Uncomfortable Asks is my infrequent advice column, where I directly address (with permission) letters or messages sent to me in a more elaborate and thoughtful fashion than I might be able in just a regular reply. Ask your own Asks here.
I’ve never been with a sex worker, and I haven’t had sex in over 10 years. I want to get back in to the dating scene but I’m out of practice. You seem cool. Can you help? Advice?– Rusty
First off – I know your name isn’t Rusty. It’s just that I see cool guys like Dan Savage always coming up with cute acronyms or pseudonyms for their askers, and I’ve always wanted to do that. Rusty is a great stand-in for “out of practice” and has a vague 70s porn swagger to it (to fit the theme set by the handsome Phillip, up there in the header image).
Second – I love this question. I love every part of it. I love the way you’ve asked it, the words you’ve chosen, and I love the motivation behind it. One of my most important goals as a male sex worker / escort guy who shows his face and talks about what he does, is establishing and promoting an idea of normalcy to sex work, and also to the idea that we are all still in process; we are all still learning.
Let’s start at the beginning. I hope you weren’t put off by the “Rusty” thing, because there is nothing shameful or embarrassing about feeling as though one is out of practice. And sex and intimate relationships are (no matter how we’ve been convinced otherwise as men) things that require practice. They involve sense and muscle memory, and function best with a breadth of active experience behind them. Nobody at all ever was just good at sex or intimacy the first go ’round. It’s hard! No matter what anyone says, or what movies tell us. It takes doing to understand the very mechanics of it, and it takes lots of doing to understand yourself well enough to feel comfortable and confident in a real way. Pornstar bravado is great, but is unmatched by the grounded confidence of an adult man who understands his own body and his genitals.
So you’re really setting yourself up for success just by saying “I’m not super comfortable with this and I might need a few laps around the track before I get there.”
Next, I think it’s entirely reasonable to view an experience with a sex professional (of any variety) as one might view a session with a personal trainer. It can be something you lean on a few times until you feel comfortable enough in certain spaces to go it alone. Ask your questions and get some answers or help in a safe arrangement. Or it can be a relationship that lasts a longer duration, designed to keep you in shape and help you safely explore new territory before you go it alone.
It’s not easy for everyone to get to that mental state though. We are socially conditioned (even by the terrible and aggressively sexual websites escort guys are forced to advertise on) to view sex workers in particular ways, and as I mentioned here, nobody really comes in with a blank slate. That you’re approaching with an open mind, and using neutral terms like “sex worker” speaks volumes about how you’re coming in.
About once a month, I think about this Quora post I answered that felt hauntingly representative of how lots of people understand sex work and the people who do it:
Luckily, lots of smart people popped in to say smart things (things which got more than my zero upvotes, lol). But that’s an especially telling phrasing (to a sex worker) and not a good start to positive, professional experience with an escort guy, or any other type of sex worker.
I asked my friend TT Baum, whose advice and work I’ve long respected and admired, what his thoughts about this idea were (part of my ongoing efforts to make this space less of a Tyler-based echo chamber) and he was as into it as I was:
“Good for him for making the decision to reclaim his sexuality! Getting back into the dating scene and finding out what pleases you after so many years can be intimidating,” TT told me.
Without knowing you personally, it’s impossible for me to say whether or not the type of encounter you’re seeking is right for you, or even if I’m understanding your imaginings correctly. But speaking from a decade of experience – and painting with an exceptionally broad brush – I would say it might be a smart move on your part. Here are some things to consider that might help you have a more positive experience:
- Be realistic about your expectations and desired outcomes. This means, be realistic with yourself before you make ANY moves at all. Take some time to think about what would be most enjoyable and important to you during a session. Are you looking to go head-first with a hardcore pornstar experience, like you’re in an aggressive and disconnected Sean Cody scene? Or are you looking for a more restrained evening where you can be yourself and have your wishes respected? Not every thing is right for every body, and having at least an outline of what you want will help you choose someone who can meet those wants. Escort guys aren’t mind readers, and you’re far more likely to get what you’re after when you have an idea what it is.
