Cougar Cocktales

by N'Tyse

  “What’s wrong, baby?” I didn’t want him to stop my love injections.

  “Turn over,” he ordered.

  I flipped over quickly. All I wanted was to feel him inside of me. He slid back into my wetness. His skin slapped so loud against mine, I knew someone could hear us. I felt his sweat dripping on my ass. My hair was even soaked. When he was ready to release, he held my waist in place and pushed deeper inside of me. He let out a sound that I wanted to hear again and again. He kissed my back softly and slowly released the grip he had on my waist. He pulled out and we both collapsed.

  “So did I make the pleasure cut?” The first question to roll from his tongue.

  “Oh baby, you definitely did.” I smiled. We lay there and relaxed for a moment before he went to flush the condom. We grabbed robes and decided to sit in front of the fireplace. With champagne and strawberries, we talked about our backgrounds and got to know each other a little better. He serviced my pussy one more time before we called it a night.

  JEROME

  I left Madison that morning after kissing her goodbye, feeling high. It was crazy when I really thought about the reality of the matter. It didn’t feel like I was with an older woman nor did it feel like she was a stranger. Being with her felt no different from being with a woman my age. I couldn’t believe she had me just after one night. This woman was incredible, and I knew my friends and family were going to have negative things to say, so I decided to keep it to myself since she was only going to be in town for a couple weeks. I didn’t even want to tell my boy, Warren. One night had me open for a woman twice my age and I’m glad I didn’t hold back because it was just that damn good.

  Her face—beautiful, her body—sexy, her personality—perfect, and lastly the sex—bananas. I was looking forward to seeing her again. I mean honestly, I didn’t want to say goodbye. I thought about calling in, but she insisted I go and handle my business. She had a busy day herself. Room service came with our breakfast. We ate, got it in again and showered. She kissed me twenty times at the door before she allowed me to go. I must have been trippin’ because I’ve had plenty of women, plenty of ass, and many, many one-night stands with women I met on pickups, but none I wanted to call back. That was not the case with Madison.

  She wasn’t your typical forty-four-year-old woman. My mother was two years older and Madison looked nothing like my mother. Don’t get me wrong; my mother is beautiful and elegant, but Madison was sexy and sensual. She gave head like she invented it and her pussy was tighter, wetter, and better than a lot of women I’d had. I was questioning my sanity. I asked myself, ‘What the fuck?’ about fifty times after I accepted the key and have been asking myself, ‘What the fuck?’ ever since I left her suite that morning.

  I walked down the halls to the elevator, waiting for one of my boys to jump out with the camera crew. I thought for sure I had been set up. After I made it to my Infiniti, I realized it was real. I had fucked a woman twice my age and I wanted to fuck her again. I was shaking my own damn head, wondering what had gotten into me. How did I feel such an attraction to her that quickly?

  Once I made it to work, I thought the thrill of the day and traffic would distract my thoughts of Madison, but I was dead wrong. I was the first one to run to clock out that evening. I chatted with her a little bit during the day when I was free, but she was busy and we didn’t get too much conversation in. I rushed up to my condo, showered and changed, then headed over to the hotel. When I walked in, the fireplace was lit, and the melodious sounds of R&B filled the room. I looked around for her, wondering where she was since I had alerted her that I was on my way up.

  I went over to pour myself a drink. She walked in.

  “Hey,” she said. I turned around. She was just as lovely as she was the night before.

  “Hey, you,” I said, rushing over to kiss her lips.

  “I am so happy to see you. It’s like the hours stood still today.” She smiled radiantly.

  “Oh you missed me, huh?”

  “Yes, to be honest. I did. It’s crazy, but I did.”

  “I missed you a lil’ bit, too,” I teased. She playfully hit my arm. “I’m joking, babe.” I kissed her again. “So what’s all this?” I asked, noticing the table was set with covered plates.

  “Dinner. I figured we’d eat, chat a little, and do what we did last night and this morning,” she proposed. I was down, but I wanted things to go down in a different order.

