Chi-Town Bosses & the Women That Love Em 1

by Anna Black

  “How old do you think I am?”

  “Looking at your radiant skin, I’d say twenty-five or twenty-six. You have amazing skin.”

  She smiled even brighter for me, and I thought, damn, I’d work ten jobs to give her whatever she wanted, just to see her smile. “Well, I’m thirty-two and will be thirty-three in December.”

  “Wow, you don’t look a day over twenty-five. I could gaze at you all night.”

  She blushed. “How old are you?”

  “I’m thirty-six, just turned thirty-six in July.”

  “Really, I didn’t think you were that old.”

  “Oh, I’m old, huh?” I joked.

  “No, no, no, baby, just older than what I imagined.”

  “Well, it’s nice to know that I don’t look my age.”

  She bit down on her bottom lip and then shook her head from side to side. “Uh-unnn, oh no, baby, you look sexy as hell for one, and I thought we were the same age. Well, how you carry yourself makes you look so damn attractive.”

  For the first time in my entire life, I blushed. I had thought about Miss Gabby every waking moment since we met. I knew it was too soon to say what I was feeling, but the attraction was so fucking intense that it was mind-blowing. I wanted to skip the meal and just have her. I cleared my throat.

  “Thank you, Gabrielle. I usually get compliments, but coming from you, I believe it.”

  “Oh, so, you think the other women weren’t truthful?”

  “Not so much untruthful, but maybe with an agenda. I don’t usually do dates and dinner. Last night, hanging with you and your peeps at the table is not my thing.”

  “What is your thing?”

  “Well, to be honest, if I see a woman I like, I’d send for her and entertain her in VIP.”

  She tilted her head to the right and her brows vaulted. “Oh, so I wasn’t appealing enough to get the VIP invite?”

  I chuckled. “No, baby, it’s the exact opposite. I’d send for them and usually a little more than conversation would go on. When I laid eyes on you, as much as I do want to have you, I didn’t want to have you that way. Women like that are one-nighters, and I usually don’t see them again,” I said, and our server returned with our wine. She poured two glasses and asked if we were ready to order. I already knew what I wanted, so I looked at my gorgeous date.

  “Ummm, I really haven’t looked over the menu, to be honest,” she said and opened it. She scanned over it and then looked at me. “How about you order for me?” she smiled.

  “You sure? I don’t mind waiting for you to read over the menu, baby,” I said and then looked up at the server.

  “That’s right, madame, you can take your time,” she agreed with a head nod.

  “Just give us a few more moments,” I said.

  “No, I’m ready,” she said and rattled off what she wanted. I told the server what I wanted, and we got back to non-stop conversation.

  I was holding on to her every word. I was so taken by Gabby, and I didn’t want our night to end. Before we left, she excused herself to the lady’s room, and I called for my car. We walked out hand in hand, and an overwhelming feeling came over me. I wanted to pull her into my arms and just tongue her down, but I kept my cool. Once the car pulled up, my driver hopped out, but I assured him that I had our door.

  Once we were rolling, I asked. “Can I take you home with me?”

  Her neck snapped so quickly when she turned to me as if I scared her. “Go home with you? I mean, I don’t- I don’t know if that’s a good idea, Gutta.”

  “Why not, baby? I won’t push. I just want to be alone with you, not in a noisy club. I want to be close to you, Gabby.”

  “And by close to me, you mean you want to sleep with me?” she said.

  “Well, yes I want to do that, but that’s not why I want you to go home with me. I’d never force you to do anything you didn’t want to do, Gabby. Baby go home with me so we can lounge on my sofa and talk. I can rub your feet, massage your scalp or paint your toes, whatever you want to do. I just want more one on one time with you.”

  She starred me in the eyes, and then the corners of her mouth curled up. “You had me at scalp massage,” she laughed. I pulled her into my arms and pressed my lips on the side of her forehead.

  “You knew you wanted to go,” I joked.

  “No, that’s not true, but how can a girl turn down a scalp massage? Plus, some more one on one time sounds nice,” she said, and I heard the smile in her voice.

