Chi-Town Bosses & the Women That Love Em 1

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by Anna Black


  I eyed the sexy chocolate ass man that stood over us eyeing me. He looked tall enough, hell, taller than my 5’5 ass, and his broad shoulders looked like he never missed a day at the gym. He reminded me of sexy ass Daniel from Insecure. He had a low fade, but a full and beautifully shaped beard. When he smiled and held up his glass, his beautiful white teeth sparkled. I knew he was what I could fuck, screw, love, or date. Shit, I had been with Mario’s bitch ass for so long, that I didn’t have a clue what my type was anymore.

  Mario was cleanly shaven because he was in the military. He had caramel coated skin and these hazel eyes that I’d get lost in but looking up at the stranger who thought to send drinks to my girls and me was definitely my new type.

  “Okay, damn, y’all. I’m so out of practice,” I confessed. “I don’t know how to mack a man,” I said nervously.

  “Relax, baby, he plans to mack yo’ ass,” Grace said.

  “How do you know?”

  “He sent drinks to your party, not just you, and he didn’t send for you to come up there.”

  “That’s true. That’s a man with some class and maybe a lil dough. Hell, it’s five of us,” Chasity said.

  “Right, right, okay,” I said, and then the waitress returned.

  “Ladies, all drinks for tonight are on the house. And my boss said if anyone needs an Uber or a ride, no worries,” she said.

  We all looked at each other, and then I hunched my shoulders. They all started barking drinks at the waitress, but I eyed him. He looked at me, and I swore he saw my soul the way he looked at me. I smiled. He gave me a smirk and a polite nod, then he moved around. I tried to keep an eye on him, but by the time he ascended the stairs, I lost him. The night progressed, and the drinks kept coming. I was taking it easy, but my sisters and best girls were getting hammered. They had all made it to the dance floor, and I sat alone wondering where my admirer disappeared to and why he hadn’t shown his face again.

  I took tiny sips of my third drink. I was a wine girl and not a friend of hard liquor, mixed drinks, or cocktails, so I nursed the drink that my girl Chasity ordered for me.

  “Can I sit?” A voice interrupted.

  I looked up to see him. I did my best to hold in my smile because this brother was finer than any man that had ever approached me in life. “Sure, hi, hello, yes, sit,” I stuttered like an immature teen. I instantly got nervous as fuck. I had been with Mario since I was a damn teen and I lived with his stupid ass since I was twenty-two, and now I was thirty-two with no game or dating skills. I knew I’d say something weird or dull, and I wished my sister’s and girls would come back. I didn’t need to be alone with this beautiful being.

  He took a seat very close to me. I prayed I wouldn’t visibly shake. “How are you tonight, beautiful?” he asked.

  “I’m good, and I have to say thank you so much for supplying the drinks for my sisters, friends and me tonight. That was extremely generous.”

  “You are welcome, beautiful.”

  I looked at him and had to tell myself to close my mouth. He wasn’t what I was used to. He was more beautiful than any man that had ever approached me, and he sat super close to me. I looked out to see my fam having a good time on the dance floor, dropping it, rolling it and getting their boogie on. I wished I had joined them because this man made me nervous.

  “I’m Gabby. I mean, Gabrielle, but everyone calls me Gabby,” I introduced myself, feeling juvenile.

  “Really? I’m Gabriel, but everyone calls me Gutta,” he said and gave me his gorgeous smile.

  “Nice to meet you, Gutta, and if you wanna call me Gabby, that’s cool,” I said and then downed my drink. I was so fucking nervous that I wanted to run to the ladies’ room. “Can I get another drink? I mean, I’m so nervous right now, and I don’t know why,” I confessed.

  “Of course,” he said and gave a wave. “I need you to relax. I just want to chat a bit and maybe get to know a few things about you,” he said, and a different waitress appeared. “What would you like, beautiful?” he asked.

  “A Chardonnay, please,” I recited.

  “Coming right up, and for you, boss?” she questioned.

  “I’m good, Lauren, thanks. Just make sure it’s the best for my lady friend,” he said.

  “Got’cha, boss,” she confirmed with a nod, and she was off.

