Geeky30s

I had the pleasure of meeting this gentleman recently. He is much more approachable and sweet than his pictures would suggest. He’s obviously gorgeous, really really sexy, but his kindness and attentiveness really take the day. He melted my considerable nerves away after just a few minutes. It was just so natural to talk to him and cuddle. He’s an exceptional kisser. He’s going to Palm Springs soon - if that’s where you are, I can’t recommend him enough!
 
Marcus_XL - Pornstar Performer, Rentboy, Gay Massage in Montreal, Quebec | RentMen
RENTMEN.EU Pornstar Performer & Rentboy in Montreal, Quebec - Marcus_XL: Masc Top Hung  

I had the pleasure of meeting this gentleman recently. He is much more approachable and sweet than his pictures would suggest. He’s obviously gorgeous, really really sexy, but his kindness and attentiveness really take the day. He melted my considerable nerves away after just a few minutes. It was just so natural to talk to him and cuddle. He’s an exceptional kisser. He’s going to Palm Springs soon - if that’s where you are, I can’t recommend him enough!
 
Marcus_XL - Pornstar Performer, Rentboy, Gay Massage in Montreal, Quebec | RentMen
RENTMEN.EU Pornstar Performer & Rentboy in Montreal, Quebec - Marcus_XL: Masc Top Hung  

I had the pleasure of meeting this gentleman recently. He is much more approachable and sweet than his pictures would suggest. He’s obviously gorgeous, really really sexy, but his kindness and attentiveness really take the day. He melted my considerable nerves away after just a few minutes. It was just so natural to talk to him and cuddle. He’s an exceptional kisser. He’s going to Palm Springs soon - if that’s where you are, I can’t recommend him enough!
 
Marcus_XL - Pornstar Performer, Rentboy, Gay Massage in Montreal, Quebec | RentMen
RENTMEN.EU Pornstar Performer & Rentboy in Montreal, Quebec - Marcus_XL: Masc Top Hung  

I truly can’t thank you enough, folks! This site has been a godsend. 

Don't be worried about touching them during the massage portion.  They'll be expecting it. 
When it comes to the "fun part", make sure to let them know what you want, it not with words, with moving theirs hands or mouth.
Most of all, relax and have fun!

https://rentmen.eu/Marcus_XL
https://rentmen.eu/Martin_MTL
links added here as per forum custom!
I know you have another thread or two going and I hope you've gotten good advice and reassurance from those......asking Martin to meet beforehand at a nearby place may seem a bit cumbersome in this case.....I know that's suggested for utter unknowns with no reviews, but, in this case, Martin has a nice set of legit-appearing reviews at RM and a fairly longstanding profile.....should be ok just to show at his place....
yes, your envelope plan seems ok and you may want to assure him ahead of time that you'll do it that way......you don't have to make a big show of flashing the envelope and announcing it, but just leave it in plain sight......it is hoped that he won't try to upsell you in the middle of the meet when you're all hot and bothered!......usually not good to talk about money at the meet
if you've already made it clear that you like "BFE" and guys taking the lead, then you've done all you can about that!......it's up to them now......without sending too many giddy communications, you may want to ask them to go over your previous notes which include those requests.....limit the communications, though!.....perhaps mention it in a final reconfirmation the day before or in a reply to their reconfirmation.......

Consider this my annual gift to the Hooboy Committee on "Newbie Appreciation" …
https://rentmen.eu/Marcus_XL
https://rentmen.eu/Martin_MTL
https://rentmen.eu/alexhxl
https://rentmen.eu/AlexHunk
https://rentmen.eu/AdrianXL_Canada
https://rentmen.eu/MalaKhai
https://rentmen.eu/UptonSterling
 

I love THIS hotel. Centrally located with a young hip crowd who aren't going to be judging your choice of company.
.https://www.hotelmonville.com/en/

I had a great time with Marcus_XL.  I've also heard great things about AdrianXL but a threesome might be a bit much for a first hire.

Seen AlexHunk before with his BF. Good guy and good service. THat was preCOVID. Adrian XL duo are fantastic but you may want to start with just one of them. They deliver but are selective and careful about who they see.
May help to provide what you want in a session and from your hire...they help in providing feedback to you. Good luck and enjoy your first time. HOpe it's a good one!

I'm very curious about the "robot" service. And do any of those "thousand attentions" involve lips and tongue?

