Charlie

Video courtesy of @Danny-Darko

Some of us are born again virgins

Does that trick still work when you tell them you're a virgin on the 2nd visit? 😆 

I for one understand.  You’re in good company.

This is my exact thought.  I was hesitant to use the phrase, “training wheel,” because it may sound a bit abusive, condescending, or offensive to some.  I am glad to hear a provider describing it this way.  I can almost liken the relationship to that of having a personal trainer in the gym: he helps me to start the engine and once I feel comfortable enough, I will go out to drive on my own.
I guess it may be difficult for the majority to understand the minority — the middle-aged novice.  I bet most of you can’t even begin to imagine how tough it was for me to express myself anonymously here, let alone to place everything in real-life context.  To me, at the very least, the providers I met have helped me take the first steps to free myself from my psychological prison.

I couldn't disagree more with this. For those who are starting off a bit late, those who haven't found their way through using the bars or the apps. Escorts make great 'training wheels'. People are fucking mean on the apps. And let's be honest, bars aren't the places to meet new people that they were in decades past. Start on 'easy mode'. Gain confidence. Then do the platforms/bars/apps. 

As a client of 20+ yrs, I make a regular practice of telling mine just as they're about to stick it in. Almost always gets me an additional 10m on the house. 😂

It’s been 8 months since I started this thread and I realize it was resurrected recently.
I was a silent bystander on CoM for a long while before I summoned the courage one day to create an account to pose a question.  I did (still do) benefit from reading others’ Q&A so I feel somewhat obligated to answer my own questions to shed some light on the subject I created myself.
1.     I did end up telling all the providers I met about my (lack of) experiences beforehand.  I am extremely lucky in that they are all kind, understanding, and receptive professionals who accommodate my needs.  It is true that there isn’t anything they haven’t seen or heard before.  It was silly of me to think that they would be surprised by my full disclosures.
2.     All my appointments have been 2-hour long.  I am not the bang-bang, hit-and-run type — at least not yet (Who knows?  I may evolve into one eventually).  I still need the time to gradually ramp up the temperature.  So to me, 1 hour would be too rush and stressful.
3.     A few providers told me they never hosted for the 1st appointment to prevent letting psychopaths and serial killers/rapists into their homes, which is totally understandable.  They prefer to meet in a 3rd party location (e.g. hotel) to assess the sanity of the clients first.  Thus, in-call versus out-call is not necessarily the client's choice.
Lastly, I do sincerely appreciate everyone’s inputs here.  I even find the ones that appear to be sarcastic, bitter, or toxic somewhat amusing and eye-opening.  Thanks for your contributions.

Some people actually say in their posting that they like working with inexperienced people. And i bet they mean that, sincerely, and that they are fun and attentive as a result. 
 
but i dont think people will have aaaannny issue with it. Most likely itll be a major net positive. I would definitely bring it up thoug , especially if you plan to bottom at some point, be cause if youve never done so, i feel like its better for the top to ease into a bit because it takes some mental rewiring to not let all your muscles seize up on confusion lol

In an ideal world. But it's so hard ... and all the more so the older you are. I wish I had the courage when I was younger. I wish the world was more tolerant / accepting when I was younger.

To be clear, I am inexperienced in terms of great, recent, and/or anal experiences.  I had my share of neutral oral-only experiences back when I was more active, and was never really into anal (until now, which is why I’m trying to get more experience topping providers since I find bottoming uncomfortable and don’t want the rectal issues you mentioned).

That's probably true. But here's the ugly truth, experience brings forth the good and the bad. An inexperienced gay guy needs to get smart about the bad, so he can make better choices for himself.
I'm all for sexual exploration, but when we're talking about the extremes, I highly recommend an inexperienced guy does his research, like having a conversation with a gay doctor if you can find one (not easy). I have too many gay friends in my age circle (over 50) who are now experiencing serious health issues with their rectums. Some of these guys are in agony, and most people don't want to talk about this stuff. Be careful what you wish for.

Congratulations! Sounds great. Next time, try fisting. That’ll really open you up. 

Shorter version: Come out. The closet kills.

I had a similar exuberance after my first time, and in fact just this past week after an amazing encounter with a provider.  Those of us who are less experienced are also less desensitized.

Sounds a little too exuberant to me, but it's been a long time since I experienced a sexual first. Or maybe I'm just too old now to get overly excited about anything. When I hear someone mention "unlocking the gates of heaven," I think about death. Not a visit with Simon Suraci.

Just want to say that's the loveliest thing I've read in a long time.  Good for both of you.

