Riding the Midnight Cowboy: Interview with a Male Companion

WHILE MINDLESSLY surfing the net in a fit of ravenous boredom, I came across a story about a paid male companion who had spent an hour of shall-we-say “quality time” with a well-known female celebrity and chose to dish about it online. Whether his salacious and less-than-flattering story about the female star was true I have no idea, but it did get me thinking about the pay-for-playboys who have been making a splash in our collective cultural consciousness recently. With shows like Showtime’s Gigolos, HBO’s Hung and Woody Allen’s latest movie, Fading Gigolo, the secret lives of daring young (and sometimes not so young) men are being pushed to the forefront of the discussion about sex and gender in this country and in the world, yet most of what we know about straight male companions is filtered through the optical illusions of Hollywood lights and glitz. What’s the real story on men who choose to hustle their time to lonely cowgirls still looking for Mr. Goodbar and willing to part with major moolah for the privilege? I decided it was high time for me to mosey on down to the rodeo to find out.

While gay men selling sex to other men is nothing new and quite common, straight men offering sex as a commodity to women may appear to be avant garde and shocking. This, however, is not the case. Gigolos have always been part of society’s secret sexual landscape. Many wealthy women have historically plied handsome young men with expensive gifts and financial assistance for romantic attention. Traditional gigolos, usually from the “servant” classes, depended on the munificence of rich benefactors to supplement their earnings from cleaning pools, trimming hedges, making deliveries or giving tennis lessons. Today’s escort, who may be college-educated and professional, is more financially and market savvy. Preferring to be called “male companions” and not willing to rely on whatever compensation their paramours might deign to dole out after the fact, they set their prices up front, anywhere from $200 to $500 per hour plus expenses. They require payment up front, too, preferably in discreet white envelopes, some even requesting a deposit when booking the meeting.

With all this in mind, I excitedly set about rustlin’ my very own real-life ropin’, ridin’, wranglin’ Midnight Cowboy. I realized rather quickly that trying to corral a bona fide bronco buster has a lot to do with the market in which you live. If a lusty lady in the U.S. doesn’t reside in or near a major metropolitan area like Las Vegas, Los Angeles, New York or South Florida, she might as well just hang her rhinestone-studded Stetson right back on the wall, because the pickin’s are slim indeed. After two days of relentlessly googling “Straight Male Escort” in my area I finally came across two guys whom I was willing to give the benefit of a doubt of not carrying some horrible disease. Although both advertised themselves as classy gigolos who were “up for anything,” with rates of $200 or more per hour, it was clear to me from their level of physical attractiveness that it was highly unlikely these two gentlemen have ever jiggled any damn thing, let alone copious amounts of hard-earned cash from some lecherous lady’s pocketbook. While I didn’t have my hopes set on finding a smoldering, Richard Gere look-a-like a la American Gigolo, I expected at least the “man-ho” lovable loser cuteness of Deuce Bigalow‘s Rob Schneider. My dreams of having an up-close-and-personal meeting with an object of desire dashed, I returned to that ever-present and faithful companion of all desperate people, the World Wide Web, to find a male escort I could at least correspond with whose barter-able flesh was worthy of sinking my teeth into.

Due to pitbull tenacity and my constant diligence at leaving no stones unturned, up popped the slick, impressive website of freelance male companion and gifted gunslinger Luke Jackson in all his glory—and I was, to say the very least, mesmerized. Although he took his moniker from Paul Newman’s character in Cool Hand Luke, there is not much about escort Luke Jackson to make you think about his hands—except perhaps the size of them, along with what must be the massive length and breadth of his feet. Amongst photos of misty beaches and bucolic pastoral scenes, Luke intersperses picturesque prose of how he is the ready, willing, and oh-so-able lover that every woman has been searching for—that is, if there’s more rattling around inside her to-die-for designer handbag besides next month’s wishful thinking and this month’s unpaid utility bills.

Convinced I’d finally found my very own verified stud, I contacted Luke and requested an interview, to which, after a few flirty emails back and forth, he agreed. Ever charming and eager-to-please lothario that he is, Luke casually informed me he would be doing our mid-morning weekend interview in the buff. His promise to be gentle with me, despite his flagrante state, instilled in me the amount and quality of optimistic self confidence I would have experienced in letting Godzilla light my cigarette. Still, like any rough-and-ready cowgirl worthy of her chaps, and determined at all costs to lasso the truth, I dusted off my hat, tugged on my boots and spurs and saddled up for what I suspected would be a long, hard and very bumpy ride.

