Cougar Cocktales

by N'Tyse

  Despite how much it felt like yesterday, that had happened two years ago. Now here I am sitting in an airport headed for Chicago at the absolute worst time of the year. I hated winters and the weather reports were terrifying, but I had to go.

  • • •

  I got off the plane and headed to baggage claim quickly to retrieve my luggage. I wasn’t in the best of moods that afternoon. I didn’t want to be in Chicago. It was freezing and our reason for moving to Arizona in the first place was to be where I could sit by the pool the majority of the year if I wanted to. Kirk and I owned a couple of hotels together in the downtown Chicago area that were doing well, but one stumbled on to some management issues, and it didn’t take Kirk long to figure out the general manager was not only doing a poor job, but he was lacing his pockets with our money. I wanted to scream when the words floated from Kirk’s lips. I looked at him with a blank stare for a few moments, hoping he was joking.

  Kirk had his hands full with our other business matters, and a trip to Chicago was too much to add to his plate, so sending me was the only option. I was a freelance photographer and had a more flexible work schedule, and sadly, more time on my hands. He and I had managed the property together years ago when we’d first married, and even though I didn’t want to make the trip, I gave in. It took a little arm twisting and a whole lot of persuading, but ultimately I decided to be a good ex-wife and go and handle our business.

  The trip was only going to be temporary; to recruit and train a qualified candidate. After I thought about it, a brief trip home wouldn’t be so miserable. I only dreaded the brutal, bone-chilling climate, but it wasn’t like I could fix the business problems from Scottsdale.

  I retrieved my two designer suitcases from the belt and fished around my purse for the key to my lock to get my coat and hat. I squatted to open the larger suitcase and thought to myself how happy I was that I hadn’t gotten rid of my entire winter wardrobe. I planned to do a little shopping, but for the most part, I had packed enough items from my storage to get me through the trip. I was all set to leave, but there was no one in sight with a sign up with my name on it. Kirk and I visited Chicago frequently to visit our family and friends and always had a driver there to meet us upon arrival. I pulled out my phone to make sure Kirk remembered to make arrangements for me.

  “Kirk, did you remember to get a car for me?” I belted as soon as he said hello.

  “Yes, baby doll, you know I set that up when I booked your flight,” he answered promptly. I then heard ruffling, so I assumed he was going through his rolodex for the number. “No one’s there yet?”

  “No, I don’t see anyone. I didn’t go outside or anything,” I said.

  “Hold on,” Kirk said. I heard the loud dial tone of his desk phone and assumed he hit the speaker button. I looked up and spotted a young man coming my way holding a sign alongside his body with my name on it.

  “Wait, Kirk. I think this is him,” I said. He came closer. ‘HEEELLLLOOO!’ I said to myself when I got a closer look at him. “Kirk, I’ll call you back,” I said quickly, ending the call. He stopped and put up the sign with my name across his masculine chest. I swallowed hard. This baby god had to be my daughter’s age, and I knew I was wrong for looking at him like he was a piece of meat, but he was too fine. I shook it off and approached him thinking, his mother would probably want to whip my ass for wanting to spank her baby boy. I knew me and his momma had to be close or even the same age. “I’m Madison Washington,” I said after clearing my throat, and then, BAM! He hit me with his sexy smile.

  “Hello. I’m so sorry I’m late. It was crazy traffic,” he explained.

  “You’re fine… I mean…ummm, it’s fine,” I stuttered. His voice was even sexier than his smile, and I just stared for a moment.

  “Can I get those for you?” he asked. It didn’t dawn on me that he was talking about my luggage. I was too busy looking at his lips. He stood over six feet, and even though he had on a heavy coat, I imagined him having an athletic build underneath. His medium-brown skin was smooth and clear and his beautiful long lashes laced the top and bottom of his eyes. His brows were thick and shaped to perfection and they laid sleek under the brim of his Chicago Bears hat. I imagined he had a nice grade of hair. He had a thin mustache and goatee, and he was definitely the type I went for back in the day when I was in my twenties.

  “I’m sorry,” I said, looking at him confused.

