I’m on the phone with an old friend from university, Preston. He’s the kind of guy most people find insufferable – a drug addicted trust fund baby with a gnarly sense of entitlement. His six figure job and beach bungalow have both been handed to him by his parents and once a year, he checks himself into Passages Malibu, the rehab center of the stars, for a reset. Cause you know being a 6’4 white dude with unlimited money and no responsibility can be really taxing on the soul. The extent to which he is out of touch with reality can get annoying, but most of the time I just feel sorry for him. Beneath his flashy, LA douchebag exterior, is a highly sensitive, sweet and intelligent man who will do anything for the people he loves. He’s just a poor little rich boy – trapped in a gilded cage of his own making.
Seemingly incapable of finding his way out of his father’s shadow, Preston’s job at the family company is little more than a glorified assistant position. Having never found a passion in life outside of spending absurd amounts of money on drugs, clothes, and shiny things, he often turns to codependent relationships to get his fix. He recently ended things with someone he knew was toxic but who he wanted so desperately to make things work with. Needless to say, he is in particularly bad spirits when we FaceTime. But things are looking up. His remedy for a lonely Sunday full of despair? Hiring an escort.
Throughout the decade we’ve known each other, he has frequently made references to his proclivity for prostitutes. Despite having never been made explicitly aware of my sex work past, he’s always known that I’m not the type of feminist to rag on him for such a lifestyle choice. That’s always been what I’ve valued most about our friendship – the whole no judgment thing.
Bonded by our black sheep status, getting candid with one another has never been a problem and today is no exception. As we touch on all the normal stuff – crazy exes, family drama, Burning Man – Preston has no hangups walking me through his escort selection technique, going so far as to send me various profiles and asking for my opinion. It’s fascinating to hear what a guy really thinks about all this.
Not just the bullshit he thinks a woman wants to hear. And while I certainly don’t agree with everything he has to say, I am more than happy to hold space for him, free from moral commentary. Because god knows the world needs more of that.
So what exactly goes through a punter’s head when choosing an escort? See below for the full scoop.
How real are the photos?
“Having more photos, like 5 or more, on a profile is generally a good sign for me – especially if they are taken in different places with different lighting and stuff. A mix of professional and candid pics is ideal because it shows consistency and gives me the sense that the person is real. Image quality is a good way for determining the age of photos.
These days most people are using phones to take pictures of themselves and since phone camera quality has improved exponentially over the last 5 years, it’s pretty easy to tell when homegirl is trying to pass herself off as younger than she actually is.
Honestly I don’t really care so much about that. It’s definitely happened before and it’s been whatever. Age doesn’t bother me as much as when she’s 20 pounds heavier than she is in her pictures.
That’s always a real bummer. Skinny girls are my thing…what can I say? When it comes to hiding the face in pictures, I mean it’s not ideal but if her body is banging then it’s not a dealbreaker. It also definitely gives off more of a girl-next-door vibe…like I’m just a normal girl who doesn’t want people to know I do this. Some guys are into that. Doesn’t really matter to me one way or another.”
How far will my money get me?
“I’m debating between three options right now. There’s Candace – the slightly chubby, 33 year blonde with huge tits. Her rate is significantly cheaper than the other two –$500 for the day.
Money is really no object but I hate feeling ripped off. Candace isn’t really my type but I’m not not attracted to her. Plus she seems like she would be down for a lot. She’s asking for a $100 deposit to pay for gas which is definitely sketch. I have no problem paying the extra gas charge in person after she’s actually showed up. But then again, it’s just $100. Seems like a risk worth taking, especially since it looks like she’s close by.”
*Sends Candace the money only to realize that he’s been scammed*
Am I actually attracted to this person?
“Candace is looking like a no go. Option number two is Ashley, who has a lot of ass pics but no face ones. She’s 22 and blonde. The thought of my ex showing up at my door and walking in on me fucking someone like that is pretty hilarious. But I don’t find her all that hot. She’s kind of fat, don’t you think? (For the record no one he describes as fat is actually fat. They just don’t have an underweight BMI).
