My Follies With The Opposite Sex – Part 1

Oh, like many burly assed dudes like myself, who auctions off head-butts to the oldest bidder, I have my problems with women. Nothing better than hearing about people blowing it with chicks, or situations that suck. I’ve got quite a few, so, let’s dish, shall we?

One of my first embarassments came from Valentine’s Day, in 5th grade. There was a girl who I was “with”, her name was Dianne. She was the coolest. She was into GI Joe, and video games, and all that cool shit. So, we had been off and on for years and we’d finally got back together. As you know, in elementary school, primary for those across the pond, we had days we’d all pass out V-Day cards. Well, being the romantic that I am, I had an Incredible Hulk card that read something “Hulk won’t stop till you are mine!” and I wrote on the back, in really shitty writing, “and I mean it!”. She hand crafted me this awesome card, and it had a ton of candy and shit, it was awesome. Fuck, I was so embarrassed. Thank God I had Mortal Kombat II to return home to. We ended up breaking up again, and never got back together. All through out middle school we’d kept in touch and such, but never ended up together again. Funny, as a kid I thought she was my soul mate. Mmm…

In 7th grade I dated a girl named Stephanie. She was the type of girl that you’d learn things from, because she’d done it all. Well, the day we started dating, her friends told me the next day that she was going to french me after PE. Funny how well thought out things like that were when you’re young.


I’d never frenched a girl before! What if I drooled? Or didn’t get it right some how? I was so nervous I didn’t eat anything from the moment I was told that, until that fateful moment. I’m honest to God shocked I didn’t puke. Oh, and I was terrible at it. I drooled, and bit her tongue. She told me she’d had worst firsts, but I think that was just her being nice. It was then I discovered the joy of doing shit with girls, because once I frenched, I wanted to do it again. And again. And again. It’s all I thought about. We broke up a week later and I was devastated.She ended up marrying an awesome dude and having a bunch of kids. Looking back on it, I think she must have had dad issues, because she was a sluuuuut.

My next girlfriend was in 8th grade. Her name was Katie, and she was awesome. She was actually a very pretty, and popular girl. I was a dork who wore nothing but Jnco, despite the fact they were so out of style, and either a Bone Thugs, wrestling, or South Park T-shirt. That was it. But, she dug your boy. Nothing funny ever came of that, really. We use to french hardcore in the hall ways and gross people out. But, I loved it. Here I was, having sex right in front of everybody. Jeeuh! She broke up with me after about 2 months, and then I found out the bad side of women. Heart break. I was really into her. She was an awesome girl. Funny. Smart. Attractive. I was pretty bummed for a while about her. It also sucked because we had a lot of classes together, and I also realized how great uncomfortableness is.

Later that year there was this attractive 9th grader who wanted to date me. But, as it turns out, she had hairy armpits, and that was beyond gross. I saw her stretching in computer class and noticed, it made me gag.

9th grade. For some odd reason, I started dating this girl who had like, this extra, crooked teeth growing out of her gums. I dunno. She had really huge titties, and was digging me. Two weeks after dating, like, on a Tuesday, she told me “Hey, this Friday I’m going to give you head”….seriously, man. What is with these young girls and planning shit like it’s a fucking business meeting?

I was so nervous this time. But not about the actual act or anything, but I was nervous that I wouldn’t get a boner. I’d heard horror stories of guys not getting wood and getting ridiculed for it. So, because I was nervous about getting a boner, I couldn’t get a boner. I didn’t want to just whip it out, in all it’s half in glory, you know? She needs to see the full 2 inches, fast and furious. Well, I just bit the bullet, and she went to work. Boy, was it horrible. Sure, I was her first, but, c’mon man. It was the age of the internet, she couldn’t research? She had a slutty sister, she couldn’t ask a fucking question? What I do remember happening is MTV was on, and a new Krayzie Bone video came on that I didn’t have recorded, so I literally threw her off of me, ran around my room with a boner, desperate to record the new Krayzie video. Oh, and I did.

She was horrible, and I was never able to get off. So, one morning she asks me to jack-off for her.

You ever jacked off for an audience? IT’S FUCKING AWKWARD. But, I made it happen. Ruined my DX t-shirt too. Ugh. There was this abandoned house right by the school where we’d go before school started, and she’d blow me there. It was rad. I promised to never tell anyone, so I told anyone that would fucking listen to me. I eventually figured out that all the stuff she said she was into was a lie, so that and the fact the way she masturbated was to dry hump me until she got off, was enough for me to call it quits. I never spoke one word to her after we broke up, and did the typical dickhead post-break up shit. I mean, who wants to be friends with a freaking girl anyways?

I ended up seeing her again about 8 years later at a party, and boy, did that suck. My friends, being like all guys, were mature and handled it well. Or, not. Because she got sloppy drunk and was hanging all fucking over me. God, it was horrible. I ended up telling her to get me a beer, then ran like all get out.

After that, came two chicks at about the same time. It was the summer of 2005, and I was a cool 21, for a good portion of my later teen years, thanks to being able to drive everywhere, and the discovery of triple stacks at Wendy’s, I became a bit of a chub scout. Well, when I was about 20 I was sick of it. So, I started an eating regimen and working out. I lost about 50lbs, and packed on some muscle. Well, it fed my ego a bit, and I wanted to start trying it out.