  “Your bags, ma’am,” he said. The word “ma’am,” for the first time stung like a bee. I was forty-four and assumed he was at least twenty-five—at least I hoped, but either way he was too young for me to be lusting after.

  “Oh yes, my bags.” I smiled, handing them over. I went into my purse and pulled out my shades and was glad I flew like I was going on a date instead of in my oversized sweats and hair scarf. I usually flew comfortable, but I knew I would be greeted by my staff at check-in and I wanted to look like the owner’s wife—well, ex-wife. I looked gorgeous at forty-four. I still looked fifteen years younger than what I really was and I knew my twenty-four-year-old daughter would have a mouthful to say if she knew I was checking out a man close to her age. “Lord have mercy,” I said softly as I followed this work of art out of the airport doors.

  “This way, Mrs. Washington,” he said, as if I wasn’t already following his lead.

  “It was Mrs. Washington, but now I’m happily divorced, so please just call me Madison,” I insisted. He opened the door for me. I got in. I did a quick mirror check before he got in and quickly removed my heavy coat to get comfortable. I fluffed my hair and he got in. It took a moment for us to pull off because there were cars everywhere, but I didn’t mind. I just checked him out in the rearview mirror.

  “Are there any other stops you want to make before going to the hotel, Mrs. Washington?” he asked as he pulled out of the parking space.

  “No, straight to the hotel is fine. And please, it’s okay to call me Madison,” I repeated.

  “Yes, ma’am,” he said and hit the button to raise the center window.

  I stopped him. “You can leave it down.” He pressed the button to retract it. He looked up and my eyes were staring, so he smiled.

  “So tell me, is this your first time visiting the Windy City?” he asked, now giving me the same eye contact in the mirror.

  “No, I was born and raised here,” I said. Now we were both watching each other.

  “Really, what side?”

  “Southside,” I replied.

  “So what brings you back? Visiting family, business, or pleasure?”

  “Mostly business. I’ll be visiting family and I’m hoping for a little pleasure,” I said, giving him my sexy girl smile. I hoped he knew what I was implying. I got on the plane that morning with thoughts of getting in and getting out; now I added getting my pussy wet to my list. I knew he was a lot younger and I never thought of getting with someone so much younger, but hell, I was now divorced after a twenty-four-year marriage, and my first sex encounter with a man half my age, didn’t sound so bad in my mind.

  “A little pleasure too, huh?” He flashed that boyish grin again. I felt my pussy tingle. I hadn’t had any in six months, and I hadn’t had it good in even longer. Things with Kirk and me went sour when he started fucking a younger woman. I knew she was with him for the money because his lovemaking began to play like a rerun of a minute man after only a few years of marriage.

  “What do you do for pleasure?” he asked.

  “Well, I travel a lot. I enjoy taking pictures and reading from time to time. That other thing I used to love doing for pleasure, I haven’t done it in a while,” I admitted.

  “How long will you be in town?”

  “A couple weeks,” I said, knowing it may be a little longer.

  “How much of that time are you willing to use in pleasure?” he asked.

  I then thought he knew I was checking him out and I hoped this wasn’t his first rodeo ride with an older woman. He was a bit cocky—I could see
that in his demeanor and in how he looked at me in the rearview. He looked damn good and I knew in this business, he may have encountered plenty of women, and I wondered if he thought I was as sexy as I thought he was.

  “It depends,” I replied.

  “On what?”

  “If it’s good,” I said, and then reached for the champagne and opened it. We were stuck in traffic, so why not.

  “Is that an invitation for a test drive?” he asked.

  “If I said yes, would I get a yes to that invite?”

  “Definitely.”

  I smiled even brighter. I filled my glass before I spoke.

  “Before you speak too soon, I gotta be honest. I’m forty-four,” I exposed. I hoped I wouldn’t turn his sexy smile into a disappointed frown.

  “You certainly don’t look it,” he replied.

  “I’m aware of that, but I need to know would that be a problem for you?” I asked nervously. I put myself out there, and if he said my age was a problem, I’d be too embarrassed.

  “Should it?”

  “I don’t know…what—you’re twenty-six, twenty-seven,” I asked. I didn’t want him to think that I thought he was more of a baby than he actually was.

