First Time With A Male Escort | International Gay Male Escort in Toronto
A bit of advice about what you can expect before we meet (our first time together, if you will). These are questions that others have fretted about and might be keeping you from reaching out already. What about rejection? Racism? Transphobia? What about money? And Hygiene? Is there going to be sex? Here are your answers...
First Time, FAQ, Stats, Questions, Escort, Male Escort, Gay Escort, New York, NYC, Gay Companion, How To
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First Time

Is it your first time?

Mine too.

(Not really. But I know what it’s like.) There’s a lot of different ideas about paid companionship and a lot of confusion about what it really means. I’d like the chance to clear up any possible confusion about me and our about time together.

The climate has changed in recent times, and internet security is more paramount than ever. Not just for you, but for your interactoins with me, as well. You might not realize that things you do and say could potentially put me in jeopardy, even when you might not mean to.

Please read through my security page for ways I’m helping keep our correspondence safe, and what you can do to help.

Beyond security measures, here’s a handful of questions guys have asked me before our first time together:

What should I expect from a meeting?

I don’t like the word “meeting,” and I definitely don’t like the word “appointment.” “Date” seems like a much more agreeable sounding thing, and a more accurate representation of what you’re in for anyway. Let’s call it a date.

And the truth is that the possibilities are endless.

I’m the sort of guy who works just as well with a quiet night at home as I do between Major Gift Donors at the Met. I love theater and opera and I’m reasonably well versed in both. I spent years at the School of Visual Arts (including a semester abroad at the Sorbonne) studying graphic design and art history, so I’m no slouch at the museum, either.

I’d love to meet you for dinner someplace cozy (I can do fancy, but what I love more than anything is someplace quiet and out of the way where I can really get to know you better) and talk about your life and how you came to know about me.

Afterwards, there’s nothing more exciting than a walk together through city streets, both of us excited to get back to your place. Toronto has some of the most beautiful new hotels and real estate in the world, so I’m forever brimming with excitement when I get to see an impressive suite or apartment with a view.

When the door closes, it’s just the two of us, and nobody needs to know what else we learn about each other (or how many times the hotel has to call to ask that we stop jumping on the bed). Maybe we build a fort with the couch cushions, too.

What you should expect is that I will be as clever and present as I’ve promised here. And that your worries about rejection or not being X enough for me will be unfounded and summarily dismissed. I’m excited to get to know you, and that is what our first date will be about.

What about money?

It’s sordid, isn’t it? There’s just no good way to talk about it without someone feeling diminished. So I prefer not to. My rates are posted, and fair, and all you should worry about is how much time you’re ready to spend with me.

I only accept cash – it’s cleaner for everyone involved, in the long run – and I expect payment at the time of service (just like the Doctor’s office). Since I don’t like discussing it, be discreet and slid it into my pocket when you kiss me goodbye.

We’ll figure out the total before we meet, so don’t be worried numbers will change from go to whoa. There will be no upsells or attempts to slyly add time on to what we’ve agreed (unless you really, really want to).

Do I need a deposit?

Many female companions insist on a deposit up front for their time. I’ve never liked to play that way and only require a deposit when I’m traveling to meet you. I like to make my own arrangements, and a portion of my consideration up front allows me to do that and to simultaneously be sure you really mean it.

What if you don't like me?

Well, what if you don’t like ME? It happens. Not often, but occasionally, you or I may realize that the chemistry between us just isn’t there, and I will need to politely excuse myself. It goes without saying that I never take my fee if I need to leave early for this reason.

If we meet and you are certain that I’m simply not what you were expecting, it’s important that you let me know as soon as possible, so that I don’t get too attached to you.

We’re all just human, after all. Sometimes it simply isn’t a match.

(If it reassures you any, I’ve only ever had this happen once, and he was a perfect gentleman about it. I think of him fondly to this day and respect his ability to be so forthright.)

Do I need to send you photos?

I would LOVE that! But no. You absolutely don’t. It always seems a little lopsided at first – me with this enthusiastically detailed site about everything I like and how I like it, and you, about whom I know nothing – so I’m always grateful when a gentleman wants to share what he does or what he looks like with me in advance. I promise that physical appearance won’t ever be a deal-breaker for me. It’s just so I know who to look out for the first time we meet.