First one I tried it out on was my good friend’s cousin.

Now, before I go further, you must understand my one weakness. Normally, women have no control over me. I’d normally rather knee a hot girl in the face than give her the time of day. However, I have a bit of kryptonite. It takes it’s form in that of a big ol’ ass. I can’t help it. If a girl’s ass is 40 inch plus, I’m all hers. I’ll settle for the high 30’s as well. From Kim Kardashian, to Elke The Stallion, the bigger the better with me. Been like that my whole life. Anyways…

Normally, I wouldn’t think to move on a good friend’s blood, unless there was a good reason. Well, the second I saw this girl walk in, and turn around, I had a good reason. Goddamn, she had an ass. Plus, she’d just turned 18, so it was all gravy baby. She was all sorts of into me, and fuck with me all the time while her cousin wasn’t looking or something. Doing stuff like grinding on me, or as we’re walking up the stairs she’d get a head of me and bend over real slow, GAH…anyways, my friend lived on the beach, so one night her and I went down there, got really drunk and high…next thing I know her cousin just heard her have an orgasm, and he came down at oh so the wrong moment. But awesomely enough, he was cool with it! He had no problem with me and her, because he knew I was a good guy. I remember one time we had to go to this formal style party thing that my friend’s wife’s parents would throw every year. Well, she wasn’t old enough to drink, so I’d just keep slipping her booze, then we’d sneak off to the bathroom and fool around. Really, there is nothing bad with this girl, I just like to relive it, because she looked like Katie Holmes but had the ass of Alexis Texas.

Now, the other girl at this time, not so much…

On my 21st birthday, I decided to take a ton of DXM. Basically, you’ve heard of people drinking a shit ton of cough syrup, right? Well, I can’t stand that taste, so I’d take these pills that had the special ingredient. Well, I’m high as hell, and my friends want to go to a bowling alley and meet up with these girls. There’s this one girl, kinda cute. Perhaps a 5, on a good day, and she’s all over my shit. Won’t stop talking to me, sitting close, touching my knee, ugh, all of that. I’m high bitch. I don’t give a fuck if you’re Gianna Michaels or CoCo [Ice T’s wife], I don’t mess with you.

Well, lucky for me she and her friends came back to my friends place. I end up in the living room with her, and goddamn, is she trying to get with your boy. All I wanted was sleep…just some fucking sleep. The sofa in the living room was in the shape of a perfect right angle. I slept on one piece, she on the other. And just as I would start to drift off, she’d open her fucking mouth and start blathering at me. What I look for in a girl, when my last girlfriend was, how often do I work out, blah blah blah…then she pulls the ol’

“I’m cold. Could you find a way to warm me up?”

Now, one of my favorite things to do is mess with chicks. Especially hot ones. Unfortunately, she wasn’t that attractive, but it was still fun to mess with her advances. So, she says that and I retort with;

“Yeah, the heating isn’t very good in here. I’m very comfortable though. Must suck to be cold right now. There’s some blankets in the hall, go get one”

“Would you get it for me?”

“I can’t.”

“Why not?”

“Cuz, I’m a man. The only thing I do for women is let’em feel my biceps”

“Can I feel your biceps?”

“Ugh, sure”

So, I get up and let her get a squeeze. She then asks me to lay with her because she’s cold. I tell her there’s no room, and that the only way I would fit is if I just laid on top of her. She said that was alright. So, I literally just laid on top of her, dead weight. I didn’t try and support myself up in anyway, just dead weight on her and tried to go to sleep. Well, the Genie was out of the fucking bottle. She started to make out with me, and I just said f it. We went down to the floor, I messed around with her boobies, which were nice, then claimed I was getting sick and had to sleep. This was thankfully before it went any further than BT’n [boob touching]. Which, we all know in man world, is the ultimate goal. As a follow up, I ended up dating her for a couple weeks because as it turns out, she gave AMAZING…let me stress this, man, AMAZING head. It was unreal. It was the type of shit you see in porn. But, after two weeks, it wasn’t worth having to sit and listen to her yell at me about doing shoorms, oxycontin, and copious amounts of pot all the time.

Now, for part two I’ll pretty much dedicate it to my greatest folly. The one that ended up with me having my heart ripped from my chest, and ending a 6 year friendship with a guy I would have taken a bullet for. Please, feel free to tell your boy about the crap that always comes with women.


~ by Caliber Winfield on February 27, 2010.

2 Responses to “My Follies With The Opposite Sex – Part 1”

  1. This is pretty cool. Made me think about when you make out when you’re like 13, 14. Sticking your whole tongue in a girls mouth and whirling it round. What the fuck was that about?

  2. Dude, no kidding huh? That’s exactly the bullshit I use to pull, because that’s what everyone in the place told me to do.

    That’s what was cool, and what sucked ass about growing up. Everything was new, you know? I’d get so worked up over having to try something new with a girl I’d damn near go into a coma. I have no idea why, but damned if it wasn’t true.

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