Simon Sheppard


Simon Sheppard is a noted author and erotica writer whose works include Hotter Than Hell, Rough Stuff, In Deep, and Homosex: Sixty Years of Gay Erotica. His short stories are also featured in Hot Cops, Truckers, Cowboys, and Best Gay Erotica 2008, to name a few. He currently resides in San Francisco.


Simon Sheppard's Taste of Leather

Author Simon Sheppard has been described by the San Francisco Bay Guardian as the "most literate and heart-poundingly romantic author to emerge from the naughty queer erotica scene in San Francisco."

Sheppard met with Cleis Press to share his insights on Leathermen his new anthology of gay erotic stories. He talks with Cleis Press about the anthologies stories, his contributions to the newly released Best Gay Erotica 2009, as well as the importance of putting a little reality into one's fantasy.

Q: Your newest anthology is a tribute to those icons of gay sexuality— Leathermen. What is it about a leatherman that makes him so irresistible?

A: Well, there are a couple of basic species of leathermen... though with a good deal of overlap. There's the über-butch, cowhide-clad man's man, who may be totally vanilla, and then there's the guy who wears leather as a signifier of his interest in kinky sex, but who may not be so butch after all. One represents the apotheosis of traditional masculinity, the other the lure of the forbidden, and both certainly have their charms. In any case, I'm not sure the book is a "tribute." I'd rather think of it as an exploration.

Q: Leathermen starts off with "Exposed, " a story by Aaron Travis. Why does he get this place of honor?

A: I'm a big fan of Travis' writing—it's sleek, sexy, and smart. "Exposed" is a story about initiation—one of several in the book—so it functions well as port of entry, especially for newbies. Actually, I'm hoping that both the leather-curious and confirmed members of the community find the book stimulating on a number of levels.

Q: We have spoken about our admiration for Jeff Mann's writing before, and you include his story "In Shadow of Devil's Backbone." What makes his work appealing?

A: Jeff writes consistently brilliant erotica, both very hot and deeply felt, and he's especially good with characters. That particular story ventures into "Brokeback Mountain" territory, though it's a whole hell of a lot kinkier. I love it. And I hasten to add there are a lot of other terrific stories in Leathermen, too.

Q: "The Village Person," your story in Leathermen, shows off the strengths of your writing: it's a puckish fantasy rooted in believable elements with satisfyingly filthy sex. How do you balance real-life concerns- in this case, about illness and death- with hot fantasy?

A: Gee, I'm not the first person to suggest there's a Big Connection between sex and death, am I? I suppose that bringing HIV into an erotic story might turn off some readers, but I love porn that's not just some airbrushed fantasy, but penetrates pretty deeply into who queer men really are, what we desire and fear. AIDS has had a huge impact on the leather community, so I unsurprisingly received a couple of other stories that deal with HIV; they're in the book, too. Not, I hasten to add, that Leathermen is depressing. Just, I hope, real. Oh, and hot. Did I mention hot?

Q: Congratulations on winning a recent Lambda Literary Award for Homosex: Sixty Years of Gay Erotica. How do you see Leathermen fitting into the grand tradition of gay smut?

A: Thanks. I suppose I might have addressed that topic by writing an introduction to Leathermen, and now—though I reasonably figured the stories would speak for themselves—I'm a bit regretful I didn't.
I think it was John Preston who pointed out that a disproportionate amount of the best erotica is SM-related, because leathersex is de facto more dramatic than vanilla is, and drama makes for swell pornography. That having been said, the whole biker icon only dates to the 1950s, and back then gay erotic writing was strictly taboo. The proto-leatherporn magazine “Drummer” came along in the mid-'70s, at a time when gay sex, erotica, and SM were all emerging from the underground, and featured a number of groundbreaking authors. And Preston, who published a lot in “Drummer” and wrote the iconic SM novel Mr. Benson, was also the first editor who put together gay anthologies that proved that erotica could not only be stroke material, but good writing, too.

Q: Pop culture personalities and even historical personages show up in your writing regularly. The leatherman from "The Village People," JT LeRoy, Che Guevara, and Subcommandante Marcos are just a few of the characters who show up in your work. Are there any other famous people that you would like to write about?

A: Lately I've been thinking a lot about beatniks, so Allen Ginsberg has had cameos in a couple of my newer stories, including the one in the new Best Gay Erotica 2009. I'm also writing an online serial, "The Dirty Boys Club," that features a number of somewhat disguised celebs: a closeted Oscar-winner, a pervy right-wing evangelist, a reactionary talk show host, folks like that. Hey, when I saw Siegfried and Roy make a personal appearance this year, I thought, "Gosh, I bet you don't know I've written a porn story about you." I try not to write about famous people unless I have some good creative reason to, beyond mere slash-type name-dropping. Actually, when you asked the question, the first image that sprang to mind was Sarah Palin as a dominatrix. We'll see.

Q: How did you start writing porn?

A: I'd been writing poetry, some of it narrative and erotic, for years. I showed some of it to Bill Brent, who was editing a sex zine at the time, and he asked me to write him a Daddy/boy story, which I did. That was picked up by the late Scott O'Hara, who put me in touch with the prolific editor Lawrence Schimel, and the rest is tedious, low-paying literary history.

Q: When you are selecting new work for your anthologies, how do you know that you found the right story? What makes good erotic writing?

A: Like any good editor, I look for good craftsmanship and authors with something unique to say. My personal preference is for erotica that's not just cookie-cutter fantasy, but that has a point of view, is perceptive about sexuality, and still will make a reader want to jack off. And I like authenticity at some level, whether factual or emotional; I've read SM porn where it was all too obvious that the writer had never, ever held a flogger or longed to be pissed on. Did you ever see the film of Anne Rice's Exit to Eden? Jesus, how embarrassing. Sure fiction is imagination-based, but your neighborhood leather dungeon, unlike Oz, is a real place. I often think that there's no fantasy as hot as actual sex can be.

Q: How have your themes or interests changed in your writing? For instance, you are one of the few erotica authors who include FTM characters, and I bet your early erotica did not.

A: Well, back when I started, there was nearly no visibility for female-to-male guys. Since then, the transmen I've known have taught me a lot about gender and the permutation of desire, and that filters back into my work. On the other hand, when I started out, Dennis Cooper-style transgressive stories were all the rage, so I wrote my share of blood-spattered porn. I've mellowed since then. Yes, I still write about erotic torture, but maybe with more heart. For one thing, I think that, yes, eros can be scary, but hell, I really love sex. And I love gay men, at least the ones who aren't assholes. I know it sounds kind of foo-foo, but I feel I have a responsibility to my fellow horny queers. So I've cut back on the horror and gore stuff, and though I still write my share of seedy stories, they often feature sentimental strophes, like the speed freak with the heart of gold. Also, as I age, I think I'm doing more work with autumnal overtones. Like the new Best Gay Erotica story. Hell, I've written four books and around 300 stories; I'm always looking for something new to say, so I don't bore myself to death.

Q: What is your favorite pick up line?

A: I was walking along Castro Street many years ago when a stranger in a passing car yelled out to me, "Is it really as big as they say it is?" Well, that was irresistible. I got in the car and we ended up at his flat, fucking. I still don't know who told him, though.
eet many years ago when a stranger in a passing car yelled out to me, "Is it really as big as they say it is?" Well, that was irresistible. I got in the car and we ended up at his flat, fucking. I still don't know who told him, though.