- Do some homework. Literally anyone can place an ad on sites like Rentmen, and that platform has an especially lax policy about what “verified” means. Think it through before you make plans with someone who lacks an online presence (websites, social media, LinkedIn – something), or who pushes or rushes to set a plan. A professional should want to know what you’re after and a little bit about who you are. Not just “when” and “how much?”
- Consider making an evening out of it. If you have the means to do so, treat yourself. We are all existing under impossible conditions every day right now. If it’s reasonable for you to take a break and spend the night in pursuit of connection, I always suggest this as an alternative to an hour or two. Even the best escort guys are gonna struggle to make that limited time feel substantial, and it can be hard sometimes to feel comfortable immediately with someone new.
- You have a right to get to know somebody a little bit before you commit to anything. I don’t personally talk on the phone, but I do my best to respond in detail to emails or encrypted messages, and I provide elaborate online resources about who I am and what I do. That isn’t everyone’s style, but you’re entitled to as much information as you need to feel comfortable. If you have questions, ask! If you have questions that may be legally or otherwise sticky, but feel they can’t wait until you meet in person, ask the best way to ask. Telegram‘s self-destruct timer is a great way to seal sensitive conversation with encryption and then permanently delete it later on.
What you’re considering is a big deal, and I’m big deal here for it. There is nothing shameful about sex or about desiring intimacy. Both things are vital and crucial cogs in our humanness. Looking for somebody who has experience to share, and will keep the stakes low for you (compared with meeting a stranger from the apps), is an intelligent and kind-to-yourself way to facilitate this.
I’m excited for you, Rusty <3
-t escort guy
A male escort is a male-identifying professional who offers companionship and time in exchange for what is often an hourly rate. Male escorts generally do not offer sexual services or other illegal goods or services in exchange for money, but instead are compensated for time and attention in the same ways as personal trainers or home healthcare workers.
This is so far from me ! Though i perfectly understand how one insecure/shy or a bit out of the whole cruising stuff person could find practical the clarity of the transaction, it supposes nevertheless a certain spiritual strengh to resist dreaming about more if the seduction is effective. I fear most guys/girls, having chosen this way to “get back in the game”, to mostly be in a state of sentimental vulnerabily that could lead to complications. Even if i deliberately tryed an encounter this way, all thought about and well planned, i know the risk of being hooked would be a serious impediment. As an escort, how can one deal if the “employer” suddenly finds himself in looove ?! After all, when you need to, there are every chances you find it ! And why not, when the date is handsome and gentle and good in bed ?!
Tyler Dårlig Ulv
It’s complicated, for sure. And it’s not the right path for everyone.
I would say that experienced companions and escorts have a set of tools for walking these emotional lines better than most people. It’s part of the care extended to those in their charge. For myself, I’m capable of experiencing and sharing love without it needing to be tethered to additional experiences in the future, or to a future commitment. Being in the moment and being honest about your feelings in the moment is challenging, though! It only becomes hard or painful when we start to project into the future and imagine that we might remain with unrequited feelings.
I find it incredibly risky; and for both parts: haven’t you ever been afraid by someone’s hesitations or even just emotive behaviors that made you think there maybe was a lot more deeper emotions involved than just the need for temporary romantic ( or not ) company ? That profession must require a lot of self-control and cold objectivity to cope with someone’s wants, in such intimate ways, while inside such vital/precise limits. Already fearful of ordinary romantic relationships, i sure know i couldn’t handle this – both ways. Escorts must be tough people – or did you just find yourself naturally at ease in this particular exchange ? Forgive me my curiosity, but my own personality’s limitations play as a extreme opposite pole to the qualities needed here; and i wonder if you’ve noticed similarities between you and some of your collegues sensibilities ?