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Tell me a little about yourself.

I’m 29, 6’3″ tall, 175 lbs. I have a master’s degree and work in a creative field.

What area do you work out of?

I’m currently based in New York City, but I’ve worked from DC as well and lived all over the world. Most of my clients have been spread out—New York, London, Madrid, Edinburgh, San Diego, Chicago, San Francisco.

What made you decide to become a male companion?

I had a friend who put herself through grad school as a high-end escort. I was just coming out of a long term relationship and she suggested I try it. I was also just starting grad school at the time and so my schedule was pretty flexible. She basically said there aren’t many straight male escorts at the high end, so there was an opportunity for someone well-educated to succeed. I put a website together over a weekend, got listed on Concierge du Monde and just started talking on the forums until I had women contact me. It was a lot easier than you’d imagine.

How long have you been a male companion?

I did it for a year and a half, then stopped when I fell in love and my girlfriend asked me to quit. I recently started again in order to pay off some loans and pay the bills while starting up a new business.

While you were in the serious relationship that you gave up being a male companion for, did you miss the work?

I missed the adventure of it, yes.

How did you approach your first encounter?

I was nervous, but just treated it like any date, being polite and friendly and being myself.

How many sessions do you have a week/ month?

Varies completely. The most I’ve had is maybe four meetings in a month. There isn’t a huge demand for high-end straight escorts and my rates are pricey, so it’s more of a now-and-then kind of thing. On average when I’m working I probably get one to two meetings a month.

What type of clients do you have?

I’ve had Swiss bankers, European diplomats, Canadian school teachers, successful New York professionals, married couples, and journalists, to name a few. It’s been fascinating and wonderful meeting people from all walks of life in such an intimate and revealing way. I even had a Thai madam from DC hire me—she ran brothels all around the country and would talk to clients and send them to addresses while we were at dinner. Crazy.

What are your rates?

They vary, but generally I charge $500 for a short meeting, $1,000-1,500 for a full evening, and $3,000 for a full day, but often I’ll discount that for a full weekend or multiple day meeting/trip. I’ve also worked with female escorts where I’ll get a similar rate for a short meeting for something specific.

Being a part of the service industry do you often get tips? Do you expect them?

I sometimes get them, but there’s certainly no expectation.

How do you get yourself in the mindset to perform with someone you wouldn’t ordinarily find attractive?

It’s just about focusing on the part of who they are that you like, and on being turned on by them being turned on. It’s not usually an issue, which is maybe why I can do what I do. But I also always make it clear that you’re not hiring me for sex, you’re hiring me for my time, and our time together, so sexual performance isn’t the only or even primary reason to get together.

Has your client base grown?

It had a few years ago, I’m in the process of re-growing it now.

Has the economy affected your client base?

Not that I can tell, but it certainly has for female escort friends of mine.

Do you have regulars? How long do they usually last as clients?

Yes, most of my clients are regulars and meet me more than once over a period of months or a year.

What do you do to put a client at ease?

Smile, be relaxed myself. Make it clear that everything is on their terms and the time is really for them. Physical contact tends to relax people, too—hugging, kissing, massage.

How often does your work involve couples?

I’ve met with quite a few couples with particular fantasies or kinks. I quite enjoy meeting with couples because it’s usually a shared experience for them, which can be more relaxed for everyone than one-on-one meetings. I’ve also put on shows with female companion friends for both men and women and couples.

Are female companions better sexually than regular women?

No, but they’re a lot of fun.

There can be something quite titillating, even liberating about being an exhibitionist. Most people, in one way or another, particularly when it is associated with their profession, enjoy putting their best attributes on display. When you are performing and there is an audience does it affect what you do?

I am an exhibitionist, that’s true, and having an audience can be quite arousing and exciting. I suppose it depends on the situation though, if you get too excited or too wound up in the moment it can be overwhelming. You have to relax into performance, I suppose.

Since you advertise as a straight male companion, I assume that you are heterosexual. Have any of your sessions had unexpected requests for homosexual activity? If so, how have you handled them?

I’ve occasionally had couples where the wife will request some involvement from the husband or boyfriend, wanting to have him guide me into her or wanting to perform oral together as a shared experience. I generally indulge the requests as I’m quite comfortable with my sexuality and feel that in these circumstances it’s more about the shared experience for the couple than it is about me. But that said, I certainly have my limits and don’t meet with men on their own or perform any sexual acts with them on my part.

How often does your work involve cuckolding (having sex with another man’s wife while the husband watches without participating)?