  My face was pressed against the side of hers, and I closed my eyes and just inhaled her scent. She smelled like flowers, and her hair was a scent of mango. Her skin smelled so fresh. I had to hold back because I wanted to lick her neck and shoulder. I held her close, and we rode to my place with minimal conversation. We just held one another. Damn, I was falling fast.

  9

  Gabby

  When we pulled into his circular drive, I was amazed. I knew a brother did well, but his mini-mansion said he did damn-well. “This is your home?”

  “It is,” he said as the car came to a stop.

  “Bullshit,” I said.

  “No, really, it is.”

  “What’s the catch? Your parents live here, or do you have something going on other than nightclubs?”

  He chuckled. The driver opened the door, and he quickly got out. “Come on, babe, let’s go inside.”

  I took his extended hand and let him help me out of the vehicle. “Moe, I think we will be good for tonight. If I need to go anywhere, I’ll take one of my other cars.”

  “Are you sure, sir?” The driver replied.

  “I’m certain,” Gutta said.

  “Okay, goodnight, ma’am and goodnight, Mr. Wilkerson,” he said and hurried back to the driver’s seat.

  Gutta took my hand, and we headed up the cobblestone walkway. His home was large, a bit too large, but I guess he could afford it. Once inside, I nervously stood in the foyer with my eyes trying to take it all in. The foyer itself was gorgeous, and I could only imagine what the rest of the house would look like.

  “Come on in, baby.” I followed behind him slowly, then he grabbed my hand. “What’s wrong? No one else is here,” he said when we made it to the family room. It was opened to the eat-in kitchen, dining room, and his place was amazingly decorated like a staged home for sale. It was super clean, and I didn't want to touch anything. “Have a seat,” he offered, and I went over to the most enormous sectional that I’ve ever seen in my life.

  “Oh my God, Gutta, your house is amazing. Why do you have something on this scale? Do you have a family you failed to mention?”

  He laughed. “No, baby, but I plan to have a family someday.”

  I sat, and he came over and pressed a few buttons on a remote that looked like a tablet. The soft sounds of Ledisi came flooding through the speakers in the ceiling.

  “Well, this is a lot of house for a single man.”

  “True and as I said, I don’t plan to be single forever. I met someone, and I have a good feeling about her,” he said and moved into the kitchen. “Would you like wine?”

  “I’d love some,” I said and then said. “So, who is this lucky lady that you have a great feeling about?”

  “Man, let me tell you. She is super gorgeous with some sexy ass lips and curves for days. She’s smart, classy and she could be Mrs. Wilkerson,” he said, pouring the white wine into a glass.

  I knew he was referring to me, but I continued to play along. “So, why did you bring me home with you if you have your eyes on another woman?”

  He came over and handed me my glass. “Because if she and I don’t hit it off, you are next in line,” he joked.

  “Whatever, Gutta,” I smiled. He leaned in, and I knew he wanted a kiss, so I gave him one. It started out slow, and when he grabbed my face, our kiss deepened. His tongue and his mouth tasted so damn delicious that I didn’t want to pull away, but I needed to put my glass down before I spilled my wine.

  “Gutta, baby,
Gutta, I,” I said between kisses. “My wine, baby,” I managed.

  He pulled back and stood. “No, babe, enjoy your wine, I’ll be right back,” he said. He went back over to the kitchen, and I sipped as I watched him make himself a drink. “Baby, I’ll be back down. Better yet, let me show you around first,” he offered.

  He gave me a tour of the entire house, and it was amazing. We ended the tour in his master where he offered me something more comfortable to put on. Gutta was tall, a little over six feet, and his arms and shoulders were muscular and tight. His dark skin was silky smooth, and his slanted eyes laced with thick lashes were mesmerizing. His gorgeous smile with nice white teeth was captivating. When he removed his slacks and button down, I tried to avert my eyes, but they were glued on his tight ass and back as he stood in front of his dresser to pull out items. He gave me a Tee and some socks and told me I could change in the bathroom, but I boldly removed my dress and wedges right in front of him.

