I can still remember the day when Eileen said to me, somewhat dismayed, “Sometimes it feels like every kinky girl who’s even close to being classically attractive decides to become a pro-domme sooner or later. Why am I the only one who doesn’t?” And of course, when she was offered a job as a pro-domme at Rapture she naturally briefly considered the opportunity. I mean, why wouldn’t she? I would have considered it if I were in her shoes, and I would have done so for a number of reasons.

The most interesting reason why I would have considered it, though, is because the thought of being a sex worker (and a sex worker is what a pro-domme is) feeds a fantasy of mine: sexual expression in exchange for money. The thought of having sex with or—even hotter—to be made to have sex with people I didn’t really know very well has long been an undeniably arousing thought. That fantasy is, to this day, one of the very few role play scenarios I can somewhat comfortably get invested in. I vividly remember the pounding of my own arousal the night Eileen came home with her half of the month’s rent in cash, pushed me onto the floor, tied me up, fucked me with a knife at my throat, and then threw the cash in my face.

Like most fantasies, the fantasy itself would probably be very different from the reality of the situation. Getting tied up in someone’s home who I didn’t know just so that I could make a few bucks is so ridiculously unsafe that I’ve purposefully avoided even getting near the possibility of doing it. Nevertheless, this sex-for-money fantasy is a rather frequent one for me, and in fact it’s pretty common among others, too. I think it’s so strongly rooted in the sexual psyches of so many people that it’s one of the most common reasons why I see bottom-ish and submissive-leaning women become sex workers, such as pro-dommes.

But that’s not what this post is about. (I could talk about inverted power dynamics of (many) pro-domme and client relationships for ages, but I won’t since there are lots of places where that’s discussed already.) This post is about the idea of the sex-for-money fantasy in general, what makes it hot for me, and some (geek-inspired) ideas I have about how to go about realizing it safely.

Perhaps it was Tristan Taormino who best explains why the sex-for-money fantasy is so hot. She recently wrote this in the Village Voice about the brothel-themed sex room at Dark Odyssey, affectionately known as “sex camp” among the attendees.

People don’t tire of the sex-for-money fantasy. Actually, there is no one fantasy, but multiple scenarios, dynamics, and roles possible within the brothel setting. I talked to a bunch of this year’s whores (who included men, women, transfolk, and cross-dressers) about what they got out of their experiences. Some said they like being a whore because it’s taboo, naughty, and transgressive; the fact that it’s illegal prevents them from pursuing it in real life. For others, being a sex worker is a longtime fantasy[…].

Playing this role can trigger other turn-ons, like having sex with strangers, no strings attached, and no pretense of romance.

[…]

A sex-worker fantasy can also fulfill a desire to be used for sex, objectified, forced, pimped out, or made to perform. Many of the whores had pimps who collected their money or made them work. There are so many power dynamics to play with. “I am turned on by the power exchange involved,” explained Ellie, a phone-sex operator in real life who’s never done sex work with physical contact. “To some extent, the worker is fully in control of the sexual encounter and can create seemingly arbitrary boundaries or limits without being expected to explain them to a partner. On the other hand, the worker is acting in service to the client, and is expected to please and satisfy them. The tension between the dominant and submissive roles in these sorts of exchanges is interesting to me.”

These excerpts showcase a couple of points. First, it confirms (yet again) that different people have the same sorts of fantasies due to a variety of different motivations. Second, when Tristan mentions that playing the role of a whore can trigger other turn-ons, she’s talking about how enacting one fantasy be a catalyst that often fulfills multiple impulses at the same time.

For me personally, ultimately the fantasy of sex for money boils down to expressions of control, just as most other fantasies do. Fantasizing about whoring is about my desire to be objectified, pimped out, and made to perform, to use Tristan’s words. Now, these aren’t things that I necessarily find directly pleasurable—theoretically I could be made to do something I didn’t really want to do—but it’s not always direct pleasure I’m after. Rather, it’s the derived pleasure I get by being controlled by my “pimp” that I find so hot, even and sometimes especially if that exertion of control is tormenting me.

While at times these desires manifest in a prostitution fantasy, at other times they fit nicely into slave, harem, or even prisoner fantasies. In some of the more extreme ones, I’m made to perform not merely for my livelihood, but for my very life. This can be very intense, but that’s because it’s this intensity of control that I lust for.

Of course, realizing such intensity in reality just isn’t practically safe. Moreover, if any of the life-or-death fantasies were to become real, they’d pretty much have to be one-offs for the obvious and very unsexy mortality issue; sometimes in my fantasies I’m killed, but that’s only sexy in the fantasy, not reality. In no way do I actually want to be in an unsafe life-threatening situation like that, and it’s a fact that there are enormous risks associated with thoughtlessly enacting these sorts of fantasies in real life.