What about hygiene?

Funny enough, this is the thing that guys hiring for the first time are often most worried about. It can be a source of anxiety and embarrassment no matter how experienced (or not) one happens to be. My policy is that I always arrive table ready; there’s never additional prep work required for anything that may occur.

I suggest getting yourself as clean as possible in the shower just before we meet up to make sure you look and feel your best. Really get in there and give everything a good scrub so you won’t ever have to make this face: 😳.

And you should really feel free to ask any questions you might have, even if they seem embarrassing or silly.

What if I do/say something that turns you off?

It happens. Not often for me, but my turn offs aren’t very many:

  • poor hygiene
  • rudeness to wait staff
  • communication failures
  • set-in-stone rules
  • having to wear underwear under a hotel robe
I'm Black/Short/Asian/Trans/Bald/Fat/Whatever. Is that an issue for you?


And you don’t need to tell me about it if you don’t want to.

I don’t require any kind of disclaimers about who you are and what you think your limitations might be in the eyes of others. If you’ve been told by a provider that you are not worth their time because of your gender or race (or any physical characteristic), you should know that is a garbage person who wasn’t worth your interest in the first place.

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First Time with a male escort, or a gay male escort.

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Tyler the Badwolf

I really want you to come say hi, but first, will you read through this and make sure we’re on the same page?

I do understand that this site may offer sexually explicit material for adult entertainment.

I do not find sexually explicit material to be offensive or objectionable. I understand and respect the standards and laws of my community.

I have a legal right to view and possess such adult material in my community, and am solely responsible for my actions.

I am obtaining material from this site solely and exclusively for my own personal use and enjoyment.

I will not allow minors to access this material in any manner whatsoever, and am of at least 18 years of age.

I am interested in this material from a purely personal, non-professional point of view.

I agree to respect the copyrights of the owners of the material that I obtain from

I understand and agree that I may archive this material only for my personal viewing, but cannot and will not distribute, resell or otherwise change, transmit, resend or reuse any material that I download from without written consent.

Additionally, I understand that any money exchanged is exclusively for time and companionship, anything else that may or may not happen is a matter of personal choice and personal preference between two or more consenting adults of legal age, and is not contracted for, nor is it requested to be contracted for, or compensated for in any manner whatsoever.

See the sun rise and set and rise again, from the comfort of my arms. A full day together to spend any way we choose; the possibilities are nearly limitless.
Additional Day
Who says the fun has to stop? Additional Day bookings must be contiguous with either an Overnight or full Day booking, but offer a deeply discounted extension of an already brilliant time together. Please ask about discounts on longer extensions of our time.
I’m glad to reserve a space for us to meet, and ask only that you add an additional 200 (240 CAD) per evening to any package longer than One Hour (Regrettably, I’m unable to play host for single hour appointments).

I will handle reservations and payment – all you needto do is arrive on time.
First Date
It can be totally intimidating to meet someone for the first time. It's often a complete gamble of chemistry and comfort. Sometimes it can be a stress reliever to know that it’s ‘just dinner’ and that there’s no pressure or reason for anxiety.

I’m a firm believer that one can sense chemistry through conversation. Let’s get a bite and see how we click before an investment in a longer session.
My most favorite package. No rushing, nothing forced. I'm terrible at sharing with others; the idea that you’ll be all mine all night is such a turn on. And while I usually do need to sleep a realistic amount, the gift of waking up in the morning in a big, comfy bed with someone who’s ready for more is absolutely magical.
In an evening we can talk and truly get to know one another. That affords us time to lead into other activities at a natural, organic clip. I love getting to know about what gets you going while we’re both still dressed and civilized. Especially in public –there’s nothing hotter than the social restraints of being in mixed company.
Lunch Meeting
I’m more than happy to swing by your private office, hotel, or home for some more focused time than my other experiences may offer (doesn’t even have to be during lunchtime! But think how clever you’ll sound declining another invitation because you have a lunch meeting with me).
Single Hour
If all we’ve got is an hour together, let’s make the most of it. I know someone like you is exceptionally busy, and might not have more time to devote just yet.

We'll get there.