  “How about you let me hit it real quick,” I said, lifting her dress. I rubbed her ass and my dick instantly got hard. “And then we chat while we eat…and then do what we did last night and this morning, after that,” I returned. Before she could dispute, I pushed my tongue into her mouth and lifted her up. I carried her to the sofa and gently sat her on the back of it. She wrapped her legs around me and I licked her down her neck to the center of her breasts. I slid both her bra and dress straps off her shoulders, exposing her erect nipples. I was impressed that her tits were not sagging, and the definition in her arms and legs was evident she worked out. I teased her nipples and put my hand up her dress and played around in her pussy, and it didn’t take long for her to get wet.

  “Take this off,” she said, unbuttoning my shirt. After I removed it and my tank, she undid my belt and jeans. My jeans dropped to my ankles. I had to bend down to get the rubber out of my pocket. We kissed and she grabbed my dick in her hand and stroked me, but I was ready to enter her body. I rolled the condom on and grabbed her ass, pulling her body into mine. I slid on in.

  “Aaaaahhhhh, baby, that feels nice…ooooh that’s good,” she panted. She wrapped her body around mine and I lifted her off the sofa.

  I carried her over to the armless chair and sat down. She began to ride me so smooth and easy. Her body felt so good, I was going nuts. “What are you doing to me, Madison,” I whispered as I sucked on her neck. “Work that pussy, baby,” I cheered as she rolled harder. She looked me in my eyes and I stared back, challenging her gaze, wondering what in the hell had come over me in less than seventy-four hours. I felt like she was already mine and I didn’t want anyone else at that moment.

  “I’m there baby. I’m there!” she screamed. She did a back-and-forth move, mixed with a circular motion before slowing her rhythm. She giggled a little and gave me a soft kiss, but I wanted more.

  “Let me bend you over,” I requested. She went back over to the sofa and bent over resting on the arm of the sofa. I spread her ass cheeks and pushed my way back in and went to work. A few steady pumps were all it took to send my soldiers into an explosion, and I was more than satisfied with what just went down. I pulled out and headed to the bathroom to flush the plastic. “Baby, fix me a drink,” I said, and inched my way to the bathroom. I still had on my tennis shoes and my jeans and boxers were around my ankles.

  “Okay,” she replied. I paused and watched her pull her straps back on her arms, thinking this woman had put something on me. When I came out, I snatched my tank up from the floor and joined her at the table. “So are you seeing anyone?” she asked.

  “No,” I truthfully replied.

  “I wanted to ask last night, but I was too nervous.”

  “Why?”

  “I don’t know. I figured since this is only going to be a fling, why ask something so personal?” she said.

  I don’t know why I didn’t like that word ‘fling.’ “So do you have flings often?” I questioned curiously, because honestly, I was digging her.

  “Absolutely not.”

  “I just didn’t want to assume.”

  “Jerome…I mean I’m forty—” she tried to say, but I cut her off.

  “I know how old you are, Madison. Our ages shouldn’t be an issue or a subject matter. We are both grown-ass people who enjoy each other,” I declared.

  “Okay, I won’t mention it again.” She smiled.

  “Okay, now let’s eat,” I said, realizing our food had gotten a little cold.

  “Let me heat that up for you, baby,” she of
fered.

  “No, let me,” I said. I took our plates over to the kitchen. The suite was a huge open-floor concept with living, dining, and kitchen open to each other. It was nice. I wanted to ask about her position, but I didn’t want her to think I was interested in her dough. “Here you go,” I said, putting her plate down in front of her. I took a seat with mine. “So you own this place?” I asked casually.

  “Yes, my ex-husband and I bought it fifteen years ago. It went under a major reno about two years ago when we settled our divorce, and since we get along so well, we have continued our business relationship.”

  “Well, it’s nice…very upscale,” I complimented.

  “Thank you…as soon as I can get a new manager in here and get things underway, I’ll be leaving this freezing city,” she said, laughing a little.

  “Anxious to leave already, huh?”

  “No, I just don’t like it here when it’s cold,” she whined.

  “Well, I can keep you warm.”

  “I’d like that.”

  I smiled at her. She had this chill persona and I liked that.

