I'm curious how many trans women others have been with? I'm not at all looking to hear about conquests and braggadocio. I'm trying to find out what is the average amount session, dates, or times with trans that others experienced, before they felt they were at another level of understanding?  

     For example; after 5, 10 or 15 times with a trans, I no longer felt as nervous or I understood the terminology and no longer felt like a newbie and so on. This applies to trans you've dated in your private life and as providers.  

     Next how many times before you felt as comfortable with a trans as you did with a girlfriend, 30, 40 times? How long before you felt you could navigate the hobby, the trans scene publicly, most scenarios and situations without hang ups or bad scenes, 50-100? And so o,n and so on, at what point did you feel like you reached a new level of understanding with yourself and with trans in and out of the hobby...  

Good question. I've seen about 150 - 200 trans escorts overall in my 9 - 10 year span of seeing Trans escorts. Most of my bad sessions were early on. Mostly because I acted on impulse & was very shy/timid. Was afraid of potentially getting caught up in a honey pot scenario and getting caught by police. I also didn't bottom my first 2-3 years because I was super afraid of contracting HIV due to a condom breaking etc. But I'm much more sexually educated now & take the proper preventive measures.  

After about my first 30 - 40 sessions I started to get more comfortable & not be as nervous. Forums like this helped me a ton! Of all the trans escorts I've seen I would say about 20% I've been a regular customer to & seen multiple times. The majority of trans escorts I've only seen once or twice max. I like variety, I tend to get bored of seeing the same girls over & over, I hope that doesn't sound shallow but it's my preference.

I’ve seen about 45 escorts intermittently over 35-ish years, taking lengthy breaks while in a relationship.  I’ve dated about a half dozen trans women and a half dozen cross dressers.  Generally I bottom for escorts, top with girls I date.  

I'm still very new to the hobby.  I've never seen a provider until I got interested in trans women.  My first experience I was scared out of my mind (but that was part of the rush).  I just had my 5th encounter, and it was the best one yet.  I wasn't scared or even nervous, and it was a 10/10.  I'd say if it wasn't for TER and you wonderful hobbyists, I might have never taken the plunge.  I read everything you and the other experienced hobbyists have wrote and it helped me understand what to expect, what to watch out for, the terminology, preparing to be bottomed and how to avoid scams.

I'd say if you don't do any research, it's going to be steep learning curve.  But, if you prepare both mentally and physically, it can be one of the best experiences of your life.

Being with trans women really opened my mind up to more possibilities.  When I first got into trans porn I was all hung up on what does that mean.  Does it mean I'm gay?  After a while I just saw all the labels as bullshit.  Who fucking cares?  I'm into feminine chicks with dicks.  That's what turns me on and I don't care what that means or what labels anyone else wants to put on me.

In the 7 or so years I have been seeing TS providers, I have seen a few dozen different ladies.  

I have never seen one more than 15 times, yet, though there are a few traveling ladies that I repeat with, the numbers just have not gotten that high.

I have never been nervous.  Proper prep ahead of time goes a long way to being ready on game day.

I have not dated any trans ladies, though, I have overnighted with a handful and taken several out socially (dinner, concerts).

I use TS4 and TSE to identify possible ladies to meet up.  I was only ripped off once.  The only other disappointments have been from some of the heavily advertised, content-rich OF models that charge $$$$ per hour.  While the time with them was not terrible, I felt that a premium was being paid to just be in the presence of their celebrity.

If I am not comfortable with a lady after the first date, I do not see her again.  I am mindful of our professional relationship and, with very few exceptions (I dug out the snow from one lady's car this past winter), I keep to that.

I've seen many trans girls. When I first saw trans escorts, I was not really nervous because I had seen many Cis escorts and had also had sex with many men. The first time was kind of a 2 great tastes that taste great together moment for me. My proclivities (and abilities) have changed a lot as I've aged. I was all top when I started, but now I'm mostly bottom. I let other people do the work. Lol. In the last few years, I've met a few girls and developed a good business relationship with them. They bring me new girls, especially new arrivals from South America, and set up group (bukkake) sessions for me. I don't use the websites anymore and most of the girls I see are not escorts, but club girls who will escort on occasion or simply join their friend for some extra cash. It's been really good and I've pushed a lot of boundaries with the girls I know. I feel like I have a pretty good handle on how this business works at this point. It's hard to put timeframes on the "milestones" you asked about, but I think they're roughly in line with what you wrote.