Cubs

Olivia

I feel exhilarated!  I feel as though I could run a marathon. It was a refreshing change from having had to deal with my non-existent husband.  Being with Tony allow my spirit to run free as we fucked the entire night and again in the morning. With him being a younger guy, he had the stamina to ravage me relentlessly.  Sharon was right, I was missing out on the younger guys. He was absolutely phenomenal and  I can't even share it with her, she would kill me to know that I fucked her son. And planned to do it again over a weekend. 

Tony hadn't told his mother that he worked for the service she suggested I try.  It was a great idea since Robert was fucking everyone else except me.  He didn't need me as his wife anymore, he had found replacements. And so did I.  I planned to meet up with Tony for a long weekend, enjoying having him between my legs repeatedly. I didn't imagine I would enjoy  myself with Tony, but he makes me feel so comfortable.

I was lounging in the backyard near the pool when Sharon called saying she was at my door. My stomach dropped as I walked through the house to the front door to let her in. I saw her standing at the door and my heart pounded loudly in my chest. 

“Sharon!” I squealed, opening the door to Sharon standing in a delicate sundress and her hair flowing. “You are glowing.”

“So are you. Did you fuck a young guy?” She walked past me heading for the patio. I froze with my mouth open while I hear myself saying, ‘yes, I fucked your son’ - in my head. 

“Sharon, is that all you think about?” I replied, trying to ignore her question and closing the door. 

I walked through the house, the cool breeze filled it with fresh, crisp air. It was a refreshing day. 

“And to answer your question,” she started. I sat down on the lounge chair next to her. “No, it is not all I think about. But I did fuck a young guy, so did you?” 

I was blushed and shocked simultaneously. Sharon was living her life and she was loving it. 

“You did, didn’t you?!” She tapped my arm.

“Yes and it was amazing!” I squealed. I had to let her know. I could talk about the situation, I just couldn’t let her know who he was. 

“Oh my goodness!  I knew it!” She screamed. “How many times?”

“From last night or from this morning?” I smiled as I laid back on the chair.

“You Bitch! Are you serious?” She was so happy that I had joined her club of older women sleeping with younger men.  I must admit, it was quite an invitation.

“Yes,” I turned towards her. “I met him and he instantly made me comfortable. I didn’t expect to be so calm, honestly.”

“I know right,” Sharon laid on her left side to face me. “I remember my first time, I was overthinking so much I almost didn’t go. But I did and it was the best decision I had ever made.”

“Yes, but he made my body feel things I had never felt with Robert.” I quivered thinking about his face between his legs.

“I don’t know how to describe it but it’s like they touch you in a manner that is delicate and taboo all at the same time.” 

“Yes! You want to feel guilty that this young man could be someone’s son but then he makes you come so hard that it makes you want to cry! It’s mind blowing!”

“Exactly!” Sharon raised her fist in exhilaration because she knew exactly what I was feeling. 

“When did this become a thing?” I asked quizzically. 

“When women started embracing their sexual prowess. As long as the man is legal, does it matter?”

“I see no problem with it. I just never imagined myself with a younger man, that’s all. It never crossed my mind.”

“Mine either, until it happened.” Sharon sat up and looked at me. “So are you seeing him again?”

“Yes, I am. I booked him for a weekend.” 

“Oh my,” she placed her hand to her chest. “I’m so proud of you!” I laughed along with her as we gave each other a high five. 

“I can’t believe it. I really enjoyed myself last night.” I looked at Sharon and I saw a bit of Tony looking back at me. I looked away, it was too weird. “How about you? Did you find a new guy?”

“Yes, in fact I did.” She fanned herself.  “I a bit embarrassed to say because he is a friend of a friend, you know kinda situation,”

“I see, so you know him?,” she nodded and I nodded as if she asked me the same question.  

“Well the less we know the better,” I said pointing back and forth between us. “We don’t need details.” 

Tony

After I received my contract for the weekend, I decided to go up to my apartment to relax a little before I figured out what I wanted to pack for the trip. To kill some time, I started looking for supplies to fill out the warehouse for the business.  With receiving the contract with Olivia, I was able to obtain some money to get the business license as well as get the website up and running. Having the overnight weekend contract will allow me to purchase those supplies I was just searching for.   My phone rang loudly on the counter. I grabbed it to see Matt giving me a call. 

“Hey Buddy, I didn’t expect you to answer at all.” I smiled. Matt is always trying to reach me but I hadn’t told him about the new job yet, I didn’t know how he might take it along with the fact that my job led me to his mother. 

“Matt, yeah I know. I’ve been busy for the past few weeks.”

“Yeah, you have,” he chuckled. “Hey do you have time to meet up today, I wanna talk to you about a few things.”

“Ah, sure. I’ve got time now if you want to meet up?”

“Yeah, now is great. Why don’t we meet up at Doc B’s in River North?” That was perfect for me seeing as I was already downtown. 

“That’s perfect.” I answered. 

“Cool, I’ll see you in about an hour?” he asked.

“Yup, I’ll be there.”  

I wondered what he wanted to tell me as I hadn’t seen him in a while. If it was something wrong with my mother, I’m sure she would have called and told me, so I couldn’t wrap my mind around what he needed to talk to me about. Anyway, I needed to speak to him because I was working on the start up money for the business and I already dropped five grand to get the ball rolling. 

