Note to family members and others who don’t want to read about my personal sex life: This one you almost certainly want to stay away from. It discusses my sex life in some detail… and discusses aspects of my sex life that you probably don’t want to know about. Really. Here’s a piece I wrote recently that you might want to read instead, about why it bugs me when people say “everything happens for a reason.”

This is Part Two of a four-part post. In Part One, “Thinking About It,” I talked about why I decided to hire a professional submissive in the first place; today’s installment tells what it was like to actually shop for, and make plans with, a pro submissive. This piece was originally published in Other Magazine, and was reprinted in Best Sex Writing 2008.

Buying Obedience:
My Visit to a Pro Submissive

Part Two: Planning It

I’ll tell you this right off the bat. As soon as I started even thinking about hiring a pro, I immediately got a lot more sympathy for sex customers. I even got more sympathy for some of those customers’ more common failings. See, as soon as I started imagining hiring a submissive, I of course started having sex fantasies about it — and one of my first fantasies was about the woman dropping her professional limits for me and making an exception to the “no sex” rule that most pro submissives have.

Now, customers who push their sex workers to do off-limits stuff is one of the big pet peeves in the industry, an absolute top-notch way for a customer to be an asshole. But now I’m not sure it is about being an asshole. I don’t think it’s about being a selfish jerk who wants what they want and doesn’t care how the other person feels. Or it least, it’s not always about that.

I think it’s about wanting to be special. It’s about wanting to not be just another customer, wanting to be the one the pro likes so much that she (or he) will make an exception and invite you across that line. For me, the pro sub in my fantasies always made the exception because I was a woman — either the “no-sex” rule didn’t apply to girls, or she was so excited about playing with a woman that she let the rule slide. As if lesbian erotic sisterhood was so powerful that it rendered professional limits obsolete. I knew rationally that this was absurd, but it was a very difficult fantasy to let go of. And it was hard not to feel disappointed about it, even before I’d booked the session. I still think pushing sex workers to do off-limits stuff is a top-notch way to be an asshole — but I now have more sympathy for the impulse.

And once I stopped just thinking about it and started actually shopping around for a pro submissive, my sympathy for customers went sky-high. It was a weirdly nerve-wracking experience, a blend of comparison shopping and answering a personal ad. I wanted to come across as respectful and experienced and interesting and fun: if for no other reason, I knew that sex workers do sometimes turn down customers, and I wanted to look like a good prospect. At the same time, I wanted to be sure I was getting the best person available for my desires, or at least some assurance that I’d actually be getting what I was paying for. To put it bluntly, I wanted to get my money’s worth. And while as a former sex worker I’m happy to advise customers, “If you don’t hit it off with a sex worker, write it off to bad luck and try again with someone else,” that advice was tough to accept when it was my own hard-earned, not-very-plentiful cash on the line.

Continued after the jump. Please note: This post includes explicit descriptions of sexual acts. If you’re under 18, please do not continue reading.

It might have been different if I’d been looking for an escort or a dominatrix. Those fields have a glut of professionals to choose from (in the San Francisco area, at least), and shopping for someone with compatible interests, good energy, and hot photos probably would probably have been pretty easy. But there aren’t a jillion people doing professional submission, even in the Bay Area. So while my filthy sex fantasies involved sorting through a large online harem of beauties and picking the one who most suited my whims, the reality was that my choices were limited.

To make things more difficult on myself, I wanted to hire someone with a lot of experience in professional submission, not just a domme who switched now and then on the side. And for reasons that are somewhat obscure even to me, I didn’t want to go to one of these brothel-y domination houses if I didn’t have to. I’m probably not being fair, but the houses seemed too much like an assembly line, and nowhere near private enough. I wanted someone who worked for herself… which of course narrowed my choices even further. It wasn’t a problem exactly — the few independent pro subs I did find seemed perfectly good — but I hadn’t realized how much of my fantasy was about the power of selection until I discovered how little selection there was. And the limited options made me that much more anxious to make a good impression when I did make my choice.

