch, you’re never too old.”

  “That explains a lot.”

  “What?”

  “Well I don’t know why it didn’t hit me that you’re Italian. Your name is Vincent Caruso, duh.”

  “It’s alright. Is that a problem? You have something against dating Italian men?”

  “Not at all, it’s just that I was wondering why I was so attracted to you.”

  “You like Italian men?”

  “I guess I do. I’ve heard that they have a lot of swag, I see that it’s true.”

  “Well that is partially what I’m known for.”

  I laughed and shook my head, “There goes that cockiness.”

  “But you like it.”

  “I do.”

  Soon our waitress came and we ordered. I was truly enjoying myself; he was so easy to talk to. I felt as if I’d known him for years. Over the next hour, he talked to me about some of the places he’d been. He was well traveled and he spoke about it without bragging.

  “I think that you would love Turks and Caicos. It’s so relaxing and when you’re there you won’t have a care in the world. The only thing that you focus on is the water, the sand, the food and luxury.”

  “That sounds divine. I’m overdue for a vacation.” I said.

  “How long has it been since you’ve been on a vacation?”

  “Twenty-one years.”

  “You’ve never been on a vacation?”

  “I’ve been out of town for funerals and a few weddings but that’s about it. I’ve never been able to afford it.”

  “That’s something else that we’re going to have to change.”

  The more he talked, the more I got swept up. He seemed to be absolutely perfect. It all felt a little too good to be true.

  “Why are you looking at me like that?” He asked.

  “Can I ask you a question and you answer it honestly?”

  “Sure.”

  “Why did you send me a message?”

  “Why wouldn’t I?”

  “I don’t know, I guess I just don’t think that black girls are your usual type.”

  He shrugged, “I haven’t dated a black woman before but color has never been a big deal to me. I’ve always found black women to be incredibly attractive. But the main reason I sent you a message was because of that big bold sign at the top of your profile.”

  I laughed loudly, “I thought that it was going to be a deterrent. You surprised me because I was giving up on the site when I wrote that message.”

  “It was very refreshing. So many women are selling themselves there and it was a little disappointing. I mean I’m not naïve, I know what the site is all about but I was still hoping for women with some self-respect. When I saw your photos and your smart-ass profile, I knew that I had to get to know you. You kept it real and it you made it very clear where you stood.”

  It felt good to hear him say that. My profile attracted the kind of man that I wanted.

  We had a wonderful meal. I have to admit that my steak wasn’t all that great, but my date, the wonderful view and the customer service offset the meal. Our waitress brought our check and I quickly glanced at it when he opened the black leather folder. I almost choked when I saw that the bill was over $400 dollars. I was shocked and I felt a little guilty. I didn’t believe in going on dates that I couldn’t afford. But Vincent didn’t bat an eyelid. He pulled out his black American Express card and paid it without fussing.

  “That bill was very steep. I almost had a heart attack.” I laughed.

  “No worries, you’re worth it. I love treating my dates, unfortunately, that can lead to me getting taken advantage of. My ex-wife was that way and that’s why we’re divorced.”

  “That’s an odd outlook, especially considering where we met.”

  “Well, I don’t want a new relationship just yet and being a sugar daddy seemed like a good temporary solution. At least that way I know what the relationship is all about from the beginning. Our expectations can be clear and we can walk away without any hard feelings. Now what I didn’t expect was that most of the women would be escorts in disguise that are looking to take me for all that I’m worth.”

  “I guess we’re both naïve.” I snickered before I finished off the last of my drink. I thought about what Jessica told me but I kept it to myself.

  We left the restaurant and headed to a new bar that was on a rooftop of a hotel. I’d always wanted to go there and now, I finally had the chance.

  “Do you want another drink?” He asked into my ear.

  “No, I want to dance. Show me what you’ve got Vinny.” I teased.

  “I don’t know if you’re ready for all of this.”

  “I’m very ready.” I said as I grabbed his hand and led him to the dance floor. We stood face to face and our bodies were pressed against each other. His hips moved with mine as I swayed them from side to side. He danced really well and it didn’t feel awkward at all.

  “You thought this white boy couldn’t dance? I’m Italian baby, dancing is what
we do.”

  “Oh, I thought you all only knew how to fist pump.”

  “Alright, no more Jersey Shore for you.”

  I snickered, “I haven’t watched that in so long.” My laugh was short-lived. I felt his bulge rising between us and my head was telling me to pull away but I got closer. I wanted to feel the blood pulsing through it, I wanted to make it twitch and I wanted to see just how big it was. I was definitely in heat and his dick was huge.

  I instinctively licked my lips and looked him in the eyes. His eyes took on a stormy blue color and my entire body felt as if had been struck by lightning. His hand went to my hair and he brought his lips to mine. I lost myself in him. The taste of him was intoxicating. He tasted like wine and passion. His lips were warm and soft and he knew what to do with them. I melted into his body and enjoyed the feeling of being close to him. It felt like it was where I belonged, which was crazy because I’d just met him. Was life really supposed to be like that?

  I was incredibly turned on. I broke my no kissing on the first date rule and didn’t care. I felt like my entire body was singing. I couldn’t help but wonder what would happen next. We spent the next couple of hours dancing, laughing and making out like teenagers. It was without a doubt the best date of my life.

  “I’m so sorry, but I have to be up extremely early. Let’s get you home.”

  “Okay.” I said casually even though I was disappointed. I was having a lot of fun.

  He obviously noticed my disappointment, “How about you come back to my place for a bit, just for coffee though.”

