I looked at the cute blonde coming our way, but she looked right past me and smiled at George. He winked at her, and she blushed. What is it about this guy that women love so much? Sure, he was good-looking, tall and fit, but I wasn’t that bad either.
The blonde wasn’t the only one who preferred George. Stacey was another woman. After I dated her for three years, she had the audacity to tell me that it wasn’t fair to be with me because she wanted George more. Thank God that she emigrated soon after breaking up with me. Imagine how embarrassing it would’ve been for me to see my friend dating my ex-girlfriend.
I’m not sure that George knew about how Stacey felt about him, and it was probably for the best. I’d hate to lose a friend over a girl.
“You’re ready?” asked George. My chest inflated as I dug deep into my lungs for air. I nodded. “Okay.” He pointed. “You go that way, and I’ll head that side. Let’s meet back here in two hours.”
That was enough time for me to cover the shopping centre and do plenty of approaches. The more approaches, the higher chances of me catching a fish. George, on the other hand, would probably need to do about two or three approaches to get an instant-date and use the remainder of the time to make out with a girl.
I got rejected by the first three girls. It’s okay. Just relax. It’ll get better once your nerves settle. I knew that motion creates emotion, so I continued walking and looking for girls who looked friendly. The fourth girl was a short, brunette who smiled but spoke to me briefly.
The fifth was happy to see me and asked for my name and if I had a girlfriend. Pity that she wasn’t my type, but I got a confidence boost from the interaction.
As I turned and walked away from her, a mature blonde popped out of a clothing store. She wore a tight blue top, jeans and sneakers. Her blonde hair came down to her shoulders, and the tight jeans revealed her round ass. I figured that she was in her mid-forties.
I swerved left and right amongst the throng to keep up with her. She was about fifteen metres away from me, but I closed the distance as she approached a coffee shop. Damn it. She stepped inside the shop and stood in line. I didn’t want others gawking at us, so I waited outside for her.
She ordered a coffee, sat at a table and then picked up a magazine. I pursed my lips and rolled my eyes, knowing that I’d wait a bit longer.
Twenty minutes later, and she was still inside. I walked in without a plan. I figured if she saw me that she’d somehow get the vibe from me that I wanted to speak to her. She didn’t even notice that I was there.
I went outside and waited.
Ten minutes later, she walked out and headed for the escalator. I was right on her tail, and I watched her go inside a clothing store. Usually, I was terrified of following a woman inside a female clothing store as the other patrons would know what I was up to, but I could have cared less.
She had her back to me and was checking a dress as I approached.
“Hi.” She turned around. “I saw you here, and I wanted to tell you that I think you’re absolutely stunning.”
She smiled, lowered her chin and gaze for three seconds, then looked me in the eyes. I learnt that it was best to be direct with MILFS. They appreciated a man, not little boys.
“Thank you. These things happen when you least expect them.”
I extended my hand. “I’m William.”
“Nice to meet you, William. I’m Charmaine.”
“You doing some shopping?”
“Yeah, before I head back home to work.”
“On a Saturday?” I asked.
She raised her eyebrows. “That’s how IT is.”
“Okay. So, you’re one of those freaks behind the geeks.”
She frowned. “Sorry?”
“You pretend to be one of those geeky types by hiding behind your occupation, but you’re a bit of a freak behind closed doors,” I said with a sly smile.
I was going for broke. She would either be repulsed or indulge me.
She smiled and said. “You think so?” That confirmed I was right.
“Definitely. I was actually on my way to get something to drink. Would you like to join me?”
“Um, I actually just had a cup of coffee.”
“I’m gonna have a juice. You can have that or something else.”
“Ya. Okay.”
I saw two guys at the restaurant opposite the store staring at me as I walked away with her. I let her go onto the escalator first so that I could get a glimpse of her ass. Man, it was so nice.
We ordered juices and spoke for about half an hour. She was friendly and reminded me a bit of Stacey. A part of me wanted to be with her just because it would feel like I was with Stacey again.
My eyes widened as she snatched the bill and insisted on paying. That was one of the perks of being with an older woman. She gave me her number, and we made plans to meet up two days later. I didn’t want to meet up the following day as it may have portrayed me as desperate.
I walked away from her with a smile on my face and feeling light-footed. Forty minutes remained before I had to meet up with George, but I didn’t bother approaching other women. I felt I had a solid thing that would result in a lay.
George smiled as I approached him. “You dirty dog, you,” he said. “Looks like you met someone.”
I figured that my face gave away my enthusiasm. “Maybe,” I said, raising my chin and narrowing my eyes.
“I also met a stunner about fifteen minutes ago. Got a date with her tomorrow at 7. You?”
“I set something up for the day after tomorrow.”
“Good stuff. Let’s head out.”
The following night, I was watching TV when my phone beeped. I stretched from the couch, extended my hand to the coffee table and then picked up my phone.
I smiled as I saw that it was a message from Charmaine. My joy devolved to anxiety as I feared that she was cancelling. I opened up the message and read: Sorry, I’m running a bit late. Traffic is hectic, but I’ll be there soon. Charmaine.
I frowned, wondering if she had mistaken me for somebody else. Then, I thought that she got the days confused and thought we were meeting up tonight, not the following day.
I typed, ‘Hi Charmaine. We’re meeting up tomorrow, not to…’ The cursor on my phone kept flashing, waiting for me to type the rest of the word as I looked at the time and saw that it was seven.
No. No ways. It can’t be. It’s impossible. This is one big coincidence. There’s no way that George also met Charmaine. I leapt off the couch and paced, wondering if I should call George to confirm. That’s stupid. He’s gonna notice my insecurity. The guy reads me like a book. I’ll call him tomorrow.