She has an OnlyFans but there’s no way I’m subscribing just to see what she looks like. I guess I might as well reach out to see what her rates are. I’ll be so fucked up by the time we meet up that I’m sure she’ll be attractive enough.”
*Reaches out and schedules Ashley then messages back saying that something came up but that he might be free later.*
How down is she?
“I think Denise is the winner though. She’s skinny and you can tell she’s the real thing based on her pictures. Her profile pic is clearly photoshopped and she’s wearing tons of makeup that kind of makes her look like a Bratz doll which is pretty weird, but then she has 6 or so more normal looking ones of her just hanging out in lingerie. The biggest green flag is that she says she’s a stripper at a place I’ve been to before, which gives me the sense that she will be way more down to do drugs than Ashley.
I’m basically a walking pharmacy — ketamine, speed, whippets, Xanax, weed. You name it, I probably have it. I’m gonna be doing hella drugs the whole time so ideally the escort I choose is down for some fun. At the very least, I don’t want to totally freak her out. It’s funny cause when they show up, they totally think “this drug addict is not gonna be able to perform,” but then I take a viagra and fuck for hours. Denise seems like she can hang and I think I’ll probably be able to convince her to stay longer than I’m paying for.”
*Schedules Denise and ends our call when she arrives*
A few hours later, Preston rings me again. “Welp, that was rather disappointing. Turns out those photos were hella outdated and she was way heavier in real life. Also I think I may have freaked her out with the drug stuff. But whatever. Think I’m gonna hit up Ashley now lol.”
*Hits up Ashley, apologizing for flaking earlier + sending a pic to indicate that he’s cooler than the other creepy old dudes hitting her up*
When we next touch base, I find out that Ashley was also a disappointment. I can’t help but wonder: “Is it the women who are marketing themselves in misleading ways or is it the heartbroken man trying to numb his feelings with meaningless sex that is the real culprit?” While I’m quick to jump to the defense of the women – who are out here risking their lives to support themselves – I can’t hate on Preston too much for not worshiping them as the goddesses they are.
His mommy issues and patriarchal conditioning are surely at play after all, and the fact of the matter is that any person who decides to become a sex worker is willingly entering a social contract where they agree to be objectified and judged by their physical appearance. Models and actors do it all the time. It can be a disempowering narrative if you let it, but it doesn’t have to be. I think a lot of that comes from not taking things personally. A man denigrating a woman based on her appearance has much more to do with him than it does with her.
There’s an unspoken understanding amongst sex workers that clients will more likely than not project their shit onto you. Here you are, a stranger who is consenting to getting to know someone in a very intimate way. There’s a closeness there but there’s also a wall – one that keeps things professional and at times, impersonal. Because of this unique dichotomy, the sex worker often serves as a stand in for a female figure in the client’s life.
This allows the punter to process unresolved emotions from a real life relationship with a safe, non-judgmental person in a refreshingly honest, albeit taboo manner. With the patriarchy constantly telling men to be strong and never express vulnerability, a few hours with a sex worker seems like it can be far more cathartic than a typical therapy session because the sexual intimacy breaks down psychological barriers much faster, allowing men to freely express themselves.
In Preston’s case, he’s definitely feeling down in the dumps about his ex. While he didn’t come out of either escort experience feeling like a rock star, he was at least able to get his mind off things and be vulnerable in a way that the real world doesn’t allow him to be – if only for an afternoon. My wokest of woke friends would look at someone like Preston with disdain but what I see in him and all the sex work clients I’ve encountered is a sad little boy. Someone who is looking for love and compassion.
As long as he pays the requested rate, treats his escort with respect, and doesn’t pressure her into doing anything she doesn’t want to do, I see nothing wrong with such an exchange. If anything, I have disdain towards the haters – the people up on their high horses who look down on sex work because they think it is inherently exploitative. I pity them for their lack of empathy and the rigidity with which they hold onto viewpoints. Life is never black and white. “Good” and “bad” are social constructs. Sex work is a far more nuanced industry than most give it credit for – one that can be empowering for the sex workers and healing for the punters seeking connection and acceptance.