I decided to go with Rachel, of rachelobeys.com (no longer online, alas). Her Website was expressive and articulate, with plenty of details about do’s and don’ts as well as about her general style. Her vibe seemed submissive and eager to please, and at the same time clear and firm about limits. And — I felt guilty about being this shallow, but there it was — her body was more my type. Voluptuous rather than skinny, with big boobs and a round, spankable ass. That wasn’t my top consideration, but it certainly wasn’t my most trivial one either — and with so little info to go on, it became even more central. I set up an anonymous email account, took a deep breath, and dropped her a line.

And the minute I started composing my email, my first question was answered: Yes, I was glad to have “Paying For It” in my hand. True, the book did give me a certain amount of “Am I doing this right?” performance anxiety, what with knowing all those damn guidelines and wanting to be good about following them. But I’d have had performance anxiety no matter what. That’s just the kind of gal I am. And while the book did give my anxiety some very concrete forms, it also gave me the tools to cope. My stomach had serious butterflies — during every step of the process, actually, not just this first one — but at least my head was saying, “You’re doing fine, you’re doing everything you’re supposed to.”

More importantly, I’d have been a lot more shy about spelling out my specific desires if I hadn’t been assured by every damn writer in “Paying For It” that spelling out specific desires is exactly what your sex worker wants you to do. They don’t want to play guessing games, and they don’t want you leaving disappointed and pissed just because they couldn’t read your mind. This makes perfect common sense, of course; but it still felt a little weird to provide a total stranger with a short but detailed list of my sexual expectations. It was good to have a clear, authoritative consensus telling me to go ahead and do exactly that.

And spelling out what I was looking for wound up handing me an extremely pleasant surprise. I knew I shouldn’t expect sex from a professional submissive; and sure enough, Rachel had “no sex” clearly stated on her Website. But since every person on the planet seems to define “sex” differently, I thought I should check with her about what, exactly, she meant by this.

“I understand and respect the ‘no sex’ rule,” I said in my email, “and would absolutely stay within your limits. But…” and I proceeded to ask about a few specifics, which she might or might not consider sex. Ordering her to masturbate. Caressing or squeezing her bottom while I spanked her. Caressing or squeezing her breasts before putting clamps on them. Masturbating while I looked at her. Masturbating while I spanked her, or while I fondled her ass. I put this list in my email, fully expecting her to say “No” to most or all of it, and half-afraid that even asking would make her blow me off as a clueless oaf who didn’t get that pro submission isn’t prostitution. I waited fretfully, obsessively checking my email, increasingly certain with each passing hour that I’d blown it and would have to start from scratch with someone else.

But Rachel finally replied… and I couldn’t have been more wrong. Not only was everything I wanted okay with her, but a number of things I wouldn’t have asked for in a bezillion years turned out to be okay as well. I could fondle and even chew on her breasts; I could rub my cunt against her ass; I could spank her pussy with my bare (gloved) hand. I could even “masturbate” her if I wanted to. That one really took me by surprise. In Lesbianland where I come from, we call that “fingering,” and it’s without question considered sex. But I wasn’t about to argue. The only things that were off-limits were body-fluid-exchange stuff like fucking and sucking, and I could happily live without those for an hour.

So the moral of the story is, “ask your sex professional for what you want.” But even if it had turned out the other way — if all the extras I’d wanted had been off-limits — I still would have been glad I’d asked. As much as I’d have hated to miss a pleasure because I didn’t know it was permitted, I’d have hated even more to try something and have it turn out to be verboten. And if I hadn’t asked ahead of time about this “borderline” stuff, I doubt I’d have had the nerve to try any of it.

Of course, now that Rachel and I had discussed details and scheduled a date, both my fantasies and my fretfulness were in sharp, vivid focus. I spent the days before the session veering between high anxiety and near-blinding horniness; between insistent, poorly-timed fantasies about the session, and a displaced fretfulness over details: what to wear, what to bring, how to get there, what if I missed my train, what if the dungeon caught fire. An hour before the session, all my planning and fantasizing and blocking out the broad strokes of the session had gone completely blank, replaced by teeth-grinding obsession over minutiae and a loud buzzing in my head. I kept chanting to myself, “This is for me, this is for my pleasure, I’m doing this for myself”… a mantra which utterly failed to sink in. And fifteen minutes before the session, everything in my brain had been obliterated by the blank, terrified hyper-awareness that I was trying to find my way through a strange, slightly dicey neighborhood with $300 cash in my wallet.

Also, did my hair look okay.

Tomorrow, Part 3: Doing It.