While lying in bed, I couldn’t stop thinking about if I had overreacted. After all, it could’ve been nothing as I had imagined it.
I woke up at six the following morning. I couldn’t remember the last time I had done that, but I guess the nerves got the better of me.
The phone kept ringing as I paced in the lounge. “Hey, George,” I blurted out.
“Hey, buddy. What’s up?” He sounded groggy.
“Sorry to call you so early. Just thought I’d check on you and see how your date went.”
He yawned. “It was good. Got back after midnight.”
“How was it?”
“I banged her.” I stopped pacing and remained silent. “William, you still there?”
“Yes, I’m here. So, how do you feel about her?”
“Yeah, she’s great. I got my hands on a naughty MILF last night.”
My eyes closed as I hung my head. “I see,” I said softly. “What’s her name?”
“Charmaine.”
I pinched the bridge of my nose and shook my head. “Right. I thought so.”
“What do you mean?” asked George.
“Was she wearing a blue top and jeans when you met her?”
“Yes. How did you know?”
“Because I also met her. I’ve got a date with her tonight.”
“Oh, man.” George chuckled. “Looks like we’re in a triangle.”
Those words told me that he would’ve taken Stacey had she professed and stayed around. He could have numerous other women, but he was joking about my love life. Since he wasn’t letting up, neither would I.
“I’ll tell you what,” I said. “After our date, we’ll set up a meeting with her and ask who she wants to be with.”
“Fair.”
“Okay. I’ll call you tomorrow.”
I had never slept with a woman on a first date, but tonight had to be the night. Since George slept with Charmaine, I had to bang her better so that she would choose me. Even if she didn’t want a serious thing with either of us, I had to know that I was the first pick. It would bring me some kind of closure.
After my date with Charmaine, I walked her to the car. There was no way I would let her slip through my fingers. “You wanna check out some photos I took while I was out in Europe.”
“Sure. Are they on your phone?” she asked.
“Um…no. Actually, they’re on my laptop. It’s back at my place. I also picked up some amazing wine while I was in France. I’d love for you to try it.” I don’t know why I said the last part since it was a lie. I was desperate. What could I do?
She smiled. “Okay.”
We got to my place, and I switched on tranquil music and poured a glass of cheap wine that I had picked up in the morning.
“Thank you,” said Charmaine as I handed her the glass. My heart was pounding my chest. I felt blood rushing to my groin, and the excitement made me inhale rapid breaths. “Nice place you -.”
Charmaine’s sentence remained incomplete as I had crashed my lips into hers and stuck my tongue into her mouth. My hand glided up her leg and brushed over her groin, then slid up under her shirt and fondled her tit. She moaned, making me even harder.
I pulled back and got the urge to stand, so I did. I unzipped my pants and pulled down my jocks. She smiled at my boner, grabbed it and then leaned forward and licked the tip.
I put my hands on her shoulders and watched her suck my dick. My lips stretched, and a vein protruded from my dick. That had never happened before. She was a champion dick sucker who must’ve gotten a lot of practice. She knew exactly the pace I liked and looked up at me with a cheeky smile as if she knew that she was pleasuring me as I had never been before.
Charmaine stood up and smiled at me while stroking my dick. She turned her back to me and pressed her ass against my dick. I grabbed her waist and clenched my teeth, wanting to stick it into her so badly. She bent over the couch and rested her forearms on top of the backrest as her ass pressed against my dick.
I squatted, pulled her cheeks apart and then licked her pussy. She shook her ass, and her cheeks slightly smacked me in the face.
I stood upright, grabbed her waist and put my dick inside. She stretched out a moan. George might’ve been better looking than me, but there was no way he would bang her better.
My dick went in all the way into her pussy, and it seemed like my pace just kept increasing.
“Oh, God. Right there!” she exclaimed while looking at the wall.
She was so wet. I wanted to lick her pussy while banging her. I couldn’t get enough of it. Looking at her hair reminded me of Stacey. It’s like I was with her again, and there was no way I’d let go of that feeling.
I wanted to feel Charmaine even closer to me, so I pulled out my dick and sat on the couch. She sat on top of me with her back facing, then put her feet on my legs and leaned back. I put my dick inside and put my arms over her stomach. Her hair brushed my face as she bounced on top of me. It felt amazing. It’s like I was with Stacey all over again.
I felt the cum bubbling up, so I pulled out my dick and came over Charmaine’s stomach.
The following day, I called George. “I spoke to Charmaine, and she said that she’ll meet us,” I said. “I figured we need privacy in a relaxed environment, so I thought the park next to my house was perfect.”
“Okay, great. What time?”
“Two pm.”
When George arrived at the park, he saw me pinned against a tree. A muscular bald guy had clutched my throat, making my face flush. I could barely breathe from the pressure that he exerted. I grabbed his wrists and tried to talk but couldn’t.
“What the hell is going on here?” asked George, standing twenty metres away.
The bald guy asked me. “Is this the other prick who slept with my wife?”
“What?” asked George, his eyes wide and eyebrows raised. “Sir, I didn’t mean to, please, forgive me. I had no idea that she was married.”
The bald guy loosened the grip. “Help me, George,” I said. George kept looking at me anxiously and was stifled. “He’s gonna hurt me,” I added.
The bald guy glared at George, released the grip and then faced him. George looked more erect than I had ever seen him and a lump had developed in his throat. With his mouth agape, George stepped back as the bald guy walked towards him. As the bald guy twitched, George ran off.
“Nice work, Lionel,” I said.
“You don’t feel bad about scaring your buddy like that?”
“Well, this was a friendship test, and he failed. You don’t leave your friend high and dry the way he just did. If he had done something to protect me, I would’ve stepped aside and let him be with Charmaine. Hell, I might’ve even told him about my ex-girlfriend wanting him.”
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