Dear comrades,
I am the OP, but I have changed my username from lostlonelysoul.  Details below.
Thanks for all your recommendations.  I eventually booked a 2-hour session with @Simon Suraci.  I have been eyeing for him on both RM platforms for weeks even before I made my post.  But his home base (SD) is way too far from me.  So I gave up until I saw his travel location coincided with my business trip.  It was meant to be.
Let me start by saying that his ad/profile pics definitely do not do him justice.  He is 100X hotter in person.  You need to see him for yourself.  Per your suggestions, I originally made a massage appointment, but as soon as I told him what I truly desired, he did not hesitate to switch gear and led me to the bedroom.
Needless to say, I was consumed by stress and anxiety initially.  He had a magical way to put me at ease.  Aside from being handsome & sexy as hell, he’s intelligent, funny, and kind.  Before I knew it, I had my first kiss, my first embrace with a man, my first time touching another man’s naked body all over, and…… I’ll let your imagination run wild to fill in the blanks (many, many, many other blanks indeed).
I was (and kind of still is) in a euphoric state for days afterwards.  Luckily, I have no important deadlines or projects on hand; otherwise, I’ll be doomed, for that session was the only thing I could think of ever since.
@Simon Suraci exceeded every expectation I have for my first rendezvous and I am so glad I made the right choice for my many, many firsts.  I bet he will forget about me very soon, but I am 100% certain I will remember him for the rest of my life.  Frankly, that was one of the most memorable experiences I have ever had.  I'll surely pay close attention to his traveling schedule from now on.
Thank you all once again.
No longer lost; No longer lonely (even though still alone); My soul has been salvaged; The gate of heaven has been unlocked; Let the wild ride begin + continue

I did too. I was going to type "Get yourself to San Diego and hire @Simon Suraci.
As a matter of fact, after reading Simon's response above, I'm thinking of flying to San Diego and telling him I'm a virgin too!

Even if the thread is fake, it's fun and funny.
The Catholic Church would love you. Look at the good abstaining has done for them.
I don't know the age of the OP, but it may be really too late for all that life.
Good advice. I see lots of ads that say, "Great with inexperienced," or something like that. There will be a lot of guys who won't want to touch you. They won't respond to your inquiry. There may be just as many up for the challenge. No, one hour is not enough! Paid "dates" could be a ton of fun. When you meet the right guy, pay him to guide you through the process, and take it slow and easy. Don't worry about the cost. If you find the right guy, the cost will be worth the experience. Prepare to pay. Just don't fall in love with a provider.
At 14, I knew what I wanted and why, and I hadn't seen much porn, certainly not gay porn. My high school gym locker room and showers were enough angst for me.
Can't imagine the pain and loneliness of the closet. Can't imagine the pain of going through life without having experienced the joy of exploring sex. Yes, sex can make a horny man crazy, but I wouldn't want it any other way. Some of the best sex I ever had was crazy sex. Bring it on.

I agree with taking the massage route.  Learn how to accept touch before you escalate to more intimate encounters

Practical advice: if it's your first time bottoming, don't go for the XXL dicks (many of them Brazilians). If it looks like it could hurt you, it probably will.
Go for an L dick, friendly and approachable 

I am in a very similar position than OP. I am certainly not very experienced, but I offer this opinion, hoping that it might help OP and others in same or similar situations.

As an older virgin, or at least sexually-inexperienced guy, I assumed that I was missing out on 'sex'. Because I am uncomfortable with my sexuality (yes, I'm still stuck in that old-school way that I grew up in, but that's a different story), I only recently started allowing myself to experience intimacy with another human, and I did it in the gradual way of massage, sensual massage, erotic massage as many of the responses here suggest. It's been great to have physical contact with another human, but I understand now that this physical contact is really what I have been missing out on. Not 'sex' as such - we can satisfy that need on our own. But touch, connection, closeness is what we're missing. And while some providers are kind and supportive and empathetic, and can provide the illusion of these things, briefly, it is not real. It is, and remains transactional. (This is not a criticism to providers at all.)

And if you are lucky enough to find a provider that is kind and caring and supportive, and one who physically also enjoys your time together, there is the danger that you might interpret it as being more than just transactional: that you might think they could be truly interested in you as a friend, a human, a boyfriend maybe ... not just a customer.

I feel like I'm rambling a bit and I'm not really sure where I'm going with this ... but I just wanted to put it out there, for some context. I guess what I'm saying is don't hire someone because you think it will fulfill what you have been missing. I'm not saying don't hire ... I'm just saying that you should temper your expectations, be clear about what you want out of it ... and be clear about what you can actually get out of it. I have had some amazing massages / interactions, and I will continue to pursue those, but I have to remind myself that I should not confuse it for real human connection, that I should not misconstrue it for something it is not.