The Penis Files

by Chester Copperpot


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Part-travelogue, part-confessional, part-examination into the soul, this essay follows one woman's pursuit for truth, justice, and the one perfect penis on the planet fit for her massive vagina. Actually, she doesn't talk about truth or justice at all. Only penises. Lots and lots of them.

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(from the archives)

"It’s not about size,” some people lie. Well, it is, goddamn it. But more so than size, it’s about what the fuck you do with that shit and what the fuck you do in bed that counts. Oral pleasure can make up for a bad dick, but it won’t last, especially on girls like me who don’t get off by having their clits rubbed until they bleed. Anal can be pleasurable, and it’s an alternative to feeling a fucking spaghetti noodle in your coochie, but I’m not a homo, and we can’t keep doing that shit for months ‘cause I’m not about to start wearing a tampon in my ass to keep me from shitting my panties. Fingers are good if you know what the fuck to do with them, but if you have nasty hangnails, rough skin and overgrown jagged nails, it’s the equivalent of having a splintered piece of wood up in your pussy. Not fun.

Sex is important to some people. It is to me. It should be to everyone. People who settle for bad sex are the kind of people who always seem to have a bad day at work. Think about it: You can tell just by looking at someone’s body and demeanor if they’re getting laid right. Meanwhile, I’m turning into a fucking hunchback with the temper of a 90-year-old woman whose cervix is rotting in her womb.

I was with a black man for 11 years. Call me spoiled, but that shit was good. Not good as in raunchy – yeah, black men do it better – but good as in “the best sex I’ve ever had with someone I loved, who loved me and wanted to please me, and in return all I wanted to do was please him back”. Well, that was then. This is now. We are no longer together for reasons that had nothing to do with sex. Unlike some people I will not stay in a relationship just because sex is good while everything else is falling apart. That’s stupid.


In the past two years since my separation I’ve sampled a number of bad cocks. Why? Because I only had one kind of cock before and wanted to see what the rest of the Cock World was like. Especially because I was the kind of girl who thought all balls were hairless, since the only pair I’d ever had were bald, smooth balls that I didn’t mind licking all the time. Now that all these months have passed, I’m starting to wonder if that sex might be the only good sex I’ll ever have. But I’m not giving up hope. Though the way this shit’s going, Lord save me!

When I was a kid, I never imagined how much cock would mean to me. In reality, it’s become a silent obsession. The search for the one nice perfect cock, with enough girth, enough length, and enough stamina to satisfy me, and (super important) attached to a body that I’m not grossed out by, and to a mind that’s fertile with imagination and intelligence with a sense of humor that makes me laugh when I’m sad.

Instead, I’ve found the following:

1) Skinny cocks on guys who think they’re actually doing something for/to me, but instead it feels like a freaking pencil trying to reach a penny that’s been stuck under a refrigerator. Get a clue! If you got pencil dicks learn how to use your hands, your tongues, your mouths. For the love of Christ!

2) Big, girthy cocks on guys that are One Minute Men. What the fuck? This type of cock saddens me more than anything! Why in the hell don’t you know how to please a woman? Is it nerves? Can I give you a chill pill so you can relax and enjoy the actual act of inserting your nice cock into a wet pussy? Loser!

3) Skinny limp cocks that feel like a boneless finger up in my cooch. Jesus, save me from this torment again! This is really an oddity. A phenomenon, if you will. Especially because said limp puny member was attached to a man who thought we “fit well”. Delusions of grandeur! Confident men with lame dicks are puzzling to me. If said person had low self-esteem, then sure, I could see why. But to be a curiously extra-confident individual with a dick that feels like a piece of dough that’s been left out in the sun too long and it’s melting … hmmm … weird.

4) Big girthy cock on a lame ass person who can only serve one purpose: a one night stand. Stupid nice cocks are a NO. This is like the equivalent of a chick who’s hot and whose pussy is nice and wet and you can fuck her forever, but don’t let her open her mouth ‘cause she makes you want to take the hammer out and pound her to death. Stupidity is not sexy. Next.

5) Average cock that makes me cum on someone’s body that jerks like they’re having an epileptic attack. Strange as fuck. That’s all I’ll say. People who don’t know how to sensually move during sex are pathetic entities swimming in their own body insecurities. These must be the same people that look spastic on the dance floor.

6) Cock that might result in orgasm, attached to someone whose feet smell like rotten cheese, has bad teeth and slobbers all over when kissing. Gross as fuck. The only redeeming thing is the actual act of getting off, but the nauseating feeling afterwards is not worth a damn. This kind of sex makes women want to crawl under a rock and never see the light of day, join a monastery and become nuns, shave their heads and pass as men, or just plain die.

7) Men who talk during sex and aren’t even well endowed and keep saying shit like, “Oh, do you feel that? Do you like it? Oh, your pussy is so good! I love the way it fits into you. I’m going to ram you with my big cock!” Shut the fuck up, moron! First of all, there’s nothing I hate more than a talker in bed. Second, if the talk is lame, I feel like my insides are shriveling up into a desert and sex becomes a fucking nightmare. Third, I find it cheesy, stupid and annoying as fuck. This kind of circumstance makes me want to start fucking corpses.

8) Funny shaped penises that angle to one side or the other. They never hit the spot. All I got to say is I might as well be fucking a banana or a gerbil. I hate angles. I never even liked plane geometry that much anyway. It always bored me.

9) Limp dicks. Yes! Why the fuck don’t you stash that shit away in a box and lock it up and let it drop until it hits the bottom of the ocean, so it never sees the light of day, eh? Men with lame limp dicks regardless of size are just so fucking disgustingly pointless and such a waste of time for all womanhood. Spare a sista’ the pain and the embarrassment of telling you that your cock is not even a cock but a midget wet wrinkled seal who should go back to the circus zoo!

10) Cocks attached to moaners, heavy breathers, or screamers. For the love of God, save the drama for Oprah. All I want is to get fucked, not hear a stupid bitch moan like their insides are being wrenched. If you moan louder than me, you’re out. I hate all that stupid noise during sex. Even when I watch a porno I turn the volume down. Why should anyone around me get away with sounding like a stupid scandalous porn star, especially if you’re ugly? Makes me want to slap that shit out of someone. There must be a cock heaven somewhere. I’m wearing my pussy halo everyday, so I can go to it.

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Honestly, Chester Copperpot is a pseudonym. That does not alleviate the author from the fact that she does, in fact, have the enormous gaping vagina everyone thinks she does.