  There was no way that we were going to his apartment just for coffee, not if I had anything to do with it. I knew the game. Men invited you over for a movie, for a drink or something innocent and you ended up having hot sex. And, that’s what I wanted.

  “Coffee sounds really good. I’m sorry I don’t mean to be a brat, I’m just really enjoying being with you.”

  “It’s okay; I don’t do anything I don’t want to do. I didn’t want to take you home just yet; I was trying to do the responsible thing.”

  We made our way out of the bar and hopped into his car. We pulled up to the Trump building.

  “You do not live here.” I said in disbelief.

  “I do.” he grinned.

  “How many small fish has your company swallowed? Oh my god, it’s super expensive here.”

  “The question is how many small fish have I turned to medium fish and then sold to a big fish.”

  I felt like I was in an urban fairytale. I could see why Jessica was addicted to this lifestyle. I’d experienced more in one evening than I had in the span of a few years.

  We walked inside of the huge building and took the elevator up to the 69th floor. I snickered.

  “I already know what you’re thinking.” he grinned, “And yes, I chose this floor on purpose. I thought that it was pretty funny.”

  “My favorite number.”

  “See, I told you that you’re dangerous.”

  “I can be.” I said in a sultry voice that I’d never heard come from me before. I was acting like a sex-crazed nympho but my body needed a release and he was setting me off. All I could think about was having his body inside of me. We walked down the hall to his condo and he opened the door. It was beautiful. We had a view of the Chicago River and Lake Michigan. I passed by all of his manly high-end furniture and stood at the window.

  “There goes that look again.” he said as he pulled my hair free from my pony tail. My hair fell over my shoulders and I was grateful because it had a mind of its own. Some days it behaved and some days it acted like a heathen.

  “This view is breathtaking.” I said.

  “It sure is.” he smiled. I looked at him and realized that he was looking at me as he said it. I smiled at him, “I like it when you look at me like that.”

  “Like what?”

  “It’s probably the same look I give when I’m looking out of the window. As if you’re seeing something new and wondrous.”

  “That’s how it feels to be quite honest. You’re gorgeous and you have the personality to match. You’re a diamond Roxie.”

  “Thank you. So are you.” I turned and looked at the rest of his condo, “Can I have a tour?”

  “Sure. Don’t judge me too harshly because I haven’t had time to do much with this place since my divorce. This was my big fuck you to her. I wanted a bachelor’s pad and I figured this was the ultimate pad.”

  “So you have women running in and out of the condo?”

  “That’s what’s so ironic about it. I haven’t had the time and I haven’t really wanted to. I went a little wild after my divorce but it got old really fast.”

  He walked me through his condo. I loved the high ceilings and open floor plan. Soon we were back in his front room and sitting on his sofa. I curled up under him as we silently watched the city. Everything felt so natural with him. He kissed my temple and stroked my arm with his thumb. ‘I could get used to this,’ I thought to myself.

  He picked up one of his many remotes from his coffee table and cut on some soft music. I was pleasantly surprised to hear neo-soul coming through his speakers.

  “Now what do you do know about Anthony Hamilton?” I asked

  “Good music is universal baby.”

  “You have a point.”

  He laughed and his hand naturally dropped towards my breast. I leaned my head back against his chest and his thumb casually circled my nipple. I quickly inhaled and my body towards his hand, I wanted more.

  “You’re so fucking sexy.” he whispered into my ear, “You’ve had me on edge all night. You make it so hard to be a gentleman.”

  “Being a gentleman means, being polite and giving me what I want.” I teased.

  “What do you want?”

  “You.” I admitted.

  “Are you sure?” He gave my nipple a gentle squeeze, causing me to gasp.

  “Very.” I quickly turned around and straddled him on the couch. I kissed him the way that I wanted to kiss him all night. I threw caution to the wind and attacked him like I was in heat! It had been so long since I’d had sex. I still wasn’t sure if I’d really ever had good sex. Most of my orgasms came from my Hitachi that was in my drawer.

  He didn’t need any more convincing, his armed wrapped around my waist tightly as he ravished my mouth. His tongue intertwined with mine as his hands found my bare flesh. He set every part of my body that he touched on fire. I’d never known passion like that before. I’d heard about it and read about it but it was foreign to me. I was completely in the moment and nothing and no one else mattered. It was the kind of experience that I didn’t think was possible. But there I was, on the couch, with a man that I’d just met, and loving every minute of it.

  He grabbed my top and helped lift it over my head. I was a little disappointed that I was wearing one of my boring bras. It’s only redeeming quality was that it was a push up, and it was clean. He didn’t seem to share my disappointment because he buried his face between them, and then unhooked my bra. My breast sprang free, and I have a content sigh.

  His mouth captured my nipple and he suckled with a sweet pressure. It felt like his mouth was all over me. My hips rocked against the bulge in his pants causing him to groan in ecstasy. He teased my nipple with his teeth and brought me to the brink of pain before he soothed it again with his wonderful tongue.

  I called out to my higher power, it felt blasphemous but the words escaped my lips, anyway. His fingers dug into my back as he went from one breast to the other. I leaned back and rested my hands on his thighs, to give him full access. Feeling his dick twitch against my center was becoming too much. I wanted more of him. I loved what he was doing but I needed more.

  I sat up and put an abrupt end to what he was doing.

  “Are you okay? Do you want to stop?” He asked breathlessly.

  “I don’t want to stop, I want more.”

  He laughed, “Impatient?”

  “Very.”


  “Too bad because there’s something that I want to do to you first.”

  His intense look paired with the licking of his lips, let me know exactly what was on his mind. I gave him a wicked grin, because I could only imagine how his mouth would feel down there.

  “Stand up, babe.” he said.