This brings me back to the first part of the title of this post: barring one’s attendance at an event such as Dark Odyssey—which I am even more intent on attending after reading Tristan’s article about it than I already was—how can one go about experiencing the thrill, nervousness, and excitement of this fantasy in a way that isn’t insanely unsafe? As it turns out, some of the best advice I’ve found on this topic came from one of Dan Savage’s Savage Love articles, in which he writes to a bisexual man who has similar fantasies as I do. (No, it wasn’t me writing in!) Dan said:

[T]he only way to safely realize this fantasy […] is by sharing it with your most adventurous [Friend With Benefits] and enlisting his help. After you tell all, ask your FWB if he would be willing to facilitate the realization of this sexual fantasy. In other words, ask him to pimp your ass out. It would be his job to find and recruit a guy you don’t know, a guy who’s trustworthy and safe but just a little freaky, a guy that he knows you would find attractive. Then your FWB/pimp tells you what corner you need stand on what night and you wait there until your pre-screened, pre-selected john drives up and rolls down his window. Be his ho, be safe (the real pros all use condoms), get paid, and run home to your pimp and hand the money over to him. Everybody wins.

I think this is sound advice, but it could be better, which is where the second (nerdier) part of the title of this post comes into play. What Dan’s advice is missing is a certain measure of protection against selective forgery attacks.

What I mean is that if I were to follow Dan’s advice to the letter there’s no way for me to be assured that the john who drives up to me and rolls down his (or her; women aren’t always relegated to the prostitute’s role in my fantasies!) window is the same john that my partner had selected for me ahead of time. Although this may be perfectly acceptable for some people, while the excitement of the fantasy would certainly be heart-pumpingly, penis-hardeningly awesome, without this added level of assurance obsessively detailed people like me would still feel an unacceptable twinge of apprehension.

Therefore, after reading Dan’s advice, I came up with a way to ascertain that the john who might (theoretically…) roll down his window in front of my slutty ass standing on the street corner was, in fact, the pre-selected person while still maintaining the fantasy’s mirage of anonymity. Since I’m an utter nerd, the inspiration of the solution came from the TCP computer networking protocol.

Here’s how the revised scenario would play out. For the purposes of this example, I’ll call my john, well, John, and we’ll assume that Eileen is my pimp (because that would be hot).

  1. After discussing this fantasy and building up the courage to actually follow through with it, Eileen would search for and pre-screen a john for me. She picks “John” and she tells me to go stand on a specific street corner at a specific date and time. She also tells me to expect a specific pick-up phrase, for instance, “Hey, pretty boy. How much for a fierce ride?” The phrase is specific enough so that it’s unlikely to be typical (but really, I have no idea what a typical line to pick up a prostitute would be). Finally, she also picks a specific amount of money that I should be whoring myself out for. (After all, she knows how much my ass is worth on the streets.)
  2. I wait at the appointed place at the appointed time (possibly wearing the appointed slutty outfit) and when John rolls his window down, I listen for the pre-scripted phrase. This step is analogous to the TCP SYN packet that computers send to initiate a connection. It’s useful because at this point I’d know whether or not this john is really my John.
  3. Assuming the phrase I hear is correct, even though I know who he is, he still doesn’t know if I’m his pre-selected ho for the night (though I suppose he could be given a picture ahead of time) so now he waits for me to respond with another, pre-scripted statement. Furthermore, this gives me the opportunity to bail if I needed to for whatever reason. If I decide not to bail, my pre-scripted response, maybe something like, “For you I could be $75. $50 if you only want my mouth,” is analogous to the SYN/ACK packet used to acknowledge a successful connection.
  4. At this point, everything is set up and we’re both reasonably confident things are going as planned, so one last pre-scripted response (“I’ve got $150, so I want all your holes, and more than once. Get in.”) from him could be used to signal the end of the pick-up precautions and start the scene, which is analogous to the final ACK in the TCP connection establishment phase.

In computing, this is known as a three-way handshake. Its purpose is to initiate a connection between two parties, and because there is a round-trip before a connection is formally established, it’s resistant to spoofing. That’s exactly the protection which is needed in any fantasy involving sex with so-called “strangers,” so it seems to me as though something like this, which could be thought of as an extension on the concept of safe-words, is just what the doctorpimp ordered.

Then, hopefully, this mysterious stranger, who would appreciate me in all my sexy nerdy glory, would proceed to treat me like the slut I am, and we’d go to a cheap motel and fuck like bunnies.