Rooms with King bed and view on Montreal, a robot to serve you and a team with a thousand attentions.

I can vouch for Alexhxl and think a couple of the others might be fine but I have only had communications with them and not able to set things up. Alex I did meet in the last year and found to be very engaging conversationally, friendly and presentable. Also very hot after we finished dinner and retired to my hotel room. I stayed at the Omni Mont Royal that time. Elevators are keyed but around corner from lobby and discreet to use.

Thanks for this, it looks great! Unfortunately, it looks like it is not available for part of my trip. Any other great hotels in the area?

It shouldn't be an issue in Montreal, especially with providers discussed favorably on this site.

Cute hotel.
Pity about the decorator’s dreadful rooftop choices though. 

Welcome to Company of Men. You are in the right place to ask questions and seek advice. 
I'm going to be direct and get to the point: Are you sure you are ready to do this?
Your post strikes me as being tinged with a sense that you are doing something shameful and wrong and will be punished for it. You aren't doing anything wrong or shameful and the likelihood of law enforcement running a male escort sting in a major US city is pretty low. Like near 0% probability. 
When I hired a guy for the first time (1996, I think - I was in my low 30's) I thought very hard about what it was I wanted and set out to get it. For me, I wanted to worship a guy's muscles, suck his dick, eat his ass, sniff and lick his armpits, kiss, and get each other off. So...I looked for providers who seemed to be into this, contacted them, expressed what I wanted, and asked if they were into a similar scene. This was pre-internet, so it was a bit of a challenge, but the approach worked. 
So, I'll ask you: what is it you are looking for? Is just a massage what you want or do you want more? This isn't about what you think you "should" do (there are no "shoulds" in this hobby), it's about what you desire to do. Also, are you looking for a regular provider with whom you can ease into what you want? If that's the case, then make sure the provider lives in the city in which you would hire him, else he won't be there the next time you want to see him.
My advice is to make a list of all the things you want to do with another man. Yes, a physical list. (You don't have to use pen and paper - MS Word or your favorite notepad app will do just fine.) Then, tick off the things you want to do on your first playdate. Lastly, when you identify guys who interest you state in your first message what you like/want to do and ask if they could get into them. Also, mention you are a first-time client and want to go slow. 
Having said all that, the most important piece of advice I can give you is "relax." 
 
 

welcome to the forum....we're here to help!........
https://www.companyofmen.org/topic/142802-etiquette-for-initial-communication/
https://www.companyofmen.org/topic/130365-caveats-in-hiring-please-contribute/
https://www.companyofmen.org/topic/83821-advice-for-a-newbie-please/
https://www.companyofmen.org/topic/103088-newbie-question/
https://www.companyofmen.org/topic/13389-recommendations-for-newbie/
 

I was with Marcus_XL last week and can vouch that he looks like his pics or better.  You can also be assured he's not entrapping you.

I remember having more of your nervousness when I was new to hiring.  I'll just throw out some ideas that will hopefully calm some of your anxiety:
There definitely aren't police stings in San Francisco for men hiring escorts online, assuming you don't go after someone who looks too young (and I don't even know if law enforcement is using their resources to address sex exploitation like that), so I really don't think there's a reason to be concerned with law enforcement here.  I cannot speak to the other cities you listed.
I think a far bigger concern would be to choose some shady character who attempts to harm/extort you.  Since you mention your career could be at risk if this came to light, it doesn't take law enforcement for your hiring to become public knowledge.  There have been previous threads here about providers who attempted to blackmail clients after having gotten personal information about them using their phone number, address, real name, etc.  I personally never worried about this because I didn't care if my family found out and don't think it would have impacted my job, but if you are in that position my recommendation is this: Stick to guys with a proven track record of providing services and getting positive reviews.  I'm not talking a few 5-star reviews on Rentmen, which can be manipulated quite easily by a shady alleged provider.  I'm talking about following forum advice and hiring guys who have a positive reputation amongst members here.
Now that I attempted to minimize your anxiety a bit, I will perhaps raise it with this somewhat scary tale from my past: I called a phone number in an escort ad on Craigslist 25 years or so ago and the number I called was answered "San Francisco Police Department."  I hung up.  I got a call back and got a "lecture" from someone saying I should be careful about what I was doing because I could get in trouble.  I don't think the call back was from the police.  I think some vigilante was just playing games and trying to scare people who were hiring escorts.