  “So what if we become more than a fling before your departure,” I asked out of curiosity.

  “Well, I don’t know, Jerome. I live in Arizona and having a long distance romance is not something I’d like to do.” She took a bite of her steak.

  “I see,” I sighed and turned my attention to the plate. I knew then to pump my brakes, because even though I knew it was too soon, I was feeling her.

  “I didn’t mean it like that, Jerome…it’s just I was married to Kirk my entire life, and if I fall in love again, or fall for you, I’d want to be where you are and not so far away,” she explained.

  “Well, it’s just day two, so we do our thang and figure out what’s next when we have to. All I know is you are sexy, smart, and beautiful. If I fall for you, I don’t want you to up and leave.” I took a drink.

  “Come on, seriously, Jerome. You could see yourself with someone my age?”

  I dropped my fork. “Madison…” She cut me off before I could finish my thoughts.

  “No seriously, Jerome, be honest with me, because the last thing I want to do is sit here and set myself up to be crushed by a young, sexy-ass, twenty-four-year-old man that is only here for a moment to have a good time.”

  “Wow, Madison, seriously? I’m sitting here asking you questions about us being more than just a fling…you think I’d be asking those questions if I was just playing with you?”

  “I don’t know, Jerome,” she said. Her eyes got glossy. “I don’t want to be a fool, you know. I don’t want this to end with me being hurt. It’s bad enough I’m opening up to a man my daughter’s age, and to be crushed by you, would be a bad thing. So not a good look,” she expressed.

  “Okay, Madison, look at it from my side. You’re like two years younger than my mom. I’m putting myself out there, too. You think I’d want to be hurt by someone I know others would talk shit about if they knew. It’s still early and we have a couple weeks, so let’s just enjoy it and see how it goes. Can you do that for me? I know this is like day two, but in this short time, I am really feeling you, Madison. So for me, can we just see how it goes?” I pleaded, taking her hand.

  “Yes, that sounds like a plan.”

  I caressed her cheek.

  “You are just as sexy, just as fine, and just as hot as a woman my age,” I said sincerely.

  “Thank you.” She blushed. We went back to our food. Room service came afterward and cleared out the uneaten food and dishes. We sat and talked for hours. That night we didn’t fuck again. I just held her all night. She came into my shower the next morning and I set her right for the day, before I headed to work.

  MADISON

  I had hired a new GM and she was good to go, but I wasn’t. It was going on week three and I had already changed my flight once to stay an extra week. I didn’t want to leave him. Jerome was smart, kind, thoughtful, and considerate. When we were together, it’s like we were the only two people in the world. We’d spend every moment we could together. I knew we did it to ourselves, but each day that went by made it harder and harder for me to leave. I had been in Chicago for a month and my family wanted to know what was keeping me there since they knew winter wasn’t my thing. I had a man that kept me warm at night, so I didn’t have any more complaints about the cold.

  “Hey, Saturday night my cousin is having a birthday party at this club out south. I want you to come with me,” Jerome said.

  Shocked, I answered, “Jerome, I thought we agreed to keep our relationship discreet.”

  “I know, baby, but I think we shouldn’t have to do that anymore. I mean, you’re my woman, and I want to show you off.”

  “I don’t know, Jerome,” I said apprehensively.

  “Why not?”

  “What will people say?” I asked afraid. We didn’t go out much because it was cold and I didn’t think I was ready to hear the whispers of people who thought I was a “Cougar.”

  “Who gives a shit what people say, baby? Look at you…you are sexy as fuck, and my boys are going to envy me when they see what’s been taking me away from them the past few weeks. They know I’m seeing someone, and it’s time that they meet you,” he said.

  I let out a deep breath. “Are you sure that’s what you want, Jerome?”

  “Baby, I’m sure. I want you to meet my family, and my mom.”

  “Hold the phone,” I protested.

  “What?”

  “I can’t, Jerome. I can’t meet your mother…baby, are you crazy?”

  “Madison, it is going to be fine. My mom is cool. Trust, she’ll be cool,” he said.