  I stood there in my bra and thongs and let him drink me in before I pulled the Tee over my head. I went over to the plush bench that sat at the foot of his California King sized bed and sat to put on the socks, not able to take my eyes off of him. He stopped showing off and stepped into some long basketball shorts then put on a tank.

  “Now that we are comfy, let’s go back down and enjoy each other’s company,” he said, reaching for my hand. I put my hand into his, and we went back down to the oversized sectional. Deciding to talk and sip, we didn’t turn on the tube. We talked about everything and gazed at each other. I had at least four refills of my wine, and I was feeling good and horny. All I could think of was riding Gutta’s ass all night long. He massaged my scalp, my feet, and when he touched my bare skin to massage my back, my pussy sprung a got’damn leak. Shit! Shit! Shit!

  10

  Gutta

  After her scalp, I focused on her feet, and then she asked me to rub her back. In my day, I knew back massages led to breast massages, nipple sucking, and then clit rubbing. I wanted all of that shit to go down. My dick was harder than a Louisville Slugger. I wanted to knock the cobwebs and dust from her pussy that night. She had shared the details of her last relationship with Mario’s fool ass and the shit she told me made me want to fly down to Texas, punch that ma’fucka in the throat and fly back. That bitch broke my baby’s heart. I was glad that his bitch ass let a good girl go because my only mission from that night on was to make Gabrielle Marie Jackson all mine. Hell, I could see me marrying her, and I hadn’t even dipped my rod into her tunnel.

  “Lower,” she moaned.

  “Baby, if I go any lower, I’ll be massaging your ass. I don’t want you to slap the shit outta me,” I joked.

  “I won’t, baby. I just want your hands all over me,” she purred.

  “Are you sure that’s what you want, Gabby? I can’t play any games tonight. If we get started, I want to finish,” I said.

  She rolled over onto her back. “Well, can we take this to your bedroom?” she asked.

  I licked my lips but still asked to make absolutely sure. I didn’t want any meltdowns or second thoughts when I was ready to push my pole inside of her. Back in the day, the good young girls used to do that shit all the time. I was too excited and too attracted to Gabby to have my dick to be deflated.

  “Gabby, are you sure you wanna go up to my bed?”

  “Either we go up to your bed, or you fuck me right here on this oversized couch. Either way, I want you to fuck me, Gutta,” she hissed.

  I didn’t ask another question. I just stood and reached for her hand. I led her up to my room, and in a matter of seconds, we were naked and in the middle of my huge bed. I wasted no time ravishing her harden nipples, and I sucked and licked her all over. It was our first night together sexually, but I still blessed her bulb and center with my tongue. The sweet sounds of my baby’s moans were harmonious to my damn ears. Gabby was the one, and I had no fucking idea how she captured me within one damn week. I never believed in that love at first sight bullshit, but now I was having second thoughts. Gabby was everything.

  After I put on the plastic, I slid my dick into her pussy, and my heart raced, and my dick stiffened harder than it had ever hardened before. I stroked her wetness as if I had been there before and she had always been mine. She moaned so loud and called out my name; it was melodic to my ears.

  “Yes, Gabby. Baby, yes. Your pussy is the best, baby, and I wanna stay inside of your pussy all night,” I said. I had fucked a lot of women. Banged the hell out of a bunch of pussies, but I didn’t pound my baby. I glided in and out, on a mission to please her and enjoy her instead of burst a nut. Women before her were just objects to get me off, but now I wanted her to get off. I wanted to feel her contract and cream all over my dick. “You like that, Gabby, you like that dick?” I asked as I slowly glided my dick in and out of her opening.

  I looked down at her. Her facial expressions and her moans heightened this session for me. My dick was in heaven. She felt amazing, and everything about this woman had me wide open.

  “I’m there, Gutta baby, I’m there!” She squealed.