  “So, this is your place?”

  “It is one of a few. Is this your first time here?”

  “It is actually. I had no intentions of going out tonight, but my sisters and girls think I need to move around.”

  “Well, I’m glad you decided to step out,” he smiled.

  I smiled at him. “Me too,” I said, and my crew returned. They all flopped down, and I introduced them to my new friend. They all exchanged ‘nice to meet you’s’ and Gutta stayed at our table as my peeps got lit. We all laughed and drank, and then the DJ slowed the music down.

  “Come dance with me,” he said as he stood and stretched his hand to me.

  “Sure,” I said and placed my hand in his. We went out to the dance floor, and when he wrapped his strong arms around me, my knees went weak. I had been held before, but something about this man’s embrace made me feel like a sexy woman. I felt like I was desirable and special; the total opposite of the feelings I had with Mario when it was all said and done. I knew he was a stranger, but when the song ended, I didn’t want him to let me go. I wanted to stay in his arms.

  “Thanks, that was nice.”

  “You’re welcome, and it was very nice for me,” he said.

  “Well, I should get back to my girls,” I said.

  “Go home with me,” he said. My body tensed. There was no way I was going home with this man.

  “I’m sorry, Gabriel, but we just met. I just can’t go to your place,” I returned.

  “My bad and I understand, but please, can I take you for coffee? I want to spend a little more time with you. I promise I’m a gentleman, and I’m even open to your crew rolling with us,” he offered.

  I studied his face. He looked sincere enough, but I lived with a two-timing bitch for ten years. I knew about a wolf in sheep’s clothing, and I wasn’t ready to spend alone time with him. He was a stranger. Hell, a sexy ass stranger that I wanted to strip naked for, but none the less, a stranger.

  “I’d love that, but I don’t know you well, Gabriel. I can’t.”

  “I understand, and I respect that. Can I have your number? And as I said, I can get you and your girls home safely. I use a great car service, and one call will get you all home.”

  I nodded, and we headed back to my table to see that no one was good to drive. I turned to him. “We valeted two cars.”

  “No worries, beautiful, your vehicles are safe here. I’ll send someone tomorrow to get your friends when they are ready to pick-up their cars.”

  “Why are you being so nice to my friends and me?” I asked suspiciously.

  “I’m a good guy,” he said.

  After I kissed my girl's goodbye, I stood near my new friend. When a car pulled up, he opened the door for me, and I climbed in. I gave the driver my address, and we rode with the smooth sounds of R&B from the speakers.

  “Can I see you again?”

  I looked at him. “Yes, I’d like that.”

  “How about tomorrow?” he suggested.

  “Tomorrow is good,” I smiled. When we arrived at my place, he got out and walked me to my door. “Thanks so much for everything: a fun night, getting my girls and fam home safely and it was a pleasure to meet you.”

  “It was my pleasure, Gabby. I’m looking forward to seeing you tomorrow.”

  “Same here,” I said. We stood there awkwardly looking into each other’s eyes. He leaned in and kissed my lips, and I allowed his lips to linger over mines for several moments. I wanted to put my tongue into his mouth, but I pulled away. “Goodnight, Gutta,” I said.

  “Goodnight, Gabby,” he returned and took a step back. He waited until I was safely inside, and then I
watched him out my window walk back to the car.

  When they pulled away, I fell back against the door. It may have been wise not to go to his place, but my pussy wished I had. She didn’t care if we had just met because all my center wanted was the dick. I was glad she wasn’t in control because if she were, we would have gotten fucked that night.

  The next day he called me bright and early, too early, but I quickly answered his call. We chatted for almost two hours, and then we got off, so I could get dressed. By three, we were sharing our first date, and all I could do is gaze into his sexy ass eyes. We sat at the restaurant for nearly three hours with non-stop conversation. Again, he wanted me to go to his place, and again, I declined. I was really feeling him, and I didn’t trust myself being alone with him. No, I wasn’t a ho’ but I wanted him to open me up. It had been months since I’d had dick, so I knew with a little seduction from that masterpiece, I would have been calling out his name.

