Jenny DeMilo

So when I started the Quaz way long ago, I thought it a good opportunity to interview people who’d normally escape my radar. Sure, I’d throw in some sports figures here and there, but the ultimate goal was to converse with the unique … the different … the extreme.

Enter: Jenny DeMilo.

I’ve been a journalist for 17 years, but never before have I interviewed a professional escort. DeMilo, however, is more than that. She’s also a photographer, a writer (actually, a really, really good one), a Dominatrix and a woman who lacks the much-needed ability to urinate on a person’s head (hey, nobody’s perfect). In other words, she’s the ideal Quaz candidate.

Here, DeMilo talks sex, money, Angel Pagan, Joe Biden and why her folks aren’t so thrilled with her chosen profession. She hosts a pretty riveting website, Confessions of a Message Board Hooker, and you can follow her on Twitter here.

Jenny DeMilo, message board hooker, welcome to the Quaz …

JEFF PEARLMAN: OK, Jenny, so this is a new one for the Quaz, where the Q&As usually concern sports, music and politics. You’re an escort and professional Dominatrix based out of Washington, D.C. You identify yourself as “a fetish enthusiast” who “can converse on most topics, from the silly to the esoteric. I can make you laugh, I can make you think or I can make you wish you were never born. The choice is yours.” You also write that, “I don’t have a heart of gold but my vagina is lined with diamonds!” So, uh, hmm … to start with—what exactly is your job? Like, what do you do? Where do you do it? And, well, why?

JENNY DEMILO: I’m a sex worker, which is a general term for someone who is in the sex business using his or her physical and emotional labor to turn a buck. Strippers, porn stars, escorts, Dommes, cam girls and phone sex operators fall under the umbrella of sex workers. Specifically I’m a GFE escort and a professional Dominatrix with a niche in erotic femdom hypnosis. I produce my own fetish content with a heavy emphasis on erotic hypnosis recordings that I sell on the tubes both on sites owned by others as well as recently opening my own site where I run the show. I recently relocated to the Washington, D.C. area and I’m still getting my feet wet here, I was working out of Los Angeles. I toured nationally visiting many cities as an escort, yup we go on tour just like rock stars (only no groupies or roadies) and I worked in L.A. out of a commercial dungeon and will do the same here in D.C. for my Domme work. I produce my fetish content out of my house. As to the why? I started my career as a professional dominatrix because I’ve always been fascinated with the fetish world; from there I slid into escorting. When that began to get a little stale for me I went back to Pro Domme work and starting making fetish content which opened up a whole new revenue stream for me, which I’m really enjoying. It’s got to be interesting and fun or I get bored and move on to something else. Oh, and for the money, lets not forget the real reason people get into the sex business … it’s all about the money.

J.P.: I took a run earlier this evening, and I was thinking about this Q&A. Specifically, I was thinking about how I’d feel were my daughter, who’s only 8, to one day become an escort and professional Dominatrix. And, to be honest, I’d be devastated. I’d wonder what I did wrong; how I led her down such a path, etc. I mean this as no disrespect, and I admit there’s much I don’t know. So tell me why I’m wrong to have such feelings—if, indeed, I am wrong?

J.D.: I wouldn’t call you wrong. My family isn’t thrilled with what I do. Admittedly, they don’t really know about the escorting though I believe they suspect. However it’s usually because people don’t know what the escort/sex business is really like. They only know what they see on Lifetime TV movies and what the media likes to represent about sex workers, which is usually inaccurate and sensationalistic. The real profession isn’t like what you see on TV at all. Many sex worker activists are working hard to try to humanize sex workers and sex work itself so that people see us as real humans with regular lives, who do a job. That we’re not all trafficked, drugged-out, streetwalkers with pimps dictating our lives being forced into sex work. That it’s a legitimate career, a needed service, and that we do it by choice not force. Of course escorts have to shoulder some of the blame for misconceptions because we market ourselves as lingerie clad, insatiable, sex kittens always looking for the next pay-for-play roll in the hay, with a healthy portion of we do it because we love sex so much because were nymphos! Plus, we’re professional liars. We create fantasy for a living and to break the fourth wall is rare. Doing so could cut into your money and the bottom line is money. Money is what really makes our panties wet. The reality is escorts are some of the savviest businesswomen I know. They run business as sole propitiators, have distinct business models and work harder then most of the lawyers, doctors and Harvard MBAs that pay me to do it. If you knew the realities of sex work you might not have the same thoughts if one day your daughter came to you and said she was working in the business. But, then again, the stigma of women using their sexuality for anything, let alone to make a living is so strong … maybe you would still feel like you somehow failed.

J.P.: What’s your background? Where are you from and what led you down this career path? How’d you end up doing what you do?