Surprisingly often. This is probably the most common request I get from couples, although some just want to live out a threesome. My size contributes to this, but it’s also a very taboo fantasy so I think some couples are more willing to try it with an escort/companion.

How do you feel about participating in cuckolding?

I have mixed feelings since it’s not really a fantasy I can relate to, but I enjoy it. The performative aspect can make it a lot like how I imagine porn must be, but on the whole it’s a fun dynamic.

What is your take on the husbands and wives involved in cuckolding?

I think it’s an interesting dynamic for couples since it seems to fulfill the needs of both partners, albeit in an unusual way. At its best, I think it can be part of a very loving relationship, but it also can cover some deep insecurities that might need to be addressed in other ways. To each their own honestly, I don’t claim to have any deep insight into their psyche, but if it’s what they and their partner want, more power to them for finding it.

How does your work affect your relationships?

I’m always open about my work with anyone I sleep with or date. Generally women find it alluring from a casual dating perspective, but for more serious relationships, they want me to stop, which I understand. At the end of the day, I do it more out of a sense of adventure and to pay off loans faster than out of true necessity, so I’m very lucky in being able to set it aside at will.

You said you once gave up being a companion for a serious relationship. Are you in a serious relationship now?

I’m not, no.

Do you miss it?

Being in a relationship? Of course, I miss elements of it, but I’m enjoying the exhilaration of possibility. You never know who you might meet or where you might end up. Uncertainty has its appeal. I have a pretty active and varied sex life. I have a few friends and lovers who I see regularly and I go on dates now and then.

Being in the companion industry yourself would you have any issues being in a serious relationship with a woman who was employed in the companionship industry and wished to remain so?

No, I wouldn’t have an issue with that. I might long term. But at least initially it wouldn’t be an issue at all. I’ve dated other escorts before.

After being in this line of work and having to be so open to sexually responding to, and even perhaps seducing women do you think it would be possible for you to have a long-term monogamous relationship or even a monogamous marriage? Due to your inherent traits that make you successful at your job and skills that you have honed over time, it is inevitable that a lot of women are going to feel sexually attracted to you, how well do you think you can deal with that temptation?

That’s a great question, and I wish I knew the answer! It’s something I think about a lot actually. I suspect I’ll end up in a somewhat open marriage, where we at least explore sex with others together, if not on our own. But only time will tell. I think monogamy in general is a fraught idea, not that it’s impossible or wrong, but I think that assuming it to be the only way is unhealthy.

How does sex that might occur during time you are being paid for as a companion compare to sex not associated with your job? Is one more personally satisfactory than the other? Has your work changed how you feel about sex as a whole?

Honestly I’d say there isn’t a big difference between the two for me. When you’re in the moment, sex is all consuming. There are certainly times when I’m perhaps a bit more selfish when having sex or doing something purely for my own pleasure, but honestly if I didn’t enjoy the sexual side of companionship I wouldn’t be doing it. And I wouldn’t be any good at it. It’s certainly taught me a great deal about the wide differences between women in terms of what they enjoy, how they orgasm, what feels good. It’s truly unique to each person, so it’s not really about tricks or anything like that, it’s about being responsive and observant, and communicating well.

What do you enjoy most about your work?

Meeting new people, getting to know their stories and I like shared pleasure. People open up with a companion in a different way. I also love the travel and exploration, seeing new cities, having great meals and adventures.

What do you enjoy least about your work?

The dubious legal status and social stigma.

Have clients ever tried to make you feel like a sex object or a piece of meat?

Yes, of course: But I quite enjoy that sometimes.

In reading interviews with other male companions, their number one complaint about some of their clients was personal hygiene. Has that ever been an issue for you?

Fortunately, no. I’ve had lovely clients pretty much across the board. I’ve been very lucky, I suppose. But I think it’s also partly how I position myself. I tend to appeal to thoughtful, adventurous women (and couples) and personal hygiene isn’t really an issue with people like that.

Suppose you were my companion for the night and it is my first time, I’m nervous and I let you take the lead. What would you do/suggest to ensure I had a satisfactory evening?

I’d suggest we have a drink together and then go for a walk. We’d talk about where we’re from, what we’re reading, the simple things. Eventually we’d wind our way back to the hotel or your apartment where I’d kiss you and suggest a massage over another drink. Things generally work out from there.

Have you experienced any consternation from any of your clients about your size?

No, no consternation, it’s often part of why I’m hired honestly, so they know what to expect… and I know how to be gentle.