  “I’m twenty-four, and as sexy as you are, forty-four is no problem.”

  I took more than a sip when he said that. Did he just call me sexy? I smiled to myself. Excited, I asked, “Okay, so…wait, what is your name?”

  “Jerome. Jerome Taylor,” he said.

  Jerome Sexy Ass Taylor, I thought. “Nice to meet you, Jerome.” I added more to my glass.

  “You too, Madison. I know it’s cliché, but everyone calls me J.T.,” he said. We both laughed.

  “I figured that, but Jerome works for me, or I can come up with another name for you later,” I flirted. He smiled shyly. We continued to make small talk. Finally, we pulled up to the hotel. The bellhop got my bags. I asked him to wait a minute and I rushed inside. When I announced myself, the staff hurried into their positions as if things were going well. I knew it was all a front. If they were doing the right thing, I wouldn’t have had to be there. After I received my keys to the master suite, I rushed out the door to Jerome.

  He got out of the driver’s seat and came around and stood in front of me. I was trembling, but I handed him a copy of my room key while I still had the nerve. “What time should I expect you?” I smiled. I had never done anything so risky in my life, and I was hoping I’d be able to go through with it.

  “I’m off at six, so about nine.”

  I nodded. I stepped in closer to him. I could smell the mint on his breath. I knew it may not have been professional, but I wanted to taste his tongue. After slight hesitation, he gave me what I wanted. I closed my eyes and enjoyed the sensations his tongue gave mine. I wanted to fuck him right then and there.

  “Can you make it sooner?” I expressed, after he planted the last gentle kiss on my lips.

  “I’ll try,” he pledged.

  I finally let him leave and then rushed inside to get acquainted with everyone. I got all of my first-night business out of the way and made sure room service knew to have my room stocked with champagne, whipped cream and strawberries. I ran myself a nice hot bath and soaked until the water chilled. I rubbed myself down with my favorite fragranced oil and slipped on some lingerie. It wasn’t the sexiest number I owned, but it would do for that night. Shopping for my young stud some eye-catching teasers were now on my to-do list.

  • • •

  At 8:27 p.m., I heard the door open. My heart stopped for a moment or two. When he walked in, my hands began to shake and I began to have second thoughts. He moved in my direction quickly and ran his hand gently across my collarbone.

  “I’ve been anxiously waiting to touch you,” he whispered. I wanted to fan myself. I wanted to ask questions, but it wasn’t time for all that.

  I swallowed hard. “What are you going to do to me?” I whispered back at him. My nerves were going crazy. Him standing that close to me, had me quivering.

  “Make you want to want me every moment that you’re here,” he said in my ear. He began to glide his tongue down the side of my neck. I then began to wonder if he had someone.

  “Is that right? Will you have that much time on your hands?”

  “I can be available if you want me to be…this is all on you. Remember, this is my test run.” He caressed my arm softly. He kissed me deeply and his fingers found their way to my pussy. I opened up for him. He gently played around in my area in a soft circular motion before licking his fingers. I wondered if he was making sure it was okay to put his tongue on my clit, or if he just wanted to taste my juices. Either way, I was okay with that.

  “Take this off,” I instructed. He took a step back, not putting a lot of space between us. My heart was pounding out of my chest. He pulled his shirt over his head, revealing a sculpted chest and rippled stomach. I bit my bottom lip at the sight of him and wanted to see it all. “These too,” I demanded, tugging on the rim of his jeans. Within seconds, his jeans and boxers were off. Chest chiseled, stomach ripped, dick enormous, and overall beautiful. “Damn, baby,” I hissed, thinking out loud.

  “Now you,” he said. I let my straps fall and slowly slid my nightie down. I wasn’t afraid to show him my naked curves because my body was thick and in great shape. My stomach barely had any traces of me having Amber twenty-four years ago because I didn’t have stretch marks. “Damn, baby, you are sexy as hell. Turn around and let me see all of you,” he instructed.

  I did a sexy spin for him. He pulled me into his body and kissed my neck from behind. He grabbed my tits firmly and massaged them. I reached behind to touch him. The action had just begun, but I was so hot, I wanted to feel him. I wanted him to please me like never before.