  I wasn’t convinced. Saturday rolled around quickly and when he picked me up, I was nervous. By the time we pulled up, I no longer had butterflies. I was nauseous and I knew I’d pass out.

  “Baby, I don’t think this is a good idea. I’m not ready to meet your family and friends,” I cried.

  “Relax.” He took me by my hands. My hands were shaking. “Why are you so nervous?”

  “Because I am twenty years older than you,” I whined.

  “And I’m twenty years younger than you. If anything, we’ll both be embarrassed,” he said, smiling at me. “Trust you’ll get more props fucking a hot-ass younger man than I’ll get fucking a sexy older woman. Now come on, baby. I got you and I’m going to be with you all night.”

  I relaxed, shook it off, and got out. We walked in, hand in hand. We found a seat at the bar.

  “Jerome!” someone yelled out. He turned around.

  “Warren, man, what’s up?” I knew that was his best friend. Jerome told me a lot about him.

  “You, man…you’ve been hiding out. I hope this young lady is worth it,” he said.

  My thoughts were, not young, but old.

  “Yes, she is worth it,” he said. He grabbed my hand. “I’d like you to meet Madison.”

  I extended my arm and the look on Warren’s face was a surprise, but a pleasant surprise.

  “This is Madison?” he asked. From his reaction, I got approval.

  “Yes, this is my baby,” Jerome boasted.

  “It is a pleasure to finally meet you,” he said and kissed the back of my hand.

  “You too,” I said. He chatted with Jerome a little longer and before I knew it, I was meeting everyone. So far there were no evil looks and I could tell Jerome’s family and friends were cool.

  “Baby, my mom just walked in,” he said. He rushed over to greet her. I turned to the door and my heart began to pound out of my chest I was so nervous.

  “A shot of Patrón,” I ordered quickly. I was glad he handed it to me before they approached.

  “Baby.” I turned to them. “This is my mom, Maxine. Momma, this is Madison,” he introduced.

  “Nice to meet you, Maxine.” I extended to shake, but she looked at my hand like I had shit on it.

  “How old are you?” she boldly asked. She rested her hands on her hips. S
he gave me major attitude and since she was full-figured and from the Southside, I became terrified.

  “I’m ummm…I’m…ummm,” I stuttered nervously.

  “Gurl, I’m just messin’ with you. Get up and give me a hug,” she joked. I swallowed hard. “J.T. already told me that you were damn near my age, but he didn’t tell me you were gorgeous,” she teased. I stood and gave her a hug. Jerome allowed her to take his seat next to me. He ordered us a round and his mom turned out to be so cool we exchanged numbers. A couple hours later, after we danced and I met everyone, I was tired and ready to go.

  “Baby, are we leaving soon?” I asked.

  “You’re ready to go? My fam was talking about hitting this other spot,” he said.

  Just then it hit me again that I was twice his age.

  “Another spot? Baby, it’s almost two,” I said, looking at the time on my cell phone.

  “Two, baby…it’s early. Don’t tell me you’re ready to take it in.” I hated it, but I was. “Listen, I can grab a cab and you can go without me. I don’t mind. I’m tired, baby.” I pouted. He gave me a quick kiss.

  “Since I don’t live far, I’ll take you by my place and I’ll just hang out for a little while longer, then I’ll be home.”

  That was fine with me. “That’s fine.” I nodded.

  When we walked in, I kicked off my shoes with the quickness. I worked out every day, but I hadn’t danced that much in a minute. My feet were throbbing. I pulled off my coat and tossed it onto the sofa and began to undress as I headed to his bedroom.

  “Okay, baby, you know where everything is. I’ll only be gone like an hour or so. I’m gone show my face and then I’ll be home,” he said. I stood in front of his dresser in my undies to remove my jewelry. “Damn, Madison, you’re making my dick hard, baby,” he said, standing in the doorway watching me. I saw him in the mirror readjusting his dick in his pants.

  “Well, you have a choice to make. Head,” I said, and licked my lips in the mirror. “Or the club?” I turned around to face him. I gave him my sexy pose and he looked at his watch.