What are some things that you do that you clients really like?

I’ve read out loud to clients before, given foot massages, made dinner…sexually the list is longer and more varied. I’m extremely good at oral sex and have made many women gush or squirt for the first time with my fingers, and due to my size I guess cuckolding could be considered a specialty. I’m also good at chess and conversation about culture or current events or philosophy.

What are some things that your clients do that you really like?

I always enjoy seeing a client truly enjoy herself (or himself if he’s watching). That can mean a mind blowing orgasm or a smile over dinner. I like knowing they’re enjoying it.

Is there anything you’ve done for a client you don’t care to repeat?

I’ve been stood up by a client before, but aside from that, no.

Do you work for an agency or are you independent? Why?

Independent, because I can manage my own time and finances. My approach is very personality based, which doesn’t come across as well through an agency.

What percentage of your clients would you be attracted to outside of work?

75% approximately.

Have you had clients that you would have seen for free but just never told them that?

Yes, I have. But it’s not about free or not, generally we never would have met if they weren’t open to hiring a companion, so it seems like a moot point. And we have fun either way!

Have you ever paid for sex? Would you? What would it take to entice you to pay for it?

Interesting, I haven’t. I’m not opposed to it but don’t currently have enough money to afford it. I’m not sure what would entice me, maybe something unusual or specific that I wanted to explore?

Have you been able to keep your personal life and professional life separate?

Yes, largely. My friends and siblings (but not parents) know about it, which was a bit “coming out” but was liberating. It’s hard to be honest about it, but it’s worth it. My actual true professional life is more important to keep separate from my companion work.

What are your health/medical considerations being a companion and how do you address them?

Safer sex is always important and a priority, so protection of course, and regular testing. It’s something I’m happy to discuss with clients and standard practice.

What’s the percentage of your sessions that include dating activities compared to sessions where clients just want to get into the thick of things?

I’d say it’s about 50/50 honestly. Most couples want to get into the thick of things after a drink, but others usually include dinner or cocktails first. And then there are the weekends and trips, which of course are more about social activities together..

Are you totally worn out the day after an amorous session? Do your clients try to wring every ounce out of you?

Often, yes… it can be quite a marathon.

What are your extended sessions (days or weeks) like? What do you do when you get bored on a long session?

I’ve never done a full week, but I’ve done a long weekend, which was really nice. I always bring a good book and we plan out lots of fun adventures. Museums, walks in the city, time exploring a zoo or a park—lots of options. Generally on trips we share a room but I have had clients get me my own room. Both options are lovely in their own way. It can be nice to have your own space, of course, but sleeping together is nice as well.

On these weekenders, I know it varies, but how often does sex usually happen if you should decide to do that with your client?

It does vary, but I’d say generally two long sessions each day, morning and night.

These weekenders, they are usually single women/married women?

Single or married, but not usually couples.

Have any of your married clients who see you without their husbands ever told you that their husbands were aware of what they were doing and didn’t care?

Yes, that’s happened before, it’s happened twice that I can think of.

When you have had couples for clients have the wives ever contacted you secretly about meeting with them alone?

Funny you should mention that—it actually happened very recently.

How do you handle that?

I’m discreet.

Have you ever had to spend an extended period with a client you didn’t particularly care for?

No, I’ve been lucky. Again, I really like all the clients I’ve met.

Have you ever been on an extended session with a client and become seriously attracted to another woman? If so, how did you handle that?

I’ve certainly seen other attractive women, but I just stay focused on who I’m with and stay in the moment.

What are some of the strangest things you’ve done during your time as a companion?

Most of it hasn’t been too strange, but I did have one client who was into prostate milking (using her fingers or toys to massage my prostrate), so that was an interesting education. Quite intense. There can be some BDSM… spanking, bondage… both giving and receiving, though I’m generally the dominant one. No roleplay yet, but I hope that changes.

What, if any, boundaries have you established in your work?

None that I’ve encountered thus far.

How many clients would you say you’ve had during your time as a companion?

I’d say fifteen or twenty. Most were repeat clients. I don’t do this every week, it’s more like once a month.

From interviewing you and seeing your photographs you are articulate, intelligent, personable and physically attractive with one particularly glaringly impressive physical attribute so I’m just curious, how many of your companionship sessions don’t progress to sex?

Only one, actually. She was one of my first patrons and we met in London for a lovely weekend, but she was very clear that she only wanted companionship, company at dinner, good conversation and nothing more. We had a great time exploring the city.