  I pulled out and put my mouth back on my baby’s bulb. I lapped up her sweet juices and loved the way she screamed my name as she released her essence all over my lips and tongue. I licked and slurped until she begged me to stop, then I smeared her juices up her stomach as I went back to her rock-hard nipples. I sucked, licked and lightly bit them as I pushed my dick back into her core. She opened wider for me. When I had her legs over my shoulders and her ass off the bed, our skin clapped as I plunged into my baby over and over again. I felt my eruption ready to explode, but I pulled out.

  “Turn over, baby,” I instructed, and my baby obliged.

  Once she was on all fours, I spread her ass cheeks and rubbed my dick up and down her crack and center before I pushed back in. Her pussy was so fucking tight and wet, my body jerked after a couple of pumps. I nutted so fucking good that I called out her name as I tried to compose myself. I felt like I had finally made love to a woman because this session was about us, not about me. I wanted her to feel just as good as I. That was the very first time I had climaxed with my dick inside of a woman’s pussy and not down her damn throat. I didn’t even know if Gabby gave head, but I didn’t care. I pulled out of my baby and fell onto my side. It was only one round, and I felt like I just had a fucking street fight. This woman had sucked the life out of me, and I smiled.

  “Baby, that was the best,” I said.

  “Oh yes, indeed it was,” she said.

  “I need water,” I said.

  She laughed. “Me too.”

  “Give me a second, and I’ll get us some.”

  “Okay,” she said.

  We laid there, and after about five more minutes, I was able to get up. I carried my naked ass down the hall to the loft area at the top of the stair landing and grabbed two bottles of water from the mini-fridge. I went back and handed her the bottle, and we both downed our water within seconds.

  “Gutta, you are the best, baby,” she said.

  I sat down on the bed. “And so are you. I want you, Gabby. I want you to be mine,” I said.

  “I’m right here,” she answered.

  “Yes, but for how long?”

  “For as long as you want me,” she answered.

  “I’d marry you,” I confessed.

  “Marry me, are you sure about that? The last man that proposed to me never married me.”

  “I’m not your last man,” I said and gently ran my thumb down the left side of her face. “I’m not him. And from what you told me, he’s a motherfucking idiot, Gabby. You are perfect. I’m glad his ass fucked things all the way up with you because you were meant for me.”

  “And you already know this after one week with me?”

  “I know it sounds crazy. I’m still trying to wrap my own damn head around it, Gabby, but I am mature enough that I’m not imagining these feelings. Trust me, saying it out loud has me shaking my damn head. Bu
t last week when I laid eyes on you, I was mesmerized, and after what just went down, I swear I’d give your ass my last name,” I said.

  “You are out of your mind, Gutta. I’m feeling you too, baby, seriously, but love at first sight type of shit happens in movies, not in real life. And I’d be foolish to believe that you have those feelings for me in just seven days.”

  I moved even closer to her. “Come here, baby,” I said and pulled her into my arms. “I don’t have all the answers, nor do I know why I’m feeling the way I am right now. I won’t start spitting game to you. That’s the shit I used to do with other bitches. Truth is, you are the second woman to ever come into my home. The second woman to ever lay in this bed. I had a piece of ass on command for years, and she was my main source, but I never felt any of these damn feelings for her. I am not going to rattle off any bullshit promises or say any fancy words because I’d never try to pull a wool over your head. All I know is at this very moment, my heart is pounding, and my stomach is doing flips; some shit I’d never experienced before. I can’t promise you a happy ending, but what I can promise is the truth. Every morning I’ll give you the truth. I’ll never hurt you, Gabby, and I’ll never break your heart.”

  “This is insane, you know that?” she said.

  “I know right and as I said, Gabby, no woman has ever had this type of effect on me. Shit, I never leaped this fast with anyone or with anything in my life, but something is telling me that you’re the one. I don’t have any time to waste with games and shit. Just let me be your man for now. I don’t want anyone else and after you put that sweet thang on me, I damn sure don’t want you with anyone else.”

  She smiled. “Oh, it’s really like that?” she teased.

  “Fuck, yes!”

  “Okay, Gutta, let’s do this shit then.”

  “Well aw’ight then,” I said and went for more water.