  That evening we Facetimed, and I agreed to go out again the next night. I had plans to go by my mom’s but still had a lot to do to get my townhouse together, so I didn’t make it by my mother’s like I said I would. The day flew by, and before I knew it, it was time to shower and get dressed for my date with Gutta.

  He took me out to an elegant restaurant. We had a delectable meal and drank delicious wine. This man was turning me all the way on. He was so smart and easy to talk to. And his kisses, oh my, his kisses made my panties wet. I got flowers every day of that week, and by Friday, this man had literally stolen my heart. And for the first time, I had already caught deep feelings for him. Every moment we were apart, I couldn’t wait to see him again.

  6

  Gutta

  I got in my car with thoughts of Gabby in my head as my driver took me home. We had gone out every night since we’d met, and I just dropped her off after a night of fun with her and her friends. I was feeling this young beauty, and I couldn’t wait to taste her center. She was so damn gorgeous, highly intelligent, and her poise was very ladylike and prim. I really like that about her, and I couldn’t wait to see her again. Holding her when we danced, inhaling her scent stirred my insides. She was literally the first woman that I’ve ever instantly liked this deep this fast. There was more than a physical attraction with Gabby. I mean, yes, I wanted to make love to her. I was craving her, but I had to control my hormones because every time I invited her to my home, she’d resist. The chemistry between us was off the fucking chain, but I had to relax and wait until she was ready.

  I’d never wanted a woman for anything more than a fuck, and this falling in love shit wasn’t a normal thing for me. Every day I wondered why Gabby made my insides do flips. Every day I was so damn anxious to see her again, and I could not figure out how this shit was happening so fast. I was only a mile away, but I wanted to hear her voice again, so I pulled out my cell.

  “Hey, you,” she said, and I heard the smile in her voice.

  “Hey,” I said. “Are you still awake?”

  “Yes, I mean, I haven’t even undressed yet,” she said.

  My dick jumped. The thought of her being naked aroused me. “Damn, maybe I left too soon,” I joked.

  She giggled. “Ummm, there won’t be any undressing in front of you, sir, for a while,” she countered.

  I cringed. Why was she resisting? I knew she was attracted to me. When I held her close, I could feel how my touch made her tremble, so why was she afraid to let me have her, I wondered. “Really, and why is that?”

  “Because I don’t just undress in front of just anybody. Only special men get that privilege.”

  “Okay, then how can I become special enough to earn that access to your body? I mean, I know you can sense how bad I want you. Just your kisses alone make my dick stiffen, baby,” I confessed.

  “Well, so far you are on the right track, and I’m enjoying this. You are wooing me, baby, so just give us a little time to get better acquainted. You are doing absolutely everything, just right.”

  I agreed. I did know how to romance the fuck out of a woman, but I hadn’t had a woman to motivate me to do so. I forgot how much work it takes to romance a good woman. “Well, I’m glad I’m getting everything right, Ms. Gabby. Just know that I’m a very persistent man and I don’t stop until I get whatever it is, I want.”

  “Is that right?” she said.

  “Yes, it is.”

  “Okay then, that is good to know. I’ll just have to play a little harder to get if that means more flowers, mouthwatering meals, romantic text messages, and your sweet kisses.”

  “Awww, baby, don’t worry, that won’t stop my pursuit. Even when you’re mine, none of those other things will change.”

  “You already know you want me to belong to you? It’s been a week, Mr. Gutta.”

  “Gabby, I knew that the moment I laid eyes on you. I plan to do whatever it is to make you mine.”

  “Is that right?”

  “Hey, that’s how you gotta be to get exactly what you want.”

  “True, and all you have to do is keep doing exactly what you are doing.”

  I smiled. “I shall, and I’d love to see you tomorrow. If you don’t have any plans, I could take you to breakfast.”

  “How about lunch? It’s late, and there is no way I’ll be up for anybody’s breakfast.”

  “Lunch is also good. How about you call me when you wake up, and we go from there?”

  She yawned. “That sounds like a plan.”

  “Great, go and get some rest, beautiful, and we’ll talk tomorrow.”