  I broke loose from him and anxiously pulled him toward the room. He stopped me and pinned me against the wall. He pushed his tongue inside of my mouth and I enjoyed kissing him. Wet, hard, long and sensual was how he ravished my mouth. At that moment I could not remember a man kissing me so well.

  He kissed my skin, heading south. He didn’t forget to please my nipples on his way down. He got to my neatly trimmed pussy and pushed my left leg up. He put his mouth on me and began to send waves through my body, applying the right amount of pressure on my clit. He lifted my thigh over his shoulder and after sucking my clit a few times, used his free hand to open me up. He pushed his tongue inside of my pussy. I wanted to cum with him inside of me, but he was on a mission to make me cum in his mouth.

  “Baby, it’s right there, and I don’t wanna cum yet,” I refuted, but he pinned me harder to the wall with his lips pressing into me. “Jerome, baby, I’m there,” I screamed, and then began to shiver. I released, and he came up smearing my juices on my stomach and tits as he made his way back to my mouth.

  We kissed deeply and I wanted more of what he had to give. I caught my breath and we went over to the bed. I asked him to lie down, but he said, “No, get on your knees,” and I did. He grabbed his dick and caressed my face with it. The heat from his flesh warmed my skin. He teased my mouth for a minute before he let me take him inside. “Aaaahhhh,” he moaned and I looked up at him, and he had his head back with his eyes shut. I wanted him to play with my hair while I pleased his dick, so I reached for his hand and placed it on my head. He pulled back and I licked his head, not wanting to give him composure time because I wanted to make him cum as hard as he had made me cum a few moments before.

  I wanted to relieve him, revive him and feel him deep inside of me again. His dick jumped, and I knew he was ready, but when he pushed it back into my mouth, I realized I was wrong.

  Surprisingly, he could hang and I was up for this pleasure match. I took him deep and then I pulled back and sucked the shit out of the tip, and he finally backed off. “Ooooh shit, baby, hold on.” He winced. I knew I had him. He reached for me and pulled me from the floor. “I want to feel your pussy,” he groaned, and then kissed me deeply, again.

&
nbsp; “How do you want me baby?” I asked, breathing heavily because I was so fucking hot and turned on.

  “Lay down.” He nudged me. I was surprised he chose missionary. He went back into the other room and came back with a Magnum. I had three under my pillow. I had gone into the hotel’s gift shop and purchased them right after I got settled in.

  “I have condoms, baby,” I whispered. I reached underneath the pillow and pulled them out. We laughed.

  “We’ll need those too,” he teased, opening the condom. I watched him roll it on. He climbed on top of me and after a few moments, he had my legs spread so wide I thought he’d break me. My pussy was aching for him. I anticipated him entering my body. I exhaled when he finally slid inside of me and instantly filled my body with pure pleasure.

  “Awww, baby. That’s so damn good,” I moaned. My pussy hadn’t felt that way in ages.

  “Can I go deeper?” he asked, pumping me like a skilled lover. His thrusts were perfect and I could feel the passion with every down stroke.“Yes, baby, yesssssssss!” I moaned. I took all of him like an eager lover was supposed to. My desire for him was so strong at that moment, it felt like we had been lovers forever instead of first encounters.

  He pressed deeply into me. So deep it pained my insides, but felt so good at the same time. “Aaaahhhh, aaaaahhhhh, ummmmm, ummmm,” I moaned, dealing with the pleasure and pain he rewarded me with. My eyes bulged when I felt my clit tingle. “Ahhhhh, ahhhhhh, ahhhhhh, baby, I’m coming,” I screamed in shock. That had never ever happened to me in all my years. I’d never came from penetration. Oral…yes. All the time, but never penetration. I figured the juices my body released excited him more because he pumped hard and then he came down and began to slow roll it inside of me. He sucked my neck and whispered, “Baby I’m close,” but then he went back up and pushed my legs back again. His sweat rolled down his chest and stomach. It was so damn sexy.

  “It’s good, baby, it’s good, baby; your pussy is so damn good,” he moaned softly, and then he slowed.