Since I was at my apartment, not far from the place, I was able to hit the gym and shower before I left to meet up with Matt. I had a car drop me off in front of the place, ironically I arrived at the same time as him. 

“Tony,” he sang walking over to me giving me a ‘bro hug’. “Long time, huh?”

“Matt, yeah it’s been a few weeks,” I grinned. He nodded and we walked into the spot and grabbed a table. 

“So how’ve you been? You look like the job’s not killing you.” Matt said, taking a sip of water. 

“The job is well, it’s not killing me. Actually, it’s going better than I thought.” 

“Good to hear,” he nodded. “Ok, I got a lot to talk to you about with the business and other things so I wanted to just jump in if you don’t mind?”

“Yeah that’s cool, shoot.” I sat back and waited patiently on Matt. He looked like he was a little kid holding a big secret. 

“I got the start-up money for our business,” he grinned from ear to ear. I couldn’t believe my ears. He got the money?

“Wait, huh?” I was working on getting the money. “How?”

“Well, that’s the tricky part,” he stammered. “I can’t tell you.”

“What do you mean you can’t tell me?” I wasn’t upset, just curious as to how he got the capital for the business. 

“It’s more like a secret investor type deal,” Matt winced. He looked uncomfortable trying to tell me bits and pieces of how he got the money. 

“What?” I scrunched  my face trying to figure out what he was trying to say. Did we have an investor now? “An investor?”

“No, it’s not like that,” he looked flustered. “I’m saying it wrong.”

“Just say it Bruh,” I looked at Matt wanting him to just spit it out.

“I met someone,” he blurted out. Our drinks arrived and he immediately took a swig of his beer. 

“Huh? You met someone?”

“Yeah, I met someone who was willing to give us the full amount over time of course,” he nervously looked at me but then gained his composure. 

“Who? Do I know them?” I was curious to find out who could give him the full amount.

“That’s what I can’t tell you, Bruh.” He shrugged and drank more of his beer. 

“What have you gotten yourself into?” I laughed. 

“A proposition to be honest with you,”  Matt leaned in, smiling suspiciously. 

“A proposition?”

“I got a question for you first?”

“Shoot.” I scooted closer to the table, I wanted to tune in on what he was about to ask.

“Have you ever been approached by an older woman before?” 

“Uh,” I smiled instantly thinking about Olivia. “As a matter of fact I have.”

“Really?” Matt sounded surprised.

“Yes. Have you?” I looked at him and he grinned from ear to ear. “Truth?” Matt nodded, closed his eyes and smiled harder. 

“Yes. I didn’t expect it at all, but she approached me and I couldn’t say no,” 

“I know the feeling. Mine was unexpected as well. I met up with her a couple of days ago. I just left her this morning.” I sat back in my chair and drank my beer. 

“A few days ago?  That’s why you said you weren’t coming home.” 

“That and work, but yes mostly her.” 

“I didn’t expect mine either. Apparently, she had been watching me for a while,” he adjusted himself in the chair and crossed his legs with his ankle on his knee. 

“Interesting, you made an impression. So is she the one giving you the money?”

“Yeah,” he answered. 

“Wow,” I chuckled. “Interestingly enough, I also have money to add for our business.”

“Really? From the woman you were with?” 

“Yes.” I was curious to find out about the woman he was seeing. Matt always had a thing for older women. “Did you sleep with her yet?”

“Yes, I did. If you must know.”

“I knew it would be just a matter of time before you would find a cougar. It’s been your thing since we were younger.” 

“Yeah, I know. Your mom and her friends were hot back then and still hot now!” He laughed. 

“And off limits.” I stated. He looked at me nervously and put his hands up, surrendering immediately.

“Ok dude. I get it.” Matt sat back in his chair smiling at his phone. 

“But I understand. It’s an incredible feeling. I wouldn’t pass it up either.”  It was magical to be with Olivia. I quickly remember her riding me and looking down at me as she kissed me softly. 

‘Yes it is.” Matt answered and we fist bumped sealing our agreement on the matter.

Our food came shortly after and I found out that apparently she was giving it to him in installments. I guess mine were installments as well, but I didn’t want Olivia to fund the entire company. Even though I believe she probably would. I wondered how far the both of us would go before things changed. 

“So, are you seeing her again?”  Matt asked.

“Of course. I’m about to go away for the weekend with her. You?” I took a bite of my burger and stuffed a few fries in right after. 

“Yeah, I’m supposed to meet up with her tonight.”  Matt chuckled and stuffed a bunch of fries into his mouth and nodded. 

I took a drink of beer and dipped another fry in ketchup and then barbeque sauce. “Quick question,” 

“Wassup?” 

“Do you think you could ever fall for an older woman?” I asked, thinking about Olivia. 

“I’m sure I could. If it’s the right woman,” He tilted his head. “I don’t need a drama queen, I don’t care how much money she has.”

“I feel you on that Bruh.” Matt took another bite of his burger. My phone vibrated in my pants. 

I wiped my hands and fished my phone out of my pocket. It was a text message from Olivia.

[Olivia] Looking forward to having you this weekend.

[Tony] I’m looking forward to taking you as well. 

[Olivia] You make me wet just thinking about you.

[Tony] Good to know. I’ll be inside you soon. Talk to you later.

[Olivia] 💦