  “Okay, goodnight,” she said before she yawned again. I said goodnight and ended the call.

  When the driver pulled up to my home, I saw a car sitting in my circular driveway that I didn’t expect to see. I wished she wasn’t sitting outside of my house. Trina was my main go to for sex, dates and just company. She had been in my life for the past six years, but no matter how great she was, I didn’t love her. I loved her pussy, didn’t mind spoiling the fuck out of her, but my heart never thumped or skipped a beat for her. Since I had been chasing Gabby all week, I hadn’t made time for Trina, nor had I answered a lot of her messages.

  My driver came around and opened my door. “Thanks, Moe,” I said and got out. “I’m in for the night,” I said as I got out.

  “Yes, sir. Goodnight,” he said, and before he could shut the door, I heard her heels clicking against the cobblestone drive. She hadn’t texted or called to ask if it was okay to come by and that surprised visit was a got’damn no, no.

  “Hey, baby,” she purred.

  Usually, that would turn me on or make my dick respond, but it did absolutely nothing.

  “Trina, you’re here without notice. What the fuck is up with that?” I questioned. I didn’t want her to think for one second that that bullshit was okay, and I didn’t want her to think it was okay to do that shit ever again.

  “Awww, baby, my battery died, and for some unknown fucking reason, that stupid ass car charger of mine isn’t working,” she pouted. “You know I’d never show up otherwise without notifying you. I know the rules, daddy.”

  “Fucking really, Trina?” I said, eyeing her. I knew she was full of shit, and I knew one day she’d try some dumb shit, so I let her follow me inside. “Trina, you and I are cool, but if you think you can just show up, that will change that shit. So, let this be your first and last time coming to my place without notice,” I blasted. She was my top choice, but her ass would get cut from the team pulling dumb shit like that.

  “I hear you, baby, loud and clear,” she said.

  I opened my front door, and she was on my damn heels. She followed me up the stairs to my bedroom, and within seconds, she was down to her thongs. Her dress, handbag, and shoes were near the door on the floor, and when I laid eyes on her vanilla skin, my dick instantly stiffened. Trina was a freak. She liked for me to spank her ass hard enough to leave bruises and didn’t mind whips and toys. I unbuttoned my shirt and then my jeans, and as soon as my dick f
ell out of my boxers, she was on her knees giving me access to her hot mouth. She had no gag reflex, so I usually grabbed her hair and fucked her mouth like an animal. The amount of saliva she’d produce while giving me head was insane. Even if I didn’t fuck her other two holes, my dick was never left unsatisfied. That was probably one of the reasons why I could never fall in love with Trina because she just stayed in freak mode. She never cooked, nor did I want her to. She was just there on command if I needed a date for a party or special occasion. She was cold, I mean tight body and beautiful face. She’d let me piss on her if I wanted and that said she wasn’t wife material.

  She pleased my dick in more ways than one, but there was no love for this woman. She knew it and allowed things to be that way. The head was excellent as always, but it took me forever to cum. As soon as I closed my eyes, I imagined I was with Gabby and nutted all over Trina’s face. It was so fucking explosive, and I wished that I could have Gabby. I wanted that woman so fucking bad. I didn’t know just how much longer I could go without having her.

  I went for the shower in my master, and she followed and went to the sink. “So, what took you so long to leave the club tonight? I’ve never known you to be at any of your clubs past three,” she said.

  “Why?”

  “No reason, baby, I’m just curious,” she said as she washed her face. She opened a drawer and got her toothbrush. If I planned to make things happen with Gabby, I’d have to get rid of her toothbrush and her other personal shit; hell, her ass too.

  I mean, I was a freaky ass muthafucka, but I’d never want to do the things with Gabby that I’ve done with Trina. I’d had threesomes, foursomes and some of the grimiest shit with Trina. She was the freakiest bitch that I’d ever fucked with in my entire life, and I knew that type of shit wasn’t going to happen with Gabby. Gabby was classy, sophisticated, and elegant. That turned me on and just made me want to love her and take care of her every need. I mean, even though Trina had just sucked the life out of my dick, I wished I could hold Gabby close that night, not just to fuck her brains out.

 

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