Why do you think women who are not seeking a more permanent attachment would rather pay your admittedly pricey rates for casual sex instead of going the traditional route of picking up some hot guy at a bar for a one-nighter?

Well I suppose that assumes first that there are hot men available who are also gentleman, safe, clean, respectful, and good in bed. Then there’s also the question of his priorities. Many men approach one night stands as being all about their pleasure, not their partner. But a companion is different. It’s about having someone focused intellectually, emotionally and physically on you and your needs, even if it’s just for an evening. It can be about particular fantasies, or about having a dashing and articulate date to a social event, but it’s all about you.

Do you ever have any clients that you suspect are really struggling to afford you, and if so, do you have any qualms about that?

Only once, and no, no qualms really, it’s entirely her choice how to spend her money. I try to be honest about who I am and what I offer, so I’m not tricking anyone.

I suspect that some emotional involvement is necessary on your clients’ part for them to continue to book you, but what do you do when you sense a client is getting too emotionally involved?

I’ve only had that happen once. It was less about the sex and more that I was an escape from some trouble she was having in her day to day life. It was more a matter of us just talking through that than anything else

What if a woman wanted to share you with her best friends for an evening? Would it still be your flat rate or would you have to increase your fee?

I’d probably provide a discount if anything. I’ve never had that happen in my work yet, but I’d love to. I enjoy the dynamic of being shared by two or more women.

How long do you plan to continue to work in this profession?

Not long! Maybe a year at most.

What characteristics would you say are necessary to succeed in this type of work?

An open mind, empathy, sexual performance and fitness, an eye for marketing yourself tactfully, and the intelligence to connect with smart, successful clients.

Would you consider yourself a master seducer who has honed his skills via trial and error or do you think just being one’s self is the best route to take for a male companion?

Definitely just being myself, I don’t feel like I have any arts of seduction at all honestly.

When it comes to sex, do you think you’re better than the average guy?

I don’t know average, but yes, I’d say from what I’ve heard and what I know, I’m quite experienced and passionate and playful in bed.

When you are in a relationship, do you make a concerted an effort to satisfy your partner on all levels as you do with a client? Is the same amount of attentiveness, active listening, attention to detail, and eagerness to please present? Or do you want to be more relaxed in your personal life? Do you think it is possible for a man to maintain that level of attentiveness and enthusiasm, to always bring his romantic A-game on a day-to-day basis in real life?

I don’t think it’s possible to maintain that all day every day, but it’s something to aspire to. It’s not superhuman or anything, it’s just very giving, attentive, and focused on her needs. That’s something to aim for in any relationship or encounter.

I’ve read memoirs of female companions before and except for a handful the women seem to either feel somewhat victimized by their sex work or seem to develop a dislike/disdain for men. However, with the material I’ve read on male companions that doesn’t appear to be the case, or at least they don’t vocalize it. Why do you think men tend to have a different view about this type of work?

That’s a great question, I think it’s partly that there are simply more women in sex work and in a wider range of situations. In our society at least, men feel entitled to sex and there’s a culture of paying for it. For women it’s a newer thing, so I think there’s still a lot of self-selection. But I don’t want to speculate too far on it. I think there are some differences between how men and women approach sex but they’re not universal, many of these differences are shaped by society, and how that plays out in sex work effects sex workers. The biggest thing we could do to change that is de-criminalize it.

Have you spoken with companions in other countries where the sex part of paid companionship is decriminalized?

A bit, yes, it makes a huge difference.

How are you different when you are in the role of pursuer rather than companion? Are there any differences as to how you proceed when it is not a foregone conclusion that a woman desires you?

Nope, there’s honestly no difference. I’m not a big pursuer, I just try to be myself and be open and honest about that and about my sex drive and desires.

Is there anything you think you know about women that most men don’t?

Women love sex more than most men give them credit for. I hear it all the time, but the idea that “women would never pay for sex” is absurd. I do think there’s a cultural ignorance about women’s sexuality. Women can enjoy objectifying men, want to explore their fantasies and enjoy sex for its own sake. Some of the women I see find hiring a companion very empowering. It shifts the power dynamic, even if they want me to be dominant in bed. They’re taking control and getting exactly what they want, when they want it.

Now for my last question, Mr. Jackson, and you can add “incredible endurance” to your resume. Having women not only want you, but willing to pay large sums of money to spend time with you must be quite flattering. Do you think that has changed your personality since you became a companion?

I hope not! I don’t feel like it has honestly. Let’s just say I don’t think it’s gone to my head.