J.D.: Born and raised in Southern California, I’ve lived there all my life until recently moving to Washington. I’m an ex-art director who worked in client side corporate advertising. I went to an expensive, well-respected art school and I have an advanced degree. My specific niche took a big hit years back and I was downsized and that’s when I started flirting with working as a Pro Domme. I dabbled but mainly because I was interested in the fetish world personally. I needed a fast job and answered an ad for what I thought was a phone sex job—“Girls with good voices get paid cash.” It turned out it was answering phones for an escort agency. I was hired on the spot, did that for a while and that’s where I learned what escorting was all about. I eventually branched out, saw a couple of clients, found my comfort level, decided it was something I could do and created “Jenny DeMilo.” I used all my skills from advertising and marketing to create the brand. I found it amusing how the skills I learned in art school, working in advertising, attending client meetings where I had to dazzle CEOs with bullshit, have served me so well as an escort. They translate better then I think anyone could imagine. Over the last couple years I’ve transitioned back into professional domination, this time taking it more seriously and started creating fetish content for sale which is a whole new world for me where I use all my advertising/art skills. Copywriting, creating graphics, marketing, advertising, branding. I enjoy learning how to conquer new things.

J.P.: It strikes me that, sexually speaking, men are much more pathetic and needy than women. In other words, it seems as if we want/need sex a helluva lot more, and will—at times—do anything to secure it. Hence, why there are so few (if any) male hookers walking the street; why strip clubs are 99 percent catered toward men. Do you agree? And why do you think it’s so—or not so?

J.D.: Women don’t pay for sex—they go to the bar and lower their standards. Men however do pay for sex and sexual attention. The simple answer is they are wired differently than women. I see this result and thank god as it’s served me well in making a living. Most men at some point have paid for some kind of sex, lap dances where the goal is for the stripper to get you off while you sit in a char as she grinds all over you, from phone sex operators who will be who ever you want and feed into what ever your fantasy is as long as you are paying by the minute, to actually going out and seeking sex from an escort where you pay for the good, good loving. Men want it, women have it and some of us will sell it. The end. There are male hookers, by the way. Lots. But they service men.

J.P.: Although the pictures aren’t clear, and your face is always obscured in one way or another, it’s certainly not out of the realm of possibilities, that one day your career bites you in the ass, no? For example—you decide you want to become, oh, a curator of an art museum, and the boss finds your old website … What I’m asking is, do you worry about the impact this can have on you, long run?

J.D.: I do worry. I do have another career and always have done regular work while doing sex work. I’m a freelance writer, photographer and I still do art work (among other things). However these are the choices I have made and I’m willing to live with them and the consequences of my choices. I highly doubt I will ever need a security clearance but you never know—stranger things have happened. I wanted to do some volunteer work for my congressmen when I was living in L.A. and I love politics in general and often want to get involved but I have to be very careful about that kind of thing. If I’m ever in a position to be outed by media or some zealot it could damage someone’s career just by being associated with me even if my secret life was a secret to them. So it is something I think about and I need to be thoughtful and careful. That being said, I’m at the point where I’m much more open about my life and my choices and I care less and less what people think. I am who I am and if I can deal with it, others will have to as well.

J.P.: I’m fascinated in your career as an escort. It seems like a confusing field—do men expect sex as part of the package? Are they told up front it’s not part of the package? Are you really just getting paid to look pretty and attend an event? And how do you make sure you’re safe and sound and not roaming the streets of Washington with some psycho killer? Oh, and how much do you charge?

J.D.: Men pay me for sex. OK, my website says “time and companionship only”—but that’s a disclaimer because prostitution is illegal. My Domme work is more legal though a lot of that depends on local laws. With Domme work there is no exchange of sex for money, though many Dommes will offer strap-on as a service, which is prostitution. Creating my fetish content is legal and I have no worries about that unless someone decides to go after me for violating obscenity laws which has happened to some people but odds are low as my content is pretty much NC17 and I don’t live in Florida. Safety is always an issue and for in-person meetings I do what’s called “screening.” I basically know who my clients are … that’s the best line of defense. If a client can’t tell me who they are and I can’t verify that information, I cant see them. Simple as that. Also, there’s an amazing network of women in the business who share safety information on dangerous clients and people to avoid. Sadly we are often looked upon as disposable people by law enforcement and as a result we can and are targeted by crazy ass-clowns who think that we have no legal recourse. There are groups like SWOP-LA (Sex Workers Outreach Project—Los Angeles) and others working to change that but it’s an uphill battle.

Rates, they are on my website but the crib notes are $600 an hour.

J.P.: How has the Internet impacted the phone sex/escort business?

J.D.: The Internet has made finding an escort so much easier, it’s moved prostitution from outdoors on the streets or having to know a madam. To indoors at your finger tips. It’s given women the opportunity to be independent businesswomen and have control over their own work and business.

J.P.: What’s the greatest moment of your career? The lowest?

J.D.: In general I don’t have great moments or low ones. Days when I count the cash and it’s staggering makes me happy or everything runs according to plan and my clients were all nice, interesting, respectful men, those are good days. I’ve had a couple of low moments, being assaulted on an outcall early on before I learned really how to stay safe, that was pretty low. I called the cops; you don’t get to do that to me. Many women wouldn’t have, though, which is a terrible shame. Being assaulted should never be accepted as a job requirement. But that’s only happened once and I learned a great deal from it and it didn’t scar me—not like my very first job working at the pizza place where my 50-year-old boss fired me because I wouldn’t fuck him in the freezer. I carry that trauma with me today. All women deal with sexual politics on the job at one point or another. Sad but true.

J.P.: Your AREA OF INTEREST LIST is riveting. You’re OK with ball busting, nipple torture, spitting and human furniture, but not getting pissed on or boxing. I understand the whole piss thing—but, being serious, how do you draw the line?

J.D.: First off, I’d do the pissing! I don’t pee on people because I’m pee shy. I might pee in a cup and pour it over someone’s head but peeing on someone? I just can’t make it happen. I don’t box because I suck at it and I’d get hurt. Too much physical contact for me. I came up with a list of things I’ll do and not do because I’ve checked It out to see how it feels … then I decide if it’s something I can offer or not. Basically, I test drive something. With BDSM or fetish work you also have to have a certain skill level or someone can get hurt. I wont offer something unless I’m sure it’s something I have skill at. The goal might be to cause pain but you never want to cause harm.

J.P.: Are you in an actual relationship? And, if so, how does your partner feel about your work? Do you aspire to one day marry and have kids and live in a nice suburban house by a park? And would you tell your husband and kids about this segment of your life? That’d strike me as an awkward conversation.

J.D.: Yes, I am in a relationship and yes my partner knows all about my sex work. He’s known since I first met him. I will marry him (we have plans) and we recently moved into together hence my move to Washington D.C. You might find it amusing to know I live in a suburban house right by a park! No Lie! Telling him was easy. When I met him I had no idea that we’d end up in love and living together and I would tell people right off the bat maybe to scare them off, I’m not sure. He didn’t scare. Many sex workers are in relationships—in fact most I associate with are. It does take an enlightened man to be involved with a sex worker and honesty is key. The more honest you can be the better for the relationship.

Kids—not for me. I have a dog. That’s hard enough.


• The best bit of sexual advice you could offer someone: Do what you like and don’t be shy. The key to good sex is enthusiasm. So if you like it you will be better at it.  Most men are just happy you want to be there. So be there and be happy to be there. That will go a long, long way.

• Your Top 5 all-time sexiest movies: Secretary, The Professional, Tampopo, Body Heat, Pandora’s Box.

• The Mets just traded Angel Pagan to San Francisco. Thoughts?: I’ll be honest and admit I had to Google that one. What I know about baseball beyond the basics is, I like to eat hotdogs and drink beer in the sun and it’s fun to sing Take Me Out to the Ball Game in lacy panties in your living room and make a video out of it.

• Three biggest turnoffs: Loud talkers, rude fucks and know-it-all ass hats (Can ya feel the theme?).

• My wife fell for the ol’ mix tape on Date Two. Are you a general supporter of music as a relationship binder?: Music matters! I cinched the deal with my boyfriend because I enticed him with my Billy Zoom story over dinner on our first date. It’s one of the things that binds us for sure. How all new music sucks and back in our day there was real music. Oh, and get off my lawn!

• Have you ever thought you were about to die in a plane crash. If so, what do you recall: I haven’t had a near flight experience but I have had a seizure disorder since I was 11 and I get weird flashes of my life on occasion because my mind plays tricks on me once and a while. Usually it feels like a dream state and I’ll get a flash of the face of a friend no longer with me and then I miss them.

• Celine Dion, Eminem, Tom Brokaw, Joe Biden, P Diddy, Martina Navratilova, Eli Manning. Please rank: Hard list umm … Joe Biden, Martina Navratilova, Eminem, Tom Brokaw, Eli Manning, P Diddy and of course Celine is on the bottom. Even though I’d probably go see her over the top Vegas show if I could find some sucker to go with me.

• Tell us a joke, please: “So a guy walks into a doctor’s office wearing a duck and says can you help me because I have a duck on my head”

• You Tweet a lot of photos of your dog. Explain: My dog is love made out of fur. He’s my constant companion and we both have epilepsy so were bonded. I have a theory about sex workers and their dogs. We have strong attachments to them because we give a lot of ourselves to others and with dogs they love and adore us with out expectations. I also tweet pictures of my boobs but only when I want new followers!

• Your Amazon wish list includes a $2,325 electric guitar. A. How long have you been playing? B. Will someone REALLY buy that for you?: That’s not just a guitar—that’s Gretsch Sparkle Jet, first introduced in 1954! I play badly and have played badly for years. The porn stars get more wish list gifts, but you never know. It could happen. A girl can dream.