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SHE-MAILING: THE ART OF THE DEPRAVED PRANK
_{By Alex Smith}

    You swish your tongue around in someone’s mouth, feeling that tension gaining on your crotch, and as you grow more aroused, you begin searching with your hand for your girl’s jeans. You finally get your fingers around the zipper and yank. That satisfying sound of the pants coming lose issues from down below. You expect to find a pair of thin underwear, the bristle of pubes beneath, and that soft, moist vagina just past, and you smile to yourself, thanking the lord that you didn’t get too drunk at the party to take it this far, and, if your penis isn’t in one of its moods, that you will have some decent sex with a total stranger tonight. But as your mind gets to spinning you notice a hitch in your plans- something extra down their in your new friend’s pants. That extra thing is a seven-inch cock.

    This isn’t your worst nightmare, because if you’re like most of us, you spend the lion’s share of your days pretending that trannies don’t exist, that they’re mythological creatures much like satyrs or tree nymphs. Yes, you’ve seen the occasional cross dresser sitting under the drying hoods at Beauty Bar when you weren’t arguing with one of their cunt bartenders. But those dudes are just gays and straights who crave attention, not, you know, chix with dix. Fact is, trannies are all around us, and I’ve watched hours of video to, um, prove it. Okay, maybe I haven’t watched hours. In fact, I’ve probably watched less than a half hour of tranny footage. When the guy or, as I like to call the male character in a porno, the “protagonist,” leans down to kiss some breast, and then gets on his knees to suck dick, I usually stare curiously numb to the act, and then go back to the video I have where Tera Patrick slaps the shit out of some protagonist’s balls before taking it missionary style.

    Thing is, I’ve developed the hobby of passing around these videos of trannies to unsuspecting friends, hoping to simulate for them something like the above scenario. It all started when my uncle, a sergeant with the Maryland police, flipped open his cell phone and said: “Oh, Alex, you’re gonna love this.” A video began playing of a decent-looking porn star with big fake breasts and blond hair-extensions. “She’s hot, right?” he said. I was a drunkard at this time, but despite the Iggy Stooge soundtrack that always started playing in my head after hitting vodka three, I could hear moaning and groaning coming from the cell phone, too. “She’s a gross pornstar,” I said. I was about to wax philosophic on my love for more natural types. If the breasts are big, great, so long as they’re real, or at least vaguely real. And if the hair is fake, fine, but no gigantic extensions. Try platinum blond or jet black instead. But before I opened my mouth the camera panned down to reveal a stringy little dick hanging off the crotch of the woman porn star. What the cruck? I smiled a bit, disgusted, and looked in my uncle’s wild eyes as he laughed. I was pleased to had been “gotten,” but more than that pleased that this man spent his young adulthood cuffing drug dealers and shaking down corner-whores, all-the-while nurturing the basest sense of humor a man in his fifties can have. He was a true American.

    Months later I’m cruising for a new porn site membership. My subscription to RealDudesFuckPeopleatParties was tiring me out, and I had lost all interest in watching animated Japanese girls with purple eyes getting raped. I decided to do it right, meaning that I went to some weird blog that rated porn sites and found that Videobox.com could no be matched. It was all about selection and easy-access, and that was what I was all about, so I quickly signed up. One of the neatest things about the site is that you can actually edit clips and download them as you like, creating what they call Custom Clips. Now, I’m not a porn-a-holic. I don’t have entire hard drives or cds filled with the shit. I have my favorites on my laptop, and I have a couple of tapes that I admittedly should get rid of (honestly, for what other reason do I have a VCR besides some shitty kung fu flicks I bought when I was 16 and Slippin’ Into Starlets?) Honestly, I barely have the time to jerk off on a given day. But this site really was fantastic, and my porn-watching certainly hit a high point the first week I was on it. Really whenever I had a couple of hours to myself I would eventually navigate over to the site to search for a star or a fetish or whatever, and really looked forward to bedtime.

    So although I didn’t spend hours editing masterpieces of porn on Videobox only to download them and whack myself silly, I duly noted the professionalism of Videobox offering such a service to its members, and did consider the convenience with great pleasure. In the end it was more convenient to download entire scenes than to labor about, cutting and pasting, guessing where these women would look their hottest, so that was what I did. But one day while scrolling through the week’s most popular videos, I noticed a tranny scene and thought to myself, Wow, these guys really do have it all, and then thought to myself I can be my uncle. I can be a true American. I remembered the skill with which he delivered the video to me, and the way it was edited- luscious lips, breasts, moaning and groaning, and then pan to weird, dangly penis. This was worth the time learning the surprisingly easy custom editing feature of Videobox. This was worth me endangering my heterosexuality by exposing myself to dudes sucking dick. This was my calling.

    My first video was a little wet around the ears. You could see the entire body of the tranny, and what kept her/him mysterious was a pair of ink-black panties, conspicuously left on well into foreplay. When they were finally slipped down the penis was flaccid, like a skin tag that had grown out of proportion, and the balls had shriveled to naught. This and the graininess of the footage—I was trying to keep down filesize to encourage friends to download my porn—all gave a strange, almost dreamy quality to the clip. It became not so much about the tranny but about the weirdness of it all, and this was not what I wanted. I wanted a simple trick, a frag grenade of sorts, that I could pop my friends with. Despite the problems with the video I went ahead and sent it out to a few close pals. I included the file in e-mails with ambiguous subject headings: “Were we supposed to meet about that?” Or “Catch-Up Stuff.” The e-mail itself was slightly dark in nature: I know you love tits this is a good one may you rest in piece.

Or something more lively and specific:

        See you at the show check out this hottie!

Perhaps my favorite was one I sent to an old professor of mine:

        Thanks, god. Should I buy you a chicken?

    Most people didn’t write me back. I had disgusted them, and I had to ask them what they thought later, in person, after giving them some time to cool off. The majority of their reactions was to be expected from a group of jaded artists and musicians: “Can you send more tit?” or “That was the greatest moment in my life.” But I also heard a lot of this: “That wasn’t real, dude.” No, dude. It was real, and so long as there are trannies out there unsure of whether they want to go under the knife, or those who can’t finance a trip to femdom, there will be these videos. Because, as Dan Savage said in his podcast: “Some straight guys want to suck cock.”

    Now you may be faulting me for misogyny or homophobia or narrow-mindedness or any other one of the cornucopia of condemnations that exist out there for people like me. You’ve already dismissed me as a sick young man with too much time on his hands. You’ve decided to punch me if you see me on the street, and you would have nothing to do with me if you ran into me at a cocktail hour. Well hate me if you wish, but know that besides a larf, I am doing something important, and something that relates directly to my heritage. Call it consciousness-raising: yes, there really are somewhat hot dudes who’ve been pumping themselves brimful of weird drugs to make them grow perky little tittywhackers and luscious lips but haven’t yet sliced their dicks in half and sent them scurrying back into their crotch, thus forming the complete image of a modern, if wonky, female. Call it gay. Yes, I’ve spent a little time developing this plan and executing it, which has required me to watch more tranny porn than the average straight horny guy under thirty. But also call it what I call it: “she-mailing.” And also do it to some of your friends and teachers. Because it’s funny, and if you weren’t such a conservative douchebag who thinks you’re an Obamaist but are really a tight-ass who’s afraid of black people and unprotected sex with hookers then you would find it funny, too

(Editor's Note: Here's what the asshole sent me... )