My follies – part 2

Alright, kiddos. Let us get back in action about my awesome luck with women.

One of my favorite stories I turned into a song, called Sucker. I swear to you, you’ll like it. People always say they’re good musicians, but I’m honest to God that I’m great. I’m no where near humble when it concerns my abilities concerning music. Anyways, back in the day when I use to play the role of the friend, thinking I’d be like a Trojan horse. Good God, was I stupid. Anyways, my last straw was me getting played really, really hard. Listen to the song Sucker, located here  . I replay the night word for word. It’s seriously how it happened.

So, my biggest folly.

I had a friend, we’ll call him Polly. He has the name of a bird, so we’ll go with Polly. Anyways, him and I were as close as friends as you could be, you know? I would have taken a bullet for him, and vice versa. I loved the guy. Anyways, he had a sister, we’ll call her Andrea. I was 19, she had just turned 17. Now, over the years she had just been my best friend’s younger sister, but as I grew older, I started to notice how incredibly beautiful she was. I mean, she’s stunning. Not just that, but she had this incredible personality. She had all these fantastic quirks that I picked up on, and adored. Goddamn, I sound like such a fag right now, but it’s true. At one point, my friend’s parents were leaving for a week long vacation, and asked me to babysit the house. You see, there was a younger son, he was about 7. He needed a ride to school every morning, and my pal worked all the time, and so someone needed to be there to take care of the little guy. Well, me being the most trust worthy man alive, and also Polly’s best friend, they hired me to stay there and watch the house.

Well, over the week I spent hours and hours with his sister. We had everything in common, it was unreal. I’d never met anyone like that. Well, after that, my feelings just got worse, to the point that I fell in love with her. It was absolutely horrible. I was mopey all the goddamn time, I couldn’t listen to ANY song talking about a girl because it would depress the fuck out of me.

I asked all my friends, and people I knew well if they’d let me date their sister. It was a resounding yes. I’m a very trust worthy guy. I’m the perfect motherfucker you’d want to bring home to mom. So, I thought, my best friend just HAS to say yes. However, I felt there was no way she’d dig me, because at the point I was at my fattest, and was a total goof. I’d dye my hair all sorts of colors. Red, blue, green, yellow, black, all types of shit. I never worked, I just sat at home and played guitar all day. What on Earth would a girl like her want from me?

Then one night at a party, I got to talking to one of my friend’s ex girlfriends. I was drunk, and let it slip I had a thing for the sister, and she couldn’t believe it. Because, apparently, the sister would talk about me non-stop. Non-fucking-stop. She was really, really into me apparently. Thought I was the cat’s pajamas, so to speak.

I couldn’t believe it. It was like, the greatest high I’d ever had. It was such an incredible feeling, I couldn’t f’ning believe it.

So, that was all I needed to hear. My friend HAD to say yes…he just HAD to. Everyone else said they would, and this guy is my best friend. He knows me better than anyone, and why wouldn’t you want your best friend to date your sister? It’s so much better than just some random creep.

So, I approached my friend, I got really high on vicodin before hand so I’d have the nerve. He told me he really appreciated the fact I came to him, gave me a hug, and said we’d talk about it. Whoohoo, good news, baby.

We went to a Greek restaurant, that we always hit up, for lunch. He then gave me his answer.


He fucking said no. I couldn’t believe it. How could he? How fucking could he? He gave me no real reason, and just left it at that. I’d never felt like that before. I was beyond heart broken, man. How could he do this? It took a lot for me to not break down and cry right there, I was so upset. I sound like such a fucking sissy saying all this, but, oh well. How fucking DARE he do this to me? Well, I was beyond bummed for a day or two. How could my so called best friend shoot me down like this? A guy I’d take a bullet for, say no?

Well, a few days later I did something a little stupid. I called her and asked her out. All I wanted was to hear her say yes. That’s it. I just wanted to hear her say yes. I wanted the yes. I wanted that to be all mine. I wanted my own proof that for one moment, her and I could have been. So, I called and asked her if she wanted to hang out next week, have a pizza and watch The Goonies [her ideal date] and she said yes. I told her that I’d have to talk to her brother, get his approval, and if he was cool with it, then we’d be set. If he wasn’t, then it couldn’t happen. She understood.

So, my plan was to call my friend and resubmit my case. To make the motherfucker understand I’m not some back alley rapist or something. The asshole. I’m his all time best friend, he had to hear me out and understand where I was coming from. That I was in love, and very serious about it. So, I called him and left a msg. Then left another. I didn’t hear from him the whole weekend.

So, Monday morning arrived. And, with it. A very, very pissed off friend. He got in my face, screaming his fucking head off about how I went behind his back, and went against his word and just did what I wanted anyway. He never gave me a chance to explain. To tell him that I would have never gone through with it if he’d shot me down a second time. That all I wanted was to just hear her say yes. My best friend, in the whole world, never gave me a chance to tell my side of the story.

I’ve maybe spoke to him once since then. He got married and everything.

So, instead of being with the girl of my dreams, I lost that, as well as my best friend. Really, this was the exact opposite of everything I was shooting for. Not exactly a slam dunk. Oh, and at one point I think she ended up dating a guy who use to hit her. So, my friend made the right choice.


Now, a lighter story.

When I was 16, I started dating a girl who was 17. She wasn’t that attractive, to be honest, but I knew she’d be down to have sex, and I wanted to make that happen. So, one night, it’s the night, baby. We’re all getting our make out on, and she stops and says she wants to have sex. Well, okie dokie. For some reason, I stood up and started getting un dressed while I preformed NWA’s Automobile. I have no idea why the song came into my head, but it did. However, that wasn’t the only thing that occurred to me just then.

Seeing her naked, repulsed me. I mean, YUCK. I don’t know how, or why. Sure, with clothes on, she wasn’t much to look at it. A 5, or a 6 if I’m being beyond generous. But naked, holy shit. We’re dipping into the negatives, son. So, I had the jimmy hat on, and the most negative boner in the world. It wasn’t happening, son. Not. Even. Close. So, you know, I do that thing where I I try and cram the fucker in anyway, in hopes of once things get going, I can get it going. Noooope. It was like trying to stuff jell-o through a key hole.

So, what’s the thing you’re suppose to do when you’re repulsed by a naked girl who’s laying in front of you?

you go down on her! Oooh yeah!

I’d never done that before, and I wanted to check it off. So, I went and did that. I was horrible, and then broke up with her the next day over AIM. Booya! That’s how a playa operates, motherfuckers!

I was 16 at the time, and didn’t end up having actual sex until I was 22. I’ve always been much more satisfied making fun of girls, and fucking with their heads instead of trying to put the moves on’em. Pretty much because I fucking hate them. But, when I find a girl worth not pile-driving, I give her the time of day. I’ve really only found about 3 or 4 in the last 10 years. Go me.

So, any awesome follies with women that you want to share?


~ by Caliber Winfield on March 2, 2010.

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