So here is a quick sample of what to do and not to do when putting together a cover letter to go with your story. That being said, remember that I'm just one of many editors out there, each with their own quirks and buttons to push. Like writing the story itself, practice and sensitivity will teach you a lot, but this will give you a start.
Don't Do What "Bad Johnny Don't" Does:
Dear M. (1),
Here is my story (2) for your collection (3), it's about a guy and a girl who fall in love on the Titanic (4). I haven't written anything like this before (5), but your book looked easy enough to get into (6). My friends say I'm pretty creative (7). If I have not heard from you in two months (8) I will consider this story rejected and send it somewhere else (9). I am also sending this story to other people. If they want it, I'll write to let you know (10).
I noticed that your guidelines say First North American Serial rights. What's that (11)? If I don't have all rights then I do not want you to use my story (12).
I work at the DMV (13) and have three cats named Mumbles, Blotchy and Kismet (14).
Mistress Divine, Goddess of the Multiple Orgasm (15)
(2) Answer the basic questions up front: how long is the story, is it original or a reprint, what's the title?
(3) What book are you submitting to? Editors often have more than one open at any time and it can get very confusing. Also, try and know what the hell you're talking about: a collection is a book of short stories by one author, and an anthology is a book of short stories by multiple authors. Demonstrate that you know what you're submitting to.
(4) You don't need to spell out the plot, but this raises another issue: don't submit inappropriate stories. If this submission was to a gay or lesbian book, it would result in an instant rejection and a ticked-off editor.
(5) The story might be great, but this already has you pegged as a twit. If you haven't been published before don't say anything, but if you have then definitely say so, making sure to note what kind of markets you've been in (anthology, novel, site and so forth). Don't assume the editor has heard of where you've been or who you are, either. Too often, I get stories from people who list a litany of previous publications that I've never heard of. Not that I need to, but when they make them sound like I should, it just makes them sound arrogant, which is not a good thing.
(6) Gee, thanks so much. Loser.
(7) Friends, lovers, Significant Others and so forth—who cares?
(8) Get real—sometimes editors take six months to a year to respond. This is not to say they are lazy or cruel; they're just busy or dealing with a lot of other things. Six months is the usual cut-off time, meaning that after that time you can either consider your story rejected or you can write a polite little note asking how the project is going. By the way, writing rude or demanding notes is going to get you nothing but rejected or a bad reputation—and who wants that?
(9) When I get something like this I still read the story, but to be honest, it would take something of genius-level quality for me to look beyond this arrogance. Besides, what this approach says more than anything is that even if the story is great, you are going to be too much of a pain to work with. It's better to find a story just as good from someone else than put up with this kind of an attitude.
(10) This is called simultaneous submission: sending a story to two places at once, thinking that it will cut down on the frustration of having to wait for one place to reject it before sending it along to another editor. Don't do it, unless the Call for Submissions says it's okay, of course. Even then, though, it's not a good idea because technically you'd have to send it to two places that think it's okay, which is damned rare. The problem is that if one place wants your work, then you have to go to the other places you sent it to in order to tell them so—which very often results in one very pissed editor. Don't do it. We all hate having to wait for one place to reject our work, but that's just part of the game. Live with it.
(11) Many editors are more than willing to answer simple questions about their projects, but just as many others will never respond— especially to questions that can easily be answered by reading a basic writing book. Know as much as you can and then, only then, write to ask questions.
(12) This story is automatically rejected. Tough luck. Things like payment, rights, and so forth are very rarely in the editor's control. Besides, this is a clear signal that, once again, the author is simply going to be way too much trouble to deal with. Better to send out that rejection form letter and move onto the next story.
(13) Who cares?
(14) Really, who cares?
(15) Another sign of a loser. It's perfectly okay to use a pseudonym, but something as wacky as this is just going to mark you as a novice. Also, cover letters are a place for you, as a person, to write to the editor, another person. Put your pseudonym on your story, but don't sign your cover letter with it.
(16) Email address—this is great, but it's also very obviously a work address, which makes a lot of editors very nervous. First of all, people leave jobs all the time, so way too often these addresses have very short lives. Second, work email servers are rarely secure—at least from the eyes of prying bosses. Do you really want your supervisor to see your rejection from a Big Tits in Bondage book? I don't think so.
Do What Johnny Does Does:
Hi, Chris (1),
It was with great excitement (2) that I read your call for submissions for your new anthology, Love Beast (3). I've long been a fan not only of werewolf erotica (4) but also your books and stories as well (5).
I've been published in about twelve Web sites, including Sex Chat, Litsmut, and Erotically Yours, and in two anthologies, Best of Chocolate Erotica (Filthy Books) and Clickety-Clack, Erotic Train Stories (Red Ball Books) (6).
Enclosed is my 2,300 word original story, "When Hairy Met Sally" (7). I hope you have as much fun reading it as I had writing it (which is a lot) (8). Please feel free to write me at email@example.com if you have any questions (9).
In the meantime best of luck with your projects and keep up the great work. (10)
Molly Riggs (11)
(1) Nice; she knows my real first name is Chris. A bit of research on an editor or potential market never hurt anyone.
(2) It's perfectly okay to be enthusiastic. No one likes to get a story from someone who thinks your project is dull.
(3) She knows the book and the title.
(4) She knows the genre and likes it. You'd be surprised by the number of people who pass out backhanded compliments or joke about anthologies or projects thinking it's endearing or shows a 'with it' attitude. Believe me, it's neither: it's just annoying.
(5) Editing can be a lonely business, what with having to reject people all the time. Getting a little compliment can mean a lot. It won't change a bad story into an acceptable one, but making an editor smile is always a good thing.
(6) The bio is brief, to the point, and explains the markets. You don't need to list everything you've ever sold to, just the key points.
(7) Everything about the story is there: the title, the words, if it's original or a reprint—and, of course if it's a reprint you should also say when and where it first appeared, even if it's a site.
(8) Again, a little smile is a good thing. I know this is awfully trite but when the sentiment is heartfelt and the writer's sense of enjoyment is true, it does mean something to an editor. I want people to enjoy writing for one of my books ... even if I don't take the story.
(9) Good email address, obviously not work, and an invitation to chat if needed. Good points there.
(10) Okay, maybe it's a bit thick here but this person is also clearly very nice, professional, eager and more than likely will either be easy to work with or, if need be, reject without drama.
(11) Real name. I'd much rather work with a person than an identity. I also know that Molly is not playing games with who she is, and what she is, just to try and make a sale.
There's more, as said, but this at least will keep you from stepping on too many toes, even before your story gets read. If there's a lesson in this, it's to remember that an editor is, deep down, a person trying to do the best job they can, just like you